E52: Winning in Crowded Markets - The CRO Playbook (Jonathan Leaf, CRO @ BambooHR)

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com. And every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes. Here's a familiar scene. A deal's in commit and the buyer says, can I talk to somebody like me? Next thing you know, sales reps are asking CSMs after hours. 5 people are in Slack trying to remember who helped last time. And that one customer who always says yes is getting burned out after 3 requests in a week. That's why this episode is brought to you by User Evidence, the platform that turns customer proof from chaos into a repeatable GTM system. With Advocate certificates, references, and real customer evidence all in one place, your team can share credible proof instantly and keep deals moving forward instead of stalling. Companies like Gong, Ramp, and Workato already use User Evidence to capture customer proof, build buyer confidence, and shorten sales cycles. See how at userevidence.com. That's userevidence.com. Today's guest is Jonathan Leaf, who is the CRO at Bamboo HR. And Jonathan spent the 18 years of his career at SoftChoice, where he started as a rep and ascended to VP of sales for Western and Central US. Uh, then he ran Central US commercial and private equity sales at AWS in a pretty exciting time, uh, at, at AWS for sure. And then was the SVP commercial sales at RingCentral before joining Bamboo as their CRO, uh, almost 18 months ago now. And today we are going to talk about two very interesting topics that I think are going to be relevant for everybody. One is how to differentiate and win in crowded, undifferentiated markets. Obviously Softchoice was a reseller of other solutions and products, which you can say a little bit more about. So not a ton of differentiation. Bamboo is in a knife fight of a market, uh, selling HR tech with a whole bunch of competitors. So you are very well placed to talk about competing in, in, uh, these types of industries. And then we're also going to talk about how to leverage culture as a revenue strategy, which I think is very much tucked in because I'm sure you'll talk about how the sales experience is a differentiator and a lot of that comes from culture. So lots of cool stuff to unpack and excited for this one. Thanks for joining.

Yeah, pleasure to be here, Kyle. Big fan of the pod. So thank you for having me.

Thank you kindly. So what did I miss in your intro? Give people like the 60-second on filling in the blanks there.

Yeah, I mean, you didn't miss much. Uh, I kind of fell into tech, admittedly. So this was at like the peak of the dot-com era, call it 2000, and, and joined Softchoice literally knowing very little about, uh, the tech industry at the time, but ended up spending 18 years there. And I served in, I don't know, 8 jobs around 5 different cities, uh, a number of the assignments cross-functional. So like, I, I couldn't have wished for a better experience. Certainly people there saw potential in me maybe I didn't see in myself. And then you mentioned AWS, like what a fascinating time. Like I had an opportunity to birth a commercial business in the central US that was largely focused on the West Coast. So the company grew so quickly, AWS grew so quickly, we had to create other organizations and other geos just to create proximity to customers and to partners. Like what an incredible experience, I was able to build that out. You mentioned RingCentral, like an effort in scale supporting 500,000 customers, a couple billion in revenue spanning SMB and mid-market. Now serving as CRO of Bamboo, and maybe just a little bit more on BambooHR, we are in the human capital management category, which as everyone could probably appreciate, a massive, massive TAM, a massive opportunity. Inside that, we're very, very prescriptive about the things we solve for our customers, in particular around HRIS, around payroll, around benefit admin, and around employee of record. So serving about 3 million users, 34,000 customers. It's been an incredible ride. We're building quickly.

What did Bamboo start as? Did they start as an ATS? Am I remembering that right?

Well, we certainly provide an ATS, but no, we, we started squarely, Kyle, in the HRIS segment. So think of that as like, best way to frame it is like, if you're an employee, it's everything from like the onboarding experience through to the offboarding, like all the process administrative stuff that would come with that employee as well, the experience of that employee.

Okay, cool. My first startup tech experience, we were on Bamboo at the time.

Oh, great.

So, you know, and it was, it was wall to wall. Um, and how big is like Bamboo and your team without sharing anything you're not allowed to.

Yeah. So we, we serve 34,000 customers, uh, roughly 3 million users. Uh, I think now the company's up to 1,600 employees and the revenue org represents about a quarter of that. And the best way to maybe describe my remit is I kind of frame it inside the customer journey. Like if the customer journey starts with that customer's initial engagement with your brand and like some awareness of who Bamboo is through to like customer support, customer success. I kind of own all the innards, like everything in between those two things. So everything from a presale, sale, kind of post-sale capacity.

Yeah. Okay, cool. All right. So let's get into differentiations. Like maybe just explain what Softchoice is so folks get an understanding of, of like that competitive space and then we'll get into some of the specifics.

Yeah. Well, You know, you and I talked a little bit about this, like you're, you've been in Toronto up until real recently. Congratulations again on your move. But, um, you know, Softchoice is based in Toronto. So, you know them and you know the space well, like talk about a knife fight. Like, so what Softchoice does at its core is provide solutions to its customers via, uh, other manufacturers and publishers. So think about it as like they're a, a very large partner to the Microsofts of the world and the Ciscos of the world and the AWS and GCPs of the world. And. Essentially what they're building is built solutions for customers that involve infrastructure, applications, professional managed services. But like none of it is the company's own IP. Some certainly is, like I don't want to discount it, but the bulk of like the hardware, the software, et cetera, is not. So you could argue like that is an incredibly crowded space and you don't have your own IP. You may or may not be paying top dollar to these people. Like what differentiates you oftentimes is how you show up to the customer and how leadership shows up to its teams and how you develop your people and how you build a culture that people thrive in, people progress in, people feel genuinely a part of. Like, that's what keeps them in seat. And I think that's what shows up to the customer. So, man, there wasn't a day that went by, Kyle, where I didn't have to like scratch and claw to like be at my best to make sure people were like firmly in seat, loving the work. Yeah. Yeah.

I had a feeling crowded market and culture as a revenue strategy were closely aligned and you're already there. So yeah, maybe unintentionally was clearly accurate. So yeah. How do you think, so let's talk about the strategy. So you're selling products that many other companies sell and you're competing with the OEMs themselves in many ways. And so how did you How, from a strategy perspective, how did you think about, uh, competing? What was the differentiation? How are you— what was the strategy?

Yeah. Well, are you talking specifically about Softchoice? Are you talking more modernly inside Bamboo?

Bamboo Pro, like, so in these environments where your product is undifferentiated, because I think the other framing that I'll give is there are more competitors in all of these categories than ever before, because it's so easy to Vibe Code, uh, some product, raise, uh, a couple hundred grand or a couple million bucks.

Yeah.

And it just seems like there's this insane proliferation, uh, in every category from AI upstarts to every incumbent wanting to now add, uh, those tools to their product. And, and so it feels to me like it, the world has never been more competitive. This is something I hear all the time from folks. And so just give people like how to, how to compete in that.

Yeah, absolutely. I mean, just think about like, if it's you or I, just think about like every day, how much inbound you get with regards to some AI solution, call it what you want. I mean, it's just like, it's accelerated so dramatically. So if I just like focus in on the space Bamboo's in, like the competitive entrants in the last 5, 10 years has just multiplied exponentially. Like it's just changed dramatically, but no matter like what happens in the market, no matter what happens with, you know, competitive entrants, like some things never change. Like at the end of the day, customers have real problems to solve. Like they have real problems to solve. And what I think about if I kind of like start at the top, it's like, okay, like how does the company show up? Like I'll use BambooHR as an example. Like I think just foundationally, the way the company shows up behind its mission, behind its vision, how it subscribes to its own values, how those values inform how we interact, how we make decisions, how we serve our customers, like that is a differentiator. And I say that through experience, like you and I've worked different places where like the company can't get out of its own way, right? Like the company at the end of the day is kind of fighting with itself. So I think it starts there. And I think it's important that you know, the company be long-term minded, thinking about where the market's going and our customers are going. But like some things will always be true. I also think it's super critical. Like, you know, I mentioned, you know, we're in the human capital management space. Okay. That's a massive, massive category. It's really, it's really important. We're prescriptive around what it is we build and who it is we sell to. And I think you're not going to differentiate the ocean you can differentiate pretty profoundly if you understand the market you serve, who you build for, and who you sell to. And I'll talk a little bit more about that. Specifically on product, I think you need to be maniacal around like what it is you build and what it is you're solving for. Like kind of back to like, who's your ICP? But like, I'm even talking maybe at a more granular level than who's your ICP. Like, what are the specific problems you're building to solve? And how is it you're doing that? And who are those customers? And like, you just need to have a maniacal focus on like, what do you build that's native? Like, what are these applications that are just going to be native, are going to be foundational, are going to be seamless, integrated? The experience to the customer is going to be world-class. And you're going to own that experience kind of end to end. And then where is it you're going to build adjacencies, whether it's through partnership or integrated solutions or otherwise, but there's differentiation across all that, but you have to be really, really intentional. And maybe the last two things I'll say is like, on people, I mean, Kyle, you talk about it a lot. I listen to the pod a lot, like who you hire matters and the type of people you bring in matter and the energy and effort you put into nailing that profile and testing against those attributes matters. And I am super passionate about people being connected to the mission because if you're connected to Bamboo's mission of setting people free to do great work, you're going to show up to your customers in a way where you truly believe we can do that. And you're not selling on features and functionalities. Selling on outcomes, like ways to help that employee live up to their own company's mission. So who you hire matters. And then, you know, as you know, like routes to market, geographies you serve, all those things are nuanced, very, very nuanced. And how you interact inside those different channels, inside those different segments, inside those different geos is differentiated, is differentiation in its own.

Okay. So there's like 6 things I want to unpack here.

I've said a lot.

Yeah, no, that's great. This is a good framework to sort of lay it out, how the company shows up to customers, being prescriptive on who you sell to and how you're solving for it, how you hire. And so now we can untangle a bunch of it. So what is the way that showing up well to a customer actually wins you deals? Like how does it actually mean that you're going to win a customer just by like showing showing up with the mission? What do you think is behind it?

Yeah. Well, I think the mission is the connective tissue. It's like, you know, most missions are, well, they're intended to be bold. They're intended to be big. But I do think they serve as a North Star, right? Like our mission is what I described. And if we do it, like our customers literally because of our technology are able to focus on their own missions, are able to focus on the work in their daily lives that's of value. So how is it like, well, stepping down from the mission, like think about the customer journey in its totality. Like I don't, I don't know that you win deals based on what I just described. I think you win deals for a series of a host of other reasons. And one of the frameworks I like to use is like, if you just think about the entirety of the customer journey, like from the start of like when they engage the Bamboo brand or they engage your company's brand, like what is it they think of? Like I want to be thought of as trustworthy. Like I want to be thought of as, um, you know, built for that customer. I want to be thought of as someone who really understands that customer and their, their challenges. And I think you and I'd agree, like, like owner is the same thing where it's, you're not, you're serving SMB. And I think you and I can both attest to the fact that I don't think SMB buyers, whether you're a restaurant owner or You know, an SMB customer that's 250 employees, like they're not looking to buy more stuff. Like they're just like, less is more, solve my problems. And they're not looking for bespoke solutions to do bespoke things. So it's like, if we can eliminate that complexity and help them consolidate in some capacity, I think that's a huge win. So when I think about like, okay, like, well, how is it you actually go and win? I mean, it's, it's all what I just described. It's, it's differentiation across the entirety of the customer journey. It's appreciating the customer's issues that they're faced with. It's not burrowing yourself in this rat race of features and functionalities. It's, it's instead like acknowledging that what these customers are faced with and pushing on the outcomes that it is you can help solve for them.

Yeah. And in, in a market where it's hard for a buyer to choose based on like technical differentiation or something that's like really obvious, then they are gonna default to the best sales experience because at the end of the day, like that's the representation of what they are going to anticipate from the rest of the engagement with that company. And so if you have a, I find like if you have a sloppy sales experience that like where you don't feel like this person is listening that well or cares that much and the follow-up emails are a little slow, then you're not going to expect that the service is going to be good with that, with that customer. You don't think that implementation is going to be any good or post-sale support is going to be very good. And so I, I find one of the things that is really meaningful is that Sales experience and people showing up and caring about the mission is the best, is the best evidence of what they can anticipate as a customer. And so if the product is almost the same, I just want to partner with good people. And this for a long time actually was why I've implemented Salesloft 5 times now. And, you know, hopefully none of them are listening to this, but like not a lot of real differentiation, but between them and Outreach. Like it was always feature for feature and tit for tat. And it was really tough to, as a buyer, to really know like which product was that much better. I think maybe Salesloft had some edge, but my experience with their team was always so incredible and they always showed up to make sure that we got a ton of value from the product and they were like highly engaged and, and, um, even the times where I explored outreach, I'm like, I should do my diligence and look at some other tools. I was like, okay, like I just, the magic of that experience was so compelling and like, why would I take a risk having not as good support and not having somebody who cares about solving my problems? So I very much resonate with what you're saying.

Yeah, I think too, Kyle, like just plain speak, like back to what I said earlier around some things will never change. Like customers are going to want to, they're going to want a fair value exchange. Customers are going to want to, they're going to want to get to that value as quickly as possible. They are going to want to have an incredible experience with your people. Like some of that will always be true. And I totally agree with you. So I don't want to minimize at all, like how the revenue teams show up is everything, is everything. And like really understanding the customer, this, the customer's shared problems and representing us in a light that they can trust and resonate with, I think is critical.

Yeah.

Yeah.

So I want to get into now being prescriptive on who you sell to and how you're solving the problem and being maniacal about it was, was, uh, was how you said it. What, um, how does that help you win and scale? Like the, the being prescriptive, where does that? Where does that lead you?

Yeah, I'm passionate about this one because it's like, you know, we, we all talk about like, okay, so you and I or other CROs would say, okay, well, how is it you grow and how is it you, you know, ultimately accomplish your long-term revenue goals and growth goals? Well, it's like, okay, you have, you have market segments you can enter and there's always a lot of talk about, well, like, let's, we should, we should go upmarket and we should find ways to go upmarket and to better penetrate enterprise. There's, there's certainly opportunity to enter into different categories, right? And to figure out how do you just generally increase your TAM and build products that, you know, satisfy other needs of your customers. There's geographic expansion, all the things. And what I have found to be enlightening, refreshing is we are just so focused at Bamboo around the customer we serve. And our mission is to be number one in that, in that segment, which is the SMB segment. So what does that mean? Well, you know, this is a massive, massive TAM, massive. I think it's probably the biggest in SaaS. And if you just were to like to zero in on the US, like for every point market share you gain, it's exponential growth to the company. And that's not even really thinking about geographic opportunity you have. So it's like, it's super, super meaningful. So then it's like, well, do you want to distract from that? Like, do you want to distract from this opportunity you have in front of you to just get incredibly fixated on the issue, the shared opportunities that these customers face and go take share. So like, what does that mean for us? Well, that means like we are, we are very much committed to who we build for in the sense of there's trade-offs dependent upon who you decide to build for. And the trade-off that, you know, often comes up in my world is, well, when you're building for that size customer, And I would say our sweet spot is somewhere between maybe 20 and 2,000. When you're building for that type of customer, like consider the journey that customer's on. Like oftentimes, you know, they're coming from very manual administrative, like there's a fair bit of overhead and there's a fair bit of things they're having to do themselves. And I think that's riddled with risk because anything that's manual is probably going to have risk. So they're coming from this, this world. And it's okay, we're now building for someone where we can be quite opinionated, where we want to be quite opinionated. And as you start to go upmarket, I think the opportunity to be opinionated, the opportunity to build what you believe is best in class, that you believe is easy to use, gets that customer to value quickly, like, is compromised in some way. And not to say it's an impossible bridge. It's not at all. Companies do it often. We've just chosen not to because we are very, very focused here. So that then aligns with our go-to-market strategy and how we resource our teams. What are the problems we narrow in on most frequently to serve our customers in and to differentiate around? Like there's a common thread I think that's pulled through across.

Yeah. The, the, and you see this fracture in so many companies where, you know, like go-to-market is chasing some, chasing a segment that has the highest ROI and product may be building for something like just a little bit different. 100%. That oftentimes leads to churn. The other reason I think this is really interesting is, you know, in these markets that have tons of competitors, if you are trying, if you are in a competitive undifferentiated market, and then there are multiple players trying to be many things to many different people, that messaging gets much more watered down. If you're the one company with something that's like much more crisp and specific, and you can speak in the language of that particular segment and have a point of view that is more resonant with that segment, even though it means alienating potentially other parts of the market, you'll win so much more in that particular niche, which, which seems to be what you guys are doing.

Yeah, we're very, very focused on it and we debate it furiously. Like we, we debate our strategy doc constantly. Like, are we doing what we said we were going to do? Is there, are we at a point in time where this needs to evolve? This needs to change. If so, why? How does the prodigy product strategy follow suit? How does the revenue follow suit? How does customer support and CX do the same? Like, I can't tell you how many times, Kyle, like my teams have put things over the fence into our onboarding implementation and support teams. And we, we haven't set them up for success admittedly. Right. So it's so important we go back to that and just hold ourselves accountable.

Yeah. Okay. This is, this is great. So how you show up being prescriptive and, and nailing a niche with specificity. The other thing you mentioned is who you hire matters and, and like nailing and testing for that profile.

So yeah.

How do you think about nailing that profile and testing for it and being able to repeat it? What, what have you put in place to make that work?

Yeah, this is one that is, I mean, I'll just give everyone a little bit of context. So I am Bamboo's first CRO and the company, yeah, the company is, it's been around 15 plus years. And in some ways I think had a bit of a first mover's advantage. Like it, it built great, great software solving a real need, especially in this segment of customer that they had, right? Like very manual, administrative heavy processes that didn't scale. Small teams trying to do that, all the things. And we fit that need really, really well and scaled very, very quickly. And I think what that allowed us to do is have a, in a way, a very narrow go-to-market strategy from the standpoint of how we acquire customers. And the best way for me to maybe frame it is super good at demand capture, like really good at demand capture. Call that like the 5% of the market that's looking for what Owner does or what Bamboo does, like that's on the market. And not super sophisticated around the 95% of the market that is not buying, likely has an incumbent, isn't thinking about this as a need, weren't super sophisticated. So, you know, when you get to our size and scale, like at some point you lose efficiency, right? Like you're, I think, you know what I'm saying? Like the bulk of that business is inbound business and throw a little bit of AI into the mix and all of that stuff is now just different. One of the first things that I started thinking about is just how do we diversify our go-to-market strategy? Like how do we create more routes to market? And the way I've been thinking about that is, you know, very typical things like, you know, outbound BDR through to how do we segment ourselves to show up differently in EMEA and in APAC and in Canada and in other markets through to how do we segment our partner channels and create better proximity to our partners and really build for those partner, those partner channels on through. Like we just weren't, we weren't all that sophisticated. So I say all that to say like. This is a chance for us to like re-script ourselves and like, how is it we want to grow up to be? Like, what is it we want to become? And, you know, we want to become something much, much larger than what we are now. But to do that, it's important that we have the right people on the bus. So said differently, like we, we went down to the studs and said, okay, like we're going to define every role. Like, what is the role? What does the role need to accomplish? What are the attributes of the people necessary to accomplishing that? How do we tease that out within, uh, an interview process on through to like, who is it we hire? Like that is all just evolved dramatically. So who we would put into an inbound acquisition seat, dramatically different from who we would put into dramatically might be a stretch, but into an expansion seat versus an outbound seat versus, you know, folks that would maybe support our partner channels. The other nuance in that is like, you gotta in some ways teach old dogs new tricks. And like, as you evolve this go-to-market strategy, you have people in seat that have largely been on the backs of inbound demand.

Yeah.

And how do we get that same workforce not to compromise conversion and, you know, the things that really matter, but how do you get that same workforce to engage the market proactively and to start to generate pipeline and to start to create demand for themselves? So we've been going through that journey for the last 16 months.

Do you think inbound people can What percentage of inbound reps can actually learn outbound?

Yeah. Uh, I, you know, there's different, I'll just say it this way. Like, I know we're just off the cuff, but, um, you know, about 7% right now of my inbound team's demand is self-generated.

Okay.

So think of that as like, it's not coming on the backs of some sort of marketing demand gen. It's coming on the backs of like them doing things and the way they're doing that isn't what you and I might deem to be outbound. It's like reference selling. It is closed loss selling. It is LinkedIn networking and connections. It is that sort of thing. I think most, if not all, can do that. Certainly.

Yeah.

When you get into like a true outbound at scale and stepping into the arena with customers that are literally not on the market, that may not know who you are. I think I'm still trying to tease that out and understand. Now there's a part of me though that just thinks, okay, well, let's get capacity. Super accurate where it needs to be in that part of the organization. And that leaves us little time for much else beyond just driving an incredible customer experience on that inbound demand gen and driving conversion up as high as we possibly can. There was a time where we, you know, had that, I think, added capacity where, you know, it's like, well, how do we want to take advantage of that? And this was one of the ways we took advantage of it.

Yeah, makes sense. And so how do you you test these profiles? You meant— you mentioned nailing this profile and testing it. So you've defined the role and the jobs to be done. It's, it's gone through this evolution. And so what are you doing to really hone in on like the specific traits that you're looking for in, in the process of identifying those traits?

Well, when we actually put pen to paper on the profiles, like, we, we draw on, well, who's serving super well in these roles. How do we have lookalikes? You know, how do we start to narrow in on the ones that have been most successful? As you start to become a multi-product organization, uh, as Bamboo has, then what, what are the requirements then of, of that profile? Like the surface area of what they're responsible for has grown. Like who's proven they're able to swim in that environment? Who's proven that, you know, it's a struggle. So we draw on what we know, which is the people we have in the building. We as a team assemble what we deem to be the most critical attributes. And some of that could just be like externally, like what do we deem to be best in class? Like who do we admire most? That's, you know, really started to show that they have grandma's recipe on some of this stuff. And how do we, how do we engage their leaders? Could be you or I just having a conversation. It could be, you know, with others in the network. And then, you know, you get people in seat, you go through like a very regimented process in my mind, like where you stick to what it is you set out to do, the questions you ask. How you, you know, go against bias and really get in on the objectives that you want to measure as you hire. And then you get people in seat and you, you talk a lot about, you know, the tech stack. I mean, certainly we have something pretty similar and it's like, we're immediately in the, in the mode of like understanding how our, how our people are showing up on calls, how our people are preparing for those calls, how it is they're executing post-call. Like, is what we thought to be true, true? And we do that through you know, a number of different AI use cases and a number of different tools. And we, and we iterate, you know, we continually iterate. Like we don't deem to think we got it right, right out of the gate. Like we learn from those who have succeeded and we learn from those that maybe have failed and continue to evolve.

What AI tools are you using to inspect whether or not they're executing the right way?

Attentions are, from a conversational intelligence standpoint, are number one. It's been incredible for us. From the standpoint of just, you know, what we're able to do and how we view our market, how we view a territory, how we engage that territory, how it is we show up to calls, how it is we exit the call. Many, many use cases that span that, that give us, I think, pretty good signal and analytics on just like how our people are showing up. We have, you know, rubrics that we use for call scoring, rubrics that we use on coaching, on deal probability, like pick your poison. Like I know I'm preaching your, your language right now. So all of that stuff, I think it's a pretty good signal and a pretty good surface area to understand who's succeeding and who has great opportunity.

Yeah, makes sense. Yeah, we're a momentum shop, but similar use case.

Yeah.

In the last 12 months, as you've been refining this profile, what have you changed your mind on in the sales profile that you're looking for?

You know, we've had pretty rigorous debate on a few things. I don't know if it's as much a profile as it much is when you're in the infancy of building some of the things that I'm describing, like you're constantly at odds with your own strategy. Like I would, it's maybe less for me about like, hey, did we get these couple handful of people right? Or is it like we just need to be going back to the mat constantly on Like, do we have the strategy right? Because in like, in the absence of signal, like in the absence of like ARR, in the absence of like a pipeline that's converting maybe at the rate you might like, it's like, how do you just keep holding yourselves accountable to being curious and to continue to dig into whether or not you're on the right path? Like I, I probably spend more of my time thinking about that than I do, you know, as a revenue leader, I'd say I'm quite impatient. So like, what is, what is that balance of, man, we're on the right stuff. We're just not maybe seeing all the things compared to like, we're not seeing all the things and I'm not entirely sure we're on all the right stuff. Like, can we, can we make two-way door decisions and be okay with that?

And so when you say, do we have the strategy right? What are you inspecting there? What are the signals and like, what are you trying to evaluate?

Yeah. I mean, the signals for me are. Like I'll just put it in like pretty simple terms. So it's like anytime you build, I think a route to market, like use, I'll use partner as an example or outbound as an example. Like, you know, I think there are certain productivity assumptions I'll make in the models to justify the investment case, right? Like here's, I want to go hire 100 BDRs. Here's what I think these 100 BDRs can produce. Here's what I think that means in pipeline. Here's how I think that pipeline will convert. And if the model or the strategy is an outbound AE zone, that pipeline, like, here it is. Here's how I think that group will show up in the sense of like yield or MRR, ARR productivity. Like, that's kind of your baseline. And I think, you know, time horizons over the top of that baseline are where, you know, things get a little bit tricky and where you can, you know, start to really question, okay. Like, are we on the right path? So what I'm looking at as, you know, quickly as possible is like, how quickly are these reps ramping? Like, do we have the necessary programs in place to like help these people succeed? Like get them to where they need to be in serving customers as quickly as possible. Do we have the right systems to do that? Do we have the right programs to do that? But are we getting them to where we want them to be as quickly as we'd like? And how do we continue to evolve and accelerate that ramp time? And then you start to get into, okay, like, well then how are we showing up to our customers? Like, is the messaging resonating? Is what what we're saying resonating? Like, do they want to hear and learn more? And then you get into like, you know, the mechanics of a pipeline, as you and I are across all the time, which is, okay, like what we deem to be a qualified opportunity is in fact, is it that? How are these opportunities actually converting? And, you know, do we have the incentives aligned and do we have the team aligned to what it is we want to drive? So we spend inside our operating rhythm, On newer initiative, you know, we're there every week cross-functionally debating and inspecting what exactly is happening in these businesses.

In all of these newer bets, like outbound or a new partner channel, you've got a weekly operating rhythm where you're unpacking the data every week.

Yeah, like one thing, you know, one thing you and I had talked about is I think there's a lot to be had out of clarity, like simplifying things for teams. And if you're someone like me, you come into a business and you're like, wow, like look at all this opportunity, like there's, there's low hanging fruit everywhere you look. Well, how do you sequence it in a way and organize it in a way where you don't, you just don't slow the organization down or put it at odds with its own culture? How do you sequence it in a way where it's, it's wildly productive? Well, it's, it's an effort in prioritization, right? And in the company right now, we have 6 key priorities, 2 of which are squarely in my remit. 2 of which are just brand new products that we have in market that we want to make sure land and that we're super efficient in our go-to-market strategy and we're learning quickly as we go. And for those types of things, yeah, like there are sprints, there are week-to-week, month-to-month cadences that just ensure we get to signal as quickly as possible and iterate when we have an opportunity. And we debate, we have strong debate on to like, as this grows and as this continues to evolve, like, do we, do we feel as though we're on the right path? And how are we holding ourselves accountable to ensuring we are?

And so you'll have 6 different meetings across all of those priorities, or one meeting where you get into all of the big rocks and it's a day to unpack? Like, I'm fascinated to hear about this rhythm.

Yeah, well, so we, you know, at any point in time you might have as a company many, many initiatives underway. Like, if you were just to go by function, yeah, we all have many, many priorities, we, uh, as an executive team held ourselves wildly accountable to just saying, okay, like, what are the, what are the critical 6? Like, what are the, just the 6 that this room needs to help own and help share? Because a lot of this is just how you're organized internally. And, you know, we're organized by function. And when you organize by function, you can have silos in the business that would really make managing things cross-functionally challenging. So what we agreed to is like with these 6, like there's going to be an executive ownership or someone who's empowered as a GM to go drive each, and they can draw on anything they need inside the company to ensure that, you know, these things remain priority, to make sure that these things are resourced exactly as they need to be. And no matter where that resource comes from in the organization, there's 2 of which that I'm in the front of. And in those specific 2, yes, it is a weekly cadence where we are underneath all the metrics associated. And then the other 4, as led by my peers, the same thing occurs. But as an executive team each month, then we're back to those, those 6 in one setting to say, okay, like, what are our key learnings and how is it that, you know, we're evolving each of these?

And so those are 6 different meetings. Are they all like an hour long? Are they 30 minutes? No. One meeting or all 6?

You would have a lead on each. That lead would probably have a cadence of sorts. To drive what it is they need to drive in that given initiative, of which I own 2, which happens to be weekly, of which then we assemble the 6 at the executive level that we review each month.

Got it. That makes sense. Yeah, it's funny because we're in the process of rebuilding what this looks like for us. We've had different, um, rhythms crop up. Like we've got our monthly business review in the revenue org, and then there's a monthly turn deep dive, and then there's a product cadence. And then we've got these tiger teams meetings, which is not quite your critical 6, but it's, it's like things that are really important across functional. And they've got biweekly meetings, but it's just like we, they've, they've spider webbed out a little bit and now we're trying to think through how do we consolidate to a tighter set of, you know, this is This is the, this is a big rock and big rocks have tiger team meetings every 2 weeks and this is going to be this. And so, cause I just think that rhythm, I think that rhythm is so important to, to prevent meeting bloat and, and maintain that coordination and that synchronicity across all of these different teams. It's really easy to fracture. And I feel like we go through this process every 12 months where we should. Yeah, things creep out, they get big, and you have to prune them all back. I did it, I did it at the very beginning of the year. We like reinstalled my operating methodology and we nuked every meeting on the calendar. Uh, that— it's called Chaos Monkey, which I borrowed from Shopify. And so we, we had every single person on the team, on the leadership team, delete every single meeting on their calendar, and they had to start from scratch. Like, oh, like what if I forget about that meeting? Well, if you forget about that meeting, it wasn't that important.

Totally.

But it's, it's just, it's interesting how we got down to like, you know, a really good rhythm and then just, we added a few things, added a few things. She's like, oh, we need a thing for this. Or, you know, we're not aligned. So like, let's put in a biweekly or a monthly or whatever. And now we got too much again. And so we're like pruning back down.

It's like good old cleaning out of the closet, right? You're like, ah, there's, you know, 80% of my stuff I've, I haven't worn in 5 years. Like, is this necessary? I think it's something we all need to do every year and it's something we're all guilty of. The other thing, Kyle, I wrestle with constantly is how do we just enable those on the edge to spend as much time as humanly possible on what matters, which is maybe in our world, it's our customers. And I'm not convinced I've done a great job of that. Like I feel like our teams, my people spend a fair bit of time away from what matters most. And I debate AI use cases inside that just feverishly, constantly, just as to like, what can we just take out for them? And you just triggered that in my head. I think it's something I think about all the time.

Yeah. And, and if we zoom back up to sort of the topic of the conversation, which is like winning in competitive environments, and this is applicable to every business, it really feels like the theme is like execution. Execution is what matters. You need to— if you want to win in these markets where there's like you know, difficult product differentiation. It's like you had just have to out-execute in terms of how you run your team, the discipline, the rhythm, the hiring profile, the specificity of the message. That seems to be a big theme here.

Yeah, I don't disagree.

Okay. I want to change gears slightly and talk about positioning. So you touched on this a little bit by by referring to like the niche and being really specific about who you're solving for and how. So how do you think about positioning products in general? And you can use Bamboo as an example, but positioning yourself in these crowded marketplaces.

Yeah, it's, man, I often see, you know, features is this thing that, you know, people love to talk about. It's a, you know, a customer says a word you're super, super familiar with. Or something that is you can solve for. And it's just like, I'm going to pounce on that and I'm going to tell them why we're the best at that. And, you know, guilty, like we're all there. I think it's just critical we get out of this concept of like chasing our tail on features. Like I could, we could build features forever. We literally, we just literally could build features forever. And I think at some point, like this checkbox mentality is just unsustainable, not interesting. And if we always just want to be checking boxes as compared to our competition, like we're just ultimately not going to win because we're going to get to a box we don't want to check. So then it's like back to your product strategy, which is like, what do you want to be? And for us, like we want to be flexible and extensible. We want to be all in one and we want the sum of the parts to be way more valuable than that feature. We think, we think there's trade-offs around like the interoperability of all the different problems we solve and the experience of that and the unified data model associated to that and the underbelly of AI associated with that is far more valuable than the feature. And I've got to get my teams and our company to make the trip on like how it is we articulate that. And I think at the end of the day, you articulate it through like, you got to like, you know, objectively speak the customer's language and it's probably an overused term, but like, you know, we, when you and I were talking, we were talking about like, we don't sell a product, we sell peace of mind. Okay, well, what the heck does that mean? All right, well, think about the customer we serve. Like the customer we serve is really worried about compliance. They're really worried about systems reliability. They're really worried about making the right decisions. Like that's what in my mind, like peace of mind might mean. So when you're, when you're engaging with a customer, it's like, well, let's push on these things. Like let's push on these things that we know are top of mind for them, are concerns of theirs, are things that have to get right. And let's quantify those things. Like, let's really get objective on like, what do these things mean? Like if you have a payroll error, like that's not super good, right? Like if there's one thing we owe our employees, it's probably, you know, timely paychecks that are accurate. Or if there's a compliance incident, I mean, those are, that's a big deal. Like these are things that can cost companies substantially, whether it's on brand or just dollars. Uptime, MPS, ENPS, like all these things matter. So you got to be able to quantify these things in the context of the challenges that these customers face. And I'm, I'm really, really maniacal on just like in customer evidence to prove that. How do we show up with stories, with soundbites, with data that resonates for those customers in their given industry and their given vertical? Could be size, could be geo. Of like, if these are the pervasive themes they face, challenges they have, this is how we solve them. And we have evidence just to show as much.

Yeah, I like that a lot. The other thing that I think is, is related in what we teach, you mentioned the word trade-offs before, but it's so easy to get into the feature battle. And in our industry, all of our competitors can basically check the box on the feature. They have online ordering, we have online ordering, they have an app, we have an app. And even though like their app is like, you know, really like so deficient in so many ways, but you can't as a rep be like, well, their app's no good. Well, how do they know? How does the customer know? There's, there's like the, you just end up in this he said, she said scenario and the customer gets paralyzed and it was like, I, I'm just gonna do what I've always done then. I'm just like not gonna make a decision. And so what, what we found to be so helpful is selling a point of view. It's like, if you care about this, you should go with this other vendor. If you care about that, you should go with us. And then having evidence to show why that's the case. Like, you know, you going back to, you want to be the all-in-one flexible extensible, it all works better together. Like that's a cohesive message. I mean, like, look, if you want to assemble all the pieces and go best of breed, you should actually go with another tool.

Yeah.

But if you want to go all in one, which is better together, we're the best solution. And here's the evidence. And I think people can internalize that. They can actually, they can understand and appreciate it versus me saying to a customer, well, like their app is no good because they're this and that. And here's the technical differences. Like it's, it's impossible to teach a rep that number one. And customers can't hear it and they can't trust it because it's so far outside of their, much of the time so far out of their like technical depth. You trying to explain the technical details of like why your HRIS is like slightly better or why your Ben Admin is like more compliant. Like how do you, how do you prove it? But you've, you go one level up to that trade-off. We call it point of view positioning. And if you can just articulate the trade-offs, then it simplifies this messaging for the customer so much.

And it demonstrates trust and I think honesty, right?

Like big time.

Yeah. You have a point of view, but it's a point of view you believe in and others have a different point of view and that point of view is fine. It's all about the need, I think, of the customer.

Yeah.

I think we're totally aligned on that. Yeah.

And there's like, there's so much psychology behind it. Like I, this I teach in, in, in our Point of View Positioning doc. It's like there's a thing called the pratfall effect. And so, or you, you'll hear it called the like 4-star effect. So people will, you will build much more trust by admitting some flaw because, you know, if you're admitting your flaws, then, then there has to be more trust there. And that's why when people read like Amazon or Google reviews, if it's 5 out of 5 across the board, people are suspicious about it versus if there's a bunch of 4s and 3s, but it's still a high rating. And so we try to, like, I try to teach this radically transparent style of sales where, where we, where we, um, are open and honest about like, look, if you want control over everything, if you want the most customization possible, that's not us. In fact, our, our value prop is that you're going to have less control, but that means that we will control it for you. And we have literally the best restaurant marketers in the world and the best people working in A/B testing every little, like, tiny piece of your experiment— experience for you. And like, that's what you should want as a restaurant owner. And people like, I do want that. I like— I don't want custom fonts. I just want to make money.

Yeah. Yeah, it sounds super familiar.

The feature function. Yeah.

Yeah, it's a tough one. I mean, it's, you know, customers want to default there oftentimes, especially like the ones that own the domain and you got to elevate it.

Yeah. Is it as simple? So going back, I was saying, you know, the, the sales experience is the evidence that the customer has for what the post-sales experience will be like and what they can count on. Is it as simple as the best sales experience wins in these markets?

I, I think that's a tough thing to just generally lay over and say, okay, yes. You know, word travels. Like, word travels. Like, you just mentioned Google reviews. Like, maybe not a world I'm especially concerned with, but like, appreciate.

But call it G2 Trustpilot era.

All the things, right? Like, word travels. And if like, if you have an incredible sales experience and you land a customer and the experience of that customer is horrible post that sales experience, like, at some point, like that's catching up to you in future bookings, in future customer engagement. It's just going to, you're going to alienate partners. You're going to alienate customers. Like it has to be, you know, something that is end to end to, you know, ensure the flywheel gets going. Like I think about, you know, one of the, I think the things we can hang our hat on most at Bamboo is like our teams are wildly confident in the fact that our customer is going to have an incredible experience through implementation, through onboarding. And if anything, any issue occurs, like they're going to be talking to someone almost immediately stateside and we're going to solve their problem. And like that becomes in a way a part of your value proposition. And so I think here you are, like, I think the sales process is super important, but I think it's a virtuous cycle with the one without one, you don't have the other and you all need to be super accountable to that in totality.

Yeah. Yeah. That, I think that's a great pushback. Okay. So I wanna, I wanna transition to talking about culture as revenue strategy. So, so interrelated ideas because if, you know, in these hypercompetitive markets, sales and reputation is so, is so much more meaningful. And so execution and culture matter a lot. And so you said in, in our pre-call prep, culture can be a revenue driver. So I'd love you to just unpack that. What does it, what does that mean?

Yeah, I think, What, what is life like if you don't have some sort of meaningful, purposeful culture in place? Like maybe the inverse is like, well, what are you left with if you don't have that? This is what I've been thinking about. Like, okay, are you operating within a world where it's just exclusively mercenaries and there's no connectivity back to the company? There's no connectivity back to the long-term vision of the company. There's no connectivity back to like What us winning and succeeding on behalf of our customers means to employees in seat, like, I think you're in a, in a really tough spot. That is the case. I think if you can align the two, there's absolute magic. And this is what I mean when I say culture can be a revenue driver. Like if you can connect the fabric of the company's mission and its values into like how we all interact, how we make decisions, how we interact, how we serve our customers. And you can combine that with a culture of winning, a culture of, hey, this is the journey we're on as a revenue organization. Should we accomplish what it is we're here to do? This is what that means to you. And this is what that means to your progression, to your career, to your development. That is magic. Like you have people willing and wanting to do the hard things, willing and wanting to go into the face of ambiguity and and go tackle something because it's, it's bigger than just the job at hand, right? It is bigger than what it was they signed their offer letter to do. It's like, no, no, we're like, we're here to build something. It's going to be hard, but we're in it for all the right reasons. I just think you find the gear inside people and they're just general psyche that maybe doesn't exist without that foundation.

And so how do you operationalize that? Like it, it's, I don't think anybody will disagree. Being connected to the mission, feeling a sense of purpose. Like, all the research shows you, like, that, that is going to drive the highest levels of engagement, whether it's like the Gallup Q12 stuff or Daniel Pink's Drive. Like, any of the research on motivation, engagement, like, you know, purpose and, and mission are great, but people struggle with the how, and they struggle with the trade-offs of, like, when the mission comes into conflict with the number oftentimes. So how do you operationalize some of this stuff?

I think it's such a good point. It's almost like we're talking about something that's just this thing and we all kind of acknowledge it's a thing, but in practice it's really hard. Like it's just really hard. It starts with like, I think values, they can be perceived differently at different companies, but if if we're steeped in our values, like if, if what we say we want to live up to be, we live those things, I think you have a pretty good foundation to go from. And we have to demonstrate those.

Yeah. What do you do tactically in the organization to bring the values to life?

Well, one, I mean, we interview behind them. So yeah, where we spend our time in interviewing candidates is in the framework of our values. Trying to draw out like what these might mean to them and how it is in their past lives they've lived up to these things or operated with, you know, these sorts of principles in mind. So that's certainly one way, but I, what I, Kyle, firmly believe in is, you know, it, it is like, it starts with myself. It starts with my leadership team and it starts with how we show up and You know, when you're in a company like Bamboo as a first-time CRO and you see opportunities to go do different things and to grow this business, how do you like maintain the fabric of the company and what got it there while building with velocity and while changing accountability, expectations, et cetera, to go drive that result? And I think that's the core of what you're asking is like, how do you, how do you get to the goals of what you need to accomplish inside revenue? Get to the change and get to the additive opportunities that you believe exist while still maintaining the fabric and the DNA of the company. I mean, none of this is going to be terribly rocket science, but I think I am highly, highly visible, highly, highly visible. Like I'm in front of my workforce as often as I can be. I ask the same of my leadership team. My workforce is largely in Utah. I'm in Utah every single week, and that's not because I have to be, it's because It's the right thing to do. It's proximity. It's visible leadership. I brought our teams back in 3 days a week. This was entirely in a remote staff. We're now in office 3 days a week. I think what you get from that is, well, you get a lot of things. Uh, one of which is just connectivity and proximity, the opportunity to collaborate, the opportunity to benefit your peers. We built groups inside the organization. I think one thing that is critical as you look to evolve, change, grow while maintaining culture is you have to empower as many people to uphold that as possible. It can't be top-down exclusively. So we've built what we call a Voice of Revenue Council, and they are cultural ambassadors. They are a bridge into product. They are a bridge to build things like mentorship programs. We have a Women in Revenue program as well to, you know, continue to provide thought leadership on our workforce and how it is we evolve that workforce and for that to be a balanced workforce. The idea being though, empowering at the edge, bringing people into being the change agents as opposed to this being on a handful of individuals to maintain it because the culture only shows up if everyone is doing their part to drive it. So there's a lot we've done, I think, to, if nothing else, draw people closer to kind of the heart of the organization and the company while communicating where it is we want to go as a revenue organization and what it is their role is in that while, you know, maintaining our character and our integrity as we go.

And does, do you bring your values into performance management in any meaningful way? How do you do it?

I mean, yeah, so we have 6 and inside those, I mean, if, if we feel like certainly you want to be as objective in some of these things as you can, but I think beyond just performance management, I think about just how do we engage in our performance reviews? How is it we assess our workforce? And we're probably in my organization, 75% objectively, like how it is you're showing up to your customers. What is it the results you are driving? Are we accomplishing the things we want to accomplish? And then a quarter of that, and I'm just spitballing, is focused on that. Like, how do you show up inside the framework of what we call ourselves bambooligans, but how it is you show up in the framework of being a bambooligan. Like, are you someone that elevates your teammates? Are you someone that elevates the function? Are you someone that operates with excellence inside, not just the numbers, but how it is you show up to your customers? Uh, all of that is in, you know, constant debate.

Yeah. Yeah. We're, we're similar where we've gotten much better at this over the last 2 years, but just baking the values into how we measure. And so it's, It's in all of our interview scorecards, the company values. And then it's in the, when we do performance reviews, we're measuring people against that. We do this thing called monthly report cards for the frontline teams where every month we sit down, review their performance, how they're showing up, their, the skills. And part of it is like how you live the values and have a conversation every single month. It's like, did you scale yourself? Did you, did, Is there evidence that you're like, these are our values? Is there evidence that you're scaling yourself and investing in your development? Did you act like an owner? Did you bring good energy? And like, it's like, actually, you like, these were scenarios where you showed up and it was, it was negative. And like, that's not really the environment we want. And, and I, I find it's like, it's not magic, but just the, the repetition and the weaving of values into as many places as you can. And people are like, well, it doesn't really make sense have it in performance management. Well, then your values aren't that good. Like, if, if, if you can't— if you can't hire against your values and you can't performance manage or review against your values, then your values probably don't mean anything.

Yeah, exactly right. Exactly right.

Um, and so you mentioned the company had a strong DNA, but now they have a CRO and you had new ideas, I'm sure. I'm sure the culture needed to change. And so how did you balance those two things? Like, and what did you want more of from your bamboulikins? I love that term, by the way. And how did you maintain the fabric while also changing?

I mean, I, okay, like we'll just go into like some of the core principles of how I think. I mean, by the way, I just totally appreciate how this is like just off the cuff. It's a good discussion. I think it's really hard to lead if you don't have credibility and trust with your teams. I think it's, well, I'm not alone. I mean, you tell it like, show me why it is I should trust you. Show it is, show me why it is I should listen to you. Like I want to influence people far more than I want to manage them as best I can. So, you know, there's, there's, there's a lesson in just listening certainly. Right. And just being wildly available, wildly present. Um, and you know, I, I think it was day 2 where I came in, Kyle. I'm like, I'm pulling everyone into the auditorium and we're just going to have a chat. And while this might seem trivial, uh, it was surprising to, I'd say, the majority of people. And I think we've both probably been places where it's like, I worked at a, you mentioned it, a reseller. Like I learned how to be so scrappy. And just to be in the trench constantly and doing everything in my power to like develop our people and make them great and make them want to be there. So then going to like one of the fastest growing companies on earth that I'm not even sure if I didn't show up one day, if that would change anything in the business. Like AWS was this. And you just see on this continuum of like how you show up in those worlds, right?

Yeah.

And I think my DNA is very much on this side of the continuum, which is like, no, no, I'm like, I'm right here with you. I'm in the trench with you. And I'm I'm going to tell you what it is that I hope to accomplish, but I'm going to bring you along and I'm going to want your input along the way. So, you know, I don't know that that may maybe earn the right to just come in and do all the things I wanted to do, but it's certainly, I think, bridged, you know, people just wanting to have connection and people wanting to understand what it is I stood for, what it is I believe in, some of my guiding principles, but opening up that line of communication and being wildly, wildly visible. And then starting to just assess like, one, how is it we show up to each other, to the company? Like, are we representing the company outward or are we representing our own internal, you know, whatever it is externally? And then starting to embark on like, where do we just have deficiency in what it is we want to do? Like, if ultimately we'll want to grow this business at the speed we're asking ourselves to do it to the size we want it to be, like, what are the things we just know are true to make that happen? You start to lay down that plan and you start to get input on that plan and you start to socialize that plan and bring others along in it. And then you start to embark on it. And what I will say is, as we started to build, being very transparent and communicative upward, peer group downward was just my constant commitment and upward. It just simply meant, hey, are like we all on this journey because this will mean change ultimately to how we show up in the customer journey, or this will mean change in the asks we'll have cross-functionally. But downward, it simply just meant, hey, this is the journey we're on. This is an incredible opportunity for so many of you. This will be a lot of fun, and this is going to be super bumpy, but are you in it with me? And here we are. So I don't know if there's a framework necessarily. Some of it's just what you deem to be right, being visible, being communicative, and being transparent and vulnerable. Like, I don't know how else to put it.

Yeah, yeah. No, I definitely think there's a lot of framework here, and it's— it is— if you want an organization to change, you have to get on the front lines. I had JD Samartin, who's the president of Lightspeed Commerce, he was like, you gotta roll in the mud. He's like, oh, he's like, I'm always there rolling in the mud, like, getting it done with people. Like I'm in there. So like that definitely seems like connectivity and earning credibility, establishing a really good vision sounds like another thing. Like where are we going and why? And here's what's in it for everybody. And then inviting people along definitely seems like a, you know, a piece that you've come back to a couple times here. And then the reinforcement and communication and updates. So people know where they are in this journey.

I think that's, it's well said.

I think there's a great framework for, for people to take away because it's tough. It's tough to bring, like, I haven't, I haven't needed to change a culture necessarily. I've, I've all, I've usually done like scratch builds. You know, my team was like zero at League and we went to, you know, it was like zero to $25 million ARR. So still quite small. And then it was like 5 to 80 people at Shopify. And then now it's like 0 to, I don't know, my team's approaching 200. And, but like, I've just got to put my fingerprints on it. And like everybody, basically almost everybody other than like 3 people I hired. And so the, the, but the, the, when I talk to friends who are coming in and trying to like make change, it seems like a fascinating, but very complicated process because especially like, you know, founder CEOs may have like certain opinions. How did you navigate that? Like, let's talk a little bit about the, you mentioned making sure that the team above was on board with the journey and what it meant. So what did you do to keep them? Is it a founder CEO today still?

No.

Okay.

No, it's two founders of which now serve on the board. And then Brad Rencher is our CEO. He came from, I think he was an EVP at Adobe for a number of years and he's been leading it for 6 years. Like, I think Kyle, this starts with like, you know, admittedly when I joined Bamboo, I couldn't have been probably a more passive candidate. Like when I initially engaged, it was like not knowing a whole lot about the company. It's just like I wasn't in a spot where I felt like a change was necessary and you go through My process was a 6-month process and it's like, I'm just like going to the mat, trying to get underneath, like the things at this point in my career matter because you're going from a public company to a private company. So if you can like get over that hurdle in your mind, yeah. Okay. Now you're into like the DNA of the company. Like, do we show up in the way that I want people to show up? Do we engage with one another in the way I hope people engage one another? Is this CEO, and this is a bit of like my decision-making framework, is like, is the CEO someone that I can learn from, but will be balanced and pragmatic and empower me to do the things that I think the company needs doing as the CRO? Like no one wants to be hand-tied coming into a role like this where you need to build. Is the TAM one we want to go win in? Like, are we willing to go invest for growth, all the things? And like, you don't, you don't know these things. Like you can try to get underneath these things in an interview process. But you really don't know these things until you're like inside the company and you're looking left and right and you're like, okay, is everything everyone said true? Is, you know, is everyone signing up as I'd hoped they would sign up? And everything for me has been resoundingly true. So then it's like, okay, like we're not here solving like all these, these dilemmas and issues that I was concerned with. We're instead trying to tackle real business problems. Like, so, okay, like we're already winning because we're focused on business problems and not things that interfere with us being able to go solve things that involve scale. So I kind of came in after a month or two, pretty clear-minded on like, I'm going to be empowered to do the things. And I give, you know, the company so much credit. They built an incredible leadership team that I have the opportunity to lead. And I think the executive team is one that, you know, looks at the opportunity the same way I do and collectively has empowered me to go do the things. So with that said, my job is to make the CEO successful, like just to be really, really clear. And so I try to bring him along. On absolutely everything that I'm contemplating. And we go at that and we look at it many different ways and then ultimately, you know, make a decision. And I'll say, you know, I've been empowered to do the things I think are necessary, but it's not as simple as like just having these things blessed. At the end of the day, it's like, well, if we have something different we want to do for a customer, it's like, well, how do the product teams make the trip and how do we inform the product roadmap? Because this is an unlock for perhaps a different customer type or a different need of our customers, or what is it we need to build programmatically to untap something within our marketing teams that, you know, we need, we know is necessary to go do the things we want. So that is where I spend a lot of my time is just trying to drive continuity across the customer lifecycle with the executive team to ensure we get to the right outcome for the customer.

Yeah. So the answer to the question it seems like I'm getting is not as much like how to persuade and influence an executive team. It's join a team that is open-minded and on the same journey that you want to go on and be very mindful about the selection process, which I very much agree with.

Yeah, I think that's right. I mean, absolutely. And that doesn't mean like we don't debate things and get to what we think is the right answer and the truth, I think that's right.

Yeah. I have this stupid saying that I, I don't know when I made it up, but like, you can't blame the lion for eating a gazelle. And so I say this to friends who are complaining about stuff or CRO buddies who are talking about their, their founders. And it's like, you knew what you were getting yourself into. Like you knew this founder was this way and the more you try to fight against what this is, like the worst things are going to get for you. Like you, you just, you can't found, especially like founder CEOs tend to have such strong convictions in many ways. And that's what has made that company great usually. And so fighting against that is like not going to be particularly productive. And you have to either like get on board or find somewhere new. And yeah, that was a a big part of my process with joining Owner, like I was the same way. I emphatically did not want to leave Shopify and things were going great. I just had my second kid. The timing was terrible to join a startup. And Adam did what he does, which is like put the tractor beam on me and pulled me in. But a big part of that process was understanding like, how did he want to build this company? What were his values? How did he think about him and I engaging? And luckily, you know, the company values almost mapped like one for one with how I view the world, which was, which I was very fortunate for. But I had like learned that lesson in congruence earlier in my career to know it's like, I'm so opinionated. I'm sure you're the same way. I'm opinionated. I have like certain ways I want to do things that are non-negotiables. And I can't ask somebody, especially a founder CEO or CEO, to do it my way if like that's not how they're built. And so I think you answered the question differently, but actually in the much, much more useful manner to this.

I hope so. I think you got to get through maybe the heart of your question before you're even in the job.

Yeah.

To your point.

Yeah. This is the, I catch flack for this sometimes because, you know, so much of like sales leadership, LinkedIn. Is people like griping and complaining, or I go to dinners and people are whining about their, their like, their bosses or exec teams or whatever. And it's our fault most of the time. Like, it's, it's like the, you picked bad. Like, there was a bad pick. You didn't do your diligence. You chased a title as opposed to, you know, like, as opposed to like holding out for the right things.

Yeah.

And the selection, everything is sort of downstream of company selection. I'm learning, like, did you pick a winning product? Did you pick a good category? Did you pick a good founder? And if you don't do that, you're sort of hooped. I couldn't possibly have accomplished what I've accomplished as an owner without great product, incredible counterparts in the exec team, like a wildly awesome founder. It's, it's only possible because I picked well.

And you've, you've said things, Kyle, in the past, I think on this pod where it's like the whole, like lack of patience, not showing mastery in a given role or in a given function.

Yeah.

You use title chasing as a term. It's like you kind of rush yourself into disaster.

Yeah. Yeah. I turned down my first CRO role 7 years ago. And I wasn't actually the CRO on paper at Owner until maybe 18 months ago or something like that. And it's because, I don't know if I've told the story on the podcast before, but like the biggest mistake I made in my career was I turned down a role at Salesforce in like 2012 because it was like a way smaller role than what I was doing at this crappy conferences and events company. And I was like, I don't know, just like didn't know how big of a deal Salesforce was and didn't understand the level of opportunity. I was like, BDR manager, like I'm a second line full cycle sales leader. No way. And like, I know a bunch of the guys who started at Salesforce at that time and a bunch of them have like 3 houses and they've made just like millions of dollars in Salesforce stock. And I was like, okay, don't make that mistake again. And so like, you know, it would've been cool to be a CRO 7 years ago, but instead I took like a senior lead title at Shopify, which was way more valuable from a learning and profile perspective. And now I'm in where I want to be, but it's, uh, that was painful lesson to learn back then.

Hey, we all have 'em. I, I tend to dwell on them. I'll just, I'll like, I'll say, I'll say one thing to you just in like, I'll match your Salesforce thing with. You know, it's not linear. It's just not linear. It's like, I, I remember when I was at Softress and people are like, why were you there 18 years? I'm like, cause they, they saw something I didn't see and they put me in positions to fail miserably. And somehow I figured it out. And like, I guess the counsel I'd give is there was a time where I'm like, hey, you move from a first line role to a second line role to a third line role. And it's just like this, like, that's what it is. And at some point you're like, I just, I don't have the skills. Like I just don't have the skills because you haven't, you haven't seen the movie and you haven't seen it from another, another angle. And where I was pushed was to go cross-functionally, to go into marketing functions, to go into sales operations functions, to like go build a go-to-market plan, go build a financial plan to understand the real guts of the organization. And I'm like, so, so thankful for that. But it was like blind intervention. Like I just did not, even think about it that way. And you're, you're describing maybe something different but similar, right?

Yeah. Yeah, for sure. Um, all right. Well, I want to move us into the quickfire so, so we can get out on time. What, in your mind, what separates a good CRO from a truly great one?

Yeah, I wish I had something incredibly novel to say. I think for me, it's like, it can be really hard to scale in our roles. Like, it can be really difficult to scale. So how do you build mechanisms for scale, for repeatability? How do you clear just put clarity into the machine and focus on what's important. And how do you make time for all the things we're talking about today? Like, how do you make time to be with the people, to be what, rolling in the mud? Yeah. Like at no point is something so big where you can't roll in the mud. And I think that's super important if you want your people to go do the things you're asking they do.

Yeah. For sure. What's the most common advice you give to like first-time VPs of sales? It's the first time with a, first time somebody managing a really big scope. What do you, what do you say to them?

Well, uh, one of the leadership principles at Amazon that just resonates with me all the time, and I don't know if it's in the context of the VP, just in life, like learn and be curious. Certainly. I think, uh, you know, anytime you're in a job for the first time, Kyle, like there's a lot you don't know. So maybe you don't pretend to know it. Like, I think you put yourself in situations where you're, you're just trying to demonstrate value, build credibility, and you're just wrong. Like, you just, you maybe don't have it right. Like, learn and be curious. Like, take it in. Like, be, be transparent, be vulnerable, you know, like, and draw on the people that maybe do know. And don't pretend to be, you know, the smartest person in the room. That'd probably be my big thing. And then second to that is maybe then trust your intuition over time. Like there's a reason you're in the role. So don't, you know, don't create paralysis at the same time. Like not everything needs to be textbook. Like you're there for a reason. Like, you know, trust yourself.

Yeah. One-way door, two-way door. Going back to your—

Totally. Yeah. You know it.

What's the hardest lesson you've had to learn in your career?

Well, I think my, my career is such a part of my personal life, Kyle, that It's like when I think about something like this, I draw on my personal life. The person I am now compared to the person I was 20 years ago, couldn't be more different. And, and in, like I say that in all sincerity, like I took me a long time to grow up is probably the way I'll, I'll clarify that one. And I think, you know, everything is hard if you're not in some sort of balance and generally speaking, taking care of yourself. And that for, for me, that transcends a few different things. And at maybe one point in time, it really transcended work. And that was about it. And I had no balance in my life, nor did I care, take great care of myself. And I think for that reason, like I learned a lesson, which is like, for this to be what I want it to be and this life to be like, you have to make some pretty profound choices in how you show up to yourself.

Yeah. Very well said.

Not to get overly deep, but like the career things matter, but there's bigger things, you know?

Yeah. Yeah, for sure. What's the best thing you've read in the last 12 months?

I just read the Bill Bryson book. Like, I think it's called A Short History of Everything. Admittedly, it took me a long time because it is somewhat complicated. I learned a lot. I don't know if it's the best thing I've read. I read a book about kind of the rise and fall of General Electric called Lights Out.

Oh, interesting.

And I, I found it fascinating. Like, it goes through like the Jack Welch era into others. And, you know, it's just like a lesson in like, man, they were Fortune 5 and now what are they? I don't know, but the large can fall and the small can grow. There's a lot that happens in business and I found that book fascinating.

Yeah, that's awesome. Well, Jonathan, this was great. We got through a ton. I still have 8 questions here that I wanted to get into on culture, but I'm glad we spent the time on company building, winning in these tough markets, getting down to the niche and and I have a whackload of notes. So this was a great one. I appreciate you coming on.

I'm super grateful, Kyle. Thank you for having me.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes and be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.