E4: Mark Roberge on Redefining Sales Leadership in the AI Era

And in terms of context setting, we're obviously in the middle of a massive platform change, and most people would argue it's bigger than mobile, internet, social, cloud. That doesn't feel like hyperbole at this point. But something that you've pointed out that I thought was really interesting, and I've been thinking about since then, paradoxically, so we're in a platform shift, and yet not all companies are running towards this change seemingly. 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. But first, a word from our sponsors. This episode is brought to you by Momentum.io. Momentum is a powerful tool for turning sales and customer conversations into go-to-market data. Using GenAI, it extracts, analyzes, and automates customer intelligence across your org. The best part? It's not a new platform for your team to adopt. It integrates seamlessly with your existing stack and writes data back to Salesforce directly. Some of the most innovative companies out there, like Zscaler, Demandbase, Ramp, 1Password, and even my company, owner.com, use Momentum every single day to capture, forecast, and churn risk, autofill Salesforce fields, share product signals, and track sentiment. So check it out with a free trial at momentum.io. Mark Roberge, welcome to the podcast. Thanks for joining.

Hi, Kyle. It's a pleasure to be here. Thanks for having me.

Yeah. Yeah. So before we jump into the big topic, which is technology strategy, most people know who you are, but give them your 60-second.

Oh yeah, sure. So I'm an entrepreneur at heart. I've done 3 or 4 startups as an operator over a 15, 20-year period. The one I'm most known for was the last one, HubSpot. I was the 4th employee, first salesperson, first sales leader, first CRO, um, did a 9-year run there through the IPO. Um, and then, um, took a break. I was honored to be invited to join the faculty at Harvard Business School where I've remained for 10 years. Uh, I was full-time for 5. Uh, great opportunity to just, uh, first off, give back with the blessed experience that I've been given, uh, but also just continue to learn at accelerated pace, uh, around lots of different patterns. And then 6 years ago, ended up in venture capital, starting a venture capital firm, Stage 2 Capital, which is the first VC fund run and backed exclusively by sales, marketing, customer success, and RevOps leaders with the intent to aggregate those folks' capital and know-how to help early-stage startups with, to professionalize their go-to-market engine. So checks a big box for me in terms of like ability to give back to the ecosystem in the place that I love. So that's what I'm up to.

Awesome. And I am a stage 2 LP, have been for almost 3 years, and it's, it's been great to see how stage 2 operates and get involved with the portfolio. I, one of the most frequently shared pieces of content with founders that I work with or advise or give advice to is the Science of Scaling PDF. That, that doc is just so incredible. Incredible. And you've literally written the book on it. You know, the Sales Acceleration Formula was one of the single most impactful things that I read as an early sales leader trying to figure things out. And I still, like, most of my hiring formula is built on that hiring formula I learned from the book. So you've done such an incredible job giving back so much knowledge. And so I'm excited to pull out some different topics which you've touched on a little bit elsewhere, but we're going to flesh out today in terms of how not just startups but revenue leaders of all sides of companies should think.

Yeah, I mean, thank you for that, Kyle. It's like so humbling to me, honestly, to, to see someone with your success and background to, to make a statement like that. So I, I do appreciate that. And even when I read the quarterly update last night, um, for Stage 2, to see your name plastered across it multiple times of helping out the portfolio. So thank you for that.

Yeah, of course. I tried to find my copy of Sales Acceleration Formula because it was just— it's covered in notes and stickies and Post-its, but it got lost. It was well worn for sure. So one more background question that I'm really keen to get your thoughts on. So you've been doing venture now for 6 years and you were advising and doing a bunch of stuff post-HubSpot. What's the biggest lesson that you have taken as an investor, advisor, board member that you really wish you had known as an operator, as a CRO?

Yeah, I know when you had first read, um, first put that out there, um, I kind of interpret it as, um, what did I don't know in my early phases of being a leader that I learned later? And, and we can, we can try to continue it into like the investor side, I have to reflect a little bit. For the first interpretation, I mistakenly thought that I had to be the best at kind of everything in go-to-market as I was the sales leader. And I have to do a lot of coaching with the sales leaders that I mentor and help develop that that is not, absolutely not true. In fact, if you're a CRO or a VP of sales at a company and you're the best salesperson at your company, You're not a good sales leader. You didn't hire well. You know what I mean? Like, to think that you couldn't go out and find someone better than you at sales, that's like, that's not good. Right? So just trying to reorient people that like, um, when you are leading a go-to-market organization, you're not, your job is not to be the best and smartest at every role in the go-to-market. Your job is to be the best at the role you are currently doing. So when you're VP of sales, you need to be the best VP of sales. You need to be the best at developing frontline managers and holding them accountable to hiring well and coaching well and forecasting well. When you're the CRO, you need to be the best at aligning the departments and managing sideways and up and down and helping with the strategy and enabling RevOps to do what they need to do. And, you know, that's what you have to be the best at. And so that, it took me a while to figure that out. And that obviously transcends beyond any job that's applicable to any leadership role is like, you're, you don't have to lead by example. There's ways to do that if you want with like your, your rigor, your discipline, your thoughtfulness, your energy, your work ethic, whatever, that's fine. But you really need to go and be the best at the current role that you're in.

Hmm. That's a great message and a hard one to, you know, as, as the company scales and you need to get further and further out of the weeds, it can be, uh, it can be challenging to turn that off.

And I, I had to develop that even in your question around, you didn't ask it this way, but like as I transitioned to investor board member is, um, you know, you're not the operator entrepreneur anymore. Like a lot of operating operators turn investors. One of the places they fumble is they have a vision they're excited about for a business and they go find an entrepreneur that is working on something similar and tries to convince the entrepreneur to like go after that vision. It's not too good. That's not our job. That's not my job anymore to have the vision. My job is to like be excited about certain problems that need to be solved, be excited about certain markets. Or even just like not even be thinking about someone and some entrepreneur comes to me with a great idea. Oh, sweet. I need to like dissect that and understand it. But if I, at this point, get into vision creation and try to push that to the entrepreneur ecosystem, that's not my job and that's going to lead to trouble.

And probably not a great sign about the viability of the startup. Yeah, very cool. So the topic for today is technology strategy and I thought this was apt because you've got such a unique position as a former CRO that went through a bunch of interesting evolutions of go-to-market technology in your time at HubSpot. You're now sort of 6 years into, well, more including the pre-Stage 2 stuff as investor advisor, board member. But there's also a very unique thing about Stage 2 is the LP base is senior-level go-to-market operators who you spend a lot of time with. Who are the buyers of technology that we're going to talk about today, buyers of some of the technologies that Stage 2 has. And so we're going to be able to look at it from all 3 lenses, which I think is why, why you're the perfect person for this topic. And, and in terms of context setting, we're obviously in the middle of a massive platform change, and most people would argue it's bigger than mobile, internet, social, cloud. That doesn't feel like hyperbole at this point. But something that you've pointed out that I thought was really interesting and I've been thinking about since then, paradoxically, so we're in a platform shift and yet not all companies are running towards this change seemingly. And maybe you can share some of the data that you had from the Stage 2 LP base about the number of AI pilots as a framing, and then we'll talk about why people seem sort of frozen.

Okay. Yeah, there's a lot to unpack here. So I'm excited about this. So yeah, to your point, Kyle, this is like, we have to appreciate the potential of the movement toward an AI tech landscape and tech infrastructure. And I'm just going to keep this into the B2B software arena because that's mostly where your audience is because there's a whole bunch we can talk about with society and consumer and like all this other stuff. So a lot of smart people, and I agree with this, are forming an analog to the major tech disruptions of, you know, like the introduction of the personal computer and the movement to the local area network and on-prem and client-server that sort of dominated sort of the '70s, '80s, and early '90s. And then eventually to the one that some of us have experience on is the transition to cloud. And it's that transition to cloud that I think we can learn a lot from as we think about the transition to AI and its potential impact. And just appreciating that it rewrote the whole landscape. You know, like every major category in B2B software was pretty much replaced whether we're talking about CRM or HR or DevOps, by a new player that didn't exist prior to the cloud. And so history suggests that that will happen again. Okay. So, so like we have to be very aware of that. And, and also just like, you know, remember if you were around, no matter how old you were in the early phases of the internet, We dialed up through AOL, we opened a Netscape browser, and we did a search through an AltaVista search engine. So just because someone's first doesn't mean they win. In fact, they don't usually. And that's really what a lot of smart people, and I agree, are saying is the big names right now will be the AOLs and not the Snowflakes. You know, Salesforce wasn't a big company at this point of the cloud realm. Google wasn't the leader, and that's a little more, you know, it's B2C. ServiceNow hadn't been created yet, right? Like, so that's kind of where I think we are is we're in a little bit of this like hype cycle. I think we're going to have a little bit of like an AI winter at some point, meaning people are going to be laughing at it, the big investments that went to zero, like be careful about AI, don't put AI in your pitch decks anymore because like all the investors are turned off from it. And that's going to be when we want to really invest in AI. That's when like the real companies are going to be built. And so, you know, what's happening now is like a lot of the stuff that's out there is a little more iterative. Just like it was with the internet. Like people were latching on like, you know, client browsers to their client-server software. They weren't rebuilding the architecture because of what is called an innovator's dilemma. You know, that's why like these cloud-first companies were able to take down the existing incumbents. It was because it was hard for the incumbents to move to the future answer given this architecture? Like, let's just take a major, like, let's take Siebel, for example, right? They're like, they, 80% of the market share in CRM in the mid-'90s, I believe, was owned by Siebel and ACT. And I illustrate this point always in front of audiences. I'm like, how many of you use CRM today? How many of you use Siebel ACT? You know, all the hands go up with the first question. No one has their hand up in the second question unless you're maybe speaking in like Europe or something. And so they, well, that's, there's an innovator's dilemma there. Like, I'm sure Siebel was like, hey, there's this thing. It's 1995. Like, we're doing really well. There's a thing called the internet that Al Gore invented 40 years ago that's like starting to be commercialized. And Should we do something about it? And they went out and did a big study and they found out that every CTO said they would never put their data in the cloud because they could never, it was not going to be secure and it would cost a billion dollars to replatform their on-premise software to cloud. So why would they do that? Why would you spend a billion dollars to go after a small market? There's an innovator's dilemma. And Mark Benioff leaves Oracle, has a vision for a cloud-first CRM. He prints money in the early stages with small businesses that were fine with the security risk, and eventually the CTOs came around, they were fine with it, and he was there to catch it. And there's endless amounts of stories like that, and that's what we have here. So now let's get back to your question, Kyle. Well, you know, I'm not sure how you wanna unpack this for a sales leader, 'cause the thing that's, so basically like just to give you the history of where we are, Kyle, with our processes, I was like, okay, this is a year and a half ago and I'm sitting here and we have our fund, you know, a third fund that we're starting to deploy at the time. Now we're deploying our fourth fund. And I was like, okay, we gotta be real careful because AI is hot, but a lot of smart people, and I agree with them, think that 95% of these businesses that are gonna be funded right now would get caught up in the hype cycle and will go under. So, but we can't like sit on the sideline for what is gonna probably be the generation, the technology of our generation. So we got to go carefully and we got to invest in places where we know well. So I stood up in front of the LP base in May of 2023 and I said, well, we all know go-to-market really well. Shame on us if we don't catch at least some of the future, you know, trillion-dollar go-to-market AI companies. Shame on us because we can make them. We should be able to see them. So here's what we're going to do. Raise your hand if you're under a lot of pressure from the street to do more with less. Everyone raised their hand. Keep your hand up if you think AI software, AI technology is a potential solution to that. Yeah, let's do it. So I said, please email me because we're going to see a lot of these go-to-market AI. Please email me if you're interested in looking at it and potentially demo, you know, trialing it in your companies. And then we can get an early view onto what's working. Right? So 110 CROs from like Snowflake and Zoom and all these great companies that are our LPs were like, yeah, I'll do that. And so I promoted that back in May of 2023. And within 4 weeks, I think I had 250 applications from go-to-market AI startups. And it like, first, the first glimpse of it like validated what we thought was happening, which was like, it was boring iterative SDR copilot stuff and forecast stuff that like the incumbents are going to win that game. You know, that's nothing new, but anyway, we picked some good teams and every Monday and every Thursday we promoted 4 of them and we did that for like 2 months and there were 50 meetings set up and 2 pilots, no rollouts.

That was, that was interesting, Kyle, because I went back and I'm like, that's the, that was the data that really caught my eye because if, if, if anyone was going to have an early opportunity to move on this.

It was, it was, it seems like that would have been an opportunity for all of us of like the big companies can't spend all day finding the new cool tech that can help. Well, we do that. And then, but they have the pilot areas to do it. And so I went back to everyone. I'm like, what the heck's going on? Like we sent you what, 8 times, probably 8, probably, probably about 75 companies over the summer. You said you needed to do more with less, and they all came back and were like, yeah, we tried it, it was awesome, but then the IT team and our legal team found out we were doing it and they shut it down because we don't have an AI policy. So that was a big learning for me in my journey to try to invest in this tech. And that is, if the incumbents are going to put up all this red tape, like that just accelerates the flywheel of disruption by the startups. So we went back to the portfolio at that point who don't have that red tape and said, hey, you should try this technology. And that's gone a lot better. We have like a lot of, you know, probably a dozen or so of like, you know, situations where the AI is beating the performance of BDRs. Like the BDR team for years was setting up whatever, 17 meetings a month and the AI is setting up 35. That's freaking awesome. That's game changing. So, so that's been exciting. And I think some of the bigger companies are probably starting to come around, but I just haven't seen a lot of great examples. And maybe in the show notes, people could paint us. If you're, if you're working a company, you feel like you've done something really groundbreaking with AI in go-to-market, that would be great to know about.

Yeah. And, and so what do you think is driving a lot of it? So you, you mentioned IT teams don't have an AI policy, but even in my comparable size companies, Series B, C type CROs that I chat with and swap notes with. I don't see tons of in-production use cases yet. What's your thought on why more isn't happening there considering we all agree this is a generational shift, we all agree this is the greatest technology we've ever seen, and yet it's just like not—

Yeah, I think there's a couple layers to it. So first off, like, let me just like, Create an asterisk for the very large companies who are— their IT teams and their legal teams are show blockers. Yeah, like, that's not dumb. They have a lot to lose. They're public companies. They have a lot to lose. They have to pay attention to those things. That's why entrepreneurship works is because we can attack without those constraints. And so like, they have to do that, and hopefully they can move fast to— like, for their own sakes, can move fast to figure those things out and to find the right balance between conservatism and innovation, right? So we'll see what happens there. You get over to your Series Bs and Series Cs. I think there's a couple layers to that. First off, I think the biggest driver is just human nature of status quo. When I talk to folks, I'm shocked because I have them on my podcast and I'm like, I want to hear, have you done much with AI? No, we haven't. We haven't really looked at it. We don't really have time for that. Like it's just, I think part of it's a little bit like coming out of our own little storm you know, in the B2B software community, in the tech community, from, you know, the massive valuations and bull run of 2021 to now the correction of 2022 and trying to recover from that. I feel like people just didn't have, like, they were working 80 hours a week trying to figure out like which 20% of their staff to keep and like, you know, like, you know, like cutting their tech budgets and barely being able to hang on to like what they think is mission critical. Like they don't have time. To look at AI. And that's just a reality. And lots of scar tissue. Lots of scar tissue. I think like, I think if they pulled 10 hours of that work back to 70 and put 10 hours a week into looking at AI, they'd be, they could have come up with something. But like there's just a timing and what's going on in these people's worlds. There's a little bit of human nature too of like most people are not early adopters. Most people are you know, late adopters, late majority, laggards, whatever. And that's happening. And like, you know, I think you should really look yourself in the mirror and try to be an early adopter now. We could talk about safe ways to do that because it can create an enormous edge. Like, I think like in the last 20 years, we haven't seen a time where investing in tech for your go-to-market motion could have an exponentially competitive advantage right now. So that's, that's important. I think the third factor is like the tools aren't great yet, Kyle. You know, like, they're just latch-ons. Like, a lot of people are like, they look at some new tool and they're like, yeah, that's cool. Like an SDR copilot. But I have like, I already have like 57 apps in my tech stack. Like, I'll just wait to hear, see what Salesforce comes out with, what HubSpot comes out with, what Clari comes out with, you know, like what ZoomInfo comes out with. And like, there's a little bit of that. And I, you know, it's like, and so anyway, I think we just gotta go through all this pain of the new infrastructure before we see the cool stuff. But those are the contributing factors I see, Kyle. Okay.

Interesting. And I very much agree with you in terms of the importance to lean in here. I, you know, I'm in a sample size of one, but I was one of the earliest Salesloft customers, one of the earliest Chorus customers. I've always had an interest in technology. And it was, you know, Kyle Porter onboarded me himself. That's how early I was with Cadence. And it was such an insane competitive advantage at the time. Like, I'll never forget that lesson. And so I might even orient too much to chasing shiny tools because I've just seen it be so productive. But, you know, I dedicate at least 2 to 4 hours a week with vendors, either companies we're doing pilots with, exploring new stuff. It's definitely a priority and it's had an incredible impact on our business. I've got a Saastr podcast on a bunch of it, so I won't talk about it here, but—

Well, Kevin, let me just make a comment there, Kyle. I think that's phenomenal. It's not talked about enough of like, how often are you learning, exploring, and experimenting? We don't talk about that much in go-to-market. And like, I would guess if we did a study that there would be a strong correlation with success and that to have been able to mobilize that operational cadence. So kudos to you and we should certainly unpack how folks who want to do that, what are some ideas on how we can, you know?

We'll transition right into that. I think that—

I didn't mean to like, oh, I just want to commend you. It is just like, yeah, that's an exciting topic that's not talked about much. Yeah.

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Yeah, and so let's talk about that. So, um, I think your assessment is, is spot on, and a lot of this is, is fear-driven. I, I love Matt Dixon's new book, Jolt Effect, and he talks about how more than half of deals are lost to no decision, close to 90%. Of deals that he's measured experience moderate to high levels of indecision. And he chalks this up to fear of messing up, basically. We've come out of a tumultuous market, much like you're saying, and the status quo bias has always been the thing that we battle against, but more so than ever in a world of tight budgets. And so The, the, and I think a lot of operators are frozen by just like not really knowing where to go or how to think about things. And so I'd love for you to help walk people through a framework. So let's just start with, you know, high level. Where do you, where should, how should operators think about where in their business should they apply technology? What is the signal that you have a, an a problem in the business that you should look for an external software solution for, as opposed to trying to solve that with people or internal process or existing, existing tech?

It's a tough one. And it's like, as you speak, it's like I've never made this connection before, but like, I'm trying to go through like 2006, 2007, 2008, 2009 at HubSpot and how we were evolving both from a team and, and a rev— even RevOps, the word didn't exist yet, right? So this is You have to go back to that moment and you're helping me to remember that I actually was living similar to you, Kyle, like the replacement of the old tech with the new cloud tech. Like I remember when we started the team, I downloaded the free copy, you know, I set up the free copy of Salesforce, like HubSpot wasn't even in the CRM business yet. And I remember I wanted to take a very data-driven approach to the business and I spent $50,000 in year 1 to— I remember we were like, you know, I was just doing it myself. I was like, okay, I want to be able to capture like how many attempts are we making against our leads? How quickly do we call the leads? Like what's the optimal next email to be sent? These are all like things that have been solved over the last 20 years, but we wanted to do that. And I was like, I kind of went into Salesforce and I'm like, okay, if a rep gets a lead or creates a lead, calls them, logs that, and then sends an email, logs that, and then sets a follow-up task to call them in 2 days. It was 17 clicks. So I call, I found this Salesforce admin. I'm like, can you make that 3? And I'm like, yeah, sure, for $50,000. So we did that with 2 reps. We spent $50,000. I know it was crazy. And it was awesome because literally they created these macro buttons, you know, macro functions in there that was custom to us, which is stupid because it was such a horizontal thing that was just like log call, boom, everything happened. Like send email. And we were able to behind the scenes suggest the right email based on the the characteristics of the lead and the attempt number. So that was sweet. The reps loved it.

In 2007?

Yeah, we were able to— it was a lot of database manipulation and stuff, dude. And like, and then it, it suggests the email, they hit send, customized it, and then it automatically set the task for when to follow up so we can control that too. So I guess like one of the like abstract learnings from that that's relevant to your question, Kyle, is Um, we found a, I, I had a, a strategic imperative on what I wanted, which was a deep data-driven measurement of how our funnel was going, especially in this example with the prospecting. Okay. And I knew if I stood up, like someone told me early on, if you ask a rep to like fill out a field because it helps you manage them better, good luck, you're screwed. So you have to find a balance between what you want and a huge what's in it for the rep. And there was a huge what's in it for the rep with this one. Because it was like, yeah, like even if you're not even gonna do the 17 clicks and like log stuff, you're gonna lose your funnel. Like your paycheck is gonna slip through your fingers. And so we've made an investment to make sure your paycheck doesn't slip through your fingers. Like from the rep's perspective, it was like, look at this, you press this button and it tells you what email to send. They're like, whoa, that's sick. And then you press this button and it automatically scheduled the task to follow up. So you never, Miss a lead. Whoa. And behind the scenes, I'm getting all the data I want, right? So like, so there's a little, that's always been a true thing when I'm advising like RevOps folks and everything is like, hey, like we can certainly talk about what we want to see from a dashboarding standpoint to help manage this business better. But like, we have to make sure if there's any reliance on rep input, there needs to be a high value for the rep. What's in it for the rep? And fortunately, things have evolved so much that there's less reliance on rep input. And just to like really bring this to life, Kyle, like I remember when I wanted to like get closure on a different, like different use case, like I wanted to get much more visibility on the frontline sales conversation. And so I literally was having reps just record calls in, what were we using at the time? Webex. So they literally had to tell people to get like legal buy-in and then the recording was too big to fit on my phone. I had an hour commute both ways to work. So I had to seatbelt in my PC, my laptop into the passenger seat and hook up a Bluetooth speaker in order to do what we do with GONE and, you know, course today, like nothing. Right. So this is just like what we were doing.

Yeah. And so when, when did you go for, when did you opt to get a solution versus solve a problem with coaching or a better business process?

Yeah, it was a little bit more like you have to have a design big, start small. Like I see a lot of like Series A companies. Companies that are like, they want to replicate the forecasting machine of say a HubSpot. It's like, dude, baby steps. Like if you can just get it, like we just need to have like 3 stages to start and if we can do that, then we know where to look. Okay, so we have like whatever, like the, you know, we've done the discovery call and there's an opportunity, you know, we've now done a presentation and we're in the buyer sequence and then we go to close. Something really high level, let's start small. And then if we see that like we're way off on the, discovery call piece. Well, we can triple-click into that and break that down into 4 pieces, right? So it's like, and then over the years, you'll start to have developed the whole thing and know where to look. So there's a little bit of that that came out. The other thing was I had enormous success around bottoms-up innovation. Like, it's hard to tops-down influence a team. To adopt the technology. You know, it's like a lot of time it's for you, et cetera. So, what I would do similar to you is I often, there was two ways that some of the best tech breakthroughs happened at the HubSpot team. The first way was I was, you know, similar to you, Kyle Porter was like, I remember when he had 6 people and we had like lunch at the Inbound in 2008 and I was like, wow, this young smart kid out of Atlanta is doing some cool stuff and like, you know, that's cool. Like I had, For every 50 of those meetings I met, you know, I had and I learned from the vendor, I learned on their take of their business, I probably allowed one through. And when I allowed them through, it wasn't like, okay, we're going to sign up to a year contract and here's my RevOps person and we're going to get this set up and we're going to train the team. That's not the starting point. It's like, I'm going to introduce you to a rep that I know is an IQ tester, high IQ, crazy tester, loves, very curious, loves to play and hack with tech. I'm going to introduce you to that rep and I'm going to have you, let you set this up with a rep. And if you can increase my connect rate by 30%, then I'll roll it out to that team, that 8-person team, and I'll tell the sales manager. And if you can sustain the same ROI, then we'll get RevOps involved and we'll do a full deployment. So like whenever I found a vendor, now you can't do that all the time if you're buying like a CRM or something. Like sometimes there are exceptions where it has to be top down. It's rare though. Most of the time it was like, dude, this is cool. I like what you're pitching, but like, I'm not going to do this if you get, unless you get a rep or a manager excited. So here's the intro, go to town. Right? So that's where a lot of tech breakthroughs occurred. Um, the other ones were just like reps found it themselves and we let them, we let them play. So you have to have a close relationship with your IT team and you know, there have been large companies like a lot of like Facebook Meta's success and Google, you know, not really as much Google maybe that have like, they're so good at carving out like sandboxes for people to play and innovate. And so like we had to do that. And I remember like our chief product officer, Christopher O'Donnell, was absolutely shocked and inspired that LinkedIn Sales Navigator within sales month, 6 months, and this is when HubSpot was a little larger, they had successfully closed a $2 million deal that started with a BDR at our team, a 22-year-old BDR downloading the free version of Sales Navigator and trying it out, and it went viral through the team, and our CFO and CTO were absolutely handcuffed because like within 2, like within 3 weeks, we had 85 BDRs that were like, I am crushing it now. And he was like so inspired by that. And that was quite instructive to how we, our venue into the sales tech arena. So those were two bottoms up like influences and experimentation type mindsets where it was like me hearing a cool pitch and be like, yeah, fine. Here's a rep. Here's a manager. Go to town. And the empowerment, the autonomy for frontline people that go find stuff, go explore, tell us what's exciting you. And that led to the tech breakthroughs.

Yeah, that's awesome. I think that's a really interesting message for folks. It's like, how do you structurally create an environment where people can tweak and iterate on the margins?

And I still didn't even answer your question, Kyle, which is how do you know when to buy or build? And that was hard. I mean, definitely had some— I remember John Marcus as an example, was a guy I hired at MIT Sloan. He wanted to start selling. And he was great at selling for a while, but he also loved to tinker with like, you know, Ruby on Rails at the time or like Python stuff. And he wrote these crazy scripts that overlaid like on Chrome browsers. And yeah, we allowed that kind of playing too, but I'm not sure I was like, it's, you know, Google did that for a while. They did a lot of building, including their own CRM. I don't think like we'd have a strong preference toward buy. You know, because like you've got enough building to do on your core product. And of course, like when we went, you know, we used our own products, of course. That was a different unique situation that probably most VPs of sales here, it doesn't apply to. But it's like your engineering team's probably so busy on just your core product. And then you've got your rev ops folks who may have some engineering bandwidth, but like, you know, if you see something that's, if you have a cool idea, there's a good chance that That's going to be more of a horizontal app down the road, and you're going to have to replace whatever you build anyway. So we had a strong preference toward like, you know, buying what's out there and configuring it.

That makes sense. So let's double-click on engaging with early-stage vendors. So you talked a little bit about encouraging a vendor to work with a small group and you could expand from there. What else do revenue leaders need to understand about how to best partner, especially with early stage startups, because oftentimes they don't really know how to like run a good pilot or, or help you buy. So what should revenue leaders know about the best way to engage to get the right outcome?

It's funny that the answer to this is the same whether you ask it as like, as a buyer, how should you set up a pilot? And as a seller, how should you set up a pilot? And it's something that like Even just in the past 2 quarters, I've communicated this to a few portfolio companies and it's completely changed, like doubled their pilot close rate. And that is to agree upfront on what the specific success criteria is and that if that is met, we are moving forward and make that as fact. Like if it's in the contract, that's great. We have a lot of success of putting that in the contract or if it has to be a general, you know, a general person's agree. A person's agreement or like a, you know, an email, that's fine. But it's just like, it's not like so many people, both buyers and sellers are like, okay, let's take the next step and let's do a pilot. And they just haven't upfront, not only like just really defined the pilot, like starting with like, what do we need to see to know that we're going to roll this out? Okay. But then there's also a bunch of other stuff like, well, who's going to set this up? Like I, before I agree to a pilot, I want to know that it's like, yeah, Kyle's in our RevOps team and he's currently booked for the next 2 weeks because we're implementing XYZ vendor. But as of July 21st, he is scheduled to work on this. Great. Let's put that in writing. And then like, I want to talk to security and IT and legal beforehand. You know, like, you know, this kind of gets back to like a give-get. And I guess I'm like, I'm letting this flow a little bit more, Kyle, into like the seller's perspective of running pilots. But I think we're jointly here together. The buyer doesn't want to waste time either, you know? And like, you know, there's an old sales framework of looking at your whole sales process through the perspective of gives and gets and equaling the gives and the gets, right? So like, what can you give to a buyer and what can you ask in return as a get that's of equal value? Like, hey, can you show me your product? Sure, that's an easy give, but in exchange, I would like to ask you some questions about your current tech landscape, some of the strategies that are happening in the company, a little bit about the decision process that might be happening. And if you can walk through that, then I'm happy to show you the product. And plus, I need to customize it. Can you give me, you know, a pilot? Well, that's a huge give. I'm happy to, but these are all the things I need in exchange. I need to know what success is. I need to know who the IT person is going to— and RevOps is going to configure this. Right? So that's usually the big thing is like work all that stuff up front to figure out what we're trying to do. And from the buyer standpoint, it's being crystal clear around the business goals and making sure that the broader team is agreed to that.

Yeah, I think that's a place people go wrong frequently is not totally understanding what this thing is supposed to do. It's an interesting piece of technology, but what is the problem that this is most targeted around? And I really like this framework that I've taught to my team. It's the opportunity solution tree framework from Teresa Torres. She's a product management author. And so essentially, it's a tree to think through. So are these symptoms of a problem and what is the opportunity that they might lead you to? And then what are then all of the solutions of that same of that same opportunity. And so, because oftentimes you're like, I want a tool to do this. And if you go one step up, like, well, what are we really trying to solve? And then you start to map out, okay, and here are all the other ways to solve that problem or opportunity. You start to say, well, actually, a tool isn't the right thing here.

I like that.

But oftentimes people don't think holistically enough about that problem and mapping it. So, like, in my project, management template. When people do a project on my team, I point them to the opportunity solution tree. Did you really map the other ways you could solve this thing so we know or not? Because what I find is people do, and I did this myself, and I would do pilots and then get to the end and it would be really interesting. I was like, oh, well, actually, I can just sort of coach my way around this problem. I can actually just solve that some other way. And, and I've wasted the vendor's time and a lot of mine too, which I try to be better at now.

Yeah. And that's a good point too, Kyle. Like one of the first principles of entrepreneurship is like, okay, and in this case, like we can, we could compare and go back to the Jolt statement of like, in a way we're being little mini entrepreneurs in our own business units when we're, we're trying to like solve a problem or bring on a new technology or something like that is it's, uh, and this is how we teach it at Harvard. Business school is it's about uncertainty management. It's really the underlying core of our entrepreneur management class that's offered in the first year. It's required by everyone. Is it the management of uncertainty? And so when you do come up with a problem that you perceive as important and you have a potential solution to go after it, your question is, how can I address the uncertainty that comes with that? As cheaply and quickly as possible. That's like beautiful framing. And so like you, you've kind of done that a little bit. And I think I can think of some examples where like oftentimes when we're like, even like I'll bring this to stage 2 for a second. I don't think it's like that irrelevant because there's so many aspects of running a venture capital firm that is similar to running a sales team. Like we have like, we look at, we look at 200, we screen 200 companies for every investment we do. There's a big pipeline there. you know, and, and so in our first version of that pipeline, like, yeah, we looked at all these tools. There's a couple standard vendors out there and you get sucked into it, but I'm like, no, no, no, no, let's not just, let's just set up a Google Sheet for like a month and just run it because that's going to allow us to know like how that's a very cheap, quick way. We can just like start to understand what we want, what's important, how we look at it. And then we, once we've got our operating cadence down, Then we can go out and look at the tools like Affinity, which is the one we ended up with, and we understand our process. So like, this is, I think those, you know, I think the way you're doing it is a really good training wheel and direction for folks is like, once you understand that problem, what is the quickest, cheapest way that we can address the uncertainty around it?

Yeah. How much time do you think a revenue leader should spend on looking at tech and tools without getting into chasing shiny things arena?

I don't know. Like, I think a lot of that, I'm not sure that I would say that aspect of sales leadership or CRO leadership is a required aspect of the job that they do and don't delegate. So I think some of that has to do with like, what's cool about leadership is in some cases you get to carve out the stuff that energizes you and do that and delegate the stuff that doesn't energize you. There's some things you just can't delegate, you know, as CRO, like if you're having like your sales kickoff, you have to give the inspirational speech. You can't delegate that, you know, like if you have to like roll out the new comp plan and get the buy-in from the team and it's a tough comp plan, like you have to do that. That is non-delegatable. But in terms of like taking on the role of evaluating cool tech that might fit in, like at some point you need to be the ultimate decision maker on it, but you can doubt, if you like doing that, do more of it. If you don't, you can delegate that to an awesome RevOps person that has a passion for it. So I'm not sure I can give you a number. I do feel though, Kyle, that is, it's a pretty high value experience, I would think, especially if you're running a high-growth team, because it will naturally keep you on the front edge of what's happening in go-to-market innovation, which is pretty cool.

Yeah. And even if you're not going to be deep in the evaluation and running the pilot, having an understanding of the broad architecture of the market and the set of opportunities, I've always felt is important.

Yeah, maybe it's like the loosest version of it, Kyle, to your point, is like I want to have a quarterly readout for an hour from this person on my RevOps team on what's new in tech and what's— why it's applicable or not to us. Great. 1 hour a quarter. Beautiful. And you stay abreast.

Yeah. Yeah. Okay. That's a really interesting view of it. Any last advice before we move into quickfire? Any last advice you'd give to CROs or revenue operators when it comes to evaluating technology, identifying the right companies to partner with? Maybe that's a good one. Like, how do you advise them on who to pick? Because it's sort of like picking a venture investment.

It really is, you know, and it depends what you're talking about. Like, there's different implications here. I think it's a lot easier to pick something that can run simultaneously for a while. So you can literally run like experiments to see what wins. I like to try to make data-driven decisions as much as I can. There's some situations like, you know, transitioning a CRM that you can't do that, you know, because it's such a system of record for you. And that just takes, you know, the bigger that decision, the more diligence that's required, the more, you know, buy-in up and down from the end user to the CFO, you know, like across the board. So I suppose just an awareness of like how much of a bet this is, how much it is, you can't get it wrong. How much is it can't be an experiment, it has to be a full rollout. How much of a broad implication is, and to your point, doing the corresponding diligence to equate to that, whatever that value is.

Yeah. Let me bounce this thought off you. So my thought has been Um, when I'm, when I'm buying a piece of technology from anyone Series A and younger, still like high uncertainty, I'm basically making a founder bet. I want to see some, like, some 10x feature, as Lemkin talks a lot about. But even if one— even if I look at two companies and one feature set is more robust, the product is better today, but company B, they have a good 10x feature, but clearly the founders are way better. And that could be signaled by your evaluation, which can sometimes be harder, or the venture capital behind them or the quality of team. My advice is often just pick the founders that you think are going to win that market, even if the product might not be quite as good. If you're buying a seed or Series A stage tool, what do you think about that?

I've never heard that before. I think it's smart. You know, I think it's smart. I'm trying to relate back to if I had situations, and I think we both told the Kyle Porter story, and I've had a couple others with folks that I had met, or the early Clary folks had talked to me a bit. And I think that's smart. I also think you have to be respectful, aware, and respect your culture that you operate as a company. Because there are companies that Like they want a culture of being first and they will appreciate that and you'd fit in well. And I think there are cultures out there as well that are, um, they don't want to be, they want to be fast followers. That's okay. But I think you're going to stick out culturally or maybe even like be a little cultural friction if you try to press on that. So I think, I, you know, I think smart what you said. I'd never thought much to too much about it. I certainly could have pulled that off because at HubSpot we were a first mover culture, but I've also seen cultures where that could have been disruptive.

Yeah, that's why I actually bet on Momentum early because there's a bunch of companies in that category. Momentum is now a Stage 2 portfolio company. I thought the founders, I'm like, these are the founders I want to bet on. Like the tooling, the tools were pretty similar. And I had met a lot of companies in the space and I just bet on those two and it's been great. Like I see the product velocity and how closely their product is following the customer need. So that—

Yeah. And your insight was extremely helpful there. And this is a very different decision. Like your decision is a little less stressful than mine because if you got it wrong, you can just part ways in 3 months and pick the winner. And if I got it wrong, I can't do that. So, but thank you, your, your insight as well as many of their LPs was, was huge too. Again, we probably screened about 400, 500 companies before we bet on that one.

So yeah, and again, it was a small pilot to start, cheap, you know, like we controlled costs, controlled blast radius. And then as we got confident, now it stretches across a bunch of different parts of our business. Okay, let's flip into the quickfire round. You answered the first question, what you wish you knew as the leader that you came to understand later, which was thinking you had to be the best at everything. So I love that. What is the most common advice you give to new leaders on your team? People that are managing people, managing larger groups for the first time. Maybe they're a first-time second line.

Um, I didn't think of the first time, second line, but I know maybe I can have another one on that. But like a big one that comes up all the time is not to try to make them like you. That comes up all the time because like, um, I see so many successful— and there's been so much research, right? They say like the successful salespeople don't make the best managers. And part of it is this reason is like there's a lot of ways to be successful in sales, and there's a lot of ways to be successful in sales, even in the same team and company. You know, I've got my people who are the activity hounds. They're, they're B-minuses at like discovery and demo, but they just have so much activity. They are always at the top. I have people who are like the most amazing discovery-oriented sellers, and they're modest or mediocre at activity. Now imagine if like you became manager now and you try to make all 8 of your people like you. That's not right. I have to always tell them, like, depending on who I'm talking to and how they connect to the world, like, maybe it's someone who's like an athlete. I'll say like, look around the NBA in basketball. You know, most of the coaches are former players. But you know, if you know basketball, there's 3 main positions. There's guard, forward, and center. I don't think any of the coaches played all 3 positions. So how can you be a guard in basketball? And then become a coach and actually coach a center. You're not going to teach the center to like dribble well and shoot from 3 points. They have to do the job of the center. The way you could do that is because you've seen other centers that are excellent and you coach them, you show them how to be a great center, even though you've never done it yourself. And so that's what you have to do is like you have to appreciate the different like personas that you might find in successful sellers, not, and not trying to make everyone like you. Just trying to make them the best of who they are. Right?

Yeah. I'm gonna—

Yeah. And I've done it all the time. That was not just like a sounds good thing. It happens all the time.

Yeah. What's the hardest lesson you've had to learn?

Oh yeah. Just, you know, a lot of times, I think this happens a lot. It certainly happened to me is like, when you start to learn what a good leader is, sometimes those are contradictory to things that are natural for you. And I think that, um, that's, that's almost— we're starting to get into like personal psychology a bit. And for me, for various reasons of like my upbringing, I have extreme conflict avoidance. I've spent a lot of time in therapy on that. Um, for the first like 20 or 30 years of my life, The minute a conflict arose, I would say whatever I could to get the conflict beyond. Terrible. That makes for terrible leadership. So I had to get through that because I knew I needed to be a great leader. And some things come naturally and some things don't. And there's this work called, what is it, authentic leadership. So you can construct situations to what you're best at. But I don't think like if you're anyone that's plucked into a leadership role and every aspect of their wiring is perfectly applicable. There's constantly things that you know that the way you have to be is not in line with how you naturally are. And that was one of the things for me. I had to have a daily task, I had a daily to-do to give negative feedback to someone. Yeah, every day I had to find someone to give negative feedback to.

That old—

yeah, you got to fix it. You got to address— I mean, I, and I have, I have extreme natural gifts in, you know, humbly saying, in empathy, um, in analytics, in, um, inspiring, in connecting. So that's fine, I could lean on those, but you're not going to be successful— you can't, you know, give negative feedback and challenge a team. So I had to, I had to force myself to do it every day.

That's awesome. Last question. What's the best thing you've read in the last 12 months?

Yeah, I would say I equate reading with listening. A lot of stuff I'm reading like lately is more like a spiritual side, which is probably not applicable here, but like, okay, well, I'll say the one that is applicable if we expand reading to like listening and all that kind of stuff. I like, let's see, Paul Roetzer at the AI Institute. He was an early partner at, so I wanna put out someone that like a lot of people might, some people may not know. He was an early successful partner, sold his agency, like his HubSpot, he was a HubSpot reseller and he did very well and jumped onto the AI world very early. I think he's been at it for 4 or 5 years, mostly from the marketing lens. And they have more recently expanded to be broader than that. They're doing some cool stuff. They, I love to listen to them and learn from them. They're a little less mainstream than, you know, top, you know, some of the ones that are out there, but like, I think there's good stuff there. Yeah, I don't know, like if you want to get into the spiritual stuff, I like go a little crazy with that stuff. I'm a big yogi and I'm reading one that like, it's actually The Forge written by Dalai Lama and it's one of his protégés and the He's studied quite a bit about, like, controlling your sleep and your consciousness in your sleep. It's just one of my side things. I like to think about those things and try them out, you know. And supposedly he has these people that are like living in the same way that we live in our awake time, in a conscious way with a family and friends and hobbies and all that stuff. There are people who are extremely conscious in their sleep world too and have a separate set of family and friends and hobbies and all that. It's crazy, dude. But like, I don't know. I just like to like pontificate about that stuff. And I do believe that there's some gems within there of things 1,000 years from now that we're going to look back and amazed that we didn't understand these things. But anyway, sorry to get too like off track and deep on that one, but you asked.

That's a topic for a different pod. I love it. Well, this was awesome. I have a bunch of really interesting takeaways here. I think this will be really helpful for folks to understand how to navigate a very interesting time in our collective business lives. So really appreciate the time, Mark. This was awesome. Pleasure to do it. And where can people find more from you?

I mostly am on LinkedIn with my stuff. I try— I don't write as nearly as much as I want to, but I try to. And that's probably the best way to get in touch with me or read some of the latest stuff I'm putting out.

Nice. All right, appreciate the, uh, the time.

Thanks, Kyle.

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