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Welcome to Calling Operator, [upbeat music] a podcast dialing into the stories of startup operators. Tune in as they share their incredible and often challenging journeys of building and scaling startups. Operator.
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Hello. It is Laura after a few weeks off the mic. My last episode published was Anna Prell at Aivo on October the 6th.
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That was my first day back at work since moving to Melbourne, and this episode with Kai Crow today was meant to publish on October the 21st. We are now over a month since that point.
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But yeah, I just needed a little bit more time settling into Melbourne, and I needed that, I guess, calibration time to settle into a new home, settle into new relationships and even work just from a new environment.
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So in my end of year wrap, I'll be bringing you some learnings and lessons from really breaking up from a country, i.e., New Zealand, where I lived for 12 years, to settling into an ecosystem where
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I feel like, oh, it's so exciting to be on the ground here, but it's pretty daunting to not have any friends and all of the above. Anyway, today is not about me.
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Today I am connecting with Kai Crow, who's customer operations and RevOps at Joyous, a Kiwi operator, and he's someone you've probably never heard of, and that's exactly the point.
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I would personally name Kai as one of my favorite humans in the Kiwi startup ecosystem. We've been connected since 2021, had many a conversation around building companies and I guess his vision for Joyous.
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But overall, he spent about 15 years building the invisible infrastructure that makes startups work. Some companies include Sonar Six, AskNicely, vmob, and now Joyous.
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At Joyous, he was the operator that turned off their entire marketing engine when he realized it wasn't working.
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He's built an AI outbound function from scratch, and he shifted the company from enterprise to product-led growth, and that journey continues today.
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But there's something that makes Kai different, and actually maybe not so different because I really resonate with this, but he's never wanted to be the founder.
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He's deliberately chosen to stay in the engine room, watching companies scale, living through acquisitions, seeing the full life cycle multiple times, and he keeps showing up to do the unglamorous work that makes everything else possible.
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Can you relate? I can relate. [chuckles] So it's funny when I'm like, "Oh, here's what makes him different," but actually here's what all makes us the same. Same, same, but different.
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But his CEO, Ruby Kalensky, told me something that really just hit me in the feels, and she said, "If it wasn't for Kai, I wouldn't be at Joyous." She describes their partnership as the reason the company moves so fast.
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They co-create side by side. He keeps everything calm when things get intense, and he's become what she calls a big light in her life.
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And I think that's a hell of a statement to come from a CEO about an operator in the business.
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And you could also see Kai as a bit of a right-hand/chief of staff/undefined chief of staff to Ruby in the business as he moves across marketing, customer, RevOps, and then I guess executive support.
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So this conversation today isn't about a hero's journey or a dramatic pivot. It's about the unsung heroes who are quite happy operating behind the scenes. I see you. You are seen. Enjoy the conversation.
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[static] Kai, welcome to Calling Operator. You are in a Joyous T-shirt, so I'd love to start off with what does being joyous mean to you?
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For me personally, like outside of the company goals, really about being part of the team. Everybody in Joyous is motivated by what we do as a business. There is no
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ego, there's no personal drive outside of trying to better ourselves and better the company. There's never somebody that says, "Oh, that's not in my role." It's sort of being willing to
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take up any challenge and do it enthusiastically and get joy out of doing it because you understand sort of how things fit into the greater purpose of the business.
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I hope everybody at the company feels in a similar way, and we all enjoy turning up to work and working with each other.
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That's really the big thing that's stuck with me and kept me at Joyous for, I think, going on seven years now, is the people, the team, the environment, and that sort of core mission of making life better for people at work.
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Nice. Help us get a feel for who is Kai outside of work. Like, who are you as a human before Joyous? Before Joyous, I've been in startups as far as my working life, uh, longer than I'd care to admit.
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[chuckles] Over ten years. My research tells me 15. That's probably right. [chuckles] When I first started in, in a, a startup, I don't think we even called them startups. It was just a, a new software company.
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Interesting. Outside of that, keen mountain biker, DIY-er, forever renovating our small beach bach- Oh, amazing... cum house. So you live in the beach bach? Yeah.
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It's a, a former beach bach that's been progressively renovated into a house. Not a big house, but... Awesome. That's all you need, a comfy little spot by the sea. Mm.
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Actually, it's funny that you say DIY because Ruby, who's the CEO of Joyous, she calls you DIY Kai, the [chuckles] the Swiss Army knife who can tackle anything.
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I spoke to one of your peers, Kyle, who says that you're the guy that will help get the boat back in water at 3:00 a.m.
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So I'd love to get to the crux and the depth of what is that origin story behind this whatever it takes and calm and steady approach that you bring to things? Yeah.
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So I guess also should note that I literally did help Kyle get his boat back in the water once. [laughs] But probably what he's talking about is more just being on call when needed.
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I've spent a lot of time working largely with teams based in the US or elsewhere in the world, and I wouldn't say I make a habit of getting up at 3:00 AM.
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[laughs] But sometimes I think you do need to recognize that you need to be flexible in these types of roles.
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I definitely don't feel like burnout culture and working around the clock is a healthy part of the startup culture that we do see in, in some areas.
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But at the same time, there definitely have been times where you sort of recognize you need to pull a few extra hours here and there and get up for things, but it's just keeping healthy boundaries in that.
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How do you keep healthy boundaries? Like when do you know when that line is from being helpful, doing whatever it takes to actually not being sustainable in your leadership? Hmm. It is difficult.
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I've definitely got that balance wrong at, at times in my career. To me, I think it's just weighing up the importance of things and being careful not to do the day-to-day stuff with that level of urgency.
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I think a company's a bit like a, a living organism in a way. Like it, it adapts and evolves and if you sort of set this expectation within the business that your capacity is 12, 15 hours a day,
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then very quickly that will become the norm and you kind of have to work at that rate to support it.
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Compared to sort of occasionally a project deadline, urgent requirement, something means you have to work a long day or work over the weekend or something like that. It's just
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making that call then, but knowing when to say no and when to just this will have to wait till tomorrow. Yeah. It takes experience to get to that point.
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Which talking about experience, so we now predict that you've got 15 years experience in tech [laughs] and in startup. So you've seen the full cycle from startup to acquisition multiple times.
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So some notable companies are Sonar Six, AskNicely, vMob. Is that how I say it? Yeah. vMob, now Plekure. Oh, okay. And then also Joyous. So I'd love for you to take us on this journey.
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What's that story of your career so far? I started out as a graphic designer, studied computer graphic design,
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spent a few years working in classic graphic design roles in a way, but even then, for me, I always had this sort of technology bent to me. Like I came from a, a family of scientists.
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I studied mainly science and mathematics at school and then went to design school. I sort of warmed naturally to like web design and interactive stuff at design school.
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And then early on in my career, sort of got more into web design and development a little bit. Started building early e-commerce sites, bespoke sites like that.
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Then took a year off, went over to Europe and, and raced mountain bikes for a season over there. Came back in the middle of the GFC and kind of had a, "Oh crap, what, what am I doing for work now?
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I've spent all my savings and then some." Started out contracting and picked up a bit of work for Sonar Six doing product design initially.
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So I took over as maternity leave cover for Karen Rayner, who I've worked with in almost every business since then as well. Started out designing the new version of the product and then it kind of went like,
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"Okay, we've built the product. We kind of need to market it now. Do you wanna stay around and do, do some of that?" I don't even know if we really had the conversation.
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It just sort of evolved from one thing to another, and I think that sort of technical lean to me really got involved when we started doing outbound marketing stuff.
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Back then, doing lead nurturing and, and what we would commonly regard as, as content marketing now was kind of a, a new thing. Like Marketo was the tool that we picked up and, and that was very new at that stage.
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I think there were one or two other customers in New Zealand. So sort of being able to not just go on that journey within the company, but within the industry as well.
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Everybody was learning at the same time and we were sort of able to test and figure things out. Marketing felt like it was highly effective at that stage. I mean, particularly in retrospect, like
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people were very happy to engage with digital content.
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There weren't many people putting out that sort of stuff, and what there was in the marketplace was very dull and boring, so we quickly created a, a point of difference and were able to be very successful in that.
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That instant gratification and, and satisfaction of seeing yourself making an impact really moved me into the, the marketing and operations piece.
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There's definitely like creative aspects to that, so I didn't feel like it was a complete departure from my creative background either. And then you stayed in marketing?
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Yeah, pretty much and, and then over time too, I think marketing has evolved into more that operational side of marketing and more support for sales team and CRM admin, RevOps type roles. Yeah.
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And you seem to have found your way in New Zealand at a time that the ecosystem has been really young here, but as part of much bigger orgs and you driving the New Zealand business. Is that correct? Yes.
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We did end up in that scenario at Sonar Six when we were purchased by Cornerstone OnDemand. Yeah. They were a thousand-person NASDAQ-listed company, bought Sonar Six.
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We became part of that business, and I think by the time I left they'd grown three times when we started in, in the space of about two years.
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That was a really interesting experience being, like you say, a, a small satellite of that. So we weren't even just the New Zealand business. They bought our product as a specific SMB target. Mm.
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So we became the SMB Cornerstone product. So we were sort of a regional team in that all of our engineers were based here, but our sales team, customer success team were all mostly based in the US.
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We had some regional sales and, and customer people based here.
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But for me, I was mainly working pe- with people in the, the US team, so whether it be the corporate marketing team or our division-specific sales and customer people.
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It was an interesting relationship too, because like the company had never acquired another business before either.
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So there was a lot of figuring out like the basics of integrating even from a brand perspective, like figuring out how you, you actually turn an existing product into one of your own.
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And systems, like we went through combining CRMs, moving all of our marketing to... So interestingly, their marketing platform was very young at that stage, whereas we had a much more mature system. So we actually moved
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the larger business into the smaller business from a- Interesting... a marketing ops perspective. But then the CRM, they had a, a massive sales team, like they were a sales-first business.
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So our CRM went the opposite direction, sort of merged into theirs. So then take me from the acquisition. What was the one or two lessons or key takeaways from that experience that then set you up for Ask Nicely?
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The basics were that understanding of how to build a scalable marketing system. I mean, that is something that I've taken everywhere to some degree.
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It doesn't directly translate obviously when you're selling, you know, like
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a SMB to mid-market sort of product at a much lower price point compared to Joist, we were selling enterprise-size deals that are, are much longer and slower. But that ethos of finding things we can automate,
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working with a small team and getting the most mileage we possibly can out of the people that we have and the resources that we have. Nice.
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So then I guess like you've learnt how to drive demand, you've learnt the content, learnt how to work on your content mix to drive demand.
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At this point in your journey, what does break versus what scales as companies grow? There's a lot of things that do break, I think.
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And one of the hardest things, and I think something that I've seen both in companies that I've worked in and, and worked with around the industry, is just recognizing when the time is to make those transitions.
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So in startup stage, you, you need people that can run fast, that can work across multiple projects, can be very multi-disciplined, turn their hand to anything.
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Whereas that type of person doesn't necessarily get fulfillment in a larger team, like, say, a, a customer success role. When you're also having to get in and like
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make database repairs or fill gaps in the product, process customer data and, and things like that, that's very different to a customer success role when you're dealing with a bunch of established accounts and just having to go through the mechanics of setting a regular meeting and
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checking usage metrics and identifying customers that are at risk. They're two quite different people. Some people can do both of those roles quite happily, but other people get bored at a point.
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I would say to an extent I enjoy the bigger part of scale, but history would prove that once we get to a certain size, that's when I move on. For me, it's always been just identifying
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when I don't feel like I'm adding maximum value, when I feel like, oh, you know, there's five other people here that could be doing this stuff. That's generally my point personally for looking to move on.
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The other thing from the outside looking in more is dev team structure. To a similar extent, like
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very agile team structures, and I don't mean agile in the agile structure sense, but the ability to be agile and work quickly is critical in the early stages of a business.
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But at some point, and it comes at different points depending on like how sensitive the data you're dealing with is, how mission-critical your product is, you just can't be that company forever.
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That is one of the big things that companies struggle with is, is making that transition to more structured architecture, better practices, better quality assurance, that sort of stuff. And it is one thing that
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impressed me early on at Joyous was how mature the company started. We started with really rigid structured processes, and we've managed to grow with that, but also maintain the ability to deliver really fast.
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And I think if anything that's evolved with time, like our, our ability to really iterate on things quickly and build small subsequent releases without breaking that sort of adherence to quality. Yeah.
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Which naturally takes us to Joyous. So you guys run very lean, so you're twenty-five people chasing a hundred mil in revenue. So in your opinion, when does it make sense to wear all the hats versus split them?
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'Cause you're currently wearing marketing, rev ops, customer success, and then also kind of playing a bit of a right-hand role to the CEO, Ruby. What's needed and where I can be most helpful.
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The big thing with the customer team to me is that's one piece where you can't stretch too hard. Anything that's gonna have a direct impact on customers, you need those people to be able to pick up things quickly.
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If they're constantly running in a state of panic, that is going to reflect somehow on your customers.
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If it's not in like a catastrophic failure, it could be just in like not having energy or not showing up to meetings, not proactively working on
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getting engagement with the product, those sort of things that you really want a customer team to be involved with.
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For me, personally, understanding when I need more help is what you're talking about, like when we should be passing stuff off to someone. It's a hard thing 'cause I quite like to be involved in a lot of things.
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But historically, it's been identifying if I'm starting to drop things or like early signs of burnout, trying to look for those and actually be proactive about saying, "We need help with this."
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Then there's a more forward-looking piece, which I think is also identifying where you could bring other people in, where there's expertise that we don't have.
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I think that's something that we've been good at in Joyous, is identifying those opportunities to bring the right new people into the team at the right time.
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And what are those systems that you've built to allow you to stay small by design? There's a lot of stuff that our engineering team have built in the product in recent times. So like
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working really closely with the customer team, understanding what are the manual pieces of work they are doing, what are the manual pieces of work that our customers are having to do, and building that into the product, sort of classic SaaS stuff of let the product do the work.
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From my side in the, the rev ops type role, it's good old-fashioned CRM type stuff, but really trying to find that balance between automating things, but not going too heavy.
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We actually try from a, a CRM perspective to keep things relatively simple. We use HubSpot. We
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had gone a long way in sort of customizing, like building a whole lot of processes and custom objects that represented our unique sales process.
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And we've actually pared that back quite a way, more just in recognizing that having good use of the tool with a little bit less data in there is better than sporadic use
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and all of the data structure, but- No data [laughs]... not enough going in there to be useful. Yeah. Yeah. Nice.
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And then before we go on to some of the projects that you've been working on, Ruby says, if it wasn't for you, she wouldn't be at Joyous.
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She names you as a big light in her life, and I'd love to break down this CEO partnership mechanic between you both, 'cause you've got such a great working relationship.
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It sounds like from her side, you really do run at projects together. So for anyone listening, how have you structured that partnership with the CEO?
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We really do just work as a, a mini team on a lot of stuff and, and that's kind of come from a broader cultural thing in, in Joyous of these sort of sub-teams.
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So like I've had at times people in the customer team working on customer operations type stuff with me.
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But in the partnership with Ruby, a lot of that is we're sort of the marketing team, the design team, the web team, any of those really public facing pieces, and it's so important and something that's often missing in, in companies,
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is that direct connection from the CEO into the public messaging piece.
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Like too often it's CEOs focused on like more the operations type stuff and maybe like high, high level strategic vision, but not on translating that strategic vision into
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your core positioning and go-to market messaging. Whereas Ruby's been a hundred percent involved in driving that, helping evolve that. Our messaging has been through several evolutions over the last few years,
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and we just wouldn't be in the place- We are now, if we didn't have that high-level strategic involvement and the grassroots marketing involvement combined together, I don't think.
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For my sort of side of the input into that, it just makes my job so much easier and more enjoyable when kind of understand where we're going and on part of that journey.
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Where if you're sort of just taking direction from above and trying to build a marketing strategy, particularly if it's around a sort of messaging or a focus that isn't necessarily what reflects
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what you're seeing in the market or what your sales team are telling you, you quite often end up in this tension between CEO strategy and sales engagement.
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Like you've got a sales team telling you one thing and the CEO telling you quite a different perspective on, on what the market says.
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And if you're trying to be that go-between, one, it takes a lot of mental energy, and two, you can end up just going round in circles or doing something in between that
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kind of doesn't upset anybody, but doesn't please anybody. It's a whole heap of time-wasting. Yeah. Yeah.
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So say an operator's listening today, and that's not the case, like you say it's not the case in most companies, what's one or two steps that they can take to have the CEO more ingrained in those pieces of work?
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I mean, get- getting the right CEO. [laughs] Yeah. [laughs] That's probably not the, the easy answer in a lot of cases.
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I think another critical part to that, I was sort of alluding to being stuck in between the, the CEO and sales, is also having that close engagement between the CEO and sales as well,
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and thinking retrospectively where I've seen that problem, just encouraging the CEO to get more involved.
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Sales is an easy point to start with that, and then you can sort of progress to that more strategic messaging architecture type side from there probably.
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I sort of jokingly say, get a better CEO, but a lot of that comes down to the right type of person. Like, not everybody is good at working on more marketing type material. So I guess
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it's also about understanding strengths and weaknesses and not trying to make somebody something that they're, they're not necessarily, but figuring out how you can best work in partnership with that person. So like
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rather than continuing to butt up against the pieces that aren't working, like figure out the pieces of the, the relationship that are working
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and figure out how you can make those stronger and the rest of the teamwork will happen as, as a result.
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I see, and that comes with a CEO being very self-aware or being open to feedback as well because there will just be some gaps that you just can't fill, but that's okay also.
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Everyone doesn't need to be an expert in everything, but at least like how are we as a business gonna like fill some of these gaps so that we can have this nice synergy happening.
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Yeah, and the biggest piece to that is the humility part. Like there's the other end of the spectrum of, of a CEO who gets involved in everything- Yeah, like Crow. [laughs]... but very one way.
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So being open to understanding what the people reporting to them understand about their parts of the business,
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being able to take that on and help work that into a strategy rather than just telling those people a strategy. Yeah, definitely. Well, let's dive into a piece of work that you're working on at the moment.
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So Joyous has shifted from enterprise to a product-led growth motion, so I'd love to hear more about this, and my first question is gonna be, as part of this, you turn the tap off on traditional marketing, and I wanna hear that story.
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What actually impacted Joyous during that decision? What broke? What didn't? Yeah.
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So as far as the traditional marketing piece, there was a little bit of moving too fast down a tried and tested content marketing approach early on.
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I mean, that's probably partly on, on me, but there are a bunch of us that have done that before. We know how to scale a marketing system, and we kind of went through the standard playbook.
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And I wouldn't say it was completely ineffective, but we were certainly struck by a few things that were happening in the market at the same time. So we were sort of starting to head into some financial crunches.
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We saw with COVID, like massive stress on, on workforces and then on company balance sheets,
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and we were very specifically targeting HR people at that point, and HR people are great to market to still. Like they still engage highly with content.
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They're easy to identify in the business, so you can build lists, you can define your target well, and you can write content for them.
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But what we saw and like we kind of recognized this having worked through the GFC at Sonar Six, HR are unfortunately one of the first departments that get their budgets squeezed when things get tough.
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So we, we started seeing an element of that playing out. Our product was getting more and more strategically driven in terms of, like, the types of feedback we were getting.
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So we moved out of the HR vertical and sort of employee engagement and more into operational type stuff. So like feedback that relates to a particular role in a particular department or a particular project.
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So the people we were targeting were further up the company chain.
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So we're, we're targeting large enterprise businesses and targeting people in the C-suite or VPs or owners of a large part of the business, like a, a field services team.
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And those people are just getting harder and harder to engage with typical marketing content. Like they don't download things. A lot of them have EAs who, if they're gonna download anything, it would go to the EA.
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Their phone will go to an EA, so you're not gonna cold call them. And that was where we really started to see more classic relationship-based sales being effective.
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That was really what started the transition to basically turning off all of that marketing activity.
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You know, it was maybe useful from a brand visibility perspective, but we had very little to back that up, and at the same time, we, we were trying to be as lean as possible from our own budget point of view.
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So we made the decision to focus on the pieces where we were getting the most engagement, and that was those really high-level
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personal introductions at the sort of buyer level in the company rather than trying to work our way up. [radio beeping] I have a quick ask.
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This show is all about creating space for tech operators and learning how to be a better operator along the way.
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Please help me reach the builders, doers, and multipliers behind great founders by hitting subscribe or follow wherever you're listening. Thank you.
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[radio beeping] We should actually probably explain what Joyus is as well. Essentially, we're an employee feedback platform, but we
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break from the traditional use of feedback in terms of being very employee engagement focused and really focus on actionable feedback on very specific topics.
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So if you're running a field services team of tens of thousands of techs who are going out installing fiber in people's homes around the US, those people are working with new tools, new technologies all the time.
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You might roll out a, a new piece of equipment that they are working with, and you need to know what are the problems with that piece of equipment.
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Traditionally, that would sort of filter back through area managers or team managers, then area managers and group managers, and as a leader you would get some very dilute
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form of that feedback possibly coming back to you in, in several months' time. Or you might run like a, a focus group or go and do ride-alongs with your people to get little pieces of feedback.
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But what we do is go out to all of those people via text or whatever messaging channel works for them and ask a couple of simple questions. Takes them five minutes to respond. Open text feedback.
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Then we analyze all that, look for common themes,
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pull out specifically stuff that's actionable, and give you a, a summary of all of the actionable suggestions that your people have made so that you can actually go, "Yes, yes, yes. That's stuff we can easily do.
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We can make an impact through that." And
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usually what we end up with is a much faster time to solving a problem or identifying problems that you wouldn't have even known existed, and therefore creating large efficiency gains or savings through that sort of feedback.
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Awesome. Thank you. I should point out, too, we do broad feedback, so not just employees. Was kind of where we started was employee and now can be customers, stakeholders, et cetera.
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It's another big shift that we've made. Yeah. Great. So we've spoken slightly about turning traditional marketing off. Nothing really seemed to break. So then how has AI had an impact?
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For us, it's helping us a lot in building marketing systems and taking some of that operational type stuff off our plates and just making it easier to scale back up again.
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We've steered clear of AI-generated content.
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That's one thing that is really important and, and another piece that I'm working really closely with, with Ruby and also Mike, who's one of the co-founders, on generating really high-quality content that we can use
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to then be distributed by tools that are powered by AI rather than dropping an article brief in GPT and having it spit out an article when we publish, like, fifteen articles a week.
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Because that sort of stuff, we're just seeing everybody do that, and there's just such a saturation of really low-quality content out there, and we see that as a point of differentiation.
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And early signs are there, there is a payback on- Quality content when it comes to the converse side of that is AI models recognizing your content, repeating that, and surfacing it to their users.
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The indications are that better quality human-curated content performs much better with AIs, ironically, than AI-generated content.
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It's about identifying the pieces where AI can make us stronger versus, like, the pieces where it sort of almost becomes something in between humans, like, if that makes sense.
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Oh my goodness, I'm so, so staunch on having just a whole portfolio of, like, amazingly written content crafted by a human, and then, yeah, like, using AI as your distribution play.
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But on this, so anyone listening who is considering building an AI outbound marketing function, what's worked for you? What hasn't? Do you have any le- early lessons? I know it's early, but do you have anything to share?
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I am quite bullish on Clay as a system, and just as a paradigm for AI tools. I'm not sure if you've used it, or for anybody that hasn't. Yeah, actually, one of our portfolio companies is the disruptor to Clay.
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They're called Freckle. So very familiar with Clay, but just from through that angle. Yeah. To me, just the paradigm of, like, a, a spreadsheet that you can run things through and have AI-driven
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cells or columns or, or, like, pull other things into it, it's such a good way of working with an AI.
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And one of the big learnings I've had just from talking to other people and some initial stuff that I've run through it is, like, the benefit just in general of having an AI check itself.
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So, like, you build a step to do this, then you pull the data out, then you run another prompt to evaluate that data that it gave against what the original objective is,
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and possibly have a human intervention in between as, as well if you need to. To me, that sort of approach of a, a spreadsheet is just like,
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it's kind of a natural interface between people and machines, and I quite like that because despite working,
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or maybe because of working for so long in tech businesses, I have a very low trust factor of computers, [chuckles] and particularly AIs.
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I think that's just an important piece of building it into a workflow that, like, helps us, not replaces us. Totally. I'm just laughing because both of our dogs are just, like, doing loops beside us.
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[laughs] Zephyr's decided right now is the time to be itching. Um, [laughs]
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so anything else that you want to pull out from this shift from enterprise to product-led growth that either you're really excited about or actually maybe is even a challenge that you're trying to overcome?
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Well, I think the whole thing's a challenge. [chuckles] That's part of what is exciting to me is just figuring out what's gonna work. There's a lot of room for experimentation.
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I still think it's gonna be very interesting to see where we are in six, 12, 18 months' time in a broader digital environment perspective. What are LLMs gonna do and agent interfaces gonna do to the buying journey?
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Will we see potentially people buying Joyous or Joyous campaigns completely through an agent? I don't know. I think there is a, a good chance that we end up in that sort of environment.
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There's a really strong possibility that we see some sort of agent operating system, browser transformation that could be, you know,
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in the near horizon that could completely change the way we interact with AIs again. And that has a huge potential to disrupt us. But I also see that a lot of the core pieces of marketing
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will still be important and, and be effective, like clear messaging, engaging content, point of difference, brand personality.
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They're all things that people have been working on building since Don Draper's era or, [chuckles] you know, since John Deere put out the Furrow magazine in 1930 or something.
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I think we will see that sort of stuff and, like, more particularly really human content like
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podcasts, in-person events, things like that coming back to the fore in marketing as all of this machine-based stuff just saturates us with online content.
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So for me, it's like figuring out where to place our bets. Again, figuring out how we can help our team scale with smart use of AI, but not trying to replace those human relationships with AI.
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I'm really hesitant to get into the sort of AI agent SDR-type pieces.
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We may experiment with that stuff, but to me, the point of a salesperson is to have that personal engagement, build that relationship that it is harder to say no to them because you've built this personal rapport.
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If they're just answering questions, maybe they don't need to be there. But so far, it's not about that. It's about building a connection with people and understanding what their challenges are.
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What drives them as a person in their business and being able to use that to hopefully drive a sale. Mm-hmm. How do you make decisions as a leader? Like, do you use a framework? Like, how are you working out,
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I guess, going through that process of making a decision on where to place those bets? No specific framework personally. I guess just weighing up all the opportunities.
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I think getting too wound up in where things might go is a danger, and it's certainly something that I struggle with a bit as, like, a fairly analytical person,
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and is also something that's good in, in our relationship with Ruby is that she really helps me, like, "Go. Do this." Then I bring in the analytical piece so that, like, once we've done the thing, we can
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understand whether the thing was effective and looking for opportunities where we can make evidence-based decisions without too much commitment.
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'Cause that is a challenging thing with marketing, particularly in an enterprise space, is that, like, you know, you could go and drop $50,000 on a, a sponsorship of
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one piece of content in a major publication or, like, $100,000 on an event and have very little indication as to whether that works on a one-off.
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Like, you might see the outcome of it after five or six of those things, but then you've blown your entire marketing budget. And if you've committed to those things and they haven't worked, you're kind of screwed.
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Definitely. And you said something there about you and Ruby thinking differently, which is what makes your partnership so complimentary.
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But if you had to think about an edge or a blind spot that you're still working on within your growth and to get wherever you're wanting to get to in your career, what would you say it was? I definitely have a few.
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Leading and scaling a team is certainly still a, a challenge, even just from the mental energy perspective. It's probably quite typical for people who are
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technical leaning that I find, you know, the most challenging is often the people relationship piece. But at the same time, it's something that I really enjoy.
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Like, that is, like I said at the start, one of the key things in Joist or in, in any team to me is that engagement with other people.
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So sort of figuring out how to be a better leader of people as opposed to just leading a strategy or a project. And- I want your phone list. [laughs] It is also a challenge of, of often working in fairly small teams.
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Probably the largest team I've led was when I was running the, the mountain bike club. So I guess part of the territory of being in small business is in one of the smaller teams in the business.
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And it's just like shifting your mindset to being your success is judged on other people's success and, like, how they're delivering their work, which is, like, such an interesting shift to think through. Yeah.
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I always thought I'm a doer, like, I like to be hands-on with stuff, and I previously have thought I don't really get motivated by facilitating the success of other people necessarily.
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But I, I think that's completely untrue because my success being part of their success is kind of...
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So, like, the outcome of the things I'm doing, helping other people, you know, like I, I think I said at the start, taking the stuff off their plate to make them able to do their job and the pieces they're good at and they enjoy,
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that's what really motivates me. So it is, in a way, that motivation of other people's success, it's just a different input to that. And on the flip side, what would you say your superpower is?
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The broad skill set is, what are you, T-shaped people- Yeah... is it- T-shaped... they like to call us now? I think just actually being happy and applying myself to a lot of things. I enjoy really technical stuff.
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I enjoy creative stuff. So it's being able to have the energy to do all those different things that I think has made me useful in the roles I've been in. 100%.
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I really see your skill set, especially because you're delivering ops from end to end really to support these different functions from pre-sales to post-sales.
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I really see you well-placed to be this AI orchestrator within your role.
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Like, whether it's people or agents you're briefing to and overseeing, I think you've got such a special skill set in that area and something that I'm really keen to watch how that evolves for you.
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So we'll check back in a year. I'll be like, "Where you at?" [laughs] And then I also really love that you are embedded in the New Zealand startup ecosystem.
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So where do you think New Zealand as a whole and as an ecosystem is heading? It's just amazing to see, particularly in the last few years, how much the New Zealand tech ecosystem's grown.
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We work in Futurehouse in Auckland, which is a deep tech startup hub. It's inspiring to see how much of that sort of outside of just software development there is going on in, in the New Zealand ecosystem.
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But, like, the growth in, in different funds that are now available, it used to be,
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yeah, you could get early-stage funding from pretty much Icehouse, and that was it locally, and then anything beyond That you usually had to go overseas, whereas like there are so many more options and so much more depth to the industry now.
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I just see it becoming more of a strength for the country. Do you feel supported from like a functional marketing/operator lens?
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Do you think there's enough happening in the ecosystem for the people working inside the startups?
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There probably could always be more, but I do think, particularly thinking from that marketing and, and rev ops point of view, like it used to be a very lonely place.
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You would struggle to find other people using similar tools or doing similar things, largely because a lot of startups will have marketing and sales functions offshore.
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But now there is plenty of people doing similar things in, in New Zealand that I can sort of go along to a user group or a Kiss My SaaS event or a Marketing Jam. There's a ton of events happening.
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So it's getting to the stage that you can just like pick up the phone and say, "I want to learn from how you've done this" to help shortcut your own learning. How exciting.
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Obviously, I'm down in Queenstown, so I don't see any of this because Queenstown's not really a tech hub, so I'm excited for you Aucklanders and for the ecosystem as a whole, even though I am about to vacate, but I will definitely be watching New Zealand very closely.
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So we're at the stage in the podcast where we're going to do a quick-fire round, and then I'm going to give you your day back. Okay. You've got 100 things that could be done, five people to do them. How do you choose?
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I tend to like to do the hardest things first, so figure out what's going to break us and then do the easy bits. But I know that's probably not always the right answer.
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[laughs] The challenge is we also like try and ship stuff fast too, and sometimes doing the big problems can get in the way of that. Kyle wants to know what's with the Post-It Note tagging system.
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[laughs] That was, uh, an internal joke that started after I, I left the apartment we had in Portland at the, near the AskNicely offices,
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and I might have left some notes for them around the apartment, maybe a few hundred of them. Um- [laughs] Amazing... I don't normally use Post-It Notes in my everyday life, though. My desk is usually very clean.
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You're like, "But I went out especially, even got a Sharpie." Yeah. [laughs] And Ruby wants to know the taco story. I think we should just say that you should be very careful what you say on a hot mic.
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[laughs] Ruby, take note, take note. Maybe leave it at that. Yeah, perfect. So a book, framework, or tool you swear by. Tools, I would have to say Zapier and Notion. Yeah.
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Anything that helps make it easy to start systemizing stuff, and Notion in particular has been great for us at Joist in terms of just being able to really quickly spin up a, a database or a process or something that can then later be transformed potentially into something more structured.
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Awesome. One to three leaders you admire, and why. I really struggle with this, so I'm, I'm gonna give a, a really bad non-answer and say all of them and none of them. [laughs] I try not to get too wound up in like
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idolizing a person.
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I know that's not what it means necessarily, but I think we do get a lot of potential in the startup ecosystem to sort of like idolize past successes and put a lot of weight on, on what other people have done.
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But at the same time, I just have the biggest amount of admiration for every person that builds a, a business and leads a company, 'cause like
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it's something, despite being around the industry, I've, I've not done myself and like it would scare the crap out of me to think about doing. Mm.
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I really like that point of view, and it kind of keeps you away from the noise as well, right? Yeah. Like I am trying to do more in terms of- Right...
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reading and listening to what other people are doing because you have to learn from what other people have done, but that propensity to like distill stuff down into like the one thing I did that changed my business sort of articles and content, and I've fallen into that trap too, like telling people, you know, about building a scalable content system and how that will solve all of your problems, and you just got to take everything with a grain of salt, right?
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Like take on board what you can and keep it in perspective and relative to your company and, and your stage. Yeah, totally.
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Well, talking about advice, what's a piece of advice that you've received over your career or in life that you'd love to pass on?
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I always go back to a, a friend of mine, and this was a really random non-work-related thing, but he was asked what, what his objective in life was, and he just replied with, "To have more fun than everybody else."
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So good. And I just thought that was such a great ethos to have, and without having thought of it myself, summarized my position. Okay, that's our objective for the week. And lastly, who would you like to hear from?
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Who should I get on the podcast next? Puhan Nathan. I worked with him at AskNicely, and he, I believe, is still at Whiparound currently, also formerly Pushpay.
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He's really been through the trenches of finance ops, setting up a business in the States to operate through and all that sort of stuff. He would be quite an interesting talk, and he's really good.
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Also, have you talked to anyone from Kami? No. They have a really interesting story. Bob Drummond was COO there. I worked with him at vMob. He might be an interesting conversation.
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[static] I love to end the podcast with a little mental wellness tip. So what's one mindset or daily practice that helps you stay grounded within the chaos of building and scaling companies?
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One thing for me, I never skip lunch and never eat lunch at my desk. So always just make sure I have some time away from the computer, and that probably extends to just like,
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you know, smaller breaks, like taking a moment to walk around the office if I'm in the office or
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wander out into the garden if I'm working at home and, you know, like a little bit of time to decompress, even if it's only five minutes. Awesome. I think that's hugely important.
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Yeah, and compounding, like it has a compounding impact on your week and month and year. Awesome. Kai, thank you so much for joining me today. Where can people connect with you after listening to your podcast?
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Probably LinkedIn is the best channel. And that's a wrap. Today's episode was recorded by me, your host, Laura Nickel, with original music composed by Stephen Shelton.
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If you enjoyed this episode, please give us a follow, and we'll see you next time. [outro music]
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Welcome to Calling Operator, [upbeat music] a podcast dialing into the stories of startup operators. Tune in as they share their incredible and often challenging journeys of building and scaling startups. Operator.
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Hello. It is Laura after a few weeks off the mic. My last episode published was Anna Prell at Aivo on October the 6th.
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That was my first day back at work since moving to Melbourne, and this episode with Kai Crow today was meant to publish on October the 21st. We are now over a month since that point.
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But yeah, I just needed a little bit more time settling into Melbourne, and I needed that, I guess, calibration time to settle into a new home, settle into new relationships and even work just from a new environment.
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So in my end of year wrap, I'll be bringing you some learnings and lessons from really breaking up from a country, i.e., New Zealand, where I lived for 12 years, to settling into an ecosystem where
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I feel like, oh, it's so exciting to be on the ground here, but it's pretty daunting to not have any friends and all of the above. Anyway, today is not about me.
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Today I am connecting with Kai Crow, who's customer operations and RevOps at Joyous, a Kiwi operator, and he's someone you've probably never heard of, and that's exactly the point.
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I would personally name Kai as one of my favorite humans in the Kiwi startup ecosystem. We've been connected since 2021, had many a conversation around building companies and I guess his vision for Joyous.
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But overall, he spent about 15 years building the invisible infrastructure that makes startups work. Some companies include Sonar Six, AskNicely, vmob, and now Joyous.
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At Joyous, he was the operator that turned off their entire marketing engine when he realized it wasn't working.
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He's built an AI outbound function from scratch, and he shifted the company from enterprise to product-led growth, and that journey continues today.
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But there's something that makes Kai different, and actually maybe not so different because I really resonate with this, but he's never wanted to be the founder.
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He's deliberately chosen to stay in the engine room, watching companies scale, living through acquisitions, seeing the full life cycle multiple times, and he keeps showing up to do the unglamorous work that makes everything else possible.
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Can you relate? I can relate. [chuckles] So it's funny when I'm like, "Oh, here's what makes him different," but actually here's what all makes us the same. Same, same, but different.
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But his CEO, Ruby Kalensky, told me something that really just hit me in the feels, and she said, "If it wasn't for Kai, I wouldn't be at Joyous." She describes their partnership as the reason the company moves so fast.
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They co-create side by side. He keeps everything calm when things get intense, and he's become what she calls a big light in her life.
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And I think that's a hell of a statement to come from a CEO about an operator in the business.
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And you could also see Kai as a bit of a right-hand/chief of staff/undefined chief of staff to Ruby in the business as he moves across marketing, customer, RevOps, and then I guess executive support.
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So this conversation today isn't about a hero's journey or a dramatic pivot. It's about the unsung heroes who are quite happy operating behind the scenes. I see you. You are seen. Enjoy the conversation.
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[static] Kai, welcome to Calling Operator. You are in a Joyous T-shirt, so I'd love to start off with what does being joyous mean to you?
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For me personally, like outside of the company goals, really about being part of the team. Everybody in Joyous is motivated by what we do as a business. There is no
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ego, there's no personal drive outside of trying to better ourselves and better the company. There's never somebody that says, "Oh, that's not in my role." It's sort of being willing to
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take up any challenge and do it enthusiastically and get joy out of doing it because you understand sort of how things fit into the greater purpose of the business.
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I hope everybody at the company feels in a similar way, and we all enjoy turning up to work and working with each other.
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That's really the big thing that's stuck with me and kept me at Joyous for, I think, going on seven years now, is the people, the team, the environment, and that sort of core mission of making life better for people at work.
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Nice. Help us get a feel for who is Kai outside of work. Like, who are you as a human before Joyous? Before Joyous, I've been in startups as far as my working life, uh, longer than I'd care to admit.
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[chuckles] Over ten years. My research tells me 15. That's probably right. [chuckles] When I first started in, in a, a startup, I don't think we even called them startups. It was just a, a new software company.
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Interesting. Outside of that, keen mountain biker, DIY-er, forever renovating our small beach bach- Oh, amazing... cum house. So you live in the beach bach? Yeah.
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It's a, a former beach bach that's been progressively renovated into a house. Not a big house, but... Awesome. That's all you need, a comfy little spot by the sea. Mm.
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Actually, it's funny that you say DIY because Ruby, who's the CEO of Joyous, she calls you DIY Kai, the [chuckles] the Swiss Army knife who can tackle anything.
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I spoke to one of your peers, Kyle, who says that you're the guy that will help get the boat back in water at 3:00 a.m.
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So I'd love to get to the crux and the depth of what is that origin story behind this whatever it takes and calm and steady approach that you bring to things? Yeah.
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So I guess also should note that I literally did help Kyle get his boat back in the water once. [laughs] But probably what he's talking about is more just being on call when needed.
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I've spent a lot of time working largely with teams based in the US or elsewhere in the world, and I wouldn't say I make a habit of getting up at 3:00 AM.
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[laughs] But sometimes I think you do need to recognize that you need to be flexible in these types of roles.
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I definitely don't feel like burnout culture and working around the clock is a healthy part of the startup culture that we do see in, in some areas.
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But at the same time, there definitely have been times where you sort of recognize you need to pull a few extra hours here and there and get up for things, but it's just keeping healthy boundaries in that.
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How do you keep healthy boundaries? Like when do you know when that line is from being helpful, doing whatever it takes to actually not being sustainable in your leadership? Hmm. It is difficult.
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I've definitely got that balance wrong at, at times in my career. To me, I think it's just weighing up the importance of things and being careful not to do the day-to-day stuff with that level of urgency.
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I think a company's a bit like a, a living organism in a way. Like it, it adapts and evolves and if you sort of set this expectation within the business that your capacity is 12, 15 hours a day,
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then very quickly that will become the norm and you kind of have to work at that rate to support it.
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Compared to sort of occasionally a project deadline, urgent requirement, something means you have to work a long day or work over the weekend or something like that. It's just
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making that call then, but knowing when to say no and when to just this will have to wait till tomorrow. Yeah. It takes experience to get to that point.
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Which talking about experience, so we now predict that you've got 15 years experience in tech [laughs] and in startup. So you've seen the full cycle from startup to acquisition multiple times.
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So some notable companies are Sonar Six, AskNicely, vMob. Is that how I say it? Yeah. vMob, now Plekure. Oh, okay. And then also Joyous. So I'd love for you to take us on this journey.
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What's that story of your career so far? I started out as a graphic designer, studied computer graphic design,
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spent a few years working in classic graphic design roles in a way, but even then, for me, I always had this sort of technology bent to me. Like I came from a, a family of scientists.
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I studied mainly science and mathematics at school and then went to design school. I sort of warmed naturally to like web design and interactive stuff at design school.
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And then early on in my career, sort of got more into web design and development a little bit. Started building early e-commerce sites, bespoke sites like that.
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Then took a year off, went over to Europe and, and raced mountain bikes for a season over there. Came back in the middle of the GFC and kind of had a, "Oh crap, what, what am I doing for work now?
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I've spent all my savings and then some." Started out contracting and picked up a bit of work for Sonar Six doing product design initially.
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So I took over as maternity leave cover for Karen Rayner, who I've worked with in almost every business since then as well. Started out designing the new version of the product and then it kind of went like,
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"Okay, we've built the product. We kind of need to market it now. Do you wanna stay around and do, do some of that?" I don't even know if we really had the conversation.
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It just sort of evolved from one thing to another, and I think that sort of technical lean to me really got involved when we started doing outbound marketing stuff.
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Back then, doing lead nurturing and, and what we would commonly regard as, as content marketing now was kind of a, a new thing. Like Marketo was the tool that we picked up and, and that was very new at that stage.
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I think there were one or two other customers in New Zealand. So sort of being able to not just go on that journey within the company, but within the industry as well.
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Everybody was learning at the same time and we were sort of able to test and figure things out. Marketing felt like it was highly effective at that stage. I mean, particularly in retrospect, like
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people were very happy to engage with digital content.
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There weren't many people putting out that sort of stuff, and what there was in the marketplace was very dull and boring, so we quickly created a, a point of difference and were able to be very successful in that.
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That instant gratification and, and satisfaction of seeing yourself making an impact really moved me into the, the marketing and operations piece.
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There's definitely like creative aspects to that, so I didn't feel like it was a complete departure from my creative background either. And then you stayed in marketing?
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Yeah, pretty much and, and then over time too, I think marketing has evolved into more that operational side of marketing and more support for sales team and CRM admin, RevOps type roles. Yeah.
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And you seem to have found your way in New Zealand at a time that the ecosystem has been really young here, but as part of much bigger orgs and you driving the New Zealand business. Is that correct? Yes.
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We did end up in that scenario at Sonar Six when we were purchased by Cornerstone OnDemand. Yeah. They were a thousand-person NASDAQ-listed company, bought Sonar Six.
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We became part of that business, and I think by the time I left they'd grown three times when we started in, in the space of about two years.
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That was a really interesting experience being, like you say, a, a small satellite of that. So we weren't even just the New Zealand business. They bought our product as a specific SMB target. Mm.
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So we became the SMB Cornerstone product. So we were sort of a regional team in that all of our engineers were based here, but our sales team, customer success team were all mostly based in the US.
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We had some regional sales and, and customer people based here.
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But for me, I was mainly working pe- with people in the, the US team, so whether it be the corporate marketing team or our division-specific sales and customer people.
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It was an interesting relationship too, because like the company had never acquired another business before either.
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So there was a lot of figuring out like the basics of integrating even from a brand perspective, like figuring out how you, you actually turn an existing product into one of your own.
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And systems, like we went through combining CRMs, moving all of our marketing to... So interestingly, their marketing platform was very young at that stage, whereas we had a much more mature system. So we actually moved
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the larger business into the smaller business from a- Interesting... a marketing ops perspective. But then the CRM, they had a, a massive sales team, like they were a sales-first business.
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So our CRM went the opposite direction, sort of merged into theirs. So then take me from the acquisition. What was the one or two lessons or key takeaways from that experience that then set you up for Ask Nicely?
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The basics were that understanding of how to build a scalable marketing system. I mean, that is something that I've taken everywhere to some degree.
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It doesn't directly translate obviously when you're selling, you know, like
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a SMB to mid-market sort of product at a much lower price point compared to Joist, we were selling enterprise-size deals that are, are much longer and slower. But that ethos of finding things we can automate,
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working with a small team and getting the most mileage we possibly can out of the people that we have and the resources that we have. Nice.
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So then I guess like you've learnt how to drive demand, you've learnt the content, learnt how to work on your content mix to drive demand.
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At this point in your journey, what does break versus what scales as companies grow? There's a lot of things that do break, I think.
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And one of the hardest things, and I think something that I've seen both in companies that I've worked in and, and worked with around the industry, is just recognizing when the time is to make those transitions.
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So in startup stage, you, you need people that can run fast, that can work across multiple projects, can be very multi-disciplined, turn their hand to anything.
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Whereas that type of person doesn't necessarily get fulfillment in a larger team, like, say, a, a customer success role. When you're also having to get in and like
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make database repairs or fill gaps in the product, process customer data and, and things like that, that's very different to a customer success role when you're dealing with a bunch of established accounts and just having to go through the mechanics of setting a regular meeting and
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checking usage metrics and identifying customers that are at risk. They're two quite different people. Some people can do both of those roles quite happily, but other people get bored at a point.
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I would say to an extent I enjoy the bigger part of scale, but history would prove that once we get to a certain size, that's when I move on. For me, it's always been just identifying
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when I don't feel like I'm adding maximum value, when I feel like, oh, you know, there's five other people here that could be doing this stuff. That's generally my point personally for looking to move on.
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The other thing from the outside looking in more is dev team structure. To a similar extent, like
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very agile team structures, and I don't mean agile in the agile structure sense, but the ability to be agile and work quickly is critical in the early stages of a business.
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But at some point, and it comes at different points depending on like how sensitive the data you're dealing with is, how mission-critical your product is, you just can't be that company forever.
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That is one of the big things that companies struggle with is, is making that transition to more structured architecture, better practices, better quality assurance, that sort of stuff. And it is one thing that
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impressed me early on at Joyous was how mature the company started. We started with really rigid structured processes, and we've managed to grow with that, but also maintain the ability to deliver really fast.
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And I think if anything that's evolved with time, like our, our ability to really iterate on things quickly and build small subsequent releases without breaking that sort of adherence to quality. Yeah.
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Which naturally takes us to Joyous. So you guys run very lean, so you're twenty-five people chasing a hundred mil in revenue. So in your opinion, when does it make sense to wear all the hats versus split them?
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'Cause you're currently wearing marketing, rev ops, customer success, and then also kind of playing a bit of a right-hand role to the CEO, Ruby. What's needed and where I can be most helpful.
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The big thing with the customer team to me is that's one piece where you can't stretch too hard. Anything that's gonna have a direct impact on customers, you need those people to be able to pick up things quickly.
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If they're constantly running in a state of panic, that is going to reflect somehow on your customers.
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If it's not in like a catastrophic failure, it could be just in like not having energy or not showing up to meetings, not proactively working on
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getting engagement with the product, those sort of things that you really want a customer team to be involved with.
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For me, personally, understanding when I need more help is what you're talking about, like when we should be passing stuff off to someone. It's a hard thing 'cause I quite like to be involved in a lot of things.
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But historically, it's been identifying if I'm starting to drop things or like early signs of burnout, trying to look for those and actually be proactive about saying, "We need help with this."
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Then there's a more forward-looking piece, which I think is also identifying where you could bring other people in, where there's expertise that we don't have.
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I think that's something that we've been good at in Joyous, is identifying those opportunities to bring the right new people into the team at the right time.
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And what are those systems that you've built to allow you to stay small by design? There's a lot of stuff that our engineering team have built in the product in recent times. So like
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working really closely with the customer team, understanding what are the manual pieces of work they are doing, what are the manual pieces of work that our customers are having to do, and building that into the product, sort of classic SaaS stuff of let the product do the work.
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From my side in the, the rev ops type role, it's good old-fashioned CRM type stuff, but really trying to find that balance between automating things, but not going too heavy.
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We actually try from a, a CRM perspective to keep things relatively simple. We use HubSpot. We
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had gone a long way in sort of customizing, like building a whole lot of processes and custom objects that represented our unique sales process.
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And we've actually pared that back quite a way, more just in recognizing that having good use of the tool with a little bit less data in there is better than sporadic use
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and all of the data structure, but- No data [laughs]... not enough going in there to be useful. Yeah. Yeah. Nice.
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And then before we go on to some of the projects that you've been working on, Ruby says, if it wasn't for you, she wouldn't be at Joyous.
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She names you as a big light in her life, and I'd love to break down this CEO partnership mechanic between you both, 'cause you've got such a great working relationship.
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It sounds like from her side, you really do run at projects together. So for anyone listening, how have you structured that partnership with the CEO?
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We really do just work as a, a mini team on a lot of stuff and, and that's kind of come from a broader cultural thing in, in Joyous of these sort of sub-teams.
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So like I've had at times people in the customer team working on customer operations type stuff with me.
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But in the partnership with Ruby, a lot of that is we're sort of the marketing team, the design team, the web team, any of those really public facing pieces, and it's so important and something that's often missing in, in companies,
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is that direct connection from the CEO into the public messaging piece.
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Like too often it's CEOs focused on like more the operations type stuff and maybe like high, high level strategic vision, but not on translating that strategic vision into
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your core positioning and go-to market messaging. Whereas Ruby's been a hundred percent involved in driving that, helping evolve that. Our messaging has been through several evolutions over the last few years,
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and we just wouldn't be in the place- We are now, if we didn't have that high-level strategic involvement and the grassroots marketing involvement combined together, I don't think.
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For my sort of side of the input into that, it just makes my job so much easier and more enjoyable when kind of understand where we're going and on part of that journey.
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Where if you're sort of just taking direction from above and trying to build a marketing strategy, particularly if it's around a sort of messaging or a focus that isn't necessarily what reflects
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what you're seeing in the market or what your sales team are telling you, you quite often end up in this tension between CEO strategy and sales engagement.
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Like you've got a sales team telling you one thing and the CEO telling you quite a different perspective on, on what the market says.
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And if you're trying to be that go-between, one, it takes a lot of mental energy, and two, you can end up just going round in circles or doing something in between that
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kind of doesn't upset anybody, but doesn't please anybody. It's a whole heap of time-wasting. Yeah. Yeah.
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So say an operator's listening today, and that's not the case, like you say it's not the case in most companies, what's one or two steps that they can take to have the CEO more ingrained in those pieces of work?
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I mean, get- getting the right CEO. [laughs] Yeah. [laughs] That's probably not the, the easy answer in a lot of cases.
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I think another critical part to that, I was sort of alluding to being stuck in between the, the CEO and sales, is also having that close engagement between the CEO and sales as well,
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and thinking retrospectively where I've seen that problem, just encouraging the CEO to get more involved.
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Sales is an easy point to start with that, and then you can sort of progress to that more strategic messaging architecture type side from there probably.
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I sort of jokingly say, get a better CEO, but a lot of that comes down to the right type of person. Like, not everybody is good at working on more marketing type material. So I guess
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it's also about understanding strengths and weaknesses and not trying to make somebody something that they're, they're not necessarily, but figuring out how you can best work in partnership with that person. So like
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rather than continuing to butt up against the pieces that aren't working, like figure out the pieces of the, the relationship that are working
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and figure out how you can make those stronger and the rest of the teamwork will happen as, as a result.
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I see, and that comes with a CEO being very self-aware or being open to feedback as well because there will just be some gaps that you just can't fill, but that's okay also.
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Everyone doesn't need to be an expert in everything, but at least like how are we as a business gonna like fill some of these gaps so that we can have this nice synergy happening.
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Yeah, and the biggest piece to that is the humility part. Like there's the other end of the spectrum of, of a CEO who gets involved in everything- Yeah, like Crow. [laughs]... but very one way.
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So being open to understanding what the people reporting to them understand about their parts of the business,
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being able to take that on and help work that into a strategy rather than just telling those people a strategy. Yeah, definitely. Well, let's dive into a piece of work that you're working on at the moment.
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So Joyous has shifted from enterprise to a product-led growth motion, so I'd love to hear more about this, and my first question is gonna be, as part of this, you turn the tap off on traditional marketing, and I wanna hear that story.
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What actually impacted Joyous during that decision? What broke? What didn't? Yeah.
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So as far as the traditional marketing piece, there was a little bit of moving too fast down a tried and tested content marketing approach early on.
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I mean, that's probably partly on, on me, but there are a bunch of us that have done that before. We know how to scale a marketing system, and we kind of went through the standard playbook.
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And I wouldn't say it was completely ineffective, but we were certainly struck by a few things that were happening in the market at the same time. So we were sort of starting to head into some financial crunches.
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We saw with COVID, like massive stress on, on workforces and then on company balance sheets,
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and we were very specifically targeting HR people at that point, and HR people are great to market to still. Like they still engage highly with content.
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They're easy to identify in the business, so you can build lists, you can define your target well, and you can write content for them.
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But what we saw and like we kind of recognized this having worked through the GFC at Sonar Six, HR are unfortunately one of the first departments that get their budgets squeezed when things get tough.
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So we, we started seeing an element of that playing out. Our product was getting more and more strategically driven in terms of, like, the types of feedback we were getting.
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So we moved out of the HR vertical and sort of employee engagement and more into operational type stuff. So like feedback that relates to a particular role in a particular department or a particular project.
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So the people we were targeting were further up the company chain.
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So we're, we're targeting large enterprise businesses and targeting people in the C-suite or VPs or owners of a large part of the business, like a, a field services team.
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And those people are just getting harder and harder to engage with typical marketing content. Like they don't download things. A lot of them have EAs who, if they're gonna download anything, it would go to the EA.
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Their phone will go to an EA, so you're not gonna cold call them. And that was where we really started to see more classic relationship-based sales being effective.
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That was really what started the transition to basically turning off all of that marketing activity.
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You know, it was maybe useful from a brand visibility perspective, but we had very little to back that up, and at the same time, we, we were trying to be as lean as possible from our own budget point of view.
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So we made the decision to focus on the pieces where we were getting the most engagement, and that was those really high-level
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personal introductions at the sort of buyer level in the company rather than trying to work our way up. [radio beeping] I have a quick ask.
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This show is all about creating space for tech operators and learning how to be a better operator along the way.
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Please help me reach the builders, doers, and multipliers behind great founders by hitting subscribe or follow wherever you're listening. Thank you.
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[radio beeping] We should actually probably explain what Joyus is as well. Essentially, we're an employee feedback platform, but we
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break from the traditional use of feedback in terms of being very employee engagement focused and really focus on actionable feedback on very specific topics.
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So if you're running a field services team of tens of thousands of techs who are going out installing fiber in people's homes around the US, those people are working with new tools, new technologies all the time.
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You might roll out a, a new piece of equipment that they are working with, and you need to know what are the problems with that piece of equipment.
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Traditionally, that would sort of filter back through area managers or team managers, then area managers and group managers, and as a leader you would get some very dilute
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form of that feedback possibly coming back to you in, in several months' time. Or you might run like a, a focus group or go and do ride-alongs with your people to get little pieces of feedback.
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But what we do is go out to all of those people via text or whatever messaging channel works for them and ask a couple of simple questions. Takes them five minutes to respond. Open text feedback.
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Then we analyze all that, look for common themes,
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pull out specifically stuff that's actionable, and give you a, a summary of all of the actionable suggestions that your people have made so that you can actually go, "Yes, yes, yes. That's stuff we can easily do.
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We can make an impact through that." And
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usually what we end up with is a much faster time to solving a problem or identifying problems that you wouldn't have even known existed, and therefore creating large efficiency gains or savings through that sort of feedback.
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Awesome. Thank you. I should point out, too, we do broad feedback, so not just employees. Was kind of where we started was employee and now can be customers, stakeholders, et cetera.
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It's another big shift that we've made. Yeah. Great. So we've spoken slightly about turning traditional marketing off. Nothing really seemed to break. So then how has AI had an impact?
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For us, it's helping us a lot in building marketing systems and taking some of that operational type stuff off our plates and just making it easier to scale back up again.
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We've steered clear of AI-generated content.
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That's one thing that is really important and, and another piece that I'm working really closely with, with Ruby and also Mike, who's one of the co-founders, on generating really high-quality content that we can use
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to then be distributed by tools that are powered by AI rather than dropping an article brief in GPT and having it spit out an article when we publish, like, fifteen articles a week.
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Because that sort of stuff, we're just seeing everybody do that, and there's just such a saturation of really low-quality content out there, and we see that as a point of differentiation.
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And early signs are there, there is a payback on- Quality content when it comes to the converse side of that is AI models recognizing your content, repeating that, and surfacing it to their users.
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The indications are that better quality human-curated content performs much better with AIs, ironically, than AI-generated content.
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It's about identifying the pieces where AI can make us stronger versus, like, the pieces where it sort of almost becomes something in between humans, like, if that makes sense.
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Oh my goodness, I'm so, so staunch on having just a whole portfolio of, like, amazingly written content crafted by a human, and then, yeah, like, using AI as your distribution play.
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But on this, so anyone listening who is considering building an AI outbound marketing function, what's worked for you? What hasn't? Do you have any le- early lessons? I know it's early, but do you have anything to share?
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I am quite bullish on Clay as a system, and just as a paradigm for AI tools. I'm not sure if you've used it, or for anybody that hasn't. Yeah, actually, one of our portfolio companies is the disruptor to Clay.
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They're called Freckle. So very familiar with Clay, but just from through that angle. Yeah. To me, just the paradigm of, like, a, a spreadsheet that you can run things through and have AI-driven
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cells or columns or, or, like, pull other things into it, it's such a good way of working with an AI.
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And one of the big learnings I've had just from talking to other people and some initial stuff that I've run through it is, like, the benefit just in general of having an AI check itself.
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So, like, you build a step to do this, then you pull the data out, then you run another prompt to evaluate that data that it gave against what the original objective is,
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and possibly have a human intervention in between as, as well if you need to. To me, that sort of approach of a, a spreadsheet is just like,
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it's kind of a natural interface between people and machines, and I quite like that because despite working,
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or maybe because of working for so long in tech businesses, I have a very low trust factor of computers, [chuckles] and particularly AIs.
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I think that's just an important piece of building it into a workflow that, like, helps us, not replaces us. Totally. I'm just laughing because both of our dogs are just, like, doing loops beside us.
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[laughs] Zephyr's decided right now is the time to be itching. Um, [laughs]
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so anything else that you want to pull out from this shift from enterprise to product-led growth that either you're really excited about or actually maybe is even a challenge that you're trying to overcome?
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Well, I think the whole thing's a challenge. [chuckles] That's part of what is exciting to me is just figuring out what's gonna work. There's a lot of room for experimentation.
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I still think it's gonna be very interesting to see where we are in six, 12, 18 months' time in a broader digital environment perspective. What are LLMs gonna do and agent interfaces gonna do to the buying journey?
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Will we see potentially people buying Joyous or Joyous campaigns completely through an agent? I don't know. I think there is a, a good chance that we end up in that sort of environment.
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There's a really strong possibility that we see some sort of agent operating system, browser transformation that could be, you know,
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in the near horizon that could completely change the way we interact with AIs again. And that has a huge potential to disrupt us. But I also see that a lot of the core pieces of marketing
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will still be important and, and be effective, like clear messaging, engaging content, point of difference, brand personality.
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They're all things that people have been working on building since Don Draper's era or, [chuckles] you know, since John Deere put out the Furrow magazine in 1930 or something.
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I think we will see that sort of stuff and, like, more particularly really human content like
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podcasts, in-person events, things like that coming back to the fore in marketing as all of this machine-based stuff just saturates us with online content.
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So for me, it's like figuring out where to place our bets. Again, figuring out how we can help our team scale with smart use of AI, but not trying to replace those human relationships with AI.
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I'm really hesitant to get into the sort of AI agent SDR-type pieces.
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We may experiment with that stuff, but to me, the point of a salesperson is to have that personal engagement, build that relationship that it is harder to say no to them because you've built this personal rapport.
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If they're just answering questions, maybe they don't need to be there. But so far, it's not about that. It's about building a connection with people and understanding what their challenges are.
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What drives them as a person in their business and being able to use that to hopefully drive a sale. Mm-hmm. How do you make decisions as a leader? Like, do you use a framework? Like, how are you working out,
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I guess, going through that process of making a decision on where to place those bets? No specific framework personally. I guess just weighing up all the opportunities.
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I think getting too wound up in where things might go is a danger, and it's certainly something that I struggle with a bit as, like, a fairly analytical person,
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and is also something that's good in, in our relationship with Ruby is that she really helps me, like, "Go. Do this." Then I bring in the analytical piece so that, like, once we've done the thing, we can
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understand whether the thing was effective and looking for opportunities where we can make evidence-based decisions without too much commitment.
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'Cause that is a challenging thing with marketing, particularly in an enterprise space, is that, like, you know, you could go and drop $50,000 on a, a sponsorship of
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one piece of content in a major publication or, like, $100,000 on an event and have very little indication as to whether that works on a one-off.
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Like, you might see the outcome of it after five or six of those things, but then you've blown your entire marketing budget. And if you've committed to those things and they haven't worked, you're kind of screwed.
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Definitely. And you said something there about you and Ruby thinking differently, which is what makes your partnership so complimentary.
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But if you had to think about an edge or a blind spot that you're still working on within your growth and to get wherever you're wanting to get to in your career, what would you say it was? I definitely have a few.
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Leading and scaling a team is certainly still a, a challenge, even just from the mental energy perspective. It's probably quite typical for people who are
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technical leaning that I find, you know, the most challenging is often the people relationship piece. But at the same time, it's something that I really enjoy.
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Like, that is, like I said at the start, one of the key things in Joist or in, in any team to me is that engagement with other people.
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So sort of figuring out how to be a better leader of people as opposed to just leading a strategy or a project. And- I want your phone list. [laughs] It is also a challenge of, of often working in fairly small teams.
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Probably the largest team I've led was when I was running the, the mountain bike club. So I guess part of the territory of being in small business is in one of the smaller teams in the business.
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And it's just like shifting your mindset to being your success is judged on other people's success and, like, how they're delivering their work, which is, like, such an interesting shift to think through. Yeah.
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I always thought I'm a doer, like, I like to be hands-on with stuff, and I previously have thought I don't really get motivated by facilitating the success of other people necessarily.
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But I, I think that's completely untrue because my success being part of their success is kind of...
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So, like, the outcome of the things I'm doing, helping other people, you know, like I, I think I said at the start, taking the stuff off their plate to make them able to do their job and the pieces they're good at and they enjoy,
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that's what really motivates me. So it is, in a way, that motivation of other people's success, it's just a different input to that. And on the flip side, what would you say your superpower is?
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The broad skill set is, what are you, T-shaped people- Yeah... is it- T-shaped... they like to call us now? I think just actually being happy and applying myself to a lot of things. I enjoy really technical stuff.
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I enjoy creative stuff. So it's being able to have the energy to do all those different things that I think has made me useful in the roles I've been in. 100%.
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I really see your skill set, especially because you're delivering ops from end to end really to support these different functions from pre-sales to post-sales.
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I really see you well-placed to be this AI orchestrator within your role.
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Like, whether it's people or agents you're briefing to and overseeing, I think you've got such a special skill set in that area and something that I'm really keen to watch how that evolves for you.
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So we'll check back in a year. I'll be like, "Where you at?" [laughs] And then I also really love that you are embedded in the New Zealand startup ecosystem.
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So where do you think New Zealand as a whole and as an ecosystem is heading? It's just amazing to see, particularly in the last few years, how much the New Zealand tech ecosystem's grown.
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We work in Futurehouse in Auckland, which is a deep tech startup hub. It's inspiring to see how much of that sort of outside of just software development there is going on in, in the New Zealand ecosystem.
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But, like, the growth in, in different funds that are now available, it used to be,
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yeah, you could get early-stage funding from pretty much Icehouse, and that was it locally, and then anything beyond That you usually had to go overseas, whereas like there are so many more options and so much more depth to the industry now.
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I just see it becoming more of a strength for the country. Do you feel supported from like a functional marketing/operator lens?
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Do you think there's enough happening in the ecosystem for the people working inside the startups?
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There probably could always be more, but I do think, particularly thinking from that marketing and, and rev ops point of view, like it used to be a very lonely place.
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You would struggle to find other people using similar tools or doing similar things, largely because a lot of startups will have marketing and sales functions offshore.
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But now there is plenty of people doing similar things in, in New Zealand that I can sort of go along to a user group or a Kiss My SaaS event or a Marketing Jam. There's a ton of events happening.
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So it's getting to the stage that you can just like pick up the phone and say, "I want to learn from how you've done this" to help shortcut your own learning. How exciting.
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Obviously, I'm down in Queenstown, so I don't see any of this because Queenstown's not really a tech hub, so I'm excited for you Aucklanders and for the ecosystem as a whole, even though I am about to vacate, but I will definitely be watching New Zealand very closely.
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So we're at the stage in the podcast where we're going to do a quick-fire round, and then I'm going to give you your day back. Okay. You've got 100 things that could be done, five people to do them. How do you choose?
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I tend to like to do the hardest things first, so figure out what's going to break us and then do the easy bits. But I know that's probably not always the right answer.
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[laughs] The challenge is we also like try and ship stuff fast too, and sometimes doing the big problems can get in the way of that. Kyle wants to know what's with the Post-It Note tagging system.
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[laughs] That was, uh, an internal joke that started after I, I left the apartment we had in Portland at the, near the AskNicely offices,
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and I might have left some notes for them around the apartment, maybe a few hundred of them. Um- [laughs] Amazing... I don't normally use Post-It Notes in my everyday life, though. My desk is usually very clean.
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You're like, "But I went out especially, even got a Sharpie." Yeah. [laughs] And Ruby wants to know the taco story. I think we should just say that you should be very careful what you say on a hot mic.
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[laughs] Ruby, take note, take note. Maybe leave it at that. Yeah, perfect. So a book, framework, or tool you swear by. Tools, I would have to say Zapier and Notion. Yeah.
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Anything that helps make it easy to start systemizing stuff, and Notion in particular has been great for us at Joist in terms of just being able to really quickly spin up a, a database or a process or something that can then later be transformed potentially into something more structured.
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Awesome. One to three leaders you admire, and why. I really struggle with this, so I'm, I'm gonna give a, a really bad non-answer and say all of them and none of them. [laughs] I try not to get too wound up in like
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idolizing a person.
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I know that's not what it means necessarily, but I think we do get a lot of potential in the startup ecosystem to sort of like idolize past successes and put a lot of weight on, on what other people have done.
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But at the same time, I just have the biggest amount of admiration for every person that builds a, a business and leads a company, 'cause like
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it's something, despite being around the industry, I've, I've not done myself and like it would scare the crap out of me to think about doing. Mm.
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I really like that point of view, and it kind of keeps you away from the noise as well, right? Yeah. Like I am trying to do more in terms of- Right...
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reading and listening to what other people are doing because you have to learn from what other people have done, but that propensity to like distill stuff down into like the one thing I did that changed my business sort of articles and content, and I've fallen into that trap too, like telling people, you know, about building a scalable content system and how that will solve all of your problems, and you just got to take everything with a grain of salt, right?
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Like take on board what you can and keep it in perspective and relative to your company and, and your stage. Yeah, totally.
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Well, talking about advice, what's a piece of advice that you've received over your career or in life that you'd love to pass on?
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I always go back to a, a friend of mine, and this was a really random non-work-related thing, but he was asked what, what his objective in life was, and he just replied with, "To have more fun than everybody else."
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So good. And I just thought that was such a great ethos to have, and without having thought of it myself, summarized my position. Okay, that's our objective for the week. And lastly, who would you like to hear from?
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Who should I get on the podcast next? Puhan Nathan. I worked with him at AskNicely, and he, I believe, is still at Whiparound currently, also formerly Pushpay.
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He's really been through the trenches of finance ops, setting up a business in the States to operate through and all that sort of stuff. He would be quite an interesting talk, and he's really good.
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Also, have you talked to anyone from Kami? No. They have a really interesting story. Bob Drummond was COO there. I worked with him at vMob. He might be an interesting conversation.
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[static] I love to end the podcast with a little mental wellness tip. So what's one mindset or daily practice that helps you stay grounded within the chaos of building and scaling companies?
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One thing for me, I never skip lunch and never eat lunch at my desk. So always just make sure I have some time away from the computer, and that probably extends to just like,
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you know, smaller breaks, like taking a moment to walk around the office if I'm in the office or
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wander out into the garden if I'm working at home and, you know, like a little bit of time to decompress, even if it's only five minutes. Awesome. I think that's hugely important.
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Yeah, and compounding, like it has a compounding impact on your week and month and year. Awesome. Kai, thank you so much for joining me today. Where can people connect with you after listening to your podcast?
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Probably LinkedIn is the best channel. And that's a wrap. Today's episode was recorded by me, your host, Laura Nickel, with original music composed by Stephen Shelton.
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If you enjoyed this episode, please give us a follow, and we'll see you next time. [outro music]
