Clear Expectations and Skill Capacity: A Sales Leader's Balancing Act with Chris Orlob

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It's time to say something real.
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I've been waiting on you to tell me how you really feel.
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Just be honest.
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Words in me Like the joke.
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I can't shake.
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I can't quit.
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It's never really what you say.
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Hello everyone, and welcome to another episode of Pillar Talk, where we build the foundations of sales leadership success and attempt to create clarity in terms of what good looks like for current and aspiring sales leaders.
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Before we jump in with today's guests, let's review the six pillars of successful sales leadership.
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It starts with talent, identification and attraction.
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Obviously, both are very difficult.
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It's also the operating rhythm, the environment that fosters the balance between motivation, engagement and accountability.
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Business planning, which is around the cross functional dynamics, so that the company can play offense instead of reacting and playing defense to things that happen around us.
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Mastering the craft, which is all about helping the team win, communication and ownership.
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Today we are lucky to have as a guest Chris Orlob, the founder and CEO of pclubio.
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That's a platform designed to help enterprise sellers consistently break into President's Club by mastering winning sales strategies.
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Now I know Chris as a thought leader focused on sales performance and analytics.
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He previously was an early employee and senior leader at Gong, where he helped shape, from my perspective, the company's narrative on conversation intelligence, which created a category Before founding P-Club.
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Chris built a career at the intersection, really interestingly, of marketing and sales, leadership and technology, sharing his learnings publicly, and I was one of the beneficiaries of that before it really became the norm to do so on platforms like LinkedIn.
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So, chris, thank you for being here today.
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On Pillar Talk.
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Yeah, thanks for having me, Rick, excited to be here.
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Yeah, excited to learn from you.
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I've been learning from you for years.
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I recall back in like 2017, you were probably the only marketer in my inbox that had a voice.
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Like you were the projection of announcements of what was happening.
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Projection of announcements of what was happening, you were, you know, sharing all kinds of stuff around your you know, around the company's positioning, and then it moved to your own sort of leadership journey and that was all kind of public.
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What made you decide to like take that approach back then, before it was the cool thing to do or a trend?
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It just seemed obvious to me.
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I don't think there was any like sophisticated insight that went behind it.
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It was just we were anonymous at Gong right, like we were a tiny little company.
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Nobody knew who we were.
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Most of our market spent time on LinkedIn.
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I had happened to spend a few years before that crafting my chops when it came to writing and public speaking and all that kind of stuff and then we were sitting on top of this data at gong right, like we're analyzing thousands and eventually millions of sales calls, and we were able to extrapolate what's working according to data.
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And so it was kind of like this perfect storm of like this is the ultimate thought leadership play and it would have been a complete waste if we weren't beating that drum loud and consistently.
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And I also think like I can't take all the credit for that, because a lot of senior leaders and CEOs will not be on board for something so polarizing.
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And it was polarizing.
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We were very polarizing where you know, even today, I mean like 90% of the people who would engage with our content loved it, and 10% of them I mean our faces were on like a dartboard that they would throw darts at, like it was very polarizing in that way, and Amit and Udi right CEO and VP of marketing at the time were very on board with that kind of narrative approach.
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Right, let's be edgy, let's put some polarizing messages into the market that are going to be both good for them and good for our business.
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And if that generates some you know trolls online, that's the price we pay.
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So that's how it started.
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Yeah, I mean I remember they were insightful.
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It was I wouldn't say controversial, but it zagged a little bit from maybe conventional thought.
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It must've gotten wonderful engagement and certainly helped with the brand as well as the swag, and I think it was a dog associated in there at some point.
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But then you know, you had seemed to be a master of like product marketing, messaging out to a large community, and then all of a sudden I'm seeing that you're in sales leadership and at the time I don't think that was a conventional move that people made.
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It's probably not a conventional move that people make today.
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Love to hear, just like what drove that decision.
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And you know what did you learn early on that you didn't expect?
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Well, I think, even to this day I'm I'm in a career where I can't really explain to my parents what I want to be when I grow up and and what I am, because my passion is not sales or sales leadership or product marketing, is not sales or sales leadership or product marketing, it's all of it, it's business.
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I like category defining business and that if you're going to do something like that, you need command over all of those functions.
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And so my background.
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Funny enough, like a lot of people in the world think like, oh, chris was a product marketer who went into sales leadership.
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It's actually not true in the world.
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Think like, oh, chris was a product marketer who went into sales leadership.
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It's actually not true, it was.
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Chris was a sales guy and then he tried his hand at product marketing by joining Gong and then went back into sales and sales leadership.
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My career before Gong was beside, you know, being an entrepreneur was sales and I wanted to try my hand at product marketing because at the time my goal was to be a CEO and one of the patterns I identified among many CEOs is they didn't come from one function.
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They had kind of like a winding cross-functional rise or ascent up to the CEO position.
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Many of them had sales backgrounds, many of them had product management backgrounds.
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A CEO position Many of them had sales backgrounds, many of them had product management backgrounds and many, if not most of them, spent some time in a couple different functions.
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And so that's where that came from.
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Right.
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When Gong hired me, they were doing about 200 grand in ARR and Amit reaches out wanting to talk and he wanted me to be an enterprise seller, right, that was like his first offer and at the time I just wasn't interested.
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I was like I, you know, I've, I've done this job.
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It's not what excites me right now, at least at this point in life.
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And so he came back and he's like look, I like how you marketed your own business on a shoestring budget, how about you lead product marketing?
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I was like great, that's that.
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And so I did product marketing for a couple of years and I still love product marketing, not necessarily as the job, but like the craft right, narrative design and all that kind of stuff.
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Love that stuff.
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I think about it all day, even in my current role.
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I didn't love the role as much though I liked being accountable to a revenue number, I liked being well I'll put it the other way and hopefully I'm not offending any product marketers out there I didn't like to be second fiddle.
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I wanted to be the sales leader who was, you know, your head's on the chopping block.
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But if your head's on the chopping block, that also means you've got some authority, hopefully to call the shots, and I was craving that kind of dynamic again, and so I can't even remember how all of that happened.
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I think I just started to talk to my boss about how I was getting bored in the current role, but I didn't want to leave the company, and so we looked for different roles.
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Leading a segment of our sales organization was the next one.
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I will say that that foresight that you had to take a product marketing role in and of itself had to take a product marketing role in and of itself, coming from a sales background.
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And, truth be told, my knowledge of your background starts with the product marketing and gong.
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So it's a lot of people fully previous.
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It's just not conventional either.
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So the storytelling and I get it.
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I mean I just looked at a post you put on today and look, I scroll through LinkedIn, like many people that listen to this do.
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It's a ton of amazing content on there and you do just have the knack for engrossing content.
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I mean I'm immediately like, yeah, people do blow their shot with the C-suite in the first five minutes.
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Yeah, these are the reasons.
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So you do have a natural knack for an ability to do that and I do like that.
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In my career also, I didn't like have purpose behind what I was going to do.
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I had the basis of like, okay, where can I make the biggest impact in the organization?
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And naturally, if I'm making a big impact in the organization, they'll likely be a lot of learning that is happening associated with that.
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So it's not like I want to get the next role.
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I just want to make sure that, as time passes, my impact is growing in the org and then I will evolve to whatever that ends up being.
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Rather than having this like purposeful journey of art.
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I want to do this, spend this much time and then it's just you can plan a pretty picnic, but like life and the changing dynamics of go-to-market are such that, like it's really hard to follow a predetermined trajectory associated with it.
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So it makes sense to me that it wasn't like purposeful, it was like that's where you were needed and it made sense.
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And then you started to talk about what that was like.
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And since this podcast is a lot about the sales leadership impact, I'd love to go back to, like when you moved into that role, anything that stood out that you didn't expect it.
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When you had to like become storyteller to people manager, quota carrying people manager.
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Yeah, I mean it's, it's just a totally different job.
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Now I will say, being a product marketing leader made me a better sales and sales leadership professional and, on the other hand, being a sales and sales leadership professional at the time made me hand.
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Being a sales and sales leadership professional at the time made me a better product marketing leader, because these aren't totally distinct skill sets.
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Right, because sales and sales leadership you're often the carrier of the product marketing artifact, which is the narrative.
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Right, you're the one talking to it.
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Product marketing is.
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You know, they're at least the best of the best, which, by the way, great product marketers really rare.
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Product marketers are common.
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Great product marketers are very rare.
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But if you're doing that job well, you craft the narrative, but you're not necessarily the one carrying the narrative, and sales and sales leadership often is.
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And so there was there's a lot of learning curve.
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It took me a little while to condense my own model of sales leadership and really understand it, and it's actually kind of similar to the pillars that you lined up at the beginning of this podcast.
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The way I I think about sales leadership for myself is really there's like three buckets there's manage the people, there's manage the pipeline and there's manage the business, and most of what you think about as far as a task or deliverable or outcome of sales leadership at least frontline and second line sales leadership falls into those buckets, right.
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Manage the people, that's well, that's hiring, that's onboarding, that's coaching, that's firing when you need to.
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Pipeline management, that's obvious.
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Right, your job is to marshal deals across a conveyor belt and make sure they close, even if you're not the one closing them, and then manage the business is kind of some of the things that you mentioned.
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There's a lot of cross-functional chops that you need to get used to.
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There's business planning, there's developing scalable playbooks used to.
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There's business planning, there's developing scalable playbooks.
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That's the part I struggled with the most was the cross-functional stuff, because I can be very stubborn, right, like if I have an idea or a way of doing things, I just want to marshal ahead and bring it into the market, and sometimes that's a very good trait to have, that's a really good trait for a startup.
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But when the company started growing and I kind of forgot that I have to align with customer success and marketing and all that kind of stuff, I think I burnt a few.
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I wouldn't say I burnt any bridges, but I scorched the earth a little bit too much.
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I was like a bull in a china shop and I had to learn some hard, cross-functional lessons.
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The china shop and I had to learn some hard, cross-functional lessons.
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And, uh, I actually remember asking my boss to do an anonymous 360 degree review of me across all my peer set.
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Right, they could like give me feedback and it was painful, like I still remember that because I I got a lot of good feedback, don't get me wrong, but there was a lot of like you know, chris, just it's kind of his way or the highway type stuff and it stung.
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But I'm really glad I asked for all of that because it stung in a way that helped me grow and I grew fast because I was willing to eat that glass, so to speak so you, I'm going to use your framing of this.
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So was managing the people pretty natural thing, because if I take it from my vantage point before you kind of get into this, the cross-functional part I'm a communicator and a little bit less of a kind of driver, so that wouldn't be a pipeline.
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Yeah, let's do pipeline.
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Less of a kind of driver, so that wouldn't be a pipeline.
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Yeah, let's do pipeline.
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I mean, I'm a sales guy.
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But the people part was the area that I was like, oh, they don't want to do it the exact way that I just do it.
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They're not clones of me.
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This is a that to me was like whoa, this is the hardest part.
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So it's super interesting to kind of frame it that way.
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Yeah, well, one of the I mean, I still struggle with this aspect of people management today.
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One of the things that I found very quickly is I like to think I'm actually great at managing and leading people who are already a players.
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I'm good at coaching them.
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I'm good at managing them.
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Um, my co-founder here at P clubs, so you can tell I'm still like working through some of these opportunity uh areas.
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He gave me feedback probably a year ago where he's like Chris, you're one of the best leaders I know when you're leading great people and you're one of the worst leaders I know when you're leading people that are not so great.
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I like to think I've grown since that conversation.
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Right, it's not like a train wreck anymore.
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But that's something I struggled with when I first stepped into sales leadership, because not everybody likes to admit this, but most sales teams have B players on them and sometimes C players, and I would get critical too fast of those people and sometimes even today, I do.
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As by far my self-criticism is almost identical to what you just shared.
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Is it more of a patience thing?
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What do you attribute that dynamic to, this ability to work incredibly well with motivated high performers and a struggle to help develop and have the patience I mean that's the word that comes to mind for me to, you know, almost slow down the velocity of your individual execution to help bring somebody along.
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Well, there's a few.
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I'll go in a few different places here.
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First, there is wisdom in knowing if somebody has the potential and drive to work out right.
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If somebody is quote unquote mediocre or a B player, that doesn't mean give up on them.
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That means assess their ability to improve and their and their drive to improve.
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And if somebody is a B player and they have those things, then it's very high ROI time for you to coach them and develop them.
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If they're not, you should just terminate them.
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You should do it compassionately and you should do it non-emotionally and respectfully.
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But it doesn't make sense to have somebody who's not great at their job and doesn't have a desire to improve or an ability to improve.
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So that's like kind of the first bucket.
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The second one is bucket.
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The second one is I can't remember who gave me this feedback, but they said you do want to be a challenging boss to work for, but you want to make the enemy the bar, not you.
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And so the wrong way to do this is you go into a one-on-one with a B player and you're all emotional and critical and you're kind of like attacking them because now you're the enemy.
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Instead, you're completely unemotional and you make the enemy the bar, the bar for performance or whatever, and you just say something with the ethos of, like, our bar's up here and it looks like what you're doing is somewhere around here, and so how do we close that delta?
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Right, that's being a challenging boss, but not being an asshole or toxic about it, and I do like I hate to admit it.
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This is kind of painful to say, especially on a podcast.
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I think sometimes I could have gotten toxic right, like in those situations I was the enemy rather than the bar, and that's probably one of the biggest growth opportunities I've had to lean into over the last five years or so.
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And is that concept making it less about what you say and more about the standard, like an application that you now are sort of prevalently using?
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Yeah, 100%, and it comes.
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I mean, this opens up a whole new can of worms.
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To be able to do that effectively and fairly, you have to document what your standards are.
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So good example of that today is day three of my new VP of sales starting, and before he started I put together what I call a wiggle doc W-G-L-L, what good looks like and it's one or two pages of of during your first 120 days on the job, between now and December 1st or December 31st.
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Here's what great looks like, here's what mediocre looks like and here's what off track looks like.
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And you can't really hold people rationally to a bar until you've documented and communicated what those are.
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So him and I you know, I shared that document with him a couple of days ago, on day one, and him, I was like go absorb this.
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I want to make sure you feel good about it.
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And then, when you've absorbed it, let's talk about it at length.
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And that's what we did this morning.
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Right, it was like you know, he's walking through his concerns.
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He's walking through why I picked certain things the way I did, I'm justifying them, and it was just a little bit of a healthy negotiation, right, like here's what I expect, and now he doesn't have to show up to one-on-ones with me guessing about how he's doing.
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We go well, let's look at the wiggle dock, and now I can refer to that and say well, you know what your ARR targets are, you know what your monthly targets are, you know what your revenue per rep targets are.
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Win rate, all that kind of stuff Looks like we're a little bit behind in this one area.
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What do you think the plan is for us?
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Closing that delta?
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That's holding people to a high bar and being a challenging leader, but being a good leader while you do it, instead of, you know, freaking out and being like you're the problem and being like all critical of them and attacking them, because now you're not on their side and they can sense that and you've just done your first step towards severing a relationship.
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First of all, love this idea of a wiggle dock.
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What good looks like Fantastic Brainstorm, or structured Like like was it something you put together quickly, based off of, like an exercise of 30 minutes of jotting things down, or is it like no, I've honed in a framework of my definition of good over months or years, or a career Like how does that all you?
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know it, it took me, I would guess, 90 minutes to perfect it and get it to where I wanted.
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I needed to rely on all of my business's context and history to get there.
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And so for me to perfect that document two years ago I probably wouldn't have been able to.
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I wouldn't have known what I could have expected because we were so early stage.
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But now I can go look at some of my historic results and what I'm paying him and therefore the economic lift I should expect from somebody like that.
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So you know, I spent a bunch of time on it.
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I, I thought, dumped a bunch of stuff.
00:20:20.538 --> 00:20:21.703
I did my own editing.
00:20:21.703 --> 00:20:23.351
I got it 90% of the way there.
00:20:23.351 --> 00:20:27.961
And then I mean, at this point, chat GPT is like my, my executive coach.
00:20:27.961 --> 00:20:32.596
I'd put it into there and I'm like how do I make this like apex level?
00:20:32.596 --> 00:20:37.984
How do I make this as good as you've ever seen when it comes to an expectations document?
00:20:37.984 --> 00:20:42.300
And I would take its feedback and redo it and probably went through that process 15 times.
00:20:42.300 --> 00:20:46.119
Wow, and you know it's, it's a bulletproof document.
00:20:46.180 --> 00:20:48.997
Now, Can you share a little bit about it?
00:20:49.116 --> 00:20:57.093
Like you know, the maybe categories or just some examples of in fact let me bring it up just so I can reference it and I'm not going off memory.
00:20:57.093 --> 00:21:01.536
So I've got let's see one, two, three, four.
00:21:01.536 --> 00:21:06.700
I've got four categories under the what great looks like section.
00:21:06.700 --> 00:21:08.441
So we've got revenue outcomes.
00:21:08.441 --> 00:21:17.626
That's one category and those are the things you would expect, right, like hitting certain ARR targets along certain time horizons.
00:21:17.626 --> 00:21:21.715
Then I've got growth efficiency expectations.
00:21:21.715 --> 00:21:30.239
So these are things like revenue per rep right, because if he hits the ARR targets by himself and the reps are struggling, that report to him.
00:21:30.239 --> 00:21:32.250
Well, that's great that we got our revenue.
00:21:32.250 --> 00:21:37.583
But that that tells me it was done through heroics and we're paying these other reps and so that's inefficient.
00:21:37.583 --> 00:21:44.884
And so I put that in place win rates, acv, sales cycle, right, making sure we're hitting certain efficiency metrics there.
00:21:45.550 --> 00:21:49.662
The third bucket was, or is, predictability and repeatability.
00:21:49.662 --> 00:21:52.758
So I'll give you one example from that.
00:21:52.758 --> 00:21:58.061
We've got this interesting dynamic in our business where we've got two revenue streams.
00:21:58.061 --> 00:22:10.871
We've got consumers who sign up for our platform and we've got businesses that we sell to and there's this bridge we call B2C2B, and we'll see a lot of deals, like business deals, come through that right.
00:22:10.871 --> 00:22:12.977
You get like six reps signing up from an account.
00:22:12.977 --> 00:22:17.115
Word starts spreading around that account and it can lead to a meeting with a VP of sales.
00:22:17.115 --> 00:22:18.760
We land those deals all the time.
00:22:18.760 --> 00:22:34.619
We've never done anything purposeful, we've never put a process in place to maximize that, and so I documented him, kind of systematizing this, and I put like a number next to it right, for every 100 B2C signups.
00:22:34.619 --> 00:22:37.473
Here's how many B2B opportunities I think we should generate.
00:22:37.473 --> 00:22:38.471
Let's put that as a target.
00:22:39.112 --> 00:22:42.721
And then the fourth and final bucket is qualitative stuff, a little bit harder to measure.
00:22:42.721 --> 00:22:47.859
But has your team taken to your leadership or has the body rejected the organ?
00:22:47.859 --> 00:22:49.963
That's one thing.
00:22:49.963 --> 00:22:51.415
Are you coaching your AEs?
00:22:51.415 --> 00:22:52.579
Do you have coaching plans?
00:22:52.579 --> 00:22:55.573
How are you showing up in senior leadership meetings?
00:22:55.573 --> 00:22:59.672
Is your influence felt, or are you quiet the entire time?
00:22:59.672 --> 00:23:01.856
And a bunch of stuff like that.
00:23:01.856 --> 00:23:04.363
And then after that I've got the same stuff.
00:23:04.363 --> 00:23:07.882
But here's what mediocre looks like and here's what bad looks like.
00:23:07.882 --> 00:23:10.550
Right, the car is driving off a cliff.
00:23:10.550 --> 00:23:18.532
The cliff is approaching very fast and we need to intervene now approaching very fast and we need to intervene now.
00:23:18.553 --> 00:23:26.134
So, yeah, so a lot of this is metrics driven and you have confidence in those metrics because you've done it before.
00:23:26.134 --> 00:23:27.980
Yeah, so you know track record.
00:23:27.980 --> 00:23:41.298
I think for our audience that one of the challenges that they get caught up in when they're being evaluated on revenue outcomes, as an an example, is like were the expectations set appropriately?
00:23:41.298 --> 00:23:46.942
And I'm sure as your organization gets much bigger, that can become a bit more challenging.
00:23:46.942 --> 00:23:57.960
But probably right now you're like I know that we can do this with the right execution and so you can have a lot more confidence in holding someone accountable to that.
00:23:57.960 --> 00:24:08.059
I think as a company with 30 reps and so on, it becomes you know, it does become a bit more challenging to kind of think through metrics that may not fully be within their control.
00:24:08.140 --> 00:24:19.719
It's just an interesting yeah, and you can always leave those out, but there's always metrics that, unless you're a very early stage startup, there's always some metrics that you should have some level of predictability around.
00:24:19.719 --> 00:24:33.182
Right, Maybe you can't do all of this, Um, but the whole point is like this document empowers you to be a challenging leader, but the right kind of challenging leader, because now you know you're being challenging in the sense of here's the bar.
00:24:33.182 --> 00:24:35.218
It's very clear and let's talk about it.
00:24:35.218 --> 00:24:41.384
It the wrong way to do it is I'm going to come after you unexpectedly and you're going to be like what the hell?
00:24:41.425 --> 00:24:55.054
like you never even told me that this was an outcome I needed to achieve yeah, yeah, people don't necessarily frequently don't know where they stand in an org and when they get you know either let go or something happens and it's a surprise like that.
00:24:55.054 --> 00:24:56.316
Yeah, yeah, it has a real impact.
00:24:56.655 --> 00:25:02.065
Yeah, and it creates unnecessary fear in your organization, which stymies performance.
00:25:04.872 --> 00:25:37.699
I mean, I think to me that is like I've always had this mindset of, you know, helping managers set clear expectations for the team, but I will concede that it's always easier said than done, but it seems like that work up front is worth it because it allows you to follow through on the element you said, which is it's not about you, it's about the bar, and that's such an easier place in which to give critical feedback or to do it from.
00:25:37.911 --> 00:25:40.378
So that effort is worth it.
00:25:40.378 --> 00:25:47.490
And you can see that also like for individual contributors with their manager, like if there's clear expectations, you'll know where you stand.
00:25:47.490 --> 00:25:49.250
We have the bar, the bars, right here.
00:25:49.250 --> 00:25:55.380
We can look at how high it is at any point in time and sort of see how you're doing against it.
00:25:55.380 --> 00:26:01.123
Fascinating to me how infrequently that simple tactic is deployed.
00:26:01.123 --> 00:26:19.538
Mostly, I observe that management and sales teams are much more chaotic and just sort of running, running, running and not necessarily having the exact roadmap and the report card that sort of says whether they're on the right, you know heading to the right city or not.
00:26:20.040 --> 00:26:22.951
Yeah, yeah, and don't look at me too close with all this stuff.
00:26:22.951 --> 00:26:29.731
Right, I've got a few things that I do really well, but I'm similar to most sales organizations.
00:26:29.731 --> 00:26:35.231
There are aspects that I haven't perfected yet, yeah, but to your point, it is common.
00:26:35.231 --> 00:26:40.583
Like most sales, there's plenty of best practice out there for sales management, et cetera.
00:26:40.583 --> 00:26:44.180
The amount of time you see that implemented well, it's pretty rare.
00:26:44.180 --> 00:26:56.001
How many sales organizations do I see that give lip service to a repeatable sales process but don't actually have one beyond just having stages in your CRM?
00:26:56.001 --> 00:26:57.474
That's the status quo.
00:27:00.473 --> 00:27:01.979
I want to pivot to that a little bit.
00:27:01.979 --> 00:27:25.134
You know, when I was thinking about your journey and your movement from product marketing to sales leadership and then, sort of, you know, starting your own company and now focused on improving the quality of sales execution in the world now focused on improving the quality of sales execution in the world my thoughts went to coaching and something that, like coaching, became something you became passionate about to the extent that you started a business around it.
00:27:25.134 --> 00:27:35.792
And you know, one of the observations you might be seeing is the fact that, like, repeatable sales process is lip service and not something that's actually adhered to.
00:27:35.792 --> 00:27:45.221
Do you want to talk a little bit about, like, how you developed a coaching philosophy and how that turned into a sort of like a passion in which to start a business around?
00:27:45.670 --> 00:27:50.762
Well I, there were a number of things that just kind of came together.
00:27:50.762 --> 00:27:53.618
I think the right word for that is a confluence.
00:27:53.618 --> 00:27:56.296
My vocabulary is not.
00:27:56.336 --> 00:27:56.656
Hey.
00:27:56.817 --> 00:27:59.131
I'm down, we'll have to.
00:27:59.131 --> 00:27:59.230
But.
00:27:59.230 --> 00:28:03.119
But the first one is just the problem I saw in the market, right Like that.
00:28:03.119 --> 00:28:11.509
That almost sounds um kind of generic because like skills, you know, skill development for salespeople.
00:28:11.509 --> 00:28:16.641
That's like the second oldest problem in business, the first of which is hiring salespeople, probably.
00:28:16.641 --> 00:28:25.854
But there's we're in a unique time in history where skill capacity across the revenue workforce is probably lower than it's ever been in history.
00:28:25.854 --> 00:28:28.941
And that's not just like founder hyperbole.
00:28:29.402 --> 00:28:34.238
There are three like macro shifts that all happened at once that made this happen.
00:28:34.238 --> 00:28:37.824
Number one is the economy changed overnight.
00:28:37.824 --> 00:28:50.939
We went from ZERP era, zero interest rate policy, where selling was easy, money was free or cheap, buyers were buying and therefore sellers did not have to be very good.
00:28:50.939 --> 00:28:52.261
They showed up.
00:28:52.261 --> 00:29:07.880
If they could fog a mirror, they could close a deal, and then immediately they were thrust into this new economy where decisions were made at a higher level, with more scrutiny, bigger buying committees, more risk-averse buying committees, and skill capacity hasn't caught up to meet that new demand.
00:29:07.880 --> 00:29:09.977
So that's one, that's only one.
00:29:10.609 --> 00:29:21.962
The second one is at the exact same time, all of this was happening, most of the revenue workforce went remote and got younger.
00:29:21.962 --> 00:29:30.017
That's not me being a boomer and criticizing Gen Z and millennials and all that kind of stuff, but let's just call that what it is.
00:29:30.017 --> 00:29:47.577
You've got all these 25-year-old AEs and 23-year-old soon-to-be AEs coming into the workforce, into a new economy, selling from their bedroom, getting coached by a manager who doesn't know what the hell they're doing in their own job and trying to sell in this economy.
00:29:47.577 --> 00:29:52.174
Right, that is a recipe for dangerously low skill capacity.
00:29:52.655 --> 00:30:06.817
And then the third element is, while the revenue, workforce got younger, a little bit less sophisticated, just because they're less experienced and remote, buyers got way more savvy and educated and they know more, and so it's like an unfair playing field.
00:30:06.817 --> 00:30:18.624
You've got economy flipped, you've got workforce went remote most of it, and you've got buyers who, essentially, you know it's not even close to the sophistication.
00:30:18.624 --> 00:30:26.269
And so now, like skill development, even though it's one of the oldest problems in existence, it's now one of the most urgent problems in existence.
00:30:26.269 --> 00:30:35.424
It is I would call it a go-to-market skills crisis, where AEs, sdrs, frontline managers, csms, even marketers hell.
00:30:35.424 --> 00:30:37.538
I mean, they've always had problems.
00:30:37.538 --> 00:30:49.000
The delta between where their skill capacity is and what is needed to win today in 2025, very big delta compared to what that delta looked like in previous decades.
00:30:50.111 --> 00:30:57.278
And so you observed this and said, hey, I think I can bring a unique perspective, because you know it's been this dynamic, been around a really long time.
00:30:57.278 --> 00:31:00.233
But you saw the need.
00:31:00.233 --> 00:31:07.820
Maybe the need increased or did you have like, hey, I've got the good, I've got the actual solution vis-a-vis everything else I'm seeing out there.
00:31:08.171 --> 00:31:09.690
Yeah, well, that led to the next piece.
00:31:09.690 --> 00:31:12.880
So there's a few passions that you know kind of play with this.
00:31:12.880 --> 00:31:17.020
One is passionate about sales, passionate about the market and passionate about learning.
00:31:17.020 --> 00:31:23.792
Right, which is our, what our business is.
00:31:23.792 --> 00:31:26.059
But then, like, our unique angle on the solution is we're not your typical sales training company, right?
00:31:26.059 --> 00:31:28.027
This isn't a one and done engagement.
00:31:28.027 --> 00:31:29.938
It's not one size fits all.
00:31:29.938 --> 00:31:38.057
It's not theoretical, where we teach you what to do without without teaching you how to do it, and it's not a bunch of trainers who haven't closed the deal since 2014.
00:31:38.057 --> 00:31:43.770
Instead, we have a platform where you learn from number one, the best of the best, right?
00:31:43.770 --> 00:31:50.230
No professional trainers, no, guys who sold Xerox in the 1980s and are still teaching the same way today.
00:31:50.230 --> 00:31:57.924
You've got, you know Nate Nesrella, kyle Norton, kyle Coleman all these like best of the best revenue experts teaching.
00:31:59.030 --> 00:32:04.891
The second thing, and what makes this unique, is we make a distinction between skills and sales process.
00:32:04.891 --> 00:32:09.790
Right, sales process is what to do, it's what do you do in this stage, then this stage, then this stage.
00:32:09.790 --> 00:32:20.863
Skill capacity is deeper it's what to do, why to do it and how to do it, and so every course you take in our platform is dedicated to one skill and it goes deep on that.
00:32:20.863 --> 00:32:40.615
So instead of learning how to sell enterprise good, which is going to be a mile wide and an inch deep, you take one short course on every component of enterprise selling Enterprise-grade discovery, enterprise grade multi-threading enterprise grade C-suite meetings, negotiating with procurement.
00:32:40.615 --> 00:32:52.922
And when you do that now you can go really deep on each skill and by the time you're done you have a very different skill set than the people who got like a surface level sales process training that dabbles across all of those topics.
00:32:54.009 --> 00:32:54.952
Yep Makes sense to me.
00:32:54.952 --> 00:32:57.530
I want to move, though, to like what you're seeing in the world.
00:32:57.530 --> 00:33:01.785
When you now cause, you're interacting with sales leaders on a regular basis.
00:33:01.785 --> 00:33:03.873
What is something that you're seeing?
00:33:03.873 --> 00:33:15.813
Any patterns that you're seeing in how sales leaders are being effective today versus what you've seen in the past, or any glaring hole that you are looking to solve as it relates to leadership impact?
00:33:16.334 --> 00:33:28.623
I mean, I think that is a subset of the problem I just mentioned, right, like revenue skill capacity across the revenue profession dangerously low.
00:33:28.623 --> 00:33:36.471
Frontline managers in particular are struggling more than others and it's not their fault, like.
00:33:36.471 --> 00:33:54.340
This is not me throwing stones, it's our current way of promoting people is broken, right, you take your super rep, who loves working alone and closing deals, you turn them into a manager and then there isn't really any rite of passage in training and development for frontline managers.
00:33:54.340 --> 00:33:55.830
You just I mean, there wasn't for me.
00:33:55.830 --> 00:34:01.021
That's not a hit at gong, but it's the truth, right, I went into sales leadership and yeah, no, I.
00:34:01.522 --> 00:34:02.171
I'm with you.
00:34:02.171 --> 00:34:10.157
You know I read every sales leadership I book I could with within like a 90 day sprint because there wasn't any other option.
00:34:10.157 --> 00:34:17.498
So I think like there's a lot of problems in sales leadership, it's a really big opportunity for people.
00:34:17.539 --> 00:34:19.626
What advice are you giving to sales leaders right now?
00:34:19.626 --> 00:34:21.532
Like, is there anything you're finding yourself saying?
00:34:21.532 --> 00:34:31.831
Like you're you're interacting with sales leaders at a far greater velocity than I am, and this whole, uh, this whole, like, everything that I'm doing is around trying to define like am I good at my job?
00:34:33.454 --> 00:34:33.994
So what are you?
00:34:34.375 --> 00:34:34.976
what are you seeing?
00:34:34.976 --> 00:34:35.836
What are you saying Like?
00:34:35.836 --> 00:34:37.039
What are people asking you for help?
00:34:37.039 --> 00:34:43.266
For I certainly know that you've got a lot of your business focused on how do we get sellers to be great at skills, and I'm all for it.
00:34:43.266 --> 00:34:51.375
I mean, I think this could be a tool to help leaders get their team to up level like fantastic.
00:34:51.375 --> 00:34:58.849
But in those interactions with the leaders themselves and their ability to impact, I would love to just get a synopsis of any advice you're giving or anything in the world we live in now, august 2025.
00:34:59.409 --> 00:35:02.760
Yeah, I mean it's not all that different than what I've already mentioned, right?
00:35:02.760 --> 00:35:06.681
Like I'm not training them on how to do their job or anything like that.
00:35:06.681 --> 00:35:20.295
The conversation I'm having with them is you went from a world of growing at all costs and hiring, and hiring and hiring, regardless of what revenue per rep looks like, and now you're in a world where you're being asked to do more with less.
00:35:20.295 --> 00:35:22.237
That's not going away anytime soon, right?
00:35:22.237 --> 00:35:23.094
This isn't a fad.
00:35:23.094 --> 00:35:34.297
This is going to be a sticky mode of operating for a while, and so your brag metric is not headcount, it's revenue per rep.
00:35:34.297 --> 00:35:43.512
Now, I'm not saying you need to jack up revenue per rep to the stratosphere, because if revenue per rep is too high, then you're probably not growing as fast as you could.
00:35:43.512 --> 00:35:47.670
Right, if you got a million dollars revenue per rep, well, you're probably hedging a little bit.
00:35:47.670 --> 00:35:57.614
But revenue per rep getting that in the right balance probably one of the most important metrics today and one of the many ways like probably a top three way to pull that lever.
00:35:57.934 --> 00:36:01.851
Skill capacity Now, I don't want to oversell that.
00:36:01.851 --> 00:36:05.628
There are other things you need to get right beyond skill capacity to drive up revenue per rep.
00:36:05.628 --> 00:36:08.885
Right, if you're targeting the wrong accounts with the wrong message.
00:36:08.885 --> 00:36:11.110
You got to fix that first.
00:36:11.110 --> 00:36:20.664
But if you've got your strategy in place and you've got some of the basics of your go-to-market, now skill capacity becomes a board level metric right.
00:36:20.664 --> 00:36:25.137
This is something you can talk about with your board saying here's where my skill capacity is.
00:36:25.137 --> 00:36:33.286
It's at the right level, which means we should hire more, or it's low, which means hiring would be a stupid idea.
00:36:33.286 --> 00:36:41.219
Let's get more out of what we can, first by increasing that number, skill capacity, and then we can start hiring again.
00:36:41.219 --> 00:36:57.369
I think this is more of a prediction rather than something I'm consistently seeing, but I think, because of the macro environment we're in, we're going to see skill capacity become not a nice to have job perk but like a requirement.
00:36:57.889 --> 00:37:16.351
So number one, chris Orlob advice to leaders is like you have to figure out a way to increase skill capacity of your team, like you need to upskill them based on the you know dimensions that you described, the three things coming together the world we live in, the more discerning buyers, the experience levels, the things.
00:37:16.351 --> 00:37:17.172
What's the second thing?
00:37:19.217 --> 00:37:20.327
I don't know if I have a second thing.
00:37:20.327 --> 00:37:22.431
All of my conversations are focused around that.
00:37:22.431 --> 00:37:29.302
So, um, yeah, I mean the first thing is like make sure you have your go-to-market strategy baked right.
00:37:29.302 --> 00:37:30.806
Are you targeting the wrong right accounts?
00:37:30.806 --> 00:37:36.438
Because having a great, highly skilled sales organization talking to the wrong people, it's not going to solve your problem.
00:37:36.438 --> 00:37:39.994
That's coming from the guy who sells skill capacity.
00:37:39.994 --> 00:37:42.273
So I know how to be level-headed here.
00:37:42.273 --> 00:37:48.188
But, assuming that's the case, it's pretty rare that I hear pushback on it, because if I did, I would go.
00:37:48.188 --> 00:37:56.945
Well, go listen to your reps' gong calls and tell me what you hear and if they're great, right, like you, don't have that problem.
00:37:56.945 --> 00:38:09.472
But you're one in 20 and most leaders I talk to they say my reps are doing surface level discovery and then transitioning to a pitch, or they're single threaded or they don't even know what the word champion actually means.
00:38:09.472 --> 00:38:14.050
Anybody who likes the product remotely, that's a champion in my, in my, rep size.
00:38:14.050 --> 00:38:18.831
So you know most of my conversations are pretty focused within that world.
00:38:19.592 --> 00:38:26.237
And do you have like learnings that you're offering around the leadership aspects, things around people, pipeline and business?
00:38:28.025 --> 00:38:40.597
We do have sales, like frontline AE manager curriculum yeah, we don't quite yet have second line leadership or like VP of sales and CRO learning paths and stuff like that.
00:38:40.597 --> 00:38:42.163
We plan on doing that.
00:38:42.163 --> 00:38:48.945
That's probably a 2026 thing, but we've got the foundations in place for AE managers to learn their job and do it well.
00:38:49.365 --> 00:38:52.250
And what are some of the high level concepts in frontline manager?
00:38:52.250 --> 00:38:54.012
You know, skill upskilling.
00:38:54.373 --> 00:38:55.936
Yes, similar to what we've talked about.
00:38:55.936 --> 00:38:59.340
Right, we've got courses that support those three pillars I've mentioned right.
00:39:01.144 --> 00:39:01.429
The people.
00:39:01.449 --> 00:39:07.896
Pipeline and the business yeah, like there's hiring and recruiting, there's skill coaching for AE managers how to run team meetings, some of the basic stuff.
00:39:07.896 --> 00:39:09.911
Then you go into pipeline management.
00:39:09.911 --> 00:39:11.833
We've got deal strategy, all that kind of stuff.
00:39:11.833 --> 00:39:17.132
Manage the business we're a little bit lighter in that bucket.
00:39:17.132 --> 00:39:22.675
Right, we don't have like deep curriculum yet on you know how to do business planning or stuff like that, but we'll get there.
00:39:23.726 --> 00:39:34.498
Well, chris, I got to say man I, you know I'm inspired a lot by just the tenacity with which you bring to the sport that you're playing in, like going after upskilling of sales.
00:39:34.498 --> 00:39:56.295
People have been doing that since the beginning of time and I think the success is A having a great product and having real operational experience and having lived it, which clearly you have, and then the rest is just the rigor with which you go to bring, and a lot of your content continues just to be as impactful and interesting and readable in 2025 as it was in 2017.
00:39:56.295 --> 00:39:57.567
So, eight years and counting.
00:39:57.567 --> 00:40:05.891
I enjoy thoroughly, you know learning from you, you know through the social media avenue alone.
00:40:05.891 --> 00:40:07.695
So it was great speaking with you.
00:40:07.695 --> 00:40:09.385
Anything else you'd want to share with the audience?
00:40:10.809 --> 00:40:13.494
No, I think that sums it up and you know I'm grateful.
00:40:13.494 --> 00:40:15.498
First of all, thank you for all the kind words.
00:40:15.498 --> 00:40:21.974
I think you're giving me a little bit too much credit, but I had a ton of fun today and I hope people got value out of this.
00:40:21.974 --> 00:40:26.155
And if anybody wants to connect with me, you can find me on LinkedIn.
00:40:26.965 --> 00:40:30.454
Yeah, I was going to say I know where to find Chris on LinkedIn or at pclubio.
00:40:30.454 --> 00:40:32.771
Chris, thanks for joining us today.
00:40:35.806 --> 00:40:38.869
We'd love to have you on Pillar Talk.
00:40:38.869 --> 00:40:41.213
Talk to you soon, man.
00:40:41.213 --> 00:40:42.034
Thanks, Rick.
00:40:50.565 --> 00:40:59.429
Reflecting on the conversation with Chris Orlob, the first thing that really stood out to me is that we have the same self-diagnosed leadership gaps, this ability to work really well with top performers and really struggle with folks that are core performers or below.
00:40:59.429 --> 00:41:08.731
It's a very real thing and it's something that has been a big challenge for me for many years that I've been in this leadership position when trying to improve as a leader in this area.
00:41:08.731 --> 00:41:15.797
Chris made this excellent point about step one determine if the team member has the raw material to succeed.
00:41:15.797 --> 00:41:27.028
Determine that it makes sense that if you do invest the time and the coaching and find the patience that's required, that there's a benefit that you can get on the other side through the skill development of that individual.
00:41:27.028 --> 00:41:42.295
When you have a history of performing at a high level and you're used to moving at like a certain speed, it's a real challenge to slow it down, to have the patience to maybe get an answer that you didn't expect to a question and be good with that and turn it into a learning opportunity.
00:41:42.295 --> 00:41:50.235
One challenge that I'll continue to have is determining who has the potential to perform and who does not and is just simply in the wrong role.
00:41:50.235 --> 00:41:52.530
It's not always cut and dry.
00:41:52.530 --> 00:41:53.474
At least, that's what I find.
00:41:53.474 --> 00:42:03.070
One thing I have to say, though, is that a key determinant of that is the will of the individual to receive coaching, versus the folks that are resistant to it.
00:42:03.070 --> 00:42:10.485
Now, the leader has to be good at coaching, and I've seen situations where there's an individual who just feels like they aren't getting the right coaching.
00:42:10.485 --> 00:42:21.217
I can't help you with that, but if we assume that the leader is actually good and has valuable information to share with somebody, that willingness to receive it can be a key determinant of whether they have the raw material to succeed.
00:42:21.217 --> 00:42:27.425
I personally adhere to a customer engagement methodology that helps me be consistent in the coaching that I deliver.
00:42:27.425 --> 00:42:32.077
I hope that helps my leadership team as well be consistent in their coaching.
00:42:32.077 --> 00:42:35.733
So I'm not saying one thing and they're saying another, and the rep's wondering what to do about that.
00:42:36.534 --> 00:42:41.552
Now, what stood out the most for me in this episode was Chris's description of how he sets expectations.
00:42:41.552 --> 00:42:44.108
He talked about the wiggle document, wgll.
00:42:44.108 --> 00:42:48.322
He made an important point Don't make the coaching about you versus the rep.
00:42:48.322 --> 00:42:51.028
Make it about the rep versus the bar that was set.
00:42:51.028 --> 00:42:52.231
And how do you set the bar?
00:42:52.231 --> 00:42:55.827
Setting clear expectations and defining them.
00:42:55.827 --> 00:43:08.228
He talked about revenue outcomes or growth efficiency, win rate, process improvements that the individual make, the team's response to a new leader, the coaching plans that were created, leadership participation.
00:43:08.228 --> 00:43:11.657
The thing that stands out isn't necessarily those individual points.
00:43:11.657 --> 00:43:19.757
It's that he took the time to define what success looks like for the individual, sat down with that person and walked through it in detail.
00:43:19.757 --> 00:43:25.764
As a result, everyone knows where things stand and the relationship can be far more productive.
00:43:25.764 --> 00:43:35.568
It can now be about the individual versus the bar that was set and can help sustain focus and execution rather than wondering where I stand and am I performing well in my role.
00:43:35.568 --> 00:43:45.670
I provide leaders in my org with a top 10 list, almost like David Letterman style at the beginning of when they join around key focus areas, and it's something that we can keep going back to and back to.
00:43:45.670 --> 00:43:53.273
Now what I need to do is take an additional step of ensuring that there are clarified expectations as part of that Now.
00:43:53.353 --> 00:43:57.641
Lastly, chris did a nice job of outlining the sales skills gaps.
00:43:57.641 --> 00:43:59.065
I'll say that 10 times fast.
00:43:59.065 --> 00:44:02.856
That he sees in the market and is the basis behind his business.
00:44:02.856 --> 00:44:08.737
I got to say it is hard to teach reps the skills it takes to succeed.
00:44:08.737 --> 00:44:20.036
When I think about sports or anything in the arts, the amount of practice that takes place is staggering, and yet in B2B sass the learning is almost entirely done by doing.
00:44:20.036 --> 00:44:27.295
Chris is passionately attempting to tackle that and if you read his content online, look, he brings a ton of credibility.
00:44:27.295 --> 00:44:28.177
So check it out.
00:44:28.177 --> 00:44:31.173
I want to thank Chris for joining Pillar Talk this week.
00:44:31.173 --> 00:44:37.996
I want to thank Ari Smolin for producing my man, isler and Sons of Summer for the tunes and I want to thank you, listener, for joining.
00:44:37.996 --> 00:44:39.385
We will see you next time.
00:44:39.385 --> 00:44:41.648
Have a good one.
00:44:42.088 --> 00:44:45.012
It hurts in me Like a drug.
00:44:45.012 --> 00:44:46.693
I can't shake, I can't quit.
00:44:54.686 --> 00:44:56.875
It's never really what you said it was.
00:44:56.875 --> 00:44:59.577
All you're doing is breaking.