E36: Why Product Thinking Beats Process Obsession in GTM with Sangeeta Chakraborty

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.

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Today's guest is Sangeeta Chakraborty, and Sangeeta was most recently the CRO at Miro for the last 3 years, and she owned the GTM function there across 600 people within sales, alliances, CX. and prior to Miro, she was a senior go-to-market leader with 5 exits to her name and held senior leadership positions at Okta and Checkr. And Sangeeta is also a very active early-stage investor and advisor. We're both LPs in the Stage 2 Capital fund. And, uh, we met months and months ago at an event, a CRO Circles event in San Francisco. And I knew then I had to have you on the pod because you had lots of interesting stuff to say. So thrilled that you could join us today.

Thanks, Kyle. I'm stoked to be here. I love your podcast.

Thank you very much for saying that. And so we're gonna cover a few different topics today. It's a slightly different approach to the podcast because people have been asking me to cover a little bit more, and you are the perfect person because you've done this pre-sales to, or post-sales to CRO transition, which I wanna dig into. I'd love to learn some of the big leadership lessons from across your career and especially dig into the Miro experience. And you're also actively on the market. You left Miro earlier this year and are in the process of assessing the right fit. And so there's so much good stuff in there for us to learn from how you're thinking about the next role, diligencing the right company, what is different today in a post-AI world in terms of company selection. So excited to dig into it. So lots to cover. Yeah. Uh, but what did I miss in your background? I, I gave just the snippet, but tell a little bit more of your story.

Yeah, yeah, happy to. So, think of me as a customer-centric sort of go-to-market leader that thinks from the outside in. And I believe in building a sales motion that is designed in the way I would like to be sold to, which means really, really come to me only when I have a need in mind, make sure you understand what I'm looking for, and sell to me in a way that makes me feel that you're my partner for the long-term journey. And so, when I build the go-to-market system, and I call it a system by design, and we can talk a little bit about what I mean by it, but essentially I think what I'm trying to do is map out that customer's buying journey and then their adoption and growth journey from the beginning, and then figure out how can I create a system where I can actually be very, very scientific at every step of the way and say, these are my target buyers. Here's, I'm gonna talk to them. Here's what makes sense for them to know. Here's how we're gonna help them do the evaluation and then the purchase, and then the real work starts, right? So, most go-to-market sales processes I see are a straight line, lot of attention on the awareness and the evaluation and the negotiations, and then there's the close, and then there's a little bit of the line that says post-sales and you're done. And I think that is so short-sighted. It is so old-fashioned. I think people are buying for the future. They're not buying a tool anymore. They're trying to buy a partner that solves all of their problems for a long time to come. And we miss thinking that the job is done when that sale is closed. So, I'm on a mission to eradicate the post-sales term. I ban it in my organizations. I think it is a term from the 1980s that we should not be thinking about anymore. Because selling is all about continuous value delivery and, you know, value communication and continuing to provide that vision to the customer. So, that's the kind of org I build. That's the kind of leadership style that I believe in.

Awesome. We're going to immediately change the order of my docket then and start there because, uh, so I listened to you on Robert's podcast, Science of Scaling, and talked about some of this. And one of the, the small things that I picked up that I wanted to dig into was you referenced that building a go-to-market or going to go-to-market motion is, is like building product. And I went to school on product stuff when I got to Shopify. I like had to get super deep just to be, you know, taken seriously there. And there were so many lessons learned. And so I'd love to start with where did you first learn about the application of product management to go-to-market team building? And then I wanna get into some of those lessons.

Yeah. So I'm a computer science engineer by training. I will say that in my early days of that technical life, I did not really understand what product management meant, right? I was given a job to do. I went and coded that. By the way, I was not good at coding at all. Luckily, I turned out to be good at the other side. But what made me fascinated about the whole science of product management was my entry into Miro. And it was by necessity because Miro is a product-led growth company and one of the best, if not the best, in the world. And I felt like, kind of like you, if I didn't really understand how product is built, I could not be really a relevant partner to the organization and a leader in in the organization. So, my first foray into that was recently, about 3 years ago. And I started reading about it and I was reading books about it. I was reading sort of literature about it. And then I started listening to people like Lenny, who's bringing constantly the best of the best. And I felt like this is what I've been missing in understanding how to build a go-to-market system because the difference I think in the way traditionally go-to-market has been built is a straight line. It's a process. And there's a process owner, and the process owner says, I'm gonna do A, B, C, D, up onto a certain number of things, and I'm just gonna be the best at that process. But if you think about the modern world of go-to-market, you are in this continuous cycle of learning. So, the best organizations are the best learning organizations. So, you are actually in a loop. It's a circular loop of never-ending learning circles. And if you think about the way people are building product, they are very focused on the user value. They have some hypotheses about how they're gonna drive that value, but they're constantly testing and doing user research and understanding, is that the right hypothesis? And they're fine-tuning and sort of creating the better and better value in the product. And that is the way I think go-to-market has to be built as well. It is a process of constant improvement. And you have to understand the customer journey and think about how you're gonna improve it in every step of the process. And the thing that was very new to me was experimentation. And I would say I was very uncomfortable with the idea because I felt like the best salespeople I know and all of these amazing podcasts I listen to, they've come from these incredible, like, insert your famous logo here companies, and they have playbooks. And so obviously it must be some playbook I need to be thinking of. But then as I understood this product management mindset and about this continuous search of optimization, what I realized is that you really don't know what playbook is going to be for your company. So, you'll have to constantly build that learning muscle in and be comfortable with testing and experimenting before you scale. And if you have a 600-person organization, you can't scale it without knowing exactly what is going to work, right? It's gonna be a very expensive mistake if you get it wrong. So, we started to build with my team's help, this sort of framework of experimentation with a set of things we needed to test. You put it in the backlog, the ones that you couldn't get to, and then constantly groom that backlog and put it forward and see what is the next thing. So, I feel like product management was sort of a skill set I needed to become a good sales leader.

I love to hear this. I'm also a raving Lenny fan. This is I, I, I've emailed him to say like, hey, I started this to be Lenny's podcast for revenue. And so he's somebody I learned a lot from. And, and this is such a— everything you're talking about resonates with me so deeply after my time at Shopify. And I think revenue leaders spending time at product-first organizations is a, is such a healthy thing to do, even though it can be uncomfortable because you're at Salesforce, sales rules the roost. You feel like the most important thing going on. And at Shopify, you definitely did not feel like the most important thing going on.

Yeah. And I think I want to give credit to the founder at Miro, Andre. He was the one who almost, I would say, take my brain sideways and challenge me differently to think differently. And I feel like just the way he was thinking about the product build was finally what I realized I was missing and it was going to make me better if I brought that in apart from obviously all the sales skills. The core skills that you would need.

So I, I'd love to double-click into this experimentation approach. So you start with sourcing ideas and there's this woman, Teresa Torres, who has this opportunity solution tree framework that I like to use for this to try to like get to root cause. But how do you, how did you figure out what you were gonna prioritize? Like what was the process of, of collecting ideas? Was it from the frontline? Was it a, offsite with your leaders? Like, how did you build that idea set? And then I'd love to get into how you actually ran the experiments.

Yeah. So, I think the way to think about it is zooming out and saying, what am I trying to do? And you could be saying, I am building a new business, a new sales motion. And I have to think about what is the first pitch I'm gonna make? What's the first sales call? What is the one that gives me the best conversion? Then how am I gonna talk about The value, how am I gonna do the demo, everything, and the pricing, the packaging, every single decision you make is based on a hypothesis, right? And so the question is, how do you know your hypothesis is true? So, you could have the conviction of a past company, but back to my point about, does the past actually even apply? You don't really know.

Oftentimes, no.

Oftentimes, no. And even if you think you know it, within 6 months, even you might be outdated, right? So, how do you continuously test your hypotheses? And where we were on the journey at Miro is we had a thriving business, very, very strong sort of unheard of strong growth numbers, amazingly successful product-led growth motion. We were trying to then put the sort of the beauty of outbound selling on top of what was working in a product-led growth motion, right? So here I needed to know if I'm not simply going to fish from the usage in the product-led pool, so to speak, And I'm gonna go talk to a buyer or a champion who doesn't really know what Miro is. They have some idea, but they don't understand the value proposition. They haven't been sold in the traditional sales process. Then I need to make those same decisions that I was talking about, and the sales plays, the pitches, the use cases. So Miro is a horizontal platform for collaboration that engineering and product teams use to build their products and take products to market. And so, that's a very horizontal value prop that has driven all of these user growth at the self-service pool. If I'm now going to a leader and saying, you should be the one sponsoring Miro and bringing it for your entire team, what is that pitch? So, we started realizing that we needed to do use case identification, sales plays and sales pitches, pricing changes, all of these needed to be decided upon. And we had two options. One is this expensive gamble that we're just going to tell the entire team, here's how you do it. Or we needed to have smaller teams run experiments where we could be much more confident about how we are going to go forward.

And so how did you come up with the set of hypotheses to go test? Is that, was that centrally done in like big brainstorms or were you pulling that from the bottoms up? Like where did that idea set come from?

So depending on what we were trying to do. So for example, sales plays, it was very much teamwork between our sales leaders, our marketing leader, the go-to-market PMM team, and our revenue operations teams coming together and saying, okay, these are the things we think are use cases that we should be honing in on and building a sales play around. And then we started to say, let's do some testing and see, does this use case actually land? Do we see conversion numbers? Getting better and better. And then that was sort of that area. For example, pricing and packaging, this was much more closely with Deal Desk and the CFO's organizations. It really depended what we were trying to build.

Okay. And so how did you test? So you have a couple of these hypotheses, like let's use new sales place, for example. Did you have separate teams of people that were like the innovation pod? That's actually what Shopify had eventually. Were you running it with groups? Like what was the testing approach?

It's a good question. So, you have to isolate the teams that are doing the experiment in some way and let them have both, I would say, two things. One is the psychological safety of going in and failing and coming back and saying, hey, that didn't work. This is not a natural thing for a salesperson to admit to. And the other thing is you have to make sure that you've taken care of them. So, they're not worried about if I miss the number, how am I gonna get my my comp for the quarter. So, the two things we did was, let's find the people that are best suited for this. They're naturally curious, they're mission-driven, they really want to bring the learning back. And the way Miro's organization is set up is we had pods. So, a set of, let's say, a couple reps, a BDR, an SE, and a renewal manager could be a pod, for example. So, what we did was we said, let's have a couple pods. And depending on what we were testing, we either did it in the US alone because we had just enough variety, or we said, let's also test in other geographies. It was one in Europe, one in the US. And what we wanted to see is, are we getting learnings back quickly from these teams that are going to test exactly what we are telling them to do? And weekly, we would review to see what have you learned? And I wanna give credit to our head of sales, Adam, who said, this is a no judgment call, so you can be safe. And that safety, I think, is crucial when you set it up. Where you can say, I learned, I tried this and I failed. And it's intimidating to say this to, you know, your C-level leaders on the call. But because we set it up, they came back and said, this isn't working, this other thing is. And we found we were wrong in our hypothesis a couple of times with very crucial decisions that then made sure, you know, we didn't send that over to the team. And then we narrowed the right use case, we narrowed the right pricing, compete strategies, all of these were sort driven by that.

Very cool. That was Adam Carr. That was your—

Adam, Adam Carr.

I think he's coming on in 2 or 3 weeks actually. So how, and how did you instrument things to get the right data? Like sales teams are notoriously creative. And so in these testing pods, were there things you were doing to really drive the control of the experiment?

Yeah. So we assigned, um, somebody from the revenue operations team to sort of be this product manager of this process. And we very carefully wanted to make sure they didn't think they were a project manager that had to do A to Z. It's about this continuous, how do you turn the dial to look for the next thing? And I would say we could have been even more insanely data-driven. We were somewhat data-driven, but there's a lot of these feedback from the call that was coming back. So, were you listening to Gong calls? For sure. But we really wanted to ask deeper questions of the rep. And said, so what did you think that was happening when they said they didn't really resonate with it? So, it was partially data-driven, but a lot of these intangibles that this live interview style of learning, I felt helped us go through it very quickly.

And so, every week— sorry, finish your thought.

Yeah, I was like, I think I'm all for data-driven inspection when you are at scale. I think if you have not scaled, it is somewhat misleading because you don't really get the entire picture and you have to do a little bit more digging that is a bit more in interview style.

And so every week you would have a meeting of this pod and the RevOps PM. Who else was in that meeting?

Yeah. So again, depends on what we were trying to test for, right? So if it was the pricing test that we were doing, I think we did it every other week and we had even our CFO on the call and we were all just constantly trying to understand from the first-person source. What were they learning? Most calls, but every other week, because every week you may not really have enough data to go surface and we needed to have like a good wealth of information to go dig in. So, revenue operations, the functional leader, and sometimes you have the CFO. And so, it really depended though, if it was a sales play, we had the PMM leader on it.

Very cool. How many of these experiments would you have going at a time?

I think about 4 or 5 major ones. There's always smaller things that we were testing, but the major ones, yeah.

Wow. And so the RevOps person as a PM, was this a separate group of people that were just running sort of innovation things or were they doing it side of desk? How did you structure it?

So we had to find somebody who could dedicate their time just to think about this process and their background is actually consulting. So, management consulting, and they came in with that natural curiosity and willingness to go into different regions. They were not, you know, this is not a process for them either. Dedicated to building this muscle up because it was all new for us. And, you know, naturally, I think go-to-market teams are uncomfortable with this concept of, I really don't know, I'm gonna go figure it out. They really want a playbook and then the enablement tells them how you do it. And then that's the management team measures that they're complying, right? So, that's the natural tendency. Here we're saying you can go out and see what you've found out and bring it back. So we needed to have people that were comfortable with sort of being in that unknown.

Was it hard to get buy-in to do things this way?

From the company leaders? No, like bottoms up. From the team?

Was it hard to get people to—

Yeah, I think it, I do think it took some, it did need some really clear communications and the risk you run is people saying, You really don't know what you're doing and you want to make sure that you help people understand. What we wanna do is be absolutely confident about what we are going to release to the teams before we release it. And that is the smart way of doing it. So, what we are doing here is a very constrained test. And we didn't talk about it with the larger team necessarily. I don't think it needed to be communicated to the entire team, but the people we brought in, they knew they were very clearly helping us discover something new.

Yeah. Was it easy to find those people? Were, were people excited about joining these innovation pods?

Yeah, I think the talent on Miro sales team was incredible and we found people that were great learners that really understood what we were trying to do here and raise a hand or we tapped them on the shoulder and they did great.

Nice. The things that you rolled out must have hit at such a higher rate than normal because you had tested it so deeply. Was that something that you found?

Yeah, definitely. We would've been, you know, doing a very incredibly wrong pricing approach if we hadn't done the testing properly. And, you know, it's very hard to reverse that. I think we could have done a much slower job of beating competition than we did because we had tested this competitive pitch. And, you know, with the general hypothesis of going against competition is you say, look at all my functions and features and look how we are so much better. I think that's not really a winnable argument at the end. It's a race to the bottom in terms of functionality or even pricing that way. So, we were experimenting with saying, look, we solve a different problem. We are just doing a very different job for you. And that was an experiment. And without going into too much details, that's sort of what we were testing to see, does that then change the direction of the conversation? So, I do feel that it hit better. We didn't really scale out the wrong version. So, can't tell you it was A/B test, but we certainly felt much more confident and we saw good results in driving out what we knew.

Okay. So you created a brand new competitive positioning in a pod, found something new and exciting, and then that rolled out well to the org.

Yeah, we tested what we thought was the right hypothesis with the pods, learned what was working, what was not. And then started to release those competitive plays out.

How many different competitive plays did you have to test before you found the one that you, you ended up rolling out?

It really depended on the competition. So we had some pure plays, we had some platforms, and we, we had a couple of hypotheses on both of them, and one of them worked better than the other.

Very cool. And so, but RevOps didn't roll directly into you, did it?

It did. Yeah.

Oh, it did. It was one of the functions. Okay.

Yeah.

And so how many people were dedicated to this like innovation team? Was it that one management consultant type person?

The one person who was dedicated is that one management person. And then there was a lot of people surrounding that. So analytics, other sort of sales operations, marketing operations, sales leadership. In some cases the CFO, me, of course. So, there was definitely a huge set of people that were brought in. And one of the things we would do at Miro was really be clear about what we were trying to solve. So, every new thing we had a dedicated kickoff that said, here's what we are trying to solve. So, everybody get on board and understand what we are doing and what your role is. And then we had an action plan that said, here's the way I expect to achieve this. These are the things we're gonna be testing. Here's how we're gonna be learning. And then we are going to be checking progress and deciding if we have finished this experiment. So it was very— what we had, these empowered pods, we had different people coming in with their different skillset, all trying to achieve a single outcome. And with one owner that was responsible for achieving that outcome, that allowed us to do all these sort of distributed team setup, but trying to solve the one problem.

Very cool. And how did you keep people's attention? Like, one of the things that I've, I've struggled with historically, and I see one of my faults is I get really excited about good ideas. And so, you know, attention can fray and you can end up doing too many things, and it's always something I'm trying to rein myself back in on.

Yeah.

How did you get people to keep their attention on these experiments that are, you know, dedicated for the RevOps individual but mostly side of desk for everybody else. Like what was the rhythm to keep people focused and making sure that those experiments are running?

I think the inspection cadence forces people to ensure that they have dedicated time for it. So when you do the kickoff, people know, okay, so the analyst will know, do I need to set up a new query or do I need to do something to make sure that we have the data for it? So they're going to go make sure that's done. And then on a regular basis, you're inspecting, everybody's on the call. They're all accountable for their part of that test. And so, because of that, it's not as much as an afterthought. It is very much a focus area. They know that they have to go talk about it. And the way you show up as a leader with your interest and your desire to move this forward, I think influences that experiment. So, the ones that work, we didn't do a ton of them at the same time, which is what you were asking me. I think we did very important ones that were very important for the organization as a whole, even to roll it out. So, I didn't see any lack of focus.

Okay, cool. So zooming out a little bit, like you and I see the world very similarly in terms of thinking about GTM as a systems engineering challenge. And so when you're looking to promote or hire senior leaders, so like second, third line plus, do you think you can teach these skills or does somebody inherently need to have this to be a viable third-line leader under your org?

So, I think that if you think about the— let's zoom out and talk about what is leadership in go-to-market really all about, right? So, I think you have to do 3 broad things. One is you have to inspire the team. And if you have, hopefully have a proper mission you're going after and the team is inspired for that bigger mission. So, it's not only about let's go make the number for the quarter, it's about Building this great business that we are building for the future. And here's how we are going and solving this massive problem in a massive market. Here's the mission we're on. So, you need that if you've got a third-line leader and like they're the head of the country, for example, or, you know, somewhere there, you need them to be very, very good at explaining the why over and over again and being really great at inspiring. That's job number one. Other two things as a leader are coaching and inspecting or inspecting and coaching. And I think the more senior you are, the more important it is for you to set direction and show people where and how we are going and why. As you become more closer to the first line, your job now is to be the world's best coach, but you are the world's best coach only if you know what you're inspecting on a regular basis. And some of the skills that I think at that point are not product management skills, you're actually looking for coaching skills. And on a side note, as I did this sort of very intentional sabbatical the last few months, I realized I personally wanted to go build some coaching skills. So, I actually signed up for a coaching session, like, for 3 days and learned, Kyle, that what we thought is coaching is actually just telling. We are telling our teams. We are not coaching. The best coaches, as you know, are making sure the athlete's on their own journey into excellence, not telling them, "Go kick the ball." They're saying, "Here's how you develop the skills that give you the best outcome for you." And so, instead of us telling the person, go do this, we really need to help them get on that journey to realize where they need to be, right? So, do you feel like these people can be taught those skills? I think absolutely hard skills like coaching can be taught. Can you ask somebody at that first level to think as a product manager? I don't think we should expect it and we shouldn't. We need to separate them from that. At that level, there needs to be no uncertainty. But the more senior you're getting up in the organization, That's where you are less of a functional leader, you're more of a company leader, and you're thinking about the company strategy and the nuances in your business, the nuances in your market. And you need to know things that I've been given, is there something I need to then get even more fine-tuned? And if I have to fine-tune it, well, that could be an experiment. Let me test it. And so, the more senior you are, the more you think about it. I think that some of this can be taught. But some of it is the mindset you come in with, right? So, most people, I think, don't think like that. They come in with this, you know, decades of being taught that there's some amazing playbooks that you have to use. But the best leaders are very creative.

And so, the 3 things for go-to-market leadership, inspire the team, inspection and coaching, and the 3rd one was the business strategy or—

So, the 3 things to me are Coaching, inspecting, and inspiring.

Oh, okay.

And depending on where you are on the spectrum, I expect you to be excellent at one of them and learn the others.

Got it. Okay. Makes sense. Because the, the, I think one of the, one of the things I noticed is you can come up through an entire sales career and be awesome at the craft and get really good at coaching, and then you hit this level and now you need to do a completely different set of things to actually be good at this new job. If you're like a first-time VP of sales, a lot of that can be just like selling day-to-day in the earliest innings. But like say you get to $20, $30 million ARR and you own the number. Now your job is so much less about that, but then no one teaches these skills.

Yeah.

And so we have a, we have a group of people that are in a job that requires something completely different from them. And we sort of like wash out and there's no, there's no place to learn that really as a revenue leader. As my winning by design, I will give them a lot of credit is doing a bunch of this, but it seems like a gap. And so my, my question for you is like maybe one, a reaction to that and two, how do you think about hiring, hiring against that profile or promoting?

Yeah. So let's see. That's a lot of questions in there. So let's take the first one, right? So if you are coming up in the sort of the traditional sales career and now you're the VP, what are the skills that you need to focus on that you've never had to do before? I would say the first thing is you have to take the trouble of doing something that's deadly boring, which is to really, really unpack your financial plan and look at everything because you are going to live or die by that plan. And it's not a comfortable area. Like we don't love spreadsheets. Generally speaking, people in sales, I certainly don't love spreadsheets. But I think if you are the owner of the number and you have been given a number based on a set of assumptions that are in that complicated sheet, you really would be best served understanding every one of those assumptions because as you're building your system up, you have to make sure those assumptions are either coming true or if they're not coming true, you're communicating immediately to the leadership saying, here's where I see risk and here's what we are gonna do about it, but you should know just as I'm seeing it, right? So, job number one, if you are coming up at that, one hard skill set to build, that would be to really, really understand your financial plan. Then as you're going from VP of sales to CRO, I think where I feel people sometimes miss is that they think that it's just a factor of working harder than you've ever been before. But it's actually a very different job. And to me, the VP of sales is the best functional leader possible. They really, really understand their function in and out. But the minute you've got a C title on you, you are now a company leader. And so, you have to stop thinking as a functional leader alone and say, I'm gonna think company leadership and see how my function can empower the strategy that drives the company strategy forward. Versus it's all about me and my team. And so, some of those places where I've seen people sort of fail and flame out is they become so internally focused on sort of protectionism around what they think is their job on the team versus thinking, if I can move the company strategy forward, my team does great as well, right? So, I think to summarize VP of sales, you really need to understand how to read the financial statements and really understand how your plan is built. As a CRO, you need to understand how the company strategy is built and how you can contribute as part of that.

Yeah. We say almost the exact same things in slightly different language. I talk about P&L fluency and you're talking about the spreadsheet. And then I'll say like, if you wanna be a CRO, you have to be about, you have to be about generating enterprise value and not hitting your number. And like, people can't make that transition and, and therefore you make local maxima type decisions about being able to hit the quarterly sales number as opposed to doing the right things to drive down churn or to ensure that NRR is in the right spot. But it's tough for people to make that change.

Yeah. I also feel that if you're a CRO, you are now no longer thinking about that straight line to close. You have to think about the entire customer journey and the lifecycle and how you're going to maximize the velocity and the magnitude by bringing everybody else along with you. So, now you're bringing product and marketing and customer success and everybody else that is responsible, operations that is responsible. That is a very different job. And that's the skill to master. How am I going to build this team together and build this systematic loop of customer value journey together?

Yeah. This was the biggest mistake I made as a first-time VP of sales. It's like bull in a china shop, hit the number, and I was too disagreeable. And it was a good lesson to learn. That was for sure. I didn't make the mistake twice.

Well, we all learn certain things, right? But I think maybe I had the benefit of not coming up the straight line and sort of coming from one of those entities that felt, hey, I could be helping, but you're not really asking for my help. And so that was sort of a lesson for me coming in where I realized that I could multiply my outcomes if I did bring in everybody.

Yeah. So last question on leadership team building. When do you promote internally versus externally? We've talked a little bit about the blueprint for these individuals. And so the question is always like, what can be taught for somebody going from director to VP and owning a function? You know, you sort of have to like project ahead. So when, how do you think about external promote people who have the skills already, you know, that you can see they've done it versus promoting internally, which has a bunch of benefits and that, but that individual, you need to make a bet on whether or not they can learn some very new things.

Yeah, it's a great question. I think, first of all, I do think that people can be taught most things. Right? So, you have a mindset you're bringing in, and that mindset can't be taught. The mindset I'm looking for are, do you have persistence, heart, and desire? I think was what John MacMahon had said once, the PhD. Do you have that innate mindset to be resilient and to be curious and sort of solve your problems? I can't teach you that. But what can I teach you? Can I teach you to think differently? If you have that curiosity, yes, I can. Can I teach you the craft and the products and what we are building here? If you have that curiosity and desire to learn, yes, I can. Now, if you ask me, would you hire from the outside or inside? I think you have to have this beautiful blend of both because if you do too much, so from the outside, what you get is new skills that you never knew you had, you could learn, right? Even as a leader, I've learned so much from external hires that have come and taught me something new that they thought was excellent. And so, not bringing in enough external expertise sometimes makes you very sort of, you know, you're really limited to the skill set that you have on the team. But if you bring somebody in from the inside, you have context, and you also set a really inspirational story for everybody else to realize there's a path for growth. I mean, that's not to be overlooked. So, I try not to have a hard and fast rule. When I look at the role description, I'm looking for a set of skill sets, and then I'm looking at the team internally first to see, is there somebody I think would be a great fit? But sometimes it's not the case. So, like, an example could be, I'm looking for a federal sales leader, and I need somebody who's sold into the federal government. Can I teach them because I've sold into them? Probably, but I would do a terrible job compared to somebody who's done it for the last 10 years, right? So, that's where I have to make a decision. Is it internal or external? Some of the hardest promotion decisions, Kyle, I find are these incredibly strong reps who want to be first-time managers and are completely unaware of what it's going to take. And they just feel it's like they have earned it. And certainly, I think, you know, you might have earned it, but be very, very aware of what this change is going to be. You can't do the job of the 8 people on your team because you were a super rep yourself. You are now a coach.

And so frequently that rep hates doing the things that a manager spends all their time on.

Yeah.

Inspecting Salesforce, attending meetings, doing the company stuff that might feel like it's not generating revenue.

Yeah.

What I've done in the past is try to give people exposure to it. So it's like, okay, you want to be a manager? You're going to find out what it's like to manage and be like, okay, this is your project. You got to go to all these meetings or you're going to coach this rep and see how It can be frustrating when people don't learn things as fast as you learn them.

I love that.

That exposure.

Yeah.

Is helpful cuz whenever I've done it, people who I didn't really think were cut out to be managers, like quickly realize you're like, oh, like actually all those things suck. Or they just like, oh, I, I can't come to that meeting. I got a demo. And you're like, okay, like that, that's your signal for what, for what you actually wanna spend your time on. But it's tough. That is, that is tough.

Yeah. Yeah. And sometimes they take a bit longer and then realize, okay, this is the new skill I have to build and they become great managers. But I love that giving them some exposure from the beginning before they get the job is great.

Yeah. Coaching, because coaching a brand new rep, if you have that DNA, it's so fulfilling and fun and exciting. And the first time I got to like teach another person sales, I was like, I loved it. But then it's the opposite for folks who have a, you know, a much more inward focus and, and are more maybe monetarily driven. That can be really frustrating, but you figure it out pretty fast.

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Yeah, um, okay, I want to change gears and talk about this transition from post-sales to CRO. And Actually, first tell me why you wanted to kill the word post-sales because we didn't get to unpack that.

I feel like I'm the one voice in the wilderness that keeps talking about it because it is so ingrained in our DNA to use this term. And it dates back, I think, from the 1980s when we sold perpetual software. And literally many people on your podcast don't even know what that is, but people would sell software once and be done. And all they did every year was to sell support for it. And so, there was a post-salesperson that did support sales and quote-unquote account management, which meant go and sell maybe one or two more SKUs or maybe more SKUs than that, but they weren't really caring too much about the customer because the customer couldn't go anywhere. They had bought it forever, right? And then, along came SaaS and SaaS said, well, now the customer has the power to decide, am I gonna keep it? Every year or every month, they make a decision. This is where customer success came in. And so, people mistakenly, I would say, but with the right intentions, said, well, if the customer has to be kept happy, let's find this person and call them customer success and say, your job is to go make the customer happy. But as you and I know, and most people know, that is a myth. Happy doesn't really mean anything. It's not measurable. And so, what is the mission? The mission really in SaaS of somebody who is now in charge of the post-land journey. So, you've landed the customer. The mission for that next leader that is taking on that journey is to make sure that the business case is achieved. And they're the best partner to the business owner, which is the champion and the EB. That's the job, right? So, but because we have created this concept of post-sales, that's essentially, it diminishes the job and it kind of also takes the customer for granted that they really are going to be satisfied by somebody that's gonna keep them happy. They're looking for hard results. So, you're looking for somebody that's going to make sure that's what their core strength is and that's what their job is to do. So, when you say post-sales, I feel like people almost minimize the work that goes into it.

For sure. And what do you want people to call it? Like the T, so onboarding customer success, which we call that organization?

Yeah, it's the question I keep getting asked. So, I think in terms of the way to call that phase, I would say you're landing the customer and then you're growing the customer. So, it could be customer growth or it could be post-land if you need to put a post word on sort of signing the first contract. But if you think about it, that is just the beginning. So, you actually are now driving all the growth of the company, right? All of the growth of that customer. So, I love the word somehow growth associated with that role. Customer success is also fine, but let's not say it's post-sales because I think it is essentially incorrect.

And it's being defined by what it is not. Oh, it's like everything but sales is that.

But I think that's also wrong, Kyle Norton, because you're never done selling. When are you done selling? You just sold the first land. You are continuously selling this customer. What are you selling now? You're either selling more value or you're selling the existing value and making sure they keep you for the next foreseeable future, right? So, you have to deliver continuously on the value you've already promised them and then show more value than they can get and show that they're still the best solution, that you're still the best solution for them. This is still selling. So, post-sales, I think, is inherently incorrect. That's one. The other thing I feel is we in go-to-market cannot say we are not in sales. There's nobody in the go-to-market team who is not in sales. You may be using different skill sets to achieve different outcomes, but make no mistake, if you're a CSM and you don't know how to position the value of your product and have commercial-heavy discussions, you're not really proving the work that you've been asked to do. And I think that's where most of the separation starts to happen because there's so many that feel my job is not commercial and I'm not going to be a seller because seller is something somebody else does. That's, um, that's not doing justice to the job that you're being asked to do.

Makes a ton of sense. And so, and you came from a world where it was much more about expansion sales and less about the traditional CS language. And this conversation comes up a lot by CS leaders who think that they should be CROs at a greater clip than they are today. What percentage of customer success leaders generally, so ones that You know, maybe have some of a team that has a number of, and some teams who are just like about company or company adoption or customer adoption. What percentage of CS leaders do you think are viable CROs?

You're going to get me into trouble with this. I, so first of all, I don't know how many of them want to be CROs, probably a very small number. And then of that number, probably an even smaller number than that would be viable CROs. But let me zoom out and tell you a little bit why I came into CS with a little unorthodox approach. So, I was brought into CS 15 years ago when like Gainsight was still forming. People were still trying to figure out what is this thing. And what fascinated me was, and I came in from a consulting angle, so I was doing consulting before that, technical consulting. So, I came and I realized a few things were happening. Companies were going to be evaluated on the recurring number. This is a new thing at that time. The customer had a decision to be made every year that whether they needed to buy us or not. And so, somebody needed to be able to be in the middle to protect that recurring number, right? So, if that could be me, I think I could add— first of all, I could learn a lot, I could build a new thing, and I could add a ton of value. So, if that's what customer success is, that's what I'll be doing, and I will define it the way I think it should be defined. And so, what I think it should be defined is I have to continuously sell the value of my product and future outcomes to the company. That I'm serving, which means I could be driving expansion and I could be doing the selling. And so, this was my first foray into selling anything, you know, and that was the 2008 dot-com bust. Things were really hard. So, I did everything from picking up the call and being a BDR for the first time in my life to actually selling and negotiating and closing deals. And what I was afraid of was this some very mythical skill set that I needed to have that was just very different than anything I've done before. What I found is if I went to first principles and I listened to what the customer's trying to get done, I inherently believe that I could solve that problem. And I could have a value creation discussion as well as a journey discussion. I strongly believe on selling to customers that you're taking them on a journey towards something. It's not the one and done. And then, if I can have the exchange of value commercial discussion then I think it is not as difficult as I thought it was. So, I could be driving all the expansions. So, that's what I started doing in all of my quote-unquote post-sales jobs. I owned the expansion. And in some cases, it was a natural outcome. So, Chekr is a consumption business. You land the account and then the majority of the work is how much they are going to be consuming your product and what more can you sell to them. And in other cases, I came and I said, here's how I'm going to be contributing to the upsell and expansion. So, I felt like I had the benefit of starting early where I could define what customer success meant differently to me. But many people that have entered customer success have entered with this being handed to them that they are post-sales, which means they're not revenue carrying, that you don't have to be commercial. You only have to drive adoption and potentially retention. And I think that's where it becomes very difficult if you've never carried a number to say, I'm now going to be a CRO one day. If that's what you want to do, then you have to proactively go into understanding what it really means to sell. The other thing that I will say is that most post-sales, again, think about their world starting in stage 4, or depending on the companies, sort of the stage of evaluation at best, and negotiation and closing the deal for most of them is when the CS teams come in. But the best CS people are going to understand the entire journey. They're gonna be curious about How did this customer find us? What was the approach? Was it inbound, outbound? What does outbound even mean? Like really learn that process and even the jargon, and then know that entire buyer journey that makes them far more situated and comfortable when they say they're going to become a seller one day.

That's great. And so the few gaps there, I want to go back to your comment around if you go back to first principles. So, being able to deeply understand what the customer's trying to solve, having, being able to have a value exchange conversation, which is uncomfortable for many. There was something in between there that I missed, but it was a great framework for—

I think you have to be inherently, first of all, a believer that you are genuinely going to solve the company, the customer's problem. So, the first thing is to understand the customer, be really, really good at listening and listen to things they're telling you, but also listen to things that they're not telling you and becomes sort of relatable to you, the problem. I found that people that are going into selling early or without really thinking about this spend very little time on building the awareness of the problem and they go jumping straight into, let me try to sell you. But the uncomfortable part is really having your customer fully feel the problem that they're in. And once you start talking to them in that sense and they're relating with you and they're saying, God, this person really understands my problem. The process of selling becomes so much easier because now they trust you and they know that you get them. And now you're saying, and here's how this product solves this particular problem for you. The next problem, the next mistake I think early sellers make when you're not a sort of a traditional seller is you try to go very broad and you try to sell everything, but try and sell the one thing that is core. And then, you know, you've got this whole expansion cycle where you can go and sell more. So, that's sort of the things that I had to learn. I did hard skills learning from force management, like, maybe I would say 8 years ago. Medpic was 15 years ago. So, you have to pick up all these skills along the way. Negotiation skills are crucial. But if you have all of that and you're in CS, I think it's not at all difficult for you to then say, I want to be a CRO or some head of sales. You just have to go learn leverage these new skills towards that.

Nice. What was the biggest surprise transitioning into a CRO role from sort of an expansion-based role?

I think the biggest surprise was most of what I saw in the CRO role was arithmetic by default. Like I need that many sales reps and this many BDRs and these many SEs and multiply this by that and here's how I get the number. Whereas I was expecting there's going to be a bit more of a science behind it. And so, that's kind of one of the things that I feel needs to be thought through. And I had to come back to first principles to start questioning and then setting it right. Another thing I felt was people did not necessarily think long-term enough. And I saw a lot of, let me just get the deal or the quarter or the number for this team done. And that was sincerely sort of surprising to me that people were not thinking long-term enough. I'm sure there's a lot more. It was just a massive learning situation for me as I walked into that role.

Yeah. What was the biggest challenge?

The biggest challenge I think is really understanding talent and how to find the right talent. And the reason I think it's particularly difficult, especially when you're going through a transition, is that what works for you at certain stages doesn't necessarily mean this person's talent did it. It could be massive inbound came in and this person was successful because they served that inbound amount. But what is, how do you actually test for talent is I think the most crucial and most difficult decisions and questions that a CRO has to go through. And that to me was the biggest challenge. That to me was sort of the longest learning cycle.

And how did you ultimately learn to test for talent? That's fascinating. Thing to say?

I think you have, so first of all, I had to sort of not get swayed by the pitch. Most salespeople know how to pitch and they'll come at you and, you know, put that in front of you. Great. I think what I looked for were really deep examples of where they had difficult situations and what they did to overcome. And you don't have to tell me it was a sales problem. Because I really want to see what do you define as a real challenge. And you'd be surprised, people came to me with things that were really not honestly that difficult. Of course, the majority of their examples were sports, but, you know, that's part of the world of sales. But people, some of them came to me with serious descriptions of things that they had to overcome. And it gave me a sense of, first of all, this person is a fighter. They are willing to do what it takes to overcome. And that to me is absolutely crucial because I think you're gonna continuously be running into obstacles over and over again. And so, if you have the resilience to run through all of those, you're gonna be a really incredible salesperson. The second thing is I'm looking for when they explore something new and they were curious about understanding it and they came and solved that in a very different way than maybe they were taught to solve. The third thing I'm looking for are examples of customers they've closed where they can tell me exactly what the customer did with what they sold. So, they didn't sell and walk away. Now, it depends on what you're doing. If you're a BDR, I don't expect you to know what your customer did, but if you're an enterprise sales rep and you can't tell me how your biggest customer used your product like 6 months ago, then that's a warning sign. And then I think the last thing that I'm looking for are how do you interview me? Like, what are you trying to understand about the business and showing that curiosity? To see if you are a fit or not. If you're just coming in for a job, I can sense that because of your questions. So those are the things I learned. I'm sure there's a lot more, Kyle, but sort of these are the way, the hard way, let's say I learned where I was making mistakes in hiring and where not.

Awesome. Okay. Last question in this category and then we're going to move to the job search. What do you wish you knew sales leaders better understood about about the world after the signature?

I wish they better understood the, the rest of the customer's lifecycle and the value journey. And they better understood how they were going to continuously build on their journey with the rest of the people on the team. And that is every other entity, product, marketing, and customer experience.

Okay, great. Okay, so I want to spend some time talking about how you're approaching this job search. So you're actively on the market having conversations with a whole bunch of companies and had the ability to step back. Amazing resume and profile. You can, you know, I'm sure you have had the pick of tons of amazing opportunities. So how did you approach the search? And we'll start with what were you ultimately looking for in a next role? And then we'll get into why.

Okay. So, to zoom back out, I went on this intentional sabbatical for a few months. And the reason I went into that is I felt I needed to give my conscious and subconscious some time to really think about what I wanted to do next. And when you are in a job, you go to the next job because sort of something exciting comes your way. You're not necessarily being very selective about it. You know, you get excited and you go after it. I wanted to take a break to, first of all, think about what is the next thing I want to do and what skills did I need to want to build in the sort of next stage in my life. I wanted to spend sort of some quiet time introspecting and understanding what is important to me. I also spent some time traveling and, you know, hanging out with my daughter in her dorm, which I thought was one of the best experiences I had. I've never stayed in a dorm in the US. I did my master's here, but Berkeley was down the street, so I didn't have to go and live in the dorm. So, I found that I had a lot of this very interesting and diverse, very, very fulfilling intentional sabbatical period. Towards sort of the first and second month, I think I did no searching at all. And in fact, the first month I fell off the internet and decided to do no LinkedIn, no podcast, nothing. I didn't even pay attention to what was happening. And, they started coming back into it and felt really, really rejuvenated. So, when I started exploring, it was both an internal exploration in terms of what do I want to do and external exploration in terms of what is exciting and how do I decide what I would like to go look for. So, in terms of internal inspection, you know, do I want to be a CEO? Do I want to be a CRO? Do I want to do something entirely different? Like, Maybe go into VC operating partner. There's so many things that I could look at that I never looked at before. Did I want to be in a venture-backed company? Did it have to be PE? So, I started looking at all of these things and I narrowed it finally down after experimentation. Talked with a lot of different people, types of companies. And I realized that first of all, the title is less important to me and I think it is The ultimate vanity metric is our title, Kyle, like what we call ourselves. What I really wanted to do is, can I build a business in a growing market for a mission-driven collaborative growth mindset company with the best leaders? And usually these are, in the ones that I was talking to, were venture-backed. There's some phenomenal PE-backed companies as well, but I really wanted to hone in on enterprise SaaS growing market. Mission-driven, massive product, market fit, growth stage. I'm not really great at the early stage. I think I'm a growth stage leader. So, that's kind of where I started looking at a very wide net and then I've started to narrow down and I am about to start something in a few, not too in the distant future. So, I feel like I've come to that end of that journey, but it was a really fun process.

How did you think about the mission? Because every company has a mission, even like companies that solve a very niche data problem dress it up as this whole big thing. And so what type of a mission was important and how much did you narrow in on a specific industry or problem that you wanted to solve?

So the type of mission that resonates most with me are missions that are multiplying value for somebody else. Like, for example, at Checker, which is a background check company, the mission is to give people a second chance. And that's wildly resonating for me because it gives people a chance to build great value for themselves. And if we didn't do our jobs, maybe they wouldn't be able to do it as effectively. I think the mission that, from my— I don't know Owner.com's mission, but I would say you are enabling these really small businesses to be wildly successful and taking away some of the minutiae of their problems. Like, there are many things to think about. Let's not have this be one of their problems. So, I love that sort of mission where I can see other human beings really benefit and fulfill their potential. That is kind of what I was looking for. What was the other question you had?

Like, how did you narrow in on industry, or did you narrow in on like a specific industry?

I did not. So, I didn't feel like I needed to narrow in. I think that there's lots of amazing businesses that fit my growing market, leading products, mission-driven, good team, good culture. And I decided not to limit on industry. I went pretty wide.

Okay. How would you stack rank product market team when venture people want big markets, incredible team, lots of product market fit, lots of product traction, but the difference between one VC fund and another is basically like, how much do you prioritize? Market size over everything versus team over everything? And how do you, how would you stack rank those as you were evaluating the right company?

The way I make the decision is almost like I am the VC with one fund to invest and I'm going to invest my entire fund into that one place. So, I pay a lot of attention to that. So I start with market and the reason I go in this right, I'll tell you why, is that I'm looking for where can I control, right? Right? So, I can't— if the market is a limited market, I personally don't know how I'm gonna go make that market a bigger market. Maybe there is, but I look for a big market to begin with. Then I look for the best team, and then I look for the product that is incredible. Now, the team and product are slightly interchangeable. If I start at a very early stage company, I feel the team is gonna make the best product. So, the team is what matters the most. At a growth stage company, I'm looking for slightly more of that product already being amazing. And then the team is also equally important because a great team can make it even more amazing. A bad team could make it worse. So, the team and product are almost equal to me, and the market is number one. What is something that I think I've never compromised on is the team culture. So, I'm looking for people that are highly collaborative learners that are trying to build something together as a team versus people that have— and they have people, there have been people that have told me that they just know the business, they know the market, and hence they're going to win. Those are the kind of people that make me worried that they're going to have all these blind spots and not be able to adapt when things change. So, I really try to look for hubris, and if I find it, then I stay away.

Nice. So I want to get into that diligencing part of it. When you talk to leaders, everybody knows what folks want to see. Oh, like, I'm a pleasure to work with. I'm very collaborative. How do you figure out who's being, who is humble and open-minded and collaborative in reality and not just like saying what people know they want to hear?

Yeah, I think the way I've seen the best matches are people that have been thinking first principles from the beginning and they come and they demonstrate that first principle of thinking versus the sort of know-it-all. It's the learn-it-all versus know-it-all. So, I'm really looking for that kind of demonstrated mindset where they're showing that they have made mistakes, they have learned it along the way, And when they're speaking with me, they're also trying to learn from me what could be beneficial for them. And that comes out pretty quickly, I think. And I see that in the difference where there's the person who is interviewing me and really testing to see if I know the right answers versus interviewing me and genuinely trying to learn something from the conversation to see if there's, you know, of course, mutual fit, but what are the things that could be beneficial for them? I think you can figure it out in the way they are talking to you.

Okay. And so what else are you diligent? So you get deep with a company, seems like a good fit. You're pretty close to an offer, but you're now trying to check a bunch of boxes. What are the things that you're diving into to do diligence?

So I go pretty deep for some of them. I've gone, so it was a good time to do the search because I could go to their company kickoff. Where they would allow me. And I got to meet a bunch of customers and got to really understand, you know, without sharing why I was there, I would show up as an advisor and really got to understand what are they getting from in terms of value. Is this company really partnering with them? Is there a journey that they're on with the customer, with the company? And so, diligencing customers, I think, is super important. You know, you can sign an NDA and ask for financial information and really understanding that, I think, is important. Making sure that the warning flags that I worry about, like the lack of interest in learning, this sort of hubris, doesn't exist. And then the thing that I think is really hardest right now is when I talked with— so I have this sort of advisory board, so to speak, and some of the people on my advisory board have given me really solid advice. I walked into the sabbatical and I was trying to now figure out what I do next. And then there's all these other people that are also giving me advice and you have to decide, you know, what do I pay attention to and what do I not? Some of it is you have to be in AI and just go. And if you're not in AI, it's a disaster. And I think that when I go look into these AI companies, so many of them have very quickly traversed the early adopter cycle and have felt like they have now the right to win the rest of the market. And it might not even be true, but they now have this somewhat unrealistic view of the world. I worry about those. I worry about the pace of compression of company lifecycles right now, because as you can see, like, from OpenAI yesterday, they probably killed like 100 companies already.

So, what are the—

Yeah. I mean, so, I think the pace of compression is extremely high. And so, the diligence I'm trying to do is, do you really have something that is long-term sustainable? In terms of the product vision, and that's what you're building, and you have built some really strong moats around it. And so some of the moats could be companies that are in certain verticals that just have specific regulatory needs or some kind of a vertical need that is really hard to just have an AI come in and replace you. I think another very big and overlooked moat is the culture that you've built in the company. And I look for those. So, it's the diligence is sort of manifold and I talk to everybody I can. I expect that's what they're doing about me. So, I try and do the same thing about them.

Makes sense. And so, how deep did you go into the financial model and what were you looking for there?

So, the sort of the first stage sort of things I'm looking for are, you know, do they have liquidity? Do they have a runway? How profitable is their financial model? Some of the companies I looked at were already profitable. Some of them are not, but they have a path towards that and I can discern that path. I get a sense of the way they think about investments and what are the investment areas and how they think that is going to be returned. So, it's different signals that I'm looking in the financial plans and some of them have shared a lot of information, some less, but that has sort of helped me understand what is the company that I think is sustainable.

And then are you digging into the unit economics and the payback periods, NRR, like all of the minutia of a growth model, or is it a higher level of abstraction than that?

So typically I get a copy of the board deck maybe for the last couple quarters, and they tend to have these unit economic numbers. I don't think like a really terrible payback period is something I would be worried about because I think that my job would come in and figure out how do you architect that, right? And make it better. But so that's not where I think I would be worried, but things like massive churn or sort of lack of understanding of why there's churn, that could be a huge flag for me. Just a lot of spend in certain areas when you're not really at the right time. Like let's say you're an early stage company and you're having a massive brand spend, or a lot of your marketing spend is on one particular source for some reason, and you're not seeing the conversion, but still happening. Those are things that I would worry, but again, so many of this is sort of things that I would expect to come in and help solve.

Yeah. Would you ever join a company that is hesitant about sharing all their financials in a board deck? Is that a non-starter?

Most likely, yes. If you have an NDA that is protecting them, I would be worried if they're super protective about what they have. Yeah.

Yeah. I got asked this question by somebody who is looking at a CRO job and I, my advice to them was like, no, don't even think about it. If you're signing up as a CRO and they won't give you a full look at the financial model, then something's up. What are your other non-starters? So like a lot of hubris and, and sort of a lack of intellectual openness, you know, you want to see product-market fit and big market. Anything else that are like big non-starters that you think that folks should be looking out for?

I think those are my main ones. You just have to make sure that your mindset is a good match for the mindset of the company. So, let's say you are a growth mindset person and to be a growth mindset person, of course, balances out profitability. But if you're going into a company all they're trying to do is sort of reduce cost and go towards profitability by all means. You've come in as this growth person who really wants to drive growth. I think that's a mismatch. So, that's where I try to see, is this a growth mindset company with a balanced approach or is it trying to do something else which probably may not be a good fit for me? So, other than the ones that you mentioned, that's what I'd look at.

Okay. And anything else that you've done to alignment, you know, you're talking about alignment in business approach, profitability versus growth alignment in sort of the day-to-day collaboration. Any, what are you doing practically to try to find that with a group of executives?

It's very revealing. A few different things are very revealing. I think one is how you spend your one-on-one time with them and what you learn from them as people. That's Absolutely crucial. Eventually, I think at the end of the day, that's what is going to either be successful and see you through the ups and downs or not. I try to learn a lot from— so many of these want kind of a workshop-style step in the process as well. So, in that workshop, they're checking to see, you know, how you're problem-solving. And I think what I'm checking to see is how are you inquiring about this problem-solving process? And are you thinking I should have a right answer or a wrong answer? There's a lot in how they interact with you. I think that gives you A sense of the collaboration and the desire to work together. Those I think are the primary things that I'm trying to do personally to try and understand other than sort of talking to as many people as you can, customers and internal people.

Last question before we get into a quickfire. How did you build your target list or how did you fill your funnel with the most interesting opportunities?

So, I went for enterprise SaaS. And I started looking at both vertical and horizontal, and I decided that I was much more interested in vertical. I definitely am very keen on a multi-product approach. I feel like I can scale those companies much better. So I looked to see for that. I looked for culture and then I talked with a ton of investors. I don't know, maybe 30 around the world, by the way, not just the US. There's some incredible businesses around the world. So, I talked with different investors, did my own research, talked with some of my advisors in terms of seeing sort of what they are seeing out there, and then started to narrow it down based on the factors that I was telling you. Like, do they really have— is it enterprise SaaS? Do they really have a sustainable business model? Because many of the investors I spoke with are super excited about companies that I really don't see how they're going to sustain that. Growth with the product they have. So, I had to do sort of my rationale there and then see what is the multi-product journey that they're on and then how is the market going to be looking like as much as I can understand. But then ultimately, you know, it's the people. So, try to do diligence on the people and narrow it down through there.

And so, getting those initial conversations, was that from the venture capital funds down? Like you start with the funds, they tell you what they have in the portfolio that's interesting or Were you building a list and cold reaching out?

It was a lot of inbound, so different recruiting companies and trying to understand what's a good fit. So definitely a ton of that. It was super time consuming too. So if anybody is looking for something, just be prepared to spend an enormous amount of time just having those conversations. So a lot of inbound and then a lot of outbound from me going to venture partners. I think the partner, the talent partners are helpful, but, and then if you talk to the partners, you get a sense of what is in their portfolio that they're excited about and why. And from them, you get insights into the founding team, into some of the challenges. I found that to be a quick learning cycle as well. So I went sort of multi-pronged inbound and outbound.

Yeah. Similar advice that I give to folks, if you have a good profile, go to venture because they're going to be excited to get you into all of the best fit companies. And there's just such an alignment of, there's such an alignment of incentives. Recruiting companies are helpful as well, but they just want to fill roles. So it's a little bit trickier.

Yeah, most of them are. I mean, I know a couple recruiters that I think are really great consultants along the way. And so they've worked with me for a while, but most of them are filling a role, you're right.

Yeah. Okay. We will move to quickfire. A couple of quick questions before we wrap. So what do you think separates a good CRO from a truly great one?

I think the good ones are the ones that work incredibly hard. They care for their teams. They bring a really strong functional leadership approach, and they want to make that sort of that number achieved. And what I think separates them from the great ones, the great ones are the ones building a system. And I use this word from the book called The Atomic Habits. Have you read that?

Oh, one of my favorites.

Yeah. In that, he says that you don't rise to the level of your goals, you fall to the level of your systems. And I think that is so true. It's been proven out to me over and over again. So, I think the great CROs are building systems and they are focused on achieving the company outcomes, not just their own. And they're focusing on learning and resilience.

Nice. What's the most common advice you give to mentees? So, people taking their first VP sales, CRO job, what do you find yourself telling them most frequently?

The most frequent advice I give to almost anybody from the professional domain that's coming to me is to get out and learn what you feel very uncomfortable doing and just embrace it. Like, if you felt spreadsheets are not your thing, go figure out how to do it. If you felt negotiations make you uncomfortable, Go take a class. I felt I didn't know enough about coaching skills, so I signed up with CoActive Coaching and got a 3-day class. Just go embrace that and you will be amazed at how much more effective and powerful and empowered you feel at the end of the day. So, that's kind of what I've been saying to anybody, not just VPs.

That's good advice. What's the hardest lesson you've had to learn in your career?

I think the hardest lesson, there's two of them. Let me pick one. The hardest lesson was how to not be defensive. Because I feel that I'm sincerely trying to do everything I can, and I've learned so much, and I'm, you know, driving this mission forward. And then, along comes somebody and says, "You didn't do this right." And my first reaction is, "No, but then look at all the things I was doing and you don't understand." But if you can let that go, That was to me the hardest lesson, by the way. Once I could let that go and say, okay, let me hear a little bit. What is it that you're saying? I have found that to be incredibly helpful for me. So, it was a tough lesson. I naturally tended to be defensive.

Yeah. I don't think you're alone in that one. I think a lot of folks, especially high achievers, can feel that way. What's the best thing that you've read in the last 12 months?

I reread Atomic Habits, actually. Then I think How We Learn is also an incredible book that I came across recently.

Yes. I just had somebody on my team read it.

Yeah.

You start to realize that the entire education system is built backwards.

So sad.

You're like, wait a second. So all of those things that I was doing in elementary and high school and university, like, that's all the opposite of how the brain develops and how things work. Yeah, it's crazy.

Yeah, it's fascinating.

We have our kids in Montessori now, largely for this reason, to like learn in a different way. And I don't know what I'm gonna do with them afterwards. Like, I don't— I'm trying to convince my wife to homeschool or microschool. Like, I just— the system makes no sense to me. If you know, it is— you know how the brain works.

So true. This system was designed about 300 years ago, I think. So And nobody dared question it. So that's the sad story. And I think there's some schools, I heard recently that Sal Khan School in the Bay Area is sort of trying to do it differently. And there's some schools that are trying, but it is nowhere at scale.

Yeah. There's one in Austin that came out of Austin, Texas, that's apparently really great and child-led and exploratory based. But those are two great plugs. Atomic Habits is one of my single most favorite books of all time. And how we learn is one that I think, uh, revenue leaders and enablement leaders, it's crazy how many people from enablement don't understand some of this stuff. So those are good ones. This was great, Sangeeta. I, I learned a ton. I could have gone deeper and deeper on the product management thing. I really hope people take this lesson to heart and learn to start thinking like product leaders and thinking about their GTM org as a system and, and finding ways to experiment. It's, it's one of the most important things that I— one of my most important evolutions over the last 6 years. So I'm glad we could get this one down and appreciate you spending the time with me.

Thanks, Kyle. It was a ton of fun.

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