Simon Rohrbach: Thank so much for having me. Appreciate it.
Andy Budd: ⁓ Thank you for coming on. I say, we chatted briefly when you were sort of delivery a few times, but we haven't spoken since. So I'd love to kind of dive into some of the sort of the founding story of Plane. But just for anyone that hasn't come across Plane yet, can you just give us a quick intro, what it does, who it does it for, what it's about?
Simon Rohrbach: Yeah, sure. So we are a B2B support platform fundamentally ⁓ built to help you power customers support wherever you talk to your customers, right? So we help our customers talk to their customers on channels like Slack, Microsoft Teams, email, chat, ⁓ forums, Discord, you name it. And fundamentally what we do is we help our customers solve three problems. Firstly, we help them talk to their customers wherever they are. Second, we help them scale the number of customers they can speak to without having to scale their accounts. We help them get more efficient with their own AI agents and also lots of just AI powered workflows. And third, we help them understand what their customers are actually telling them at scale, right? Because I really believe that customer support is your link to your customers. And so it has a very kind of unique position where it can really help you understand what are people actually asking of you. Other than just getting in touch about like say a refund or like a bug report, how many bug reports are you getting each week? ⁓ What feature requests do people have of you? What's making them happy about your product? What's making them unhappy? So we help people with that as well. So these are three problems that we solve and we now do this with lots of different customers from all over the world. So we work with companies like Cursor, Roussel, Eniden, Ashby, Granola ⁓ and many, many others. So a really good set of companies that we're very, very excited to be partnering with.
Andy Budd: I think that's an excellently crafted pitch. I'm sure you've done it like, you know, so many times it's off by heart now, but that's a really good, I think everyone gets a really good understanding of what it is that Plane does. But I'd like to start just by having sort of taking you back a little bit. So like I said, when we met you were leading designer at Deliveroo. It was a fast growing company. The team was sort of scaling really quickly. At what point did you decide that you wanted to move out of working for somebody and starting your own tech business?
Simon Rohrbach: I'll Yeah, I think it's something that I've always sort of been wanting to do, had sort of been a bit of like a burning fire inside of me to kind of like try my hand at. know, previously, before I joined Deliveroo, I was running my own like very, very small design consultancy for a while and really enjoyed that. But ultimately ended up joining Deliveroo because I was like, really want to see how this is done with almost like, know, learning from someone else and sort of... See a company grow around me. So I sort of I know how it's done and Joined Delibroo when I was, know, 10 people was the first designer there first higher in tech saw the company grow to 2,000 people actually 3,000 people of which 1,000 was customer support by the time I left five years later and In that process ended up building and leading the design team Content research and design which by the time I left was around 40 people 45 people And so kind of like felt like, you know, I'd sort of seen that journey and was very grateful to almost had, have gotten this MBA that was being paid for in terms of like how to build a business and what that looks like. And took like a few months out to kind of like just recharge and recover because it was a fairly intense experience. I was like, okay, like what do want to do now? And I sort of felt like, okay, the options in front of me were either
Andy Budd: Hehehe.
Simon Rohrbach: to sort of go and do something like this again. So to join a company and be a designer there and lead a design team or something like that. Or it was to maybe expand my skillset and sort of, and actually kind of now not only build the product, which is what I've been doing, but also build a company. And it always felt very strongly that the skill set of a designer,
Andy Budd: Hmm.
Simon Rohrbach: actually translates really nicely ⁓ to building a company because fundamentally as a designer, ⁓ the essence of what you're doing is you're building systems and fundamentally solving pixel problems ⁓ for people. And in building company, ⁓ you're also building but you're solving people problems. You're building a system of people to build really good pixels. ⁓ So ⁓ almost kind of like reversing sort of the order ⁓ and I'd sort of found that dynamic really interesting. So was like, okay, ⁓ where I go and do that? ⁓ Ended joining Index Ventures for a year, ⁓ which one of the first investors ⁓ at was mentor and residence there like other VC firms called us ⁓ executive residence where ⁓ your basically is to ⁓ help the portfolio companies with building product, building teams ⁓ and on. Did that for a year and by the end of that was like, actually I think now I feel like I have the energy and I have the idea, more importantly, to go and do this. reconnected with somebody who joined my team at Deliveroo, his name was Matt Wagner, and we'd always stayed in touch and got along really well. He was a designer engineer on my team, had transitioned into engineering actually after leaving Deliveroo. And we always wanted to do something together, we didn't know what it was. we sort of connected over this idea ⁓ doing something ⁓ ultimately ended up starting playing together so that's kind of how playing came to be.
Andy Budd: I mean, that's a wonderful story. Like going from being the founding designer to scaling a team, I think you're absolutely right. It would have been easy for you to, you you would have been incredibly in demand to go to dozens of other companies and repeating the same story and plenty of people we know have done that. They've made a career out of scaling teams from one or five to 50 or a hundred or whatever. So that would have been easy, but I love the idea of like, I've done that. Why would I do that again? I'm wanting to learn something new. It sounds like the time in VC was probably quite interesting as well because it gave you a little bit of a view from the other side of the, I guess, the window or the curtain. So what was that year like? What were you doing there? Were you advising other companies? Were you also kind of starting to play with your idea for Plane or did Plane come completely after your time index?
Simon Rohrbach: Yeah, sort of all overlapped really nicely. fundamentally I spending my days doing was ⁓ meeting lots of companies in the index portfolio and ⁓ helping them with was on their minds in the product domain. ⁓ Sometimes that was hey, I think we need to build much more of a product or design discipline there. We need to help with that. Sometimes it was as simple as a one hour conversation with a founder around, I'm hiring a design leader. What should I look for? What does it look like? Help me calibrate on what the job should be, what it shouldn't be. And that would be that, right? Like just one hour conversation. Or it be like a bit more of sustained engagement of just like helping a company through shifting the part of strategy or refocusing some of their teams onto like different problems. or figuring out what's good operating model for a product team at a certain stage or certain scale. So it was a really nice range of different problems and it was really interesting see it from the outside looking in because on one hand what's really nice is you're able to stay intellectually really engaged and you're able to solve lots of different problems across your desk every single day. So you learn a lot and you build pattern recognition, I think, very, quickly. And at the same time, you also still have very, you know, current knowledge from like having run a team yourself. So you kind of know what the other side of that conversation looks like internally. So you kind of almost able to kind of be at right at the intersection of like, what does the business need to do? Where's the business at? What problems are you trying to solve with and for the business as a founder?
Andy Budd: Hmm.
Simon Rohrbach: but also how do you actually set your teams internally up for success and have to have conversations there. So it was a really interesting mix of like thinking through systems problems with people, thinking through business problems with people, helping them with organizational design almost, but also just like reasoning through, yeah, like for a D2C e-commerce business, like a great design discipline looks very different than it does for a B2B SaaS business. And so kind of being able to like flex ⁓ in both directions was really fun and really engaging. I think the thing ultimately kind of came back to was ⁓ there were so many conversations I had there with all these amazing companies and all these amazing founders where consistently it like ⁓ like the half hour call ended or whatever it was, I kind of felt like, ⁓ let me just, like, ⁓ me try and involve myself more. Like I really want to help more. Like I know how to do this. ⁓
Andy Budd: Yep.
Simon Rohrbach: And that kind of told me, okay, maybe this is a sign that maybe I just have to go and do this. Because I don't want to be the person that is backseat driving, right? That's not helpful. ⁓ to try my hand at this myself now. ⁓ And yeah, it's always had that kind of itch that I really want to scratch. And ⁓ the way we of ended up ⁓ starting something like playing was that Matt and I were kind of throwing a few ideas around and ⁓ I think... what Deliveroo had taught me was there's a very, very big and important difference between a good product and a good business. And more importantly, I there's maybe a third dimension to it as well, which is the company. And I think in order to build a really successful entity overall, something that has a big impact in the world, I think you have to have all three. You have to have a good product.
Andy Budd: Yep. Hmm. ⁓
Simon Rohrbach: a good business that's underlying the product, and a really good company. And if you fail at any one of those three, the entire thing is toast. And I think that the company, or the world, think is littered with startups that are great products that will never be good businesses. And so the thing we sort of ended up toying around with was, where do we think is the really big market that can be a really good business? where we can also build a really cool product. And then hopefully we'll do an okay job of building the company around it. And we're talking about with a few ideas, like one of the ideas we're kind of looking at was payroll software. know, payroll software, extremely boring, most people would say. Huge market, because anyone that employs people needs payroll software by definition. You can't get past it. And so...
Andy Budd: Mm-hmm.
Simon Rohrbach: Then actually sort of like the business factor is almost kind of a bit of a given right and Then actually that frees you up to like go and build a really cool product around it so we're kind of looking at like water markets where this is the case and a very Distinctly remember Matt in random text conversation. We had we still have a screenshot of it somewhere Going like you know, what's horrible customers report software? like every team you speak to doesn't like using the tool that they're using. it would be really cool to do something in this space. And so that's kind of like when we landed on this idea of like, okay, this is a big market. Everyone that has customers has some form of customer support, no matter whether you want it or not, by definition. And actually, as designers, there is a really cool product to be built here. We can really flex that muscle in this domain. And that never really left us.
Andy Budd: I mean, so many amazing things out. think the product business company sort of ⁓ triumphant is absolutely right. I think so many founders go into it focusing on just building the product and actually aren't very good at building a business and actually not very good at scaling a company. And it's one of the things I want to talk about a little bit later in the call about how you've gone from product focused to business and company focused. But I guess the other thing with the idea, you were launching, you know, not into kind of a blue ocean, you were launching into a world where they were all very ready, very kind of established players in this space. Intercom is a classic example of a kind of European incubated designer led company. You've got all the Zendesk and various other kind of companies in the world. So what was it that you thought you could do differently the other companies weren't currently doing? What was the sort of the space that you carved out for yourself?
Simon Rohrbach: Yeah, I think for a long time we didn't really know. ⁓ We sort of knew, okay, we want to do something here, but we don't know what exactly it is. I think the thing we kind of centered around was that ⁓ Deliveroo, we customer support grow from essentially being a collective effort ⁓ where was kind of chipping in and helping out through to being an org of 5,000 people. ⁓ And I remember very, very distinctly, ⁓ this moment, was some kind of management meeting that we were in where a data analyst was showing a chart. chart showed the headcount ⁓ of RCS ⁓ and had overlaid on top of that order growth. ⁓ And the two were linear. So what this meant was that for every hundred or a few hundred orders we were adding to our order volume per day ⁓ We could guaranteed another one or two people and customer support ⁓ like something crazy like that, right? So ⁓ in this really paradoxical position where? The more successful you are ⁓ the you get to bankruptcy because like this is like a ⁓ business that's a high volume low margin ⁓ Right. So ⁓ every single every single penny
Andy Budd: Mmm. ⁓ Mmm. Well. ⁓
Simon Rohrbach: of like margin starts the matter at that point. And if you have a really high contact rates and therefore you need more people and customer support, therefore you have more costs than where you grow. Actually the less healthy the business becomes. And we were looking at like, okay, why is this the case? And it turned out that all of it came back to tooling. We were using...
Andy Budd: Hmm.
Simon Rohrbach: Zenesq at the time, we built all kinds of tooling around it. And Zenesq is, be clear, a great product from many, many companies. But every company is a little bit different, right? And we were a very engineering-driven ⁓ And what we wanted was to almost have ⁓ building blocks to build on top of, ⁓ something we could build our own sort of customer support tooling around. So ⁓ we of started centering around this idea of, ⁓ hey, if we build what we call Stripe for customer support, like an API for customer support?
Andy Budd: Mm-hmm.
Simon Rohrbach: They can build on top of and build lots of internal tooling on top of And we sort of went after this idea of like building infrastructure basically And for the first couple of years this didn't make sense like it actually disastrously failed had no revenue two years in no customers of no like nothing it felt like being banging her head against a brick wall So we were like Okay, like this isn't working We have to sell to people like ourselves because it feels like the market for a solution like this is Deliveroo, DoorDash, Kubernetes, maybe Monzo. ⁓ Those are the only companies that actually need something like this and are of the size where they can actually build their own internal tooling. So let's go sell to companies like ourselves. ⁓ are we? We are a developer tool. ⁓ what we were at the time. ⁓ let's go and talk to DevTools ⁓ see what they need. And it turns out all of them talk to their customers on Slack. Microsoft Teams, Discord, and these sorts of channels, but no one's really built anything for those channels. And we suddenly started realizing that all of these B2B companies more broadly, removing all their customer communications to channels like Slack, Microsoft Teams, et cetera, because you just build way richer, way more interactive, way more multi-layered customer relationships there. actually a really great channel that you support on. ⁓ So started building integrations for all these channels, ⁓ and really when revenue started taking off. ⁓ And now a very, very funny way, what's happening is... ⁓ AI has changed the cost side of the equation. So all of a sudden, software is really cheap and easy to build. And so all of a sudden, all these companies are coming to us going like, hey, what we really want is something we can build on top of, because it's not really easy for us to build our own internal custom tooling. So suddenly, the very thing we started with, which didn't make sense at all at the time, and led us to kind of going off to B2B, is now actually causing us to win.
Andy Budd: Hmm You
Simon Rohrbach: a lot of amazing companies that really want to build, like they want a lot of pain out of the box, but they also want to build a lot of stuff on top of it. So ⁓ we're becoming this infrastructure ⁓ for these companies ⁓ in a very kind of funny full circle way.
Andy Budd: I mean, that's amazing. That's a brilliant story. ⁓ How much of that challenge was a positioning challenge versus how much of it was a product challenge, do think?
Simon Rohrbach: Yeah, I think... 40 % product challenge, 60 % positioning challenge, I'd say. The product challenge is when you say you are a customer support platform, people immediately mentally compare you to like a Zendesk or Intercom. And they go, OK, you say the word customer support platform. That must mean, of course, that you multilingual support.
Andy Budd: Hmm. Mm-hmm. Mm-hmm.
Simon Rohrbach: Yes, and it must mean that you have multi-level SLAs for teams that run in different regions, right? And surely it means that you have really grandly reporting, right? And the list becomes endless, none of which you have when you start. So you have to build all those things. And so took us a long time to actually build the foundations there. So I think that's kind of the 40%. Do you even become viable as a customer support platform? That's why this market, yes, it's very large and it's crowded.
Andy Budd: Mm-hmm.
Simon Rohrbach: But it's also like the players out there are very, big. And there's not many tiny players because it's such a big moat that you have to overcome first to actually become viable. Many companies fail before they make it past that. And we now have. And so I think that's kind of like the 40%. I think the 60 % is around, if I say to you,
Andy Budd: Hmm.
Simon Rohrbach: hey, build more stuff internally. ⁓ Get your engineers to build more customer support tooling. You're going to get no way. going to go and build products for our customers. ⁓ We're not going to spend time on what's often perceived as a cost center internally. ⁓ I say to you, hey, right now you're losing customers ⁓ because the state of your tooling is so inflexible ⁓ and not meeting the needs of your business, ⁓ we giving you more flexibility. ⁓ giving you more power to do whatever it is that you want to do. To have tooling that's completely custom to you, that works the way your business does, that maps how you think by your customers. In a fraction of the time it took you previously, suddenly that value prop is very, different. ⁓ And think for a long time initially we were saying, write more code. No one wants to write more code. Everyone wants to write less code. ⁓ And when flipped it to like, we give you more flexibility, ⁓ which is we're doing now.
Andy Budd: Hmm.
Simon Rohrbach: value prop becomes very, different.
Andy Budd: I mean, think getting the value proposition, getting the positioning right is so vital. I think something that most founders kind of assume is in the bag. I talk about this idea of like, you need to get language market fit before you find product market fit. And so many people just assume the product is amazing, but then really struggle to articulate who it's for, what its value is, why it's different. In a really crowded marketplace, got to, you you set up problematic comparisons with other platforms because you a certain set of language and it really can paint you into a corner. So it's fascinating that you kind of had that experience. Just rolling back a little bit, I'm just kind of curious, like in the early days of the product, like how long did it get you to build something usable? Because from what you've described, these platforms need to be all singing, all dancing, kind of like behemoths. And so did it take a long time? Were you kind of one of these classic like, you know, we've got funding and it's going to take a year before you get to see anything useful or did you have a working prototype immediately out of the gate when you went to raise funding?
Simon Rohrbach: ⁓ So we had a prototype fairly quickly. We raised our very first round of funding from Index Ventures. Obviously, we had a pre-existing relationship there, so it was a great relationship to be able to kind leverage, and they've been great partners since. And so we able to kind of get to like actually work on something, work on the product very, quickly, ⁓ which was great. I think what we did afterwards is we were like, great, now we have the prototype ⁓ of like the full We're gonna go and build a full platform ⁓ I think therein was the mistake instead of lesson number one ⁓ which is ⁓ think many founders ourselves included They start with the end state ⁓ And I think that can kill you ⁓ You because like ⁓ if have this gap between ⁓ We have ⁓ This that we have in our heads. ⁓ We need to build a full thing before we go to market yeah, there's a year in between like
Andy Budd: Hmm.
Simon Rohrbach: that first point and that end point, And originally you might think, okay, it's gonna take us six months. We all know these estimates are not accurate and six months turn into seven and then into eight. And it's the classic kind of like metaphor of like, you're refurbishing like a flat or a house, right? And you lift up the floorboards and there's rats. Like, what do you do now? Like all this stuff is hard to build and like, know, plans change. So.
Andy Budd: Mmm.
Simon Rohrbach: The longer you have this gap between having the idea and having it out in market, the more you open yourself up to things coming out of left field. don't know where someone beating you to market, someone doing it faster, assumptions changing. And so I think the job is to compress that as much as possible. And I think in retrospect, I think probably what I would do differently next time we get this and what a Netl founder is to do is...
Andy Budd: Hmm.
Simon Rohrbach: Yes, the endstay that you have in your head is a customer support platform, but the thing you can probably start with is you could just build a really great email inbox for bootstrapped, indie, B2B SaaS founders that have a couple of emails a week and need a nice email inbox to help them, like a nice shared email inbox to help them manage their support in a really nice UI that helps them manage those 5, 10 emails a week. And you charge like nine bucks a month for it, like done. ⁓ And suddenly, that's a thing that you can now build in probably a couple of weeks and you can have something come through running fairly quickly and get that validation. And then you sort of yarded the gates and you can start to gradually mature that product and add more things. If you look at most successful products in history, many of them did not start with the end state. They started as something much more smaller and then started adding more and bits ⁓ as they went on. ⁓ And I think oftentimes, you know, as a human, especially as a product person, you have a tendency to look at like, okay, like, you know, Facebook or whatever, like, what is Facebook to me now? ⁓ That's what we're gonna build. And you realize that's not how it started. It started something way, way smaller and very, different.
Andy Budd: I think you're absolutely right. mean, think there's a tendency, you know, a lot of founders have a vision of what the future wants to be like, and they try and build that vision. And that vision is huge and all-encompassing. And I think you're absolutely right. Starting with something small to give you the time to build out that vision and also make sure that the vision is right, makes sense. But I do sometimes wonder whether designers are particularly susceptible to this because, you know, we're really good at kind of like brainstorming and kind of like visioning the whole picture. And we don't want to launch until things are perfect. we know we've done the competitive analysis. We know all the features and functions that all of the other people have on the market. And we want to kind of reach feature parity. But by the time we've reached feature parity, all the competitors have now added another dozen features. And so it feels like there's this kind of arms race. And so I just wondered, like, do you find that this is a thing, like, was there anything about being a designer that you had to kind of deprogram yourself almost out of habits that you always thought were right, but now as a founder, you're like, oh, Maybe I was wrong there when I was a designer.
Simon Rohrbach: Oh, completely. So many things. I think the way I always think about it is as a designer, you have an eye for certain things and you're trained to spot imperfection. And that eye can become a lot of baggage in the wrong environment. Because ultimately, your job when you build a company is to like, what's the be all end all? It's revenue. Frankly, how you get there doesn't really matter. And to put it bluntly, whether you get there with buttons that look kind of shitty and where the drop shadow is not that nice, if someone's paying you for it, you're good. That's the only thing. And I a lot of people, including ourselves, get stuck in polishing the drop shadow of a button of a feature that does not do the right thing. And... the job is to validate that the feature is the right thing and that someone's gonna pay you for it. And then you can go and make the button really nice. And I think that's something I always try and remind myself of now. And actually just recently we've introduced new operating principles in the company, ⁓ which sounds really stupid, but like for me is a big shift, big mental shift, which is like, ⁓ of them is ⁓ today over perfect tomorrow. ⁓ I think... ⁓ As a designer, think often times you kind of go to like perfect tomorrow. know, tomorrow I'll put in a bit more polish and make it really nice. ⁓ Not the job. The job is to get it out today. Even if it's bit hacky, a bit rough around the edges, but it gets you the feedback.
Andy Budd: I see this time and time again. I always sort of joke that like whenever there's a release in a large company, the product team are really happy, the engineer team are really happy. You look over to the designers and they're sat in the corner feeling really sad in the morning. And when you go and understand what's going on, everyone else is really excited because they're looking at the 80 % that wasn't there before that the designers have been able to build. But the designers are mourning the 20 % that they couldn't get through. If only they had a bit more research, if only had a bit more time, if only they'd had not to make so many ⁓ often designers see the bigger picture and they feel that everything goes out as a compromise. That can be really quite challenging and disheartening. So I'm kind of curious, do you find yourself saying things to your design and product team now ⁓ as executive that when you were on the receiving end of that, it would have kind of like driven you crazy?
Simon Rohrbach: Absolutely. we have, ⁓ with all our product teams now, have product reviews every week ⁓ we all go through, okay, what's the roadmap? ⁓ What are we shipping? ⁓ is it at? ⁓ And we demo ⁓ we all talk through it together. And it's like, you have to imagine it like sort of ⁓ big crit where people are from sales, people from customer success, people from operations, people from violence, everyone's involved. ⁓ it's opt-in, so like nobody has to join, but people who find it useful do. ⁓ And ⁓ I use that forum ⁓ as a way of setting the tone, as a way of ⁓ driving a certain standard. My operating model myself now ⁓ a CEO is like every meeting I'm in, I'm either setting a standard or I'm tolerating a different one. ⁓ It's actually very simple. So the standard I want to set ⁓ is let's it out now. ⁓ And ⁓ do we feel like if we ship to stay, we'll learn something? Great. Let's get it out. And ⁓ so the thinking, like I'm trying to drive here, is really one of like, do we have a question in mind that we want to ask our customers when we ship this thing? ⁓ And if we have that question in mind, great. Let's go and ask the question. And then we can always make it better afterwards. And I think this is kind of thing where, yeah, that would have really brought me the wrong way as a designer in my previous life. I was kind like, no, but the design system's not there yet. The button's two pixels off, right? It's that sort of stuff. But again, the job is to actually save you and save yourself from almost polishing the thing that nobody needed in the first place.
Andy Budd: Thank
Simon Rohrbach: And I think that's often the far bigger failure mode for product development is you build the thing that nobody needed. So I think that's our job ultimately as designers is to find the thing that people need.
Andy Budd: Absolutely. The way I liken it is a lot of my friends have got kids and they find themselves saying the things that their parents used to say to them when they were kids that used to annoy them. But now they're on the other side of the equation. They're like, ⁓ I get it now. I get why that they were saying you should do X or Y or tidy your room or this or that. So I think there's a kind of a new perspective that you bring coming from that sort of business leadership role. there kind of one of the things I tend to find with operators that become leaders like If you're an engineer and you're a founder, like every problem is an engineering problem. If you're a marketer and a founder, every problem is a marketing problem. Is there a tendency that when you come from a design and product background, like every solution becomes the product solution and you end up kind of like delving into this area that you love and finding more excuses for doing product stuff when actually as a founder, you need to be looking at something else. You need to be looking at go to market strategy. You need to be focusing on building the business. You need to be focused on culture. but you're constantly drawn back to this thing that you're good at and makes you feel kind of successful and powerful and have fun.
Simon Rohrbach: Yeah, 100%. I think that probably continues to be the biggest challenge in my day to day because I've done the hard 180 towards go to market and like... ⁓ sales and success and like building sales team and all these sort of things. ⁓ So my day to day now is probably 90 % those things and 10 % product, if even. I don't think we'll always remain that ⁓ but I think right now it's kind of what the company needs. ⁓ the thing I try and remind myself of ⁓ your job ultimately as CEO, right, is to work on the company's biggest problem. ⁓ I find this a very kind of useful like mental stopgap for kind of going like for a mental check for kind of like ⁓ doing this thing right now that I'm being drawn to with the product, am I working on the company's biggest problem? And if the answer is no, then I probably shouldn't be working on it. ⁓ of course, ultimately, everything lives and with the product. If you don't get the product right, ⁓ good can't fix that. ⁓ And so everything ultimately comes back to that. But... ⁓ that kind of eps and flows, I think, the company grows, right? Like, you'll have moments where the product's in a really good spot, then actually, all the teams are totally running the right direction, and everything's just execution, and then it's time to go and build sales, right? And then you might be in a time where actually the product needs to be reclarifying, be readapting, and shifting in the market, and so that you have to go and spend time over there again. But I think the... Yeah, like the big sort of like muscle thing to build ⁓ as a founder is ⁓ you have to like increase your tolerance for stuff that lives in spreadsheets and like processes that are ⁓ in the product and things that ⁓ scrappy, very manual, ⁓ but they get the job I think that has to kind of be. ⁓ You're always to do those things first and then multi-seater the things that are working. You can build them in the product. You can build tech around them and like all these sort of things, right? But that's not how you start because code is hard to change, ⁓ know, manual process or not. So I think it's a good sort of mental model.
Andy Budd: Absolutely. ⁓ I'm curious, again, back in the early days, when did you really truly feel you were onto something? There's a lot of conversation on product market fit, you know when you've reached product market fit. So when did you suddenly realize, ⁓ we're seeing demand, things are growing, we're onto something?
Simon Rohrbach: ⁓ It's sort of... ⁓ There was a point where ⁓ we started people ⁓ up for the product ⁓ and talking to us. ⁓ That were companies that we never thought ⁓ have the privilege of ever being able to talk to. And they were companies that we had looked up to. ⁓ when we started the company, we were like... ⁓ We're like, OK, if we really make it one day, maybe we'll be lucky enough to forget even work with the company, but just meet some of the people there the loan from them. ⁓ And ⁓ few these actually express interest in what we're doing. like, hey, ⁓ we really like your We like what you're doing. We're moving from such and such platform. We'd love to do a trial. ⁓ And I think that was kind of the first one, I was like, hold on a second, this is now exceeding our expectations that we had of ourselves. you have this kind of, oftentimes it's a weird duality as a founder where, or a sort of cognitive dissonance between you starting this thing because you think it can be really big and your vision is to build a really big company. But that's totally divorced from like, where do I think we're going to be next month? and sort of like, ⁓ the level of, ⁓ ⁓ like short-term ⁓ pessimist, long-term optimist at all times. ⁓ you can live in both worlds at the same time. And it was, yeah, that's at a point where ⁓ these started inbounding us and were like, hey, we'd love to do trial, this looks really, really cool. ⁓ almost started taking the product out of our hands. despite its imperfections and despite all the things they did in their two and they were ⁓ to look past that because they saw what came beyond that. ⁓ That's really when I felt like, this could really go somewhere.
Andy Budd: Hmm. So you're really starting to feel this sort of market pull. It's not you pushing anymore. It's like you're starting to see brands that you really admire, that you've always wanted to work with, kind of start to have those conversations. Before you got to that market pull, like how did you get your first customers? Like that's a real challenge at the moment, I think. Like channels are saturated. You know, what might've worked on Twitter or kind of five, six, seven, eight years ago isn't working now. ⁓ What was your initial go to market strategy like and what was the thing that kind of really clicked when you're like, hey, we're, talking about things in the right way or we found the right channel that works.
Simon Rohrbach: Yeah, the best way to sum it up is that the way we got our first customer was never how we thought we'd get our first customer. ⁓ So ⁓ we had this really elaborate plan for like, OK, we're to start outbounding all these companies, maybe we'll launch in a month's time. And let's work towards that. And here's all the great things we have to have in place, like a really nice website so we can make a big splash. you know, really great onboarding experience and like all that sort of stuff. ⁓ Classic kind of like, I think, designer mistake of like everything has to be just right until we can launch. ⁓ And suddenly this ⁓ colleague of ours from Deliveroo, ⁓ like he left Deliveroo and he started the site project with a couple of friends of his. ⁓ And I remember it was.
Andy Budd: You
Simon Rohrbach: They were building a platform that allowed you to send out voucher codes for participants in user research. Oftentimes in user research, you can send out people with a voucher, an Amazon voucher or something like that. Oftentimes it's a really big pain to go to this much organized expense and all that stuff. So they built up a really nice platform that essentially you point and click and go, I want to send a voucher to this person, this person. They automate the whole process. And that started getting with some traction. And so they're starting to some embeds from the customers and some emails. they knew that we were building plane. ⁓ suddenly I get this random WhatsApp message ⁓ like Thursday afternoon or something ⁓ ⁓ actually Graham was the name like Graham kind of goes like hey like ⁓ Come use you guys We need a custom support tool and ⁓ I just like what like ⁓ no, I yeah sure ⁓ and ⁓ Immediately everything changed like The launch no longer happened. We're like, okay, let's get a call going now and we'll get you set up. we just like, YOLOed the whole onboarding. It was completely manual, completely broken. We got them up and running within like an hour. Turns out we didn't need a nice onboarding process or a nice website. We just needed people around us to know that we were up to this thing and that we're building this thing that could help them solve this problem. And so it was this completely unexpected just... being pulled into the market by friends of ours that I'm still really grateful for because I think without that we probably would have still been at this like two more months and built a really nice website first. And for me it's a good lesson of just like, most thing you need is just like the forcing mechanism to pull you out of that mode and like make it live now despite all its faults.
Andy Budd: Absolutely. In my book, I talk about kind of this quote from Paul Graham that says, at the start, you don't need to get the word out, you need to get the word in. And by that, he means that so many of your early customers are going to come from your network, probably. I think this is one of the reasons why a lot of VCs are really interested in founders who understand the problem space really well or are really connected to other people that might want to use the product or, you know, in terms of hiring as well, being connected to really amazing talent. Like those first, you know, 10 customers or 100 customers, or if it's B2C, 1,000 customers might be coming from your direct network and friends and friends. So that's really important. ⁓ Beyond that, was go-to-market easy? I'm just thinking companies ⁓ like Intercom, they had a really big play when it came to content strategy. What were the early motions that were working for you and Plane?
Simon Rohrbach: Yeah, I think a couple of things. think the first thing I think is just to show velocity. Because I think ⁓ in very crowded market, ⁓ people buy the current state of the product, they buy what it's going to be. ⁓ And making fundamentally a bet on your team. ⁓ And The thing that really helped us, which was like every week posting something to changelog and kind of like, here's what's new and making some noise about it. That was kind of the first thing. think the second thing was, and I hesitate to recommend this because I think it can be a bit of a trap, but we were designers, so we were like, okay, how can we make this look and feel really nice from a marketing perspective? And actually we started getting lots of love for... the way we done our website and like all these other things right so like despite what I said earlier on like it actually getting a first customer inbound pulled us out of that mode of like having a really nice website later on that actually helped us because it was us playing to our strengths and it was us trying to convey the quality of the product with the quality of our marketing and our positioning ⁓ and that resonated with people that were like us who valued nicely built tools and like you know well designed products which is a lot of dev tools and lot of tools that are for builders. So we definitely sort of tried and sort of like took a bit of inspiration from like the linear playbook almost of ⁓ trying to build this perception of this is a really high quality product. ⁓ That really worked ⁓ it got us a whole bunch of customers because website started being shared around and lots of stuff. Again, I think there's a trap there because that's not ⁓ always in every single market. you know, think ⁓ as customer base grows, not everyone cares about this, but you can get either. to start.
Andy Budd: I was just going say, I was curious how much you think the brand, the name played in. I spoke to Sam Stevenson recently from Granola who talked about how the name Granola was almost an accident, but in a weird kind of way. There's something really nice, simple, clean about the name that is really, attractive. I think the same with plain. It's really, there's really, just it feels natural. And so how did the name come about? And could you have... ⁓ you know, become as big as you were, as successful as you were, if you were kind of like supportpro.com or something instead.
Simon Rohrbach: ⁓ Yeah, like think naming was a bit of an obsession of ours. ⁓ So we actually started the company as Juniper. Like Juniper Berry, right? ⁓ ⁓ just throw everybody a nice ring to it and then sort of went for that first. ⁓ out there's a very big company called Juniper Networks that a lot of lawyers with like a dedicated section on their website ⁓ to the trademark. so we're like, that's maybe not such a good idea. but went through a bunch of names and ultimately landed on Plane, I think, we sort of felt like there was something really nice to having a bit of a blank canvas, a word that can make you or is a word that many other people probably would not pick. And actually, if you do it right, you can lean into the meaning of that word. And in our case, we felt very strongly, and I feel that still to this day, and I say this to everyone who joins, A lot of customer support software feels like filling in the attacks return. It's not, it does not spark joy. And when you're a support team or someone who works in support, you use a tool like this eight hours a day. And so every interaction really matters. And over time, a of these tools have become full of all this fluff and all these clicks and all this stuff that feels like you're wading through mud. And all of that is just to talk to your customers, which is the single most important thing your company can possibly ever do. And so, playing in that kind of landscape, we call it CS without a BS. ⁓ It's customer support without any of the fluff and any of the BS there. And we really wanted to lean into that. think the name Plane speaks to that really nicely. that plain and simple. It what it does really well. ⁓ And you can use it forever. You can use it however you want. It's really flexible. It's really adaptable. But it's just plain. And so, yes, 100%. I think the name is a big thing. I think it's also, yeah, it's a bit like, I don't know, you know, buying a property, right? You can change many things about it, but the one thing you can't change is the location. And the name is like that. It's like, can't, I mean, you can change it, but it's expensive.
Andy Budd: I was going to ask you actually, in terms of the location, with such a simple name, how difficult was it to get the domain name?
Simon Rohrbach: ⁓ It was actually reasonably straightforward. We got plain.co first because that was sort of available for sale and not that expensive. Plain.com was listed for sale so we just contacted them and negotiated the price down. I got this really great ⁓ which is firstly don't contact them from your main company email because then immediately the price goes up. Second, ⁓ name your price and then walk away. It's the only And so I named the price and I walked away and ⁓ the person that we bought it from negotiated themselves down and sent me several emails like, know, this and then actually I'll go lower. How about that? How about that? How about that? ⁓ Until they met the price ⁓ and then we bought it. it was ⁓ feels like a sort of a stupid investment upfront. But then if you think about it, it's like it's the cheapest it will ever be because you have to assume that like you'll be successful.
Andy Budd: you
Simon Rohrbach: And if you are successful, someone's gonna sit on that domain name knowing that you exist and waiting for you to raise some more funding and then go like, great, like it's now several million pounds. And you don't want that. actually in proportionality, ⁓ amount of funding that we had at the time was actually one of the cheapest purchases we've ever made. ⁓
Andy Budd: That's amazing because you could have quite easily said, yeah, it was a couple of million pounds and it was a really harsh negotiation. So I think the value you've got from that domain name is huge. I think having a really strong domain name that is searchable, that's findable, that's memorable, that isn't kind of really complicated. You see so many domain names where the way it's spelled is very different from how you vocalize it and you can't ever find those companies. So I think that was a really good purchase. ⁓
Simon Rohrbach: Yeah, we're gonna for like 40k USD or something like that in ⁓ the end. From what I'm being told, not bad for like anything like this.
Andy Budd: That's good. That's One thing I haven't talked to you about, because you said that fundraising, basically you'd done a year at ⁓ a VC fund index. They were your first investors. Did you actually formally have to go out? Did you do the kind of dog and pony show? Did you go and speak to 40, 50 VC funds? Did you get lots of rejections and door slams? Or did you just go to index, say, hey, this is what I'm building next, and they wrote you a check on the spot?
Simon Rohrbach: I think maybe something in between. It's one of these things where when you join a fund ⁓ to be an executive residence or some funds will have an entrepreneurial residence, success, the success definition of an engagement like this is that either you join a company in the portfolio or you start a company. ⁓ And if you start a company, The idea is that you'll talk to them about it first. And there's no obligation there or anything like that. has to invest or whatever. You can have really bad ideas. That's not the goal. It's more just like, that's kind of like part of what makes this so beneficial and such a great experience. So it's definitely the kind of conversation where you can be like, hey, I'm starting this thing. What do you think? And actually what's really nice is you can actually have all these amazing people around you. that can help you stress test the idea and kind of go like, you know, here's like, what does this make sense, what does not make sense, how would it make sense, like, ⁓ here's what might be a bad idea, etc. So ⁓ it kind of like makes that, ⁓ stage ⁓ actually more kind like, ⁓ more beneficial to like the thing you ultimately kind of building. ⁓ So ⁓ we did go out and like, you meet lots of investors, but it was more just like after we kind of knew, okay, like we'll probably, we'll do this within Dex and you know, they're excited about this and we are excited about this. ⁓ And then it's more just about getting other investors ⁓ to ⁓ join around. So there was a bit there and it still took us like, you probably a month or two to kind of get everything fully wrapped. But ⁓ on the whole, we definitely am very thankful for this. Like we had. probably an easier experience getting started than many other companies just because we had that kind of relationship.
Andy Budd: I mean, this is a much more common thing in the US. I see a lot of times in the US, a founder or senior executive will leave a company that that investor has backed. They will come in as an entrepreneur in residence or executive residence for a year. They maybe start working on their next project. And then they've almost got like a, guaranteed, but they've got a really good in for that round. I'm curious, the reason I was asking is like, If you were talking to a young designer now that was thinking of leaving their job and raising funding, what advice would you give them? How would you help them navigate through that process?
Simon Rohrbach: Yeah, think the first thing I'd say is like spend time on the business and on the product. Like the product will come easy to you, right? Like it's literally your job and literally like we do every single day. ⁓ not why this will fail ⁓ if you have that skill set. Like reason this will fail is because, you you're picking a really cool product idea in a really bad market. ⁓ I think that's the far more common failure mode. ⁓ So... My biggest piece of advice would be really make sure that the thing you're going after is in the market that can support a very large public traded company. Because if you're swimming upstream against the market, that just never will be good. ⁓ there's many markets like this, right? Where, I don't know, ⁓ ⁓ verticals where ⁓ just like you look at it and go like, it's just hard ⁓ make money in a space like this. ⁓ You see, for example, ⁓ . . Yes, you might have a breakout success, but there's also a history of many, many companies having tried and not really having been able to make it work as a standalone thing. And so, it's not to say you can never turn into a great business, but it's much harder. So I would say spend time on that really make sure that ⁓ going after a market that can support a very, large company. ⁓ And where does the money does a portal by a large company where transactions are so big and these sorts of things so really go deep there I think the the second thing I probably say is ⁓ Really make sure that like the ⁓ The thing that you're picking, the thing that you're going after is the thing you can see yourself spending a decade on. And it sounds kind of extreme, but I think it really has to be that. This can't be a thing in the moment where it's hot right now, but in years time you're gonna lose interest. For me and for Matt, for both of us, this was always customer support to this day. Continues to be like a thing we very very deeply like have a very very strong conviction in because we think fundamentally it's but fairness like in a company it's like why are you giving the people who Are you linked to customers and work so hard trying to fix things when they go wrong? Why are you giving them the worst tool and the worst equipment the lowest budget the lowest share in the world or share a voice in the company and Ideally outsource so you never have to talk to him ever again like like it's completely upside down. It makes no sense
Andy Budd: Mm.
Simon Rohrbach: And so if we can build better tooling for a space like this, we can actually make someone's work day just that little bit better. that alone is massively worth it. And ⁓ has to be something that we deeply believe, it has to resonate with you deeply in what ⁓ of world you believe in, so that ⁓ year five, six, seven, eight, ⁓ you can be an all-hunting company and inspire the company and rally the company around why this really matters. Case in point, this is year five for us. ⁓ I've to SF ⁓ together with my wife and my dog. ⁓
Andy Budd: Hmm.
Simon Rohrbach: to open up the office here. most of my life in London, right? Like, ⁓ it has to be the kind of thing that you're prepared to do these really big things for, and if doesn't meet that test, ⁓ it's probably the right idea.
Andy Budd: I was actually going ask you about the SF move. Was it difficult deciding to, I guess this came off an expansion in North America. Obviously when people expand, there's a real desire for the leadership to be there, be seen and be connecting with customers, et cetera, et cetera. So was this a tough decision or was this always going to be inevitable with success? ⁓
Simon Rohrbach: Hmm. I think it's like... It's one of these things where sort of as your horizon expands and as you kind of go Hey, we're starting to get like, you know a lot of inbound especially from from the states and actually case in point of one of our first paying customers was from the US And since they won the lava revenue like majority of revenue was always from from the US You kind of go like hey, we should probably be where our customers are and and then actually becomes like very for me being a very logical decision, which is My job ultimately is to improve the odds of success for the company. ⁓ There are many things I can do in my day that frankly don't move the needle on that. Like I can go and polish a feature, doesn't really affect the director of the company. ⁓ Being where your customers are and being, or especially right now, is kind of the epicenter of software for a large part of the world still, at least in tech. ⁓
Andy Budd: Hmm.
Simon Rohrbach: Being there and building a team here and having exposure to that and being next to your customers, many of our customers literally stand the road, I think that alone improves the odds of success for the company by one or two percentage points. And that is greater than any other thing I can do in my day, in my week, in my month. And so I think from that perspective, then it just becomes very obvious, obviously, that's the thing that you'll do. And so, yeah, was kind of like, was it hard? Absolutely. It's like it's a different culture. You are learning a new way of communicating, like what you do and a new environment where you don't have any of the network, et cetera. ⁓ And ⁓ time zone shift is kind of rough. ⁓ ⁓ AI is behind London, right? ⁓ So my mornings are like insane. ⁓ And that's hard, but I absolutely believe it's worth it.
Andy Budd: I'm getting a sense from your social media, from LinkedIn, that you're really, really enjoying being there. feels like you're in the epicenter of something. And ⁓ I can just tell from your demeanor that it's really good fun. In terms of sort of philosophically, mean, again, a lot of European companies will inevitably, if they're successful, move to the US because it's just a huge market with a single language or a couple of languages. Some people... They just move their sales out to the US and keep like product back home. Some people they want to go to the valley because to the Bay Area because there's so much engineering talent. But then it's also a bit of an arms race with everybody else there. Like, what's your philosophy at the moment? Are you is it just a sales team? Are you replicating all of the functions out there? How are you pulling this together?
Simon Rohrbach: Yeah, big piece of advice we've gotten early on from one of our investors was it's really important to cluster. And they kind of go like, hey, where do we want to headquarter each function? So right now we're headquartering GoToMarket here in SF. ⁓ That is not to say. And we're headquartering ⁓ EPD, Engineering, Product, and Design in Europe and London. And ⁓ we have people all over Europe, so it's quite distributed. That is not to say that this is the only place where you have to have functions. And we're now hiring a first engineer here. I think that's going be really important to also support the team here. We're going to have more go-to-market in Europe. So my goal really is to have almost three HQs. It's to have London, Europe, Remote, and NSF, and to make sure that we have functions that are strongly located in each of those. because I think it's sort of, for me, it's kind of the new operating model of many, many companies where you can have an in-office presence, and that's really useful as like a hub for your customers, your community, the people that you're trying to do things with. And at the same time, you can also still have access to the very best talent in the world by opening yourself up to a remote. So I think both those things are possible at the same time.
Andy Budd: I mean, that's exactly the kind of the approach I would recommend. So it's great to hear that that's sort of what you're doing so brilliant. Sort of last question or a couple of questions. Like obviously AI is huge at the moment. There's loads of opportunity in the support space. I'm curious, like how is the product evolving in the face of of AI? And then my second question to that is how are your internal practices, particularly around design and engineering, kind of evolving?
Simon Rohrbach: Yeah, I'll take the second one first. think ⁓ everyone in our company now codes, ⁓ they write the lines of code themselves. ⁓ We've always kind of had this to some degree. We've always hired designers to be technical and ⁓ of that. It's something I very deeply believe ⁓ in. But now, we've really taken it to a new level. Every designer, ⁓ we do ⁓ mocks ⁓ wireframes anymore. be fair, we never really have done wireframes or anything like that. But we don't do prototypes. We open up Cursor or Claude or anything else, and we kind of go, let's make a prototype of this UI and how we want it to work. And it's available in the browser. We can all click around with it and reason about it. And suddenly, within a couple of minutes, you have something that you can share around, you can give to customers, and they can actually validate something. So we do this all the time now, and I think that's become like a really big boost. Obviously, the entire engineering team uses AI every single day, ⁓ like in every single line of code almost at this point. So that's become a big accelerator for us as well. ⁓ So ⁓ think we're really, pushing internally a lot. ⁓ And that also extends to all internal processes and sort of like automating things that previously ⁓ hard to automate. So ⁓ do this a ton. On the first part of the question, ⁓ how is the product changing in the face of AI? I think a couple of things ⁓ have shifted us ⁓ over the six, 12 months. ⁓ They're really down on now. ⁓ Firstly, ⁓ what's happening that ⁓ software is cheaper and easier to build. ⁓ And that means that for straightforward use cases, it's pretty straightforward now to actually like vibe code your own thing ⁓ that does most of the thing that you previously bought a SaaS tool for. ⁓ And so what's the value that like a platform can offer you in that ⁓ Well, ⁓ like you probably don't want like own ⁓ constant maintenance and like all of the bugs and like all that stuff that becomes really big distraction. ⁓ I think even beyond that, like... I think it basically means that a lot of SaaS platforms are now turning into infrastructure, or I think the good ones, in my opinion, will. And so we are in an unusual position here. We started the company API first. We started the company's infrastructure. And suddenly, the infrastructure we've built over the last five years is now actually really coming to the fore. And so what we're really doubling down on is giving people
Andy Budd: Hmm. Hmm.
Simon Rohrbach: the tools to build their own support system. We are no longer a support system, we are system for building your support system. ⁓ We're really excited about that. We're giving people the flexibility, the extensibility to build whatever it is that they need to support their business and to talk to their customers. Almost give them Lego blocks that they can assemble themselves because now it's way, easier to do this. We want to bring the same level of flexibility that engineers today have with vibe coding. We want to bring that to the support space. ⁓ I think that's a really, really fundamental shift.
Andy Budd: Yep. Yep.
Simon Rohrbach: And I think the second thing to be honest, I think that's gonna happen is you have a lot of like AI agent companies right now, especially in the support space that you can point your support to, right? You're gonna be like, hey, like, do solve this ticket, talk to this customer, give them a response. At the same time, you have to operate from the position of assuming that, you know, all the foundational models that are out there, like TractorBT, Claude, etc. ⁓ get an order of magnitude better ⁓ every three six months. And if they do, ⁓ and you as a company are not training your models, what's the moat that you actually have ⁓ when these models get so much better? ⁓ not that far from being able to point ⁓ of the foundation models ⁓ your support and go like, ⁓ Attributee, ⁓ Claude, do support.
Andy Budd: Hmm.
Simon Rohrbach: That world is not that far away. And very few companies in this space have the resources to be able to train their own models. So what's the value that a company like us can provide in this world? Well, we can give you the building blocks to be able to orchestrate all these different things, all these different agents that might be using all these different foundation models in a way where we all play together. And you can actually build a system for talking to your customers, a system that talks to your customers for you. And I think that's very much the world that we are embracing is one where ⁓ I think that the future is very multi-agent. ⁓ I think in the future you'll have a platform where you orchestrate lots and lots of different AI agents next to lots of different human agents. ⁓ And we want to build the orchestration layer for all of that. it's a really ⁓ time ⁓ be in a space. It feels to me a bit like, well, I'm old enough to remember ⁓ ⁓ everything first came online and it feels a bit like that, know, where everyone suddenly had a website and then was like, now we're online, we have a website, you buy from us online. And it feels a bit like that, so it's a really fun time to be in the space.
Andy Budd: Yeah, absolutely. think there's so much renewed energy at the moment, so much opportunity. I think you're in a brilliant space. ⁓ I can see the energy and enthusiasm there. So look, I can't wait to see what the next sort of five years of playing will be, ⁓ I'm sure it's going to be amazing. Thank you so much. If people want to follow you, if they want to follow your journey, ⁓ ⁓ ⁓ designer out there that's kind of harboring the idea of being a founder, if there are founders out there that... really love the kind of attitude that you've brought to the conversation, where can they follow you?
Simon Rohrbach: Yeah, So send me an email, simon.plan.com. Very happy to ⁓ help or chat in whatever way I can. ⁓ Follow us. ⁓ planning support on LinkedIn ⁓ or X. And then me, Simon Roebuck, on ⁓ LinkedIn or Twitter.
Andy Budd: Well, look, Simon, thank you so much for joining me. It's been great having you on the show.
Simon Rohrbach: Thank you so much for having me, really appreciate it. Great conversation.
Andy Budd: Brilliant. And thanks to everyone else who's listened. Thanks for tuning into the Design VC. If you enjoyed this episode, please subscribe, leave a review, share it with someone you know who cares about the intersection of design, startups, and venture. And I've been Andy Budd, and I'll see you next time. Goodbye.