E34: Why Enablement Is the Most Overlooked Growth Lever with Luke Arno, CRO of Transcend
28 May 2025 · 77 min
Luke Arno, CRO of Transcend, explains why sales enablement is the most under-invested growth lever. He breaks enablement into three chapters: onboarding, ongoing development, and field-sales strategy. Measuring impact means tracking onboarding ramp, conversion rates, pipeline coverage, and revenue.
Chapters
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.
This episode is brought to you by Momentum, the revenue orchestration platform that helps revenue teams actually execute.
If your pipeline is clogged with admin, buried insights, and disconnected tools, Momentum fixes that. It automates workflows, structures customer signals, and drives next steps with AI. See how Zscaler, Owner.com, and Demandbase are supercharging revenue execution at Momentum.io. Today's guest is Luke Arno, who's the CRO at Transcend. And Luke has spent almost 2 decades in SaaS sales, having been an early employee at a bunch of legendary companies like Salesforce, Yammer, Box, Segment. And Luke spent 7 years at Box, eventually becoming the VP of North American mid-market sales. Then 4 years at Segment before Transcend, where he was the VP of global sales for Twilio Segment, having gone through the acquisition and a bunch of the integration. So I'm excited for this one because we're going to talk enablement, which is a topic near and dear to my heart. I know it is for you. And we're going to talk about the business case for enablement, how to build a great program, and really unpack a whole bunch. So excited for this one and thanks for joining.
Thanks, Kyle. Appreciate you having me on.
Yeah. So what did I miss in your background? Give folks a little bit more color and then we'll jump right in.
I mean, you covered it incredibly well. As mentioned, I'm serving as the chief revenue officer at Transcend. I've been here for coming up on what will be a year and a couple of months. I think the key things to call out, one, I have felt incredibly fortunate to be able to work for the companies I've I've served time at. It's been the best of the best in the Valley. I've learned from the best. I've benefited from building internal champions who have helped me develop throughout my career. Um, I've been able to take on projects at a stretch and, uh, and have seen great outcomes. I've learned from an incredible cast of leaders, and it's put me in a great position to see the world through a 360-degree view as I have stepped into this role at Transcend. And as we're going to talk about today, enablement's a big part of that.
Yeah. Yeah. The value of working for world-class businesses, I still think is underappreciated. You know, the network that you develop, the lessons you learn growing at that speed. I give this advice all the time, just like, just get into the best company you possibly can. Worry a little bit less about the role and the comp because it'll all work out in the end, as we've seen with your career. So We're going to talk enablement. And so I'm curious, in sort of our pre-call discussion, this was like a really big area of focus for you. And where did you first come to understand the impact of world-class enablement? How did you become an evangelist like this?
Yeah, it's a great question. I mean, early in my career, when I first started at Salesforce, which was my first role in enterprise software sales. I mean, the first day I stepped on the floor, Doug Landis was the head of enablement, and Doug is incredibly well known throughout all of these companies. In fact, I was able to learn from Doug at Salesforce, and then he also was at Box when I went over there and was retrained by Doug there. And, you know, and then later in my career as I'm building out teams, I was able to work with some really, really strong enablement leaders, Mac Rotaliers at Segment and now Lane Carruthers at Transcend, who also spent time at Twilio Segment. Outside of the direct enablement function, I've just always taken a liking to understanding the psychology of selling and the psychology of how to be successful in this role. And there are some outside trainers who I've you know, I, I have effectively, uh, spent a lot of time researching and just becoming a subject matter expert on, and like Jeff Hoffman and, and John Barrows and the work they do and, and the, the force management team. So, uh, I, you know, outside of the, the professional job I have, I spent a lot of years coaching youth sports. And to me, enablement is very comparable to how you teach anybody to focus on just the core fundamentals of, of being successful.
When it's done right.
What's that?
When it's done right, for sure.
And when it's done right and, and not looking too far past, you know, the basics. And, and there's always an opportunity to, to focus on ways to get better every day. So, um, for me, enablement's always had just a direct impact on, on my outcomes, my team's outcomes. So, um, Yeah. Anyway, I'm excited to get into it.
Cool. So, I knew we were going to have a lot of, like, overlap here, and your analogy to sports is one that I use a lot. I think, like, great enablement looks way more like sports training than it looks like HR learning and development. So, that's a cool framework for us to come back to. So, I first want to make the business case because I think what I commonly see in what's out in the market is enablement is criminally underinvested in. It's oftentimes an afterthought, not something that's given the level of primacy. So, just give the business case for investing heavily in enablement. Like, what are the outcomes people should be expecting and why should they take this more seriously than they do today?
Yeah, I think John McMahon says this in in many of his engagements, Qualified Sales Leaders, a book he wrote, and he references the dollar spent on enablement is the most leveraged dollar you can get back a return on. And I think what he means by that, similar to how I think about this, is if you can force multiply sales productivity in your organization, what better way can you add dollars to the top line? Right. And so as we look at the most important metric in the business, when we're talking about revenue growth, it is sales productivity. So perhaps the business case is underinvested in. I think there are trade-offs at certain periods of a company's growth. Earlier stage companies, you have a different set of responsibilities that you're focused on. Where we're at at Transcend, it made, it made great sense for us to bring in Lane and start building this out from the ground up as we're scaling the organization. It's a complex sale. We brought in value selling. There were just things that I myself or my sales leaders couldn't do all on our own at the capacity that we wanted. And the return, the business case is we're going to improve sales productivity. That is the metric we're holding ourselves accountable to. To. So onboarding, acceleration, and productivity.
Makes a lot of sense. Why do you think enablement is so underinvested in? And maybe like you can agree or disagree with that statement.
Yeah, I mean, it's probably similar in terms to how you quantify a value metric to a piece of infrastructure, right? There's an indirect correlation to putting your data in the best position possible to be efficient or productive at the end state. So with a sales rep, a sales, a sales enabler sits at that layer of infrastructure. They're building systems and processes and workflow automation that impacts a direct rep. The direct rep is the, is the person who gets the credit for, for productivity and gains and revenue, not the enablement person. And so, you know, In a world where that is off-kilter, it's easy to say why invest in enablement when we can just go invest in a rep and assume they're going to get to the outcome we need. But I, you know, I frame a lot of how we get to the end state through the investments in the process. In fact, one of my favorite books is the biography or autobiography of Bill Walsh, And it's the score will take care of itself. And it's a, it's a great framework to think through process and practice and perfect practice makes perfect and, and all those things. And that's all enablement. That's not hire the best rep in the Valley and expect them to produce, you know, $2.5 million in a year. So I think we have a lot, a long way to go to help educate you know, the, the people we have to go get approval on the business case, but it's not an insurmountable conversation. It just requires the right framing.
Yeah. How closely do you try to measure the impact of enablement? Are you able to just make the business case and say, this is how we're going to get great as a sales team. These are the investments I want to make. Or if you had to build an ROI model about the stuff you're spending dollars on, like how far down that path do you go? Yeah.
So upfront to get approval for the business case, I didn't need to put a lot of— I didn't have to put metric quantifiable metrics into that model. However, I did anyway because we run our enablement program with a really tight measure on the metrics we're tracking. And so I, the co-founder or the, the founders at Transcend and the executive leadership team that I've stepped into, we all share a very similar vision for how we're going to force multiply and grow. So that was the easy part of the conversation. Where we are now is measuring the impact of enablement. And we're early. I mean, we're still only 6 months in from our enablement hire. And but we have a whole course of metrics that we stay really close to, of which are curriculum. So there's 3 chapters to enablement, which we'll get into. But onboarding is really where we are now. With the class that has come in or the cohort that has come in since we've hired our enablement lead and the work they're doing. So we're tracking very deeply curriculum, certification, prospecting, outcomes from prospecting, first calls, which are S1s or SALs in our book, conversion at S2, and then more mature pipeline S3+.
And how do you find the enablement impact on those metrics?
So what we tried to do was pull baseline from what historical showed, which is, I mean, it is what it is. You can pull it and you understand from time of hire to productivity and time of hire to pipeline for the classes that existed prior to enablement. And we're going to measure against that. I think it'll be probably a pretty dated or that data set won't matter as much as in 12 months when we're measuring this class versus the next class and the impact enablement's going to drive.
Okay. So you have a set of baseline metrics.
We do.
You're running an enablement program against those metrics and you're looking at trends.
Yeah, we do. And the primary metrics, I mean, sales productivity is the outcome metric, but the leading indicators are pipeline coverage, pacing to ramp plan, with pipeline progression and then revenue.
Okay. So you mentioned there's 3 chapters to enablement. What are those 3 chapters?
So onboarding is you welcome someone in the door, you set the expectation for how they're going to get up to speed over a set period of time. Ongoing is the consistent rigor for how we're going to continue to introduce or refine on the sales enablement So of which can be sales methodologies, prospecting, building a point of view, working through negotiation, however you frame sales enablement. And then there's the intersection of cross-functional enablement, which is product, product marketing. How do they want to get in front of our sales team to take the new messaging to market? So that's ongoing. The third is what I would just call is field sales strategy. So as we're taking into consideration the inputs for enabling the field, what are we learning? Where and how do we pivot? Or how do we build on the programs we've run to make our reps even more effective? And that to me is probably the most dynamic course of building the enablement program. And I think this is where you see great sales enablement leaders shine. Versus just running static programs.
So what's the difference between field sales strategy and ongoing?
So I follow that.
Yeah.
So on, so ongoing, let's, let's take into consideration when we're running a QBR process, we'll have our reps come together in person and we'll spend usually a day and a half to two full days together. And I'd say no less than probably 50% of that time is actually spent on some form of enablement, whether it's direct, like, call discovery improv sessions or new first-call deck messaging and certification, or we're all together going through deal reviews or building points of view and getting, you know, some updated curriculum from how we're going to use new tools to do that. So 50% of our time is there. The other 50% is within our team going through the quarter and the deals. That's an example to me of ongoing enablement.
Okay.
Field sales strategy is we are mid-quarter and we're looking at the pipeline we have and we are evaluating how do we move the needle or how do we win this stage and get this from stage 3 to stage 4 where our close rates accelerate up to 85% and how do we help the field execute on or evaluate the gaps where they are and help them execute to get across the line. Most of the deals we sell into the enterprise primarily, enterprise, large enterprise, strategic segments, and many of these deals, as much as you want a cookie-cutter sales process, which we have a very tight-knit sales process, the deals themselves, the customers themselves are all snowflakes. And so there is some dynamic nature within each of these cycles. So my head of enablement now, Lane, is very close to the pipeline. We run office hours every week. He's taken the lead. I stood these up when I got here, but he's taken the lead. A lot of those office hours are pipeline reviews. What, where, and how can enablement help? Where and how can field sales strategy help progress deals? And that could be in creating new assets, i.e., total cost of ownership model or an ROI model, or working with product marketing on a revised business case deck. Or, you know, a fine-tuned value pyramid. How does this look against the current state, negative consequence, future state PBOs? So that's where an example of field sales strategy is just ongoing dynamic. It is, or it differs from ongoing in its dynamic.
It's in-the-moment problem solving for the quarter. Oh, I like that. I haven't heard it structured in this way, but it makes a ton of sense. It's certainly different than ongoing. Like building a program on, you know, better value prop presentation or closing mechanics. And so is that a different person in the team that will run— or it sounds like Lane has got his hands on all of it, but eventually is that, is there somebody that's dedicated to just like in the quarter deal help?
In our current state model, we just have a single resource in enablement. So Lane is We're very tight at the hip and, and he's running both these programs in a future state. As we scale out, we will bring in new resources and assuming we get to where we want to be, we'll have at a minimum 3 total in the next year. And that'll be for onboarding, that'll be for ongoing, and then one for field sales strategy.
Okay, really cool. So I want to talk about the hallmarks of a great enablement strategy? So we talked about the components. There's 3 things: onboard people well, ongoing craft development, and then field sales strategy. What makes these things good versus great or not so good versus great in your mind?
Yeah. I mean, if you're doing it right, I think your enablement team has spent time in the field or has empathy and a true understanding for the challenges the field is facing. And, um, and when not— and because as you scale, you're— you need to hire people to do certain functions within the job, um, but you, you lose a little bit of direct connect or, or relation to perhaps the true challenges that are surfacing in the field. And so the more you can empathize with your sellers to find a path to help make them successful, the more adoption and buy-in you're gonna get from your team. So that's just a core principle. I think the closer the DNA is, the more effective you're gonna be in outcome.
It's a great one.
I think second to that, as we talk about process and frameworks, When we go into enabling the sales organization, we have to be very clear with intent. We have to be very clear on what the expectations are on both sides, right? Our expectation for delivering enablement is going to have a direct impact on your productivity. However, there's a mutual commitment here. You have to lean in and open yourself up. Be vulnerable to pursuing a path of mastery to get better at your craft, because what was working yesterday may not work tomorrow, let alone today. And the numbers typically show that, right? The average productivity per rep is down over the last few years, and every company is in a position to need to inflect that. So whether you're new to an organization or you've been here for a year or 2 or 3 years, ideally, It is all about pacing to the productivity metric up in the right. And so a clear set of expectations and then the curriculum. I think the curriculum has to be dynamic and it has to be engaging. And this is probably the most challenging thing that has come out of COVID moving from in-person bootcamp-style enablement on the floor, osmosis, whether it's in the bullpen with the BDR or SDR team or the commercial sales team or inside sales reps working with their strat AEs, you lose all of that knowledge transfer when you— when we move to remote and we're a remote company today. So we struggle with this too. And we struggle with this at Twilio Segment. How do you capture the time and attention of people for the right period of time? And then how do you get them to also take ownership and action of the content? So that's probably the— there's no silver bullet to this one, I think. That's why we try and get our team together quarterly in person. We stand up a lot of field events. We just, we try and get face time as much as we can. But in the absence of day-to-day face time, it's— this is a gap area.
Okay. Let's get into this right now. I had it later in my docket, but I want to talk about securing mutual commitment. So, one of the things that I think many leaders are familiar with is you spend a bunch of time building an enablement program, you think it's pretty good, and then the reps are on email and Slack all the way through it and just like the engagement's not there. How do you drive rep buy-in and engagement in— and this is more ongoing, I think, like for onboarding, everybody's pretty dialed in, they're on their best behavior, but especially like ongoing programming, how do you drive that engagement?
So for me, it starts with the first call in an interview process. And when we're bringing someone into an organization and you imagine what you're going through, if you're a new employee or a new candidate in a process, you're evaluating a company as your next employer as much as the employer is evaluating the individual. And so for me, whether I'm on the first call in the process, which I'm not anymore, but I'm in every single one of our sales hire calls at some point, and the conversation I have with the rep will give me the context I need on whether I think they have the right persona commitment and attributes to lean into a mutual accountable model. But I'll also walk them through what I believe to be the journey they're going to go on. And so I— there's a few, you know, conversation notes I take away from that and I share with them upfront what I'm looking for. But assuming that plays through and they come aboard, the expectation working in the organization that we've built here is this is the choice they've made. They have made the decision to join us. We're going to embrace them in. With a tremendous amount of love. But on the other side of that, there's accountability that comes into the equation. So one of the leading principles I share with the team is love and accountability. You're here. We've hired the best of the best. You've chosen to be here. But we know the job we have to do and we have a great playbook for how to do that. And it's not a scripted playbook, but it's a competency model we've built to go get the best out of people. And then a training program with, with Lane and enablement to make sure people are skilling up, right? So when you look at the 4-box quadrant, skill and will, we've hired high will. We have to get them to high skill as quick as possible. And if we've done all that, then there's no excuse, right? They are— they're in it to get better every day, and we're going to put them in the best position possible to be successful. It's one of the other pillars of leadership, the intersection of data and psychology. And then we're just going to continue to pursue mastery in the function and role. And so, I mean, in the companies I've worked at over my career, every company has presented something new for me to learn, whether it's the sales process or the product or working for new leadership or new competitors or a new economic market. If we're not inspiring that same level of learning in the reps, and they're unproductive or they fail, one of two things have happened. We've either hired the wrong rep or we have failed to enable them on the way. And therefore their productivity drops, their connection to the company drops, and then we have to make or have a tough discussion about what to do next. So short answer to your question, to get mutual commandment starts on the first call. The first call when we're going through an interview process. As I came in to Transcend, I think the conversation changes a bit, right? There's an existing team of sellers here. Who have done great things. And so how do I, how do I earn that commitment from the team up front? I mean, this is probably— I think this is the earliest stage company I've worked at. And the one thing that has stood out more than anything is the aptitude of the team is very high. It's a high-skilled team, but the appetite to learn and to create efficiency and optimize for where they recognize their own deficiency, especially being remote in a highly complex sales cycle. It was just like wide open. So I just, I was able to jump right into it. And now we have this team highly committed to learning and we've seen the result and so forth. So a lot of it's mindset and a lot of it's open and upfront clarity and transparency on, on what the expectations are on both sides.
Yeah, couldn't agree with you more on that. I, I also interview every sales candidate that we hire all the way to SDRs. And part of that interview process is me telling them what's not great about Owner. You know, I talk about, okay, it's really easy to be excited. We are in the news a lot, bunch of awards, like company's growing like crazy, but like it's not for everybody. And I go through all the reasons why people don't end up being great fits here. We're not a big work-life culture company. Like we work really hard. There's high expectations. It's a performance culture. So, you know, everybody's held to a high standard. And I didn't realize I had to say this until like a while ago, but even if you're good at your job, you're gonna get coached. I figured that was like an accepted thing, but you know, it's definitely not, especially if you're hiring more seasoned reps. You know, I tell people, I'm like, look, even if you're hitting your quota, even if you're smashing your number every month, you're gonna be getting coached on something. You're gonna have, we call it a secret sauce. Every month you're gonna have your secret sauce. You and your manager are gonna work on improving that thing with a whole bunch of different tools at our disposal. And if you're, you're the type of rep that just wants to like hit the number and be left alone and be like, look, if I'm crushing, don't even talk to me, just like let me do my thing, then you won't like owner. And that certainly helps this, certainly helps create the environment where you have the right people that are leaning in because what I find is it doesn't take too many people acting too cool for school to then have everybody else be like, oh, I don't really want to do that program. Oh, it's like, that's not, that's not our priority. If your top reps aren't leaning into enablement, it's that cascades pretty rapidly. But let me ask you about the, how the programming is built. So I think I totally agree, getting the right people, setting the right expectations, like massively important. But what about the type of programs you're running? What, what are you doing to make it engaging and dynamic for folks so that they actually want to spend the time?
Yeah. And this is where I, I look to some of the best in market for help. And Lane brings a tremendous amount of experience having done this at Twilio Segment. And so we'll probably— in fact, I know because I've seen the next chapter of this, we're going to continue to incorporate the dynamic ways of learning from the models we've seen in the past. But the most important things that stand out when you think about onboarding, there are so many different tracks you can take a rep through, but you have to pace at a pretty good rate. You have to give them real-world experience and exposure. Some of the tools we use in-house, Gong's a great tool for us, call recordings and catching up to speed on the customer conversations is a critical part of it. Sit with in team calls and forecasting calls early in their journey. Just getting a pulse of how the organization operates on the ground floor at the intersection of our team talking to customers and then reporting back on that is really important. And reps will develop their own point of view on where and how they'll fit into this new world. So that to me is really important. And after we bring people on, there are several set of tracks we put them through. So we have our product enablement track, we have our competitive track, we have our sales process track. So Lane is also administered as a command of the message lead. So we take people through value selling, we take people through pipeline generation, what it means here, how to build a point of view. And what's great is a lot of people come with experience on how to do this. But to your point, there's still an expectation to be coached up because it's a different company with a different set of problems we're solving for a different set of customers. And so we'll put people into those tracks. That's onboarding. Ongoing, we take PG, we take value framework, we take sales process. We always are touching on this. And this shows up in quarterly certifications if we're rolling out new sales content. If we're, I love, you know, when we talk about coaching, My favorite part of the sales stage is from account identification and account planning through prospecting to first call. So that those 3 steps— who is the company in my book that I'm going to call on because I have an incredibly confident point of view, we can add value to this company? How am I going to get their time and attention? And then how am I going to command the cycle or the call or the message when I have that mutually agreed-upon call. And, and then there's a whole psychology of discovery frameworks and discovery flow. And I don't think anybody in their career can ever say they have that entirely dialed in because it's, it's, it's a super dynamic state and changes so fast.
Today is a wild time to do it.
Yeah, yeah. And yet it's like, it's the— in my mind, it's the same as teaching someone how to catch and throw a baseball or getting a 3-point stance to block. Like, this is the core fundamental of selling. You have to be able to quantify or have a point of view on the problems you solve, how you're solving them different and better in the market, and the customer proof points to, to showcase that. And then develop a point of view on how you can take that across any of your key target accounts depending on industry and size and and where they are. I mean, that's, that's a required capability to be successful in today's market. And then doing that and then progressing conversations and building champions. So there's just, there's a tremendous amount of opportunity for ongoing that we lean into and we'll continue to scale. A lot of that we try and do in person, as I talked about. A lot of that we try and do on our quarterly basis. So those are, those are the programs. The field sales strategy one we've talked about, this is more dynamic in nature. So there's no playbook here. This is read and react. What's happening in the field in these mid-cycle deals to ensure we're improving conversion and progressing from multiple stage out of, uh, into, um, more accelerant high close rate stages. And, uh, that, that one, that one will be fun to see how it tracks over time.
So I'm gonna come back to a couple of things here. Command of the message, which you talked about, and I want to talk about acquiring the right methodology, but you mentioned Lane a couple of times. You're talking about this field sales strategy piece, which I think is— that's a very specific type of individual in enablement who can do it. So I want to hear about your framework for leadership hiring and enablement. What are you looking for? How do you find this person? And then we'll talk interview process. So like, what do you— what's your ideal person look like here?
Yeah. So someone who effectively is a trainer or a coach at heart, someone who gets gratification out of helping others, which you'll find in most sales enablement resumes or conversations. The caveat, though, is I look for someone who carried a bag and I look for someone who spent time in the field. And not only that, I look for someone who sold very complex data infrastructure technology. So someone who was whip-smart to the problems we're solving and yet all of the complexity around our platform. And there were very few people in my network that actually stood out against that criteria that were either in enablement field sales strategy or wanted to move to enablement field sales strategy. And, um, we just— we happen to be very fortunate that, uh, the person we brought in happened to be, um, actually in the market as well. So, uh, it was, it was just a great, uh, a great match rate for, for where we are now. In a future state, if I were to do this all over again, I probably wouldn't straight too far. But again, I think enablement differs on size and scale and complexity. We needed someone across all three of those areas. Yeah. And former roles, when I was, for instance, at Box after Doug left and imprinted upon us just the concepts of how to command a strong sales process and sales discovery flow, you know, we, we had, we thought about enabling it a bit differently. And some of that was competing in the market against, you know, a lot of the incumbents and the big file storage companies or cloud storage and the rise of, you know, the, the consumer applications with Dropbox. And so our path through enablement took a variety of different routes. And, you know, would, would the same persona apply in that role? I don't know. Probably not. And And I think the more you are in tune with the problems you're trying to solve and the people that would be the best fit to solve those problems, the more successful you'll be with hiring the right person.
So really being thoughtful about your specific environment.
Oh, 100%.
Yeah. And so say more about the— so enablement could have taken a different path at Box. What do you mean by that? Like, how would it have looked different? Given sort of the competitive dynamic there?
It's not that it couldn't have, it just took a different path at Box. And this was, Doug is one of one. And when Doug moved on, it was, you know, we had a more of a traditional framework for enablement, but a lot of the processes had already been built. And by that time we were a public company. And so we just, we slotted more into the programmatic enablement.
Okay. What, so I'm a big fan of Doug as well. And known him since the early Salesloft days. Um, what, what made him so special as an enablement leader?
Yeah, I think he, he embodied a lot of the same attributes I looked for when I brought in my head of enablement here. Uh, Doug carried a bag. Doug worked at the, the most complex and, um, in, in most— some of the most well-known companies. And then he decided to move into a different part of the, the organization and create value at scale by taking ownership. I mean, I joined Salesforce, they were still only about 2,000 people, and I think Doug— and that they were growing rapidly at the time, but I think Doug was responsible for enabling every single one of those people who came through. And you just, you look at the success of that company, um, he cared, he had heart, uh, he still does. You know, anytime you talk to that guy, he's filled with energy. He understands the exponential gains you can get out of the just the marginal investments to the core fundamentals. So, you know, I think he's special for those reasons. And, and I, again, I think people who embody some of those attributes have a great opportunity to be successful in a similar role.
Yeah, boatloads of charisma helps too, for sure. You don't see a lot of guys, you don't see a lot of people in enablement that have that like captivating of an approach and can hold a room like that.
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This summit combines cutting-edge insights and actionable strategies. Learn from industry pioneers covering all aspects of sales and revenue growth into 2026 with sessions from Andrea Kahl of Help Scout, Guy Rubin of EBSTA, Wendy Sturgis of Cleverbridge, and more. Visit joinpavilion.com/cro-summit to secure your spot today. Oftentimes I think enablement is just like underpaid, you know, like we under-resource it as a function. And so it's, it's harder to pull in, you know, the, the elite talents, um, that you really want doing it. So that makes sense. What are your big red flags? So, so when you're, what's the flip side of the coin on what should people look out for? Where have you seen enablement programs go wrong? In terms of the leadership profile specifically?
If you put yourself in the shoes of your best seller in the field and they're coming for coaching on a specific topic, is the person who's running enablement able to, one, field the request and provide a valuable response or program or not? And so to answer that question, I think you have to think through when would that happen? When would there be an example of someone who has not been there, not seen that, or prepared to answer that question? And I think if we maybe due to, you know, compensation or whatever the driver, if we hire the wrong people in enablement, it is very easy to lose trust. So red flags are ensuring that you have the right people who are taking responsibility of teaching, training, building the force multiplication in the sales org. If you get that wrong, you will lose a lot of time, you'll lose a lot of faith, and you'll lose perhaps people, valuable people at your organization.
Yeah. Any tips for the interview process? How do you go about unpacking some of this stuff?
Yeah, part of— I mean, no matter the role, I think motivation is critical. So understanding what drives people in, in their pursuit of, you know, commitment and becoming the best of who they are. So we ran through a series of different questions with the funnel we evaluated for this role. I think you have to go tactical at some point and understand how do you build programs, especially in a remote company, for engaging people, keeping them stimulated, making sure they're leaning in, and then testing against, you know, perhaps that curveball scenario. Where and how have they work through or embrace some of the most challenging enablement scenarios from some of the best reps. Who do they call in for support? How do they tackle that problem? How do they learn to get better? So I think covering your base on making sure people are committed to a long-term journey with enablement, you know, as we think about rep retention versus attrition, everybody you hire in your organization is going to have some degree of a profit loss. Formula, right? You are, you are underwater on that hire for a set period of time. And if you can accelerate that, great. Um, but with regard to this hire, this hire has to be a very strong hire. This was when I came into Transcend, this was actually the first hire I made. I, without any doubt, I, I knew exactly where I was going to put dollars in the business. I spent a lot of time making sure we got the right person, but Anyway, so the interview process, I think I covered the main thing. Yeah. Yeah.
And I just want to unpack how to get tactical. So you mentioned you want to figure out how do they build, how do they keep people engaged? How did you do that in the process?
Yeah. So if I'm looking at this objectively, I had experience, direct experience with Lane. So I've seen the programs in the past, but objectively it would be Walk me through the 3 workstreams for enablement. Well, actually zoom out. I mean, if I showed you my deck, the first part of the meaningful stage of the interview is walk us through your philosophy of enablement, right? Take me through the philosophy of enablement. And then the click down is how did you institute these principles or this philosophy inside of X organization? And then what did you learn? What worked well? What didn't work well? I have a great deck I can actually share with you if you care to poke through it. I would love to see it. It helps frame a discussion and then allows both sides to get into the detail, not too dissimilar to what we're doing here, right? Help me understand how you think about this and then let's get into the meat of what you learned and so forth.
Very cool. So let's talk a little bit about how do you build this thing from scratch? You're in the midst of it. I'm, you know, 2 years into doing the same thing here at Owner. What are the first things that you prioritize and how do you think about the sequencing?
Yeah, it's a great question. And you can't do it alone. As you know, you need someone who's going to put 100% dedicated time on it. And so in this framework of a RACI, although ultimately I am the responsible party for the metric of sales productivity, My head of enablement and field sales strategy is the responsible party for building the program. And I provide a tremendous amount of agency for them to execute. But the key things we consult on are what are the most important things we're building for today and what are the next set of important things we're building for tomorrow and next year and so forth. And for me as a head of revenue here, we need to have high command of the message and high command of our sales process, full stop. Like that is priority number one. Do we have a common language across the organization about how we talk about deals? Internally, and then how do we talk to customers externally about the problems we solve, how we solve them, how we do it better than others, and where we've done it. So that therefore brings in the, the concept of command of the message or the value-based conversation, how to work through that discovery flow, that internal evaluation of med pick. And then we get into sales process, winning the stage, customer verified outcomes, how to progress with high confidence stage by stage, bringing resources around. So that's where we anchored. And in fact, before my head of enablement came in, I started to chip away at that on my own. And, and I worked, you know, sales ops and rev ops and brand and marketing. We actually rolled out the Value Driver series right when I first started working here. And then, and then we got into sales process and started to introduce MedPic programs. But we are now full instituting with high consistency, the same rigor. And what's great about this as the beachhead and the staple for us is as we bring new products or if we're shifting messaging at all in market, the framework and structure is there, right? It's just about filling in the quads. What is the problem we're solving? How do we do it? How do we do it better? Where can we show that we've done this before?
And that's the end of the message stuff. Yeah. Yeah.
Yeah. And so the field has well adopted this.
Say that last thing again.
And the field has come a long way in adopting this. This wasn't the common language within the organization 9 months ago. And so we're now at a pretty good place. I think we can build upon and just get tighter on the message, really understand what we're looking for in sales calls. Coach to that ongoing framework in our quarterlies, make sure we're improving. You know, it's at this point it's aggregation of marginal gains in that program that make a big difference over time. But anyway, so that's it.
Where is that phrase from? Aggregation of marginal gains? I've never heard that.
Yeah, it's, it's— what did I just read? Oh, it's an old, uh, an old, uh, it's an oldie but a goodie about— it's, it's not The Power of Habit, but it's, um, Compound Effect? No, uh, I'll, I'll get it for you in a second. Okay. But yeah, aggregation of marginal gains.
That is a great, uh, term. I've never heard that before. Brailsford.
Uh, Atomic Habits.
Oh, it is Atomic Habits. Oh, that's so— oh, this is the cycling guy. Okay.
It's funny. That's right. That exactly. Exactly. That's right. Tour de France.
I've read Atomic Habits multiple times and I never picked up that term. That's funny.
The things you pick up, especially when you read books a couple times through, just different things stand out.
I talk about this a lot, you know, like we, especially we're an SMB business and you're really just trying to pick up basis points across all of these little touchpoints and instrument and tweak and finesse. But Aggregation of Marginal Gains is— that'll be a good one to fit into our language because we're big— Atomic Habits is one of our big must-read books. So we were talking building from scratch. So the components you mentioned, What are the most important things for today? What are the things that you need for tomorrow? How do you prioritize those things? Like, how did you go and identify what were the most important things for today and what's tomorrow? And just like walk me through how you think about prioritization.
Perhaps you agree, as a sales leader, as mentioned, sales process, sales framework methodology was, was high priority number one. Just driving consistency in the language. Building for tomorrow, I think, is a—
And was that intuitive? Like, you just, you're like, yeah, you just, yeah, you're just like, look, like methodology is my first thing. I don't need the data. That's, that's where we start.
Well, the data fed that. So without enablement, I spent a lot of time running an assessment just on— so if I were to back up, running an assessment on current sales engagements, close rates, progression, accelerate the ACV, all that stuff. It takes you to a point, right? And usually in early stage companies, you're spread really wide and you have very inconsistent, predictable process you can build upon. And so you try and understand what is the root cause of that. Are we communicating with high efficacy and consistency in the market. So is marketing aligned with sales, aligned with product, to make sure we're telling the right story to our customers? And largely, you are, but in a sales forecasting model, you're not, right? Because you're, you're selling to— like, we sell to, I'd say, all in maybe 3 to 4 at max verticals with, with, uh, high success within our ICP. So part of the work was dial in the ICP, get a ton of focus on the right accounts, and then in these accounts or these industry verts, how are we talking about the problem? And then how do we build a scalable process where we can govern and forecast and inspect and provide the right guidance on deal management? And all of that takes me to sales methodology and the way we talk to our customers, which is command of the message. We extended that internally cross-functionally. So it's spread across our products, our marketing, our CS, our CX team. So yeah, it's well adopted now, the way we think about value drivers and differentiators and so forth. Cool.
So I want to talk about command of the message a little bit. So you're certified. You can clearly tell you're deep in this. How did you come to force management? How do you think about the decision to take an off-the-shelf methodology like Command of the Message and implement it versus like giving it your own spin? Um, talk to me about just like building your methodology that you use.
Yeah, the, um, I mean, I, I, I try and maintain the perspective of being a student at every company I've been at. I've just been really lucky. So I mentioned Jeff Hoffman and John Barrows, and Jeff came to us at Yammer, which was just so much fun. And, and I brought Jeff into Box and then Segment. And, you know, we studied Challenger at Box and implemented that. And then when I got to Segment, I think what was more unique about force management was, uh, I, I just had the fortune of working under Joe Morrissey, who's now at A16Z, but, um, he was our CRO at Segment, and he had worked directly with John McMahon, John Kaplan, and rolled out force management, I think, at a couple companies— CloudEra, uh, Mongo— and clearly he had high confidence in this program. And so as someone who was just trying to absorb as much as I could from a, a really strong revenue leader. I saw his conviction for it, and then we went through the program, and it was a live training in Las Vegas, my first week there. And, um, what I took away from that was they demystified the whole conversation of just the core concepts we've talked about into a way that not only connected the front end of discovery, which I've so deeply appreciated Jeff Hoffman's approach through the deal management and inspection of MedPick. And then right in the middle of all that is Champion Development. So they just took this end-to-end process and stitched it all together with a, a language that had strong continuity throughout. Is digestible for salespeople. It's digestible for cross-functional organizations. And so for me, I thought, wow, this is an incredible way to help people. And at the time, I had the commercial organization. My first year at Segment, I had the commercial organization, and we were going from a, uh, a cycle where we had a tremendous amount of inbound demand to to enrolling this out and introducing this methodology. And then in my second year, we were— I took over the enterprise team to now having to go outbound to find opportunities. And this was the bridge that helped us get there. So anyway, the proof point, the success came with it. I leaned in deeply to the methodology. When I came over to Transcend, it was a no-brainer to introduce the core concepts. We rolled it out on the back of just our experience without any professional engagement. We've tweaked it, you know, we use a lot of the same core principles, but, you know, there's a bit of a spin on it. Uh, not spin selling spin, but a lot of these, a lot of these converge in, in certain talk tracks anyway. I mean, you have to understand pain, you have to understand negative consequences, you have to understand what the requirements are, you have to understand who the competitors are. So as long as you're conversationally fluent in the problems you solve, how you solve them for other customers, how you stack up in the market. You can call it force management, command of the message, or anything else. It's effectively just being able to have that conversation.
Yeah. And John McMahon, was he a PTC guy?
Yeah. Yeah. Okay.
So hence the minute.
Okay. Okay.
Um, that is really interesting. I've, I've been through a ton of Challenger stuff. We did a little bit of messaging work with force management when I was at Vision Critical way back in the day, but it was like pretty light touch. And so I've always erred towards like assembling my own methodology and maybe that's because I'm a control freak and I just like want it to be my specific like variant of it. But I think for a lot of folks, this is a really interesting accelerant to get them to skip a bunch of steps and have something you can implement day one across the customer journey. And how much Challenger, or are you now basically like, okay, we're all in on Command of the Message. This is our one methodology. We're not going to use Challenger language because you're trying to simplify and create that shared language. Or are you pulling pieces from here and there, or is it really about like one central philosophy?
No, we pull, we pull from everywhere. So, okay, for instance, Jeff Hoffman's framework talks about the perfect meeting, and the perfect meeting is a great way to think about first call engagement, right? And a framework to work through a funnel of discovery that shifts the paradigm of what this is, a sales call where I'm a seller, you're a buyer. To something more like a teacher-student. And he has a great playbook of ways to do that. We, we've incorporated that into how we think through first call. Challenger finds itself in our model in when we're talking about maybe second, third call or just ongoing engagement. The key elements with Challenger that stand out to me are teach, tailor, and take control. And when you're selling disruptive technology, which we are, we're selling a new way to do something that has an existing incumbent. And so we have to teach our prospects or our customers the value of, or inversely, the pain or consequence if not.
Yeah, that challenger story arc makes a lot of sense there.
Yeah, totally. And then we circle back to command of the message. When we're thinking through new business meetings, sales process, framing back champion development, economic buyer, and then the MedPick framework, all that I frame into the force management playbook. But so we use it all. And then, and then frankly, like we seek to hire the best in the market and I trust my team to exert and, uh, and apply the skills they've acquired over time. And the only thing I ask for in return is if, if you're applying SPIN Selling in the field to get to the outcome you need, I have zero problem with that as long as we're incorporating what I believe are critical, our value drivers. So how we communicate to the market, the value we drive, and then that's externally. And then internally We're talking about the deal as we're going through pipeline and forecasting against MedPick.
And then when we—
so those are the two connective tissues there. Like, get to where you need to go with your discovery frameworks and your champion development exercises. But when we talk about what we do to the, to the market, make sure we understand our value drivers. And we have a whole pamphlet on how we've enabled the team on this. And our differentiation and all that good stuff. And then internally, you know, we talk about the deal integrity against the sales process framework. Yeah.
Flexibility within a framework, I think, is so much of it. I mean, finding that Goldilocks, that Goldilocks point between like, hey, we only do it this way, these are the only things you can say, can be overly rigorous. It can take away people's feeling of autonomy and agency, which actually has very negative motivational consequences versus no methodology, no way to systems engineer and tweak and change things. So, I think that makes a ton of sense. And I think it's underrated, the internal language we use, you know, having a framework like MedPick or just the language you use to talk about a deal, the types of words that we describe certain situations. Like, even I really like from Challenger, their champion frameworks from the Challenger Customer, the second book. So, you can really have that shared language like, "Okay, is this a skeptic, a blocker? Are they a coach?" Because then you can get— you can just the shared language accelerates things so much. I don't have to explain, well, this guy was kind of a dick, but like, I actually think he's interested. No, no, that's just a skeptic. That's somebody who's legitimately interested, is going to ask hard questions, and we can just— we can shortcut the way that we're moving internally. So much of this stuff I think people find is like boring or like overkill, but I think it is the oil that really like lubricates an organization to move quickly.
This is my favorite part about the job. Like this is, this is a, you have to tie your shoes before you get on the basketball court, right? Like this is it. You have to, and this is the most elusive skill to continue to be a master at, at least earlier in your career. I think reps are very quick to overlook some of these core fundamentals and apply other principles to seeing if they can get deals done. But if you master this part of it, what is the problem the customer is facing? Put your shoes in the self of the customer. How are they thinking about their options? What do they think of us? How do we show up to have a good, educated conversation with them? How do we advise them on their own optionality? I just, to me, it's the fun stuff. It's like psychology of selling.
Yeah, yeah. The basics. The basics is everything. Like the little flourishes are cool and interesting to talk about, but there's, this is one of the negative outcomes of like LinkedIn and sales social media is like everybody gets obsessed with the shiny stuff and it's like, no, you know, having rock-solid discovery and very concrete ways to communicate your value in succinct language and a way to navigate a sales cycle. That's 95% of it. Okay. I want to quickly loop back to two interesting things that are only semi-enablement related. So you mentioned greatly, you said very offhand, great leadership is about the intersection of data and psychology. Say more about that. What do you mean?
Sure. So paraphrase data and psychology with putting your people in a position to do their best. Right. So as revenue leaders, you and I have access to a tremendous amount of data. And it's either qualitative anecdotal or system generated, like but you know where the market is, where the opportunities are. And then on the other side of that, you know the team you have and you know their personas and you know their motivators and you know their strengths and you know where they have growth areas and you know if they're going to lean into those or not. And so as a leader, or put yourself in the position of, you know, being a baseball coach or a football coach, you're going to put the right person in the right position. To make the play. In a sales organization, why can't you do the same thing? Right? Just because you have a headcount plan to hire 20 reps this year and the market is only bringing you a certain cohort of talent, who's to say you can't change your plan and get 2x productivity from the talent you're bringing in in a different way of cutting the pie? So that's one example of it. Just put your people in the best position possible to be successful. Don't overlook it. That's the people management side of, of leadership. And, and stay close to your team. I, you know, I try and run skip levels. I try and get into deal reviews with reps as much as I can. I try and run office hours just to understand how they're thinking and the overall just the overall sentiment from the field and if they feel like they have a chance to be successful. And if not, that's where I work hand in hand with enablement to ensure we're shoring up those gaps.
Nice.
I think, yeah, does that make sense?
For sure. And so this is all about like you have two jobs. Look, understand the data, make good decisions. Navigate the organization and be able to deeply empathize and understand your rep so that the people in the right spot can actually do, do the thing you, you all want to do together.
Yeah. And find the intersection. So based on what you see from the data, make sure you're putting your reps in the right roles to go maximize productivity. Yeah.
Makes a ton of sense. Um, any other comments about like what makes great what makes great revenue leadership?
Based on my experience working under great leadership and things I've tried to take away and incorporate, whether I succeed at that or not is a different question. But I think great leaders can inspire people to do their best work. I think, I think good leaders, table stakes are running, running the business against all of the different ways you and I think about it. And, but I think great leaders are the ones who get you to wake up early. You got a pep in your step. You're out to get it, not just for yourself, but for the company, the vision, the mission that's put in front of you from, you know, your founding team, your sales team, your sales manager. They hire the best people around. So you're constantly challenged to be better. I think that's what separates good from great.
Yeah, yeah. One, one of the things that I've been talking to my leaders about a lot is how to foster intrinsic motivation and how to foster an internal locus of control. Because I find, especially newer managers, it's always about like carrots and sticks. It's always about, okay, you know, run a spiff, have a tough conversation, push people, push people. And there's a time and place for that, of course. Sometimes you just need to give, give people a little bit of a shove in the right direction. But being able to foster this like much more deep-seated motivation in people to be the best versions of themselves, to like pursue greatness, pursue mastery. And this all comes back to this internal locus of control, all the All of this psychology research would tell you that that is by far the most durable and most powerful motivation. And so, I find one thing I'm spending a bunch of time on is tweaking the conversations that my reps, my managers are having with their reps to try to stoke the fire within somebody as opposed to lighting a fire behind them and totally getting them to run.
Yeah, I think there's— Daniel Pink wrote about this a long time ago in his book Drive. Yeah, it's purpose, mastery, autonomy. And if you just use those core elements of how to, how to get the most out of people, the way we think about it here, everyone who comes in at owner.com doesn't know how to do the job on day one. And so enablement's a core part of that. And giving them the tools to develop mastery is a core part of that. So your ability to teach or your sales manager's ability to teach them, skill them up is a core part of that. The purpose piece, I think, is where great leaders stand out over good leaders. This is what I'm talking about, inspiring people to feel like they have purpose. Within this company to achieve whatever that intrinsic motivator is. Maybe it's to help buy a home for their family. Maybe it's to pay down student debt. Maybe it's to develop skill to get to the next role. Everyone's unique intrinsic motivator is different. So I think— I mean, I love it. I love the way you're thinking about it. On the skilling people up, though, this is oftentimes an overlooked element where this is the phase 2 stuff of enablement. You didn't ask about phase 2. Or you asked about what's phase 1, phase 2, and I gave you a bunch of phase 1.
The phase 2 stuff—
yeah, the phase 2 stuff, like what's not burning fire today, although it could be, it is developing the competency framework at my— the new company Transcend for what it takes to be successful in this role. And the core competencies really rarely change in my mind. You need to be effective as Somebody who can generate PG, who can manage complex deal cycles, and who can have an operator's mindset around if you have a territory, how do you become the CEO of that territory and increase NDR? And then the sub-competencies are the core training elements within that, right? How do you build an account plan? How do you prioritize outreach? How do you work with your BDR to crack into key accounts? How do you progress stage 1 to stage 2 deals with discovered. And that, Kyle, I've realized, is one of the great unlocks to helping people develop mastery. Because when I came in as a seller, I didn't know how to do all that. Doug Landis helped me a lot in those early days and some of the great reps before. But 15 years later, 20 years later, the world's changed. And some of the core principles are the same, but the world's changed. And we have a different set of leaders and enablers trying to teach back that stuff. So Making sure you have a consistent framework for how you teach mastery and skill for the company you're at, I think, is an important part of the, you know, the Daniel Ping story, right? And so that's the next phase for us. We're going to get deep into the competency framework. We're going to use it as a bridge to performance measurement and management and, you know, the skill will stuff and professional development, career career ladders, but it's all interconnected and hopefully it unlocks motivation.
Yeah. We're rebuilding this ourselves.
Nice.
Rebuilding our competency matrix. So, we'll have to swap notes on it. Yeah. I love Drive and all things Daniel Pink actually. And so, I wrote an engagement strategy document for my team so they can understand the psychology of rep engagement. And so, Instead of AMP, autonomy, mastery, purpose, it's CRAMPPS because I read a bunch of other engagement research and it talks about the importance of community. So, it's community recognition, autonomy, mastery, purpose, and then steps. Steps is like career progression to try to round out that full picture because it's such an underrated— it's such an underrated part of this whole picture, being able to— we think about the machine and instrumenting and the hiring profile and all that stuff, but what is the thing that gives people that sense of fulfillment? And you mentioned getting up with a pep in your step every morning. What is the framework for that? And for me, it's cramps, giving people— plus, it's funny because I can say to engage employees, you got to give them cramps. But, It's give them a sense of community, give them a connection to their peers and leaders. Recognition we know is like a massive motivator, but do it in a way that's resonant with how people operate, not just their outcomes. And then autonomy, mastery, purpose, which you were talking about. And then steps, like what is the career progression? How do you make that as clear as possible? Because oftentimes, it's very unclear, um, and giving people like— and promoting from within, you know, like as much as you can promoting from within. I feel like— yeah, agree, that's a good way to round it out.
Yeah.
Um, okay, let me move into quickfire, uh, and then we'll wrap it up. So I already asked you what separates good to great in terms of a CRO. We got some good stuff there. What is the most common advice you find yourself giving to new leaders of yours? So like new second-line leaders, somebody who's a first-time VP of sales, what do you find your most common advice is to them?
Yeah, it's a good question. There's a lot of things you try to not say to new second-line leaders, but I think the number one thing I do say and segment we had experienced bringing up a couple first-time second-line leaders, it's to find where your value-add is in the chain of command. What is it that you're now most responsible for doing as the leader in this position now? And more often than not, you'll see growth here over time. But in the early days, it's— there's a lot to be there's a lot of pain in growth, and usually it takes— it roots in the form of first-time, second-line leaders are working 20 hours a day because they're trying to do everything.
Yeah, they're trying to be the manager and be the director, VP. Yeah, yeah.
And it creates a ton of confusion in the organization as well, all the way down to the rep level. And so, uh, it is just to understand deeply what your, your value-add is in the chain of command here and how do you maximize and optimize company productivity and outcome and leverage.
That's a great insight. That's the first time somebody's mentioned this. That's good. Um, what's the hardest lesson you've had to learn?
Um, I— so, you know, I've gone through a few different phases of my career growth, uh, selling different products from application infrastructure, going through acquisition, going through public companies from private. Like, there's, there's been a lot of things there Hard. I mean, they're all hard. Valuable. They're all valuable. I would say the most challenging thing I've had to go through is in my former life before I came here, post-acquisition compounded with market dynamics post-COVID era was, you know, it was, it was an integration. It was a separation. It was a reduction, it was a growth. Like there was so much thrash in such a short period of time that it, you know, it took a toll on, on me. It took a toll on a lot of the people that I brought in and helped develop. And so that was, that perhaps was the hardest thing I've had to go through professionally.
And what did you learn from that? What was the big, big learning that you took from that, that period of time?
Yeah, I think looking, I mean, transparency is key and critical. Everybody you bring into your organization, As mentioned, first pillar of leadership is love and accountability. And everybody I brought in, I loved. I wanted them all to be successful. And as we were going through hard times, you had to be open and you had to communicate with clarity and with context and let people know, you know, the hard truths about certain things. And, you know, a lot of it wasn't personal and, and then embrace them and help them, you know, get to the next phase. And then on the flip side of that, as we were going back through growth, It's, you know, a degree of transparency on there's nothing guaranteed, right? We are going to go through the motions and the decisions our people make to rejoin us on this journey have to be rooted in their own intrinsic motivation for what they're trying to achieve through this next phase, regardless of what is out of their control. If we were to hire again and fire in 2 months, like, how does that impact you? Are you okay with that? What do you have to gain? So it really helped me just create clarity and more so challenged me to have a high degree of transparency for the purpose and decisions that the company at the time had been going through. So it was hard though.
Last question is, what's the best thing you've read in the last 12 months?
It's a reread that I took up 5 years ago, but It's a great book by an author named Owen Eastwood. If you haven't read any of his stuff, you might like it. I was first turned on to him from a podcast listener, which I'll share with you as well. But Owen Eastwood wrote a book called Belonging, and it profiles the story of the old New Zealand Māori tradition of this term called waka papa.
Oh, somebody else mentioned this to me a couple of weeks ago.
No way.
Yeah.
Anyway, it's a great way to think through uniting people on a mission and a journey together. So, I have found it. I've read it once before. I used a lot of these principles in former roles and I'm finding it really inspiring again right now.
This has to go on my list. Two people in like three weeks and both super sharp folks. I'm going to read it.
I think you'll enjoy it.
Well, this was awesome, Luke. Pete Kazanjee said that we would get along well and we'd have a lot to chat about, and he was very right. I mean, you're clearly just such a thoughtful guy about all of this stuff. It was awesome to go deep with you, and this was an awesome episode. I learned a ton. It's no surprise why you've been as successful as you have been. So appreciate you jumping on, man.
I love it. Thank you. This was super fun for me too. And I love to, love to rap about these subjects. Thanks for the platform to talk about them. For sure.
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 you, share it with your network, and please join me next Wednesday for another great conversation.
More from Kyle


E74: Your Agent Isn't Broken. Its Foundation Is. | Jonathan Moss, EVP Growth & Partnerships @ Experity


E73: The AI Enabling 600 Customer-Facing Reps | Lauren Hughes, VP Revenue Effectiveness @ Justworks
E69: Stop Paying For SaaS: The AI Playbook Driving A $1B Trajectory | Ghazi Masood, CRO @ Replit
E68: Are You UNINVESTABLE? The New GTM Reality | Cassie Young, General Partner @ Primary Venture Partners
E67: Your Buyer's AI Is Pitching YOUR Product (Badly) | Adrian Rosenkranz, CRO @ Webflow
E53: Sales Capacity Planning That Doesn't Suck (Jenny Dingus, SVP Global Sales @ Clio)
E62: CRO Life: from a $20B Exit, to a Hyper-Growth AI Org (Michelle Donnelly, CRO @ Crescendo)
E58: Replacing Your Sales Team with AI Agents (Jason Lemkin, Founder & CEO @ SaaStr)
