---
title: "Why Circle's Co-Founder Ran 1,500 Sales Demos Before Hiring a Single Rep"
episode: 107
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Andy Guttormsen"
guest_title: "Co-Founder & Chief Revenue Officer"
date_published: 2026-08-31
date_modified: 2026-09-03
duration: 00:54:11
word_count: 9086
topics: ["gtm-strategy", "revenue-operations", "ai-in-gtm", "brand-positioning"]
canonical_url: https://www.leanscale.team/knowledge/podcast/andy-guttormsen-circle-1500-founder-demos/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# Why Circle's Co-Founder Ran 1,500 Sales Demos Before Hiring a Single Rep — Full Transcript

> Episode 107 of The LeanScale Podcast, with Andy Guttormsen.
> Published August 31, 2026 · 00:54:11 · 9086 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://www.leanscale.team/knowledge/podcast/andy-guttormsen-circle-1500-founder-demos/

## 00:00 — Cold open + intro

**[0:00]** Doing eight to ten demos a day, you think sounds like the fastest way to go out, acquire your first hundred customers, two hundred customers, and it totally was, but actually that wasn't the goal.

**[0:14]** My guest today is Andy Gudermsman, co-founder and chief revenue officer of Circle, the creator community platform now home to 15 million members and names like Jay Shetty, Mel Robbins, and Ali Abdaal.

**[0:28]** Obviously, content is valuable and has been valuable. It's how we at Circle grew for a really long time as we shared our ideas with the world, people resonated with them, you build that relationship one to many over time.

**[0:41]** And that's great, that still exists, but obviously with AI, there's so much more content, content's being diluted over time.

**[0:49]** From your experience and perspective, what are some of the major components of a well-run community? What are some of the best ones doing right?

**[1:00]** Probably a helpful approach for folks who are just starting out is to think, afraid about building a community, more just like, I want to deliver value to people, I want to ensure that part of the value I deliver is those folks connecting with each other.

**[1:17]** How do I nail an offer? Like, I would nail an offer for any other business community or not.

**[1:32]** Andy, you ran more than 1500 demos yourself in 18 months, 8 to 10 demos a day. At what point did that stop being the founder pitching in and start being your actual go to market strategy?

**[1:46]** Doing 8 to 10 demos a day, you think sounds like the fastest way to go out, acquire your first 100 customers, 200 customers, and it totally was.

**[1:58]** But actually that wasn't the goal. So the goal is completely different, very counterintuitive. The goal was actually product feedback and brand.

**[2:06]** So, you know, imagine this is 2020 and, you know, COVID hit. People are wanting to build online communities. Our product is just getting started. We have a landing page up.

## 02:10 — 1,500 demos: why the goal was feedback and brand, not revenue

**[2:21]** And we've got all these folks coming in. There's not much of a description for what the product even is. It's a home to build your community.

**[2:28]** And we've got to figure out there's only one of me. There's all these leads coming in. Who are we actually going to build the product for?

**[2:36]** And so I've got 100 people reaching out every single day saying like, hey, I think I want to build a community online, but I've got eight slots.

**[2:45]** And so start to ask folks like, hey, do you check these boxes? Are you trying to do this kind of thing?

**[2:52]** Are you willing to pay for the product if we solve the problem for you? And so what we realized was that if I start to have a conversation with eight folks every single day,

**[3:04]** and they have an amazing experience, by the way, with one of the founders, they feel really heard. They give us great product feedback.

**[3:11]** They would go and start to talk about it online. So you would go on Twitter, I guess at the time, or LinkedIn or whatever, and they'd come off a call and be like, hey, I just had this amazing conversation where I saw this product and kind of got a really good sense of where it's heading and all that.

**[3:26]** And then it would kind of build this flywheel on social and create even more lead gen for us.

**[3:32]** But then at the same time, every single one of those calls, like I'm going back, I'm talking with my two co-founders, they're building the product.

**[3:38]** And we've got a nice little feedback loop going there. And so we realized, you know, you do a month of that, and there was so much benefit to it. It's like, why even stop, you know?

**[3:49]** No, 100%. And I think there are so many founders in tech that they literally can't wait to hire their VP of sales and then hop out of demos and get into everything else that is likely on their plate.

**[4:03]** What felt like some of the things you were gaining that just kept you wanting to continue to do that? Anything specific that was like, if I hand this off, I'm not going to get the same experience?

**[4:17]** Yeah, so I think, you know, part of it was just we really wanted to grow quickly. We wanted to prove to ourselves that there was going to be a real business here. And the way to do that is to stay incredibly close to those initial customers who are kind of taking a bet on you, right?

**[4:35]** If they decide to use your product, which is three or four or five months old at that stage. And so, you know, I kind of knew, like, our approach was going to be, we knew we wanted to be venture, like, build like a big scale, you know, venture back to business.

## 04:45 — Staying close to your first 100 customers

**[4:48]** We were kind of coming off of our time at Teachable, which was a really great outcome, but we thought it could have been so much bigger. And so we kind of knew, like, I knew, hey, if we want to get to 1,000 customers, the fastest way to get there first to get to 100 customers.

**[5:03]** And if we want to get to 100 customers, like, what would it take for us to add, you know, five or 10 customers a week? Could we do that one on one? And I knew we could do that one on one. So, you know, if we have 100 customers and they're paying us $50 a month at the time, now they pay us, you know, a lot more than that.

**[5:18]** The product is completely different. There's so much more, but, okay, 10 customers a week might be $500 an MRR a week that we're adding. Okay, we can get to $2,000 MRR by the end of the month. And then the next month, I bet you we could go from, you know, 2,000 to 5,000.

**[5:34]** And that's kind of what it would take for us to be like, oh, 100 customers, 200 customers, 300 customers, like, we can do it in this kind of unscalable way to get to that first milestone and be like, hey, we got something here. Like, let's raise money. That's really, that's really go for it.

**[5:52]** When did it feel like, okay, I've probably done enough. I think you've taken it way further than anyone I've ever heard of. So when did it feel like, okay, now's probably the time I can start to hand off.

**[6:06]** And was there any trigger point or threshold that you hit that made it clear that it was time to start getting a team in place to help you?

**[6:15]** Yeah, so I'm sitting in a closet in a one bedroom apartment with my fiance at the time in Hoboken, New Jersey. And the closet is, you know, five by five feet. And that's where I'm doing these demos all day long.

**[6:34]** Not great for the brand, right? But it was fine. And, and so I got to a point where my calendar all day is sales calls, right? And again, like, I wasn't doing as much marketing then because the sales calls themselves were creating the top of funnel.

## 06:43 — The closet, the full calendar, and knowing when to hand off

**[6:51]** So they were kind of knocking out like three or four important parts of our function, like our GTM function at the same time. Again, this is all like first year, but it got to a place where I was having to cancel my one on one calls and throw group coaching group group demo calls on the calendar.

**[7:09]** And I'd have like 12 people show up to that group demo call because there just were not enough one on one slots. And when I started to have almost like all these one on one slots booked all day long, but then also would have to have two group demo sessions where now there's 10 people on each one.

**[7:24]** And I was like, I'm dreading these by this point. I'm like, I just did seven demos. I got 10 people showing up here. You know, one of them is somebody who's incredibly sophisticated. Like it might be some celebrities manager who wants to build like a digital community business online

**[7:39]** with this guy who's building a backyard gardening community from scratch and he's never done any of this before. And it's like, all really tough. And at that point, I was like, we got to find a fix here. Now at the same time, I was also figuring out like sales lead motion is going to be really key for us.

**[7:57]** Today we're about 50/50 split between sales lead and self serve kind of more product lead, but I hadn't overseen a sales org before formally. And so I went out to hire a coach.

**[8:09]** I was actually giving a demo to a guy who's running an SDR community online and it was really successful SDR community and had a great conversation. He ended up moving his community over to circle and I reached out to him and I was like, hey,

**[8:22]** I need some help. I want to hire you as a coach and I want you to coach me on how to go out and find my first couple of reps and really turn this into an actual sales function here at circle.

**[8:34]** And then probably within, you know, three or four months, I tricked him into becoming our VP of sales at circle. He actually sold his community. It was acquired.

## 08:36 — Hiring a coach who became VP of Sales

**[8:48]** Wow. I love that. I absolutely love that.

**[8:52]** One thing I think a lot of founders have a tough time with, with that transition from founder lead sales to starting to scale out the sales, I've gone through it too. So starting lean scale, I started in 2021 and did all the sales for a few years and then getting other people into that motion was very, very challenging.

**[9:17]** How, how did you prepare him to take the lead and transfer all the knowledge that you built from 1500 demos and make sure that he could not only take it and run with it, but also continue to improve upon it.

**[9:35]** So I think my biggest realization watching him come in and then also our first reps who were really good reps that he hired, by the way, not me, is so my win rates were really high.

**[9:52]** Right. But those are also the earliest adopters are the easiest folks to close. And I thought a lot of myself when I'm doing those early demos, I'm seeing the win rates.

## 10:00 — Hire the leader, not the reps — why founder win rates mislead

**[10:00]** But then when I saw him come in, what I realized is he had an actual sales process that was repeatable that could very predictably generate results that he could, you know, hand off to other folks.

**[10:12]** And so I think if I went out and I hired the first rep or two, it wouldn't have been possible because I wouldn't have been able. First of all, I didn't have a formal sales process.

**[10:23]** I wouldn't have been able to train these folks on the formal sales process. I would have probably made the wrong hires. I would have hired for the wrong skill sets and things like that.

**[10:32]** And so he's the one who made it that so that we could actually scale this thing. By the way, we have about a 15, 20 person sales team right now, still the same guy right over the last five, five years, Charlie on our team.

**[10:45]** But it just wouldn't have worked if I tried to be the person to hire the next few folks versus hiring the leader.

**[10:53]** That's a really good size sales work. And that's when like there are complexities that come into play. But I think that is an interesting insight to say, hey, rather than going and getting a handful of reps, because that's usually what happens.

**[11:06]** It's like, oh, okay, I'm going to go get two, three AEs, but bringing in someone specifically to lead it. And I'm assuming when Charlie started, he probably took the reins of doing his own demos for a handful of time or for a bit of a time, and then and then started to hire the team underneath him.

**[11:25]** And it really helped. So think about this unfair advantage. And it's something we've taken into our other hiring for even other functions, but he had run his own community business before he sold that community business, he moved it to circle.

**[11:43]** And and so that was a really like hard one experience and a great kind of story that he could tell on every single call. And people really resonated with people because he had some real skin in the game.

## 11:52 — The unfair-advantage hire: empathy from lived experience

**[11:57]** And so I think, you know, it's really something actionable that we've kind of learned from that we take into all sorts of, you know, functions. It's like, does this person really understand our space and like, have they lived in and experienced it, experienced it them themselves so that it will actually be a big advantage for them, kind of in their day to day role.

**[12:23]** I love whenever you have a deep empathy story like that. It's pretty rare for someone who's not actually the founder to have that level of empathy for the problem.

**[12:33]** But that definitely goes a long way. The story can resonate and then you can really help coach on the messaging when you're building the team and what hits and what doesn't when you're trying to position the product well.

**[12:49]** Yeah, 100%.

**[12:52]** One thing I want to move into a little bit because I think especially with AI flooding, the outbound portion of go to market flooding the quote unquote hyper personalized outreach to strangers, a lot of tech companies are scrambling to find their moat and a lot have leaned into content.

**[13:18]** But I think there's a nuance that a lot of people don't really understand. Can you break down the difference between content and community and where you think the advantages lie in both of those fields.

## 13:26 — Content vs. community in the age of AI

**[13:36]** So, the obviously content is is valuable and has been valuable. It's how we had circle grew for a really long time as we shared our ideas with the world.

**[13:49]** People resonated with them you build that relationship one to many over time, and that's going to still exist, but obviously with AI, there's so much more content content being diluted over time.

**[14:02]** And that's actually, it's a hard thing to say and it's really close and personal to a lot of you and I are literally doing a podcast right now we're creating content right now, right.

**[14:12]** And so, the, our customers at circle for instance they are content creators. In many ways and most of them are actually, but, um, but community goes one step further, which is connecting the people in your audience with each other.

**[14:31]** And what's really interesting there is that you unlock so much value and like shared expertise and, you know, between the people in your audience with each other that just like wouldn't be there if it was only a one to many relationship.

**[14:47]** So, to make it a lot more tactical though and just like to share like a real example here. You know there are folks like Dr. Becky from good inside.com, who, you know, has a business that's doing 10s of millions dollars a year in revenue and she's an amazing content creator

**[15:04]** and of course like she puts out all of this parenting guidance and it's amazing content and helps us all the time. We're, we have a two year old here, we're trying to potty trainer this week. It's not fun at all, but Dr. Becky her content's been super helpful.

**[15:20]** The thing is though is Dr. Becky she also has this community Dr. Becky's only one person so all of these folks that follow her advice and have these problems that brought people to Dr. Becky, well, they can go on this journey together.

**[15:37]** And so, if you're creating content, a big opportunity is to bring those people together. And so, that's something that I think is becoming very obvious to a lot of businesses out there is like, Hey, we've got all these customers you know we've got people that are kind of along

**[15:58]** on this journey with us but like, how can we unlock all the value between those folks.

**[16:06]** And again, I do think there's something powerful and magical when your community starts teaching themselves, engaging with themselves, and then sharing things that are good for the business as well that you can probably keep your eyes on.

**[16:21]** I've seen.

**[16:23]** I've seen a lot of communities done wrong and done poorly.

**[16:31]** From your experience and perspective. What are some of the major components of a well run community, what are some of the best ones doing right that others should take note of.

**[16:44]** And what are some real big things to avoid to make sure you're not making a vapor community that's not really adding value.

**[16:54]** So, I think, too many people can fleet and over generalize what building a community even is. And, you know, one of the things that we realized at circle we have 20,000 plus paying customers and 10s of millions of, let's call it like members of those communities

**[17:22]** but actually if we're being really honest like we don't even think of ourselves as a community platform if you go to our website right now.

**[17:28]** You'll notice, we talked about, we're a place to build your digital business and that could be a coaching business it could be a education business it could be a community first business or a membership.

## 17:30 — A community is just a business — nail the offer

**[17:40]** They're all I mean there are newsletter businesses right and so I think our realization as we looked at like who's really winning and then who's just kind of starting a community and it just kind of fizzles out and doesn't work is that it's really just, it's just a

**[17:55]** business first of all, it doesn't, it really needs a great offer, like the offer itself needs to be more than just, hey, come in here pay me every single month, and then talk to each other, like that never works, it's got to be anchored around really great specific value

**[18:14]** props and rituals and it's probably going to be hard to get people just to talk to each other but if there's like, let's say a recurring event or I get some outcome, and there's maybe education that goes along with it, there's a transformation that I get by being part of the

**[18:29]** community. And I show up every single day and I'm really like actually connecting with people. By the way, it doesn't have to be every day, it could also just be once a month like is that a community if I show up once a month, I have kind of a almost like mastermind style like session

**[18:44]** and people where we all share our problems and get feedback and we help each other. That's all community like generally speaking, and I think what's probably a helpful approach for folks who are just starting out is to think, afraid about like building a community

**[19:03]** like I want to deliver value to people. I want to ensure that part of the value I deliver is those folks connecting with each other. How do I nail an offer like I would nail an offer for any other business community or not.

**[19:19]** I like thinking about it that way. It's like, hey, the same approach you would take to running a business all the components that are important to offer the messaging, managing the operations of the business as well like making sure you're on top of those rituals

**[19:33]** that you put into the offer. Are there any communities, maybe thinking that would be a helpful example for a B2B SAS or B2B AI company. Do you see any companies in that space that are doing an exceptional job at building community.

**[19:57]** 100%. So, one of my favorite examples would be a company called growth X. So, growth X.

**[20:08]** We're actually a customer of theirs, they're a customer of ours, but they are building a community. So what they do is they're actually kind of more of a services agency, where they're kind of AI powered and they help you with your content, your AEO, SEO, you know, things like that.

**[20:26]** And they use AI to essentially kind of like optimize all of the processes around your AEO, SEO. Now, they have all of these clients and customers who are running their marketing functions.

## 20:34 — A B2B example: how GrowthX builds community

**[20:45]** They have, you know, bunch of like directors of marketing, head of content type folks in there, they've got founders in there, and they're all trying to do the same thing. They're trying to like get improvements and get more traffic and get more visibility through search.

**[21:03]** So, even though their main service is one thing and their actual product is kind of software in some ways too, they still have a whole separate kind of a world and part of their offer where they bring all these folks together and just deliver a ton of value, which I would imagine for them creates really

**[21:25]** stronger attention. And it makes it really hard to kind of say like, "Hey, I'm only getting value from the product itself," because they're educating people about how to actually use their product as well.

**[21:39]** So you get so much more from them than just the service, basically.

**[21:45]** It's a huge value add. And I think something that people may be misinterpreted to is they look at their audience. So maybe they're looking at their YouTube following, their LinkedIn following, if they're on other socials, they look at how many people are subscribed to their newsletter.

**[22:03]** I think a lot of people would think of that as their community, if you will, and would look at the big numbers and be impressed by it.

**[22:12]** But I think one of the things that you mentioned is you don't have to have scale for it to add a ton of value. You could have a smaller tight-knit group.

**[22:22]** Maybe just because I think some people might not totally get the nuance, the difference between having an audience versus having a community and what the numbers mean on either side of the house.

**[22:33]** So we've got lots of our customers who have their own audiences, and they have really fancy numbers on social where you see these big audience sizes, maybe they have 600,000 followers on Instagram or something like that.

**[22:49]** And those folks, these creators, they'll put out a post. They'll get tons of engagement on the post. Maybe they'll get thousands of replies and things like that. And that's great.

**[22:58]** Those audience members, they're learning from them and all of that. But if you look at that creator a lot of times, their business, well, on the back end, it might only be that one out of a hundred of those 600,000 people.

## 23:10 — Audience vs. community: 600K followers vs. 1,000 members

**[23:14]** Maybe there's like a thousand people there on that broader list, but they're in some type of membership experience. And those folks are paying a couple thousand dollars a year. And that creator for them, like that business might be a multimillion-dollar business and might be, you know, 5 or 10 or 50 times the size of, let's say,

**[23:41]** the brand sponsorship business that they get from selling ads, essentially, against that kind of broader audience on social.

**[23:52]** So, yeah, it's like the community itself a lot of times is much more down funnel. But again, I really think it does come down to, are the people in your audience, are they connecting with each other? Because that's really where the community lives, once you kind of unlock those connections between your audience members.

**[24:12]** Yeah, and using that example, let's say a company has a decent following that doesn't immediately translate to an effective community, right? There's much more work that needs to be done to convert your audience into an engaged community.

**[24:28]** 100%. I mean, again, it comes back to having like a real offer value prop. And you're kind of wanting to almost get like hand raisers in there. Like, okay, I got 600,000 of you following me or, by the way, like your YouTube following, right?

**[24:43]** Like hundreds of thousands of folks there, but and that's, you're covering such a broad range of all these interesting topics. And you have so many people that are at different stages, solving like wanting different problems solved and all of that.

**[24:57]** But a lot of times it's like, all right, like, can I identify what's the big, like, what are some of like the core problems? Like, what are some of like the through lines amongst my audience? And who happens to right now, kind of be at a moment in time where they like really have high

**[25:14]** value and they really want to solve these problems? And then how do I design an offer for them and really show them why I but not just me also like them being connected with the other members here who are also in the same boat can add values that the members themselves

**[25:32]** add to the offer. That's the thing that's often a small percentage of the broader audience, but just as powerful as the big audience.

**[25:43]** It's a big opportunity for a lot of companies that are really not taking advantage of large audiences that they have. And I think it's a huge lever of growth that people are leaving on the table.

**[25:56]** Yeah, you know, it's, it's, it's interesting, like, of our actual customers themselves. So we, you know, it's very meta, but we had our own dog food, of course, we have our 20,000 customers, we have this customer community. And for us, what's happened is, and we're, think of us as a technology

**[26:14]** that we're more of a AI native software company. And for us, though, about 30% of our leads and our new customers that come in are already part of another circle community.

## 26:32 — Circle's 30% referral loop from eating its own dog food

**[26:32]** Whatever we're part of our existing customer community, it's just so like a big referral loop because we have all these customers who are, you know, talking about their experiences they're connecting with each other, we do in person stuff where literally just the customers

**[26:47]** are running the show kind of connecting it with each other. And so they have all those experiences if you can really empower them and enable them to go out and kind of show what they're doing and teach almost on your behalf.

**[26:59]** It could be a huge channel and in the early days it wasn't even as exciting because then you don't, it's kind of brand, it feels kind of brandy, right, like it feels like a brand thing and so you don't get the instant gratification all the time.

**[27:14]** But, but now like you really start to see a compound and you have better rev ups teams and you have better data and like you can actually like see the proper attribution you're like oh wow, this really works.

**[27:29]** One of those bets that take the longest to pay off, pay off in the biggest ways. And one that people are, I feel just starting to come around to in some businesses I think others were early on to it but the content game.

**[27:44]** It takes years to build it properly and to, to keep it going and you're not going to get it right away like you're going to get absolutely nothing for the first three to six months.

**[27:56]** And then it just slowly starts to build and then all at once it feels like it's this exponential network effect thing that you can't imagine running your business without.

**[28:06]** And I think the same applies to the community side where, like you said it's, you have to make a bet on it, but still go all in you have to do it properly you can't do it haphazardly or else it's going to fizzle out like a lot of them do.

**[28:20]** And eventually you those network effects will start to pay off, but it takes some time, and I don't know if a lot of people have the stomach to wait it out.

**[28:34]** Yeah, and you need to know how to look for the leading indicators the early signals that, you know, things are kind of working and yeah it's hard you can only do so many of those types of long term bets at the same time, you know like.

**[28:50]** So, it's hard to have like four or five of those different long term bets all kind of in motion and you're just hoping that a good chunk of them pay off 12 or 18 months from now versus like it's easier to have like one of those big long term bets.

**[29:06]** Yeah, that's true. That's true. And one thing that you, you talk about it's related to this, because on the flip side, it is important to be able to forecast, it's important to know how you need to resource the team.

**[29:20]** So yes, you don't want to over invest everything into a long term that and then you have no predictability anywhere else.

**[29:26]** And one of the things that you said that this kind of stuck out is you hate not knowing where revenue is going to come from.

**[29:32]** I'd love to hear what type of processes systems, things are you putting in place. So you always know where that revenue is coming from.

**[29:45]** Yeah, so one of the things I'm not proud of, but was a big learning opportunity for us was at my former company teachable. We didn't really have a rev ops function. Right. And so, kind of towards the end of my time at teachable me my co founder Sid who is one of the

**[30:04]** three MPs at teachable. And then on core, who on coordinate quality was the founder and CEO of teachable we're all very close friends still to this day. By the way, on core was the first check into teachable.

**[30:16]** When I let him know that I was going to be moving on to start this thing and wanted to kind of fill him in on my thinking around it. We're having a lunch at a little Thai place in New York City and his first response was, I'll be the first check in.

## 30:21 — The Teachable RevOps regret and when to bring RevOps in

**[30:27]** And so he wrote a check the next week, but we're like, man, we really missed the ball by not having rev ops. Like, of course, you know, this could have been such a bigger business had we really invested in rev ops.

**[30:40]** And the truth is, is like, I had never directly overseen a rev ops function. And that was a big learning curve for me. So today circle we have 280 team members across the world we have are doing $60 million in ARR and we're going very fast and, you know,

**[30:59]** I've had to learn a lot and scale myself a lot and hire really great leaders who could compliment me in areas supplement me in areas where I didn't have that experience and so we've had a couple of really great rev ops leaders.

**[31:13]** But now we call it internal AI, we can talk about that, but that was one of the big bets that we made early on was kind of over investing in in rev ops.

**[31:29]** I'd love to hear from your perspective. And obviously as someone who's I ran rev ops for three companies then started the rev ops company in 2021. And we were on rev ops for companies anywhere from series eight pre IPO or augmenting rev ops teams.

**[31:46]** I definitely see the value I have probably an assertive opinion on when you should bring it in and when you should start investing and what roles you need. But when should a team be bringing in rev ops, how do you think about the first hire that you bring in.

**[32:04]** And then when you're talking about a company doing 60 million ARR, what is a rev ops team look like and what does that level of investment look like?

**[32:13]** So, I mean, you've probably thought a lot more deeply about when to bring in rev ops. Here's, here's maybe but I'm also a little bit more biased because I'm like such a connoisseur of the function, but I'll tell you how I thought about it.

**[32:28]** As soon as we started to as soon as we start as I really wanted to ensure that from a demand gen perspective, we were going to have pipeline, and it was the first time I had a sales or that was going to be reporting and to be and this was when we were probably

**[32:47]** about, you know, 2 million $3 million in ARR so, and I really wanted to ensure from a capacity perspective doing all the capacity modeling I didn't want to mess that up because I really didn't want to over hire we were still a small team 2030 people.

**[33:02]** And so, you know, as I'm doing that I'm realizing like, all right, I'm creating all these capacity models working side by side with our new newly minted VP of sales that by the way actually not even VP he was VP level responsibility.

**[33:16]** But we didn't even have VP titles back then it's all just kind of head of, you know, all very flat, but I'm like man.

**[33:25]** This seems like this kind of like operational rigor and the cadence and the model like it's taking me a lot of time and this is just like a capacity model at this point.

**[33:36]** We're wanting to do better reporting and kind of like funnel tracking in our, like, self serve kind of like PLG product funnel, and I'm sitting there with Charlie our head of sales at the time like, yeah, so what's our plan for rev ops and all that I'm like,

**[33:57]** I want to get back to you on that right and I like I wasn't thinking about rev ops and he's like rev ops was the most important function like they're like my closest partner in his lab so he had been, you know, VP of sales probably three times before he was like got Salesforce, you know,

**[34:10]** and all that and so he had seen excellent rev ops functions before and he was telling me he's like, Andy, we have to absolutely nail this so we went out we started a search we hired a head of rev ops it was a small team to start it was, you know, maybe two or three people.

**[34:26]** And then today we have what we call our internal AI team which just went through kind of a little bit of a rebrand but I would call it's much more than that like the scope of a lot of various roles and stuff has changed.

**[34:39]** But essentially we have a VP of data and rev ops kind of oversees that org, that is now our internal AI or it's, I think it's maybe 12 or 13 folks today and it's just like critical for us.

**[35:00]** It's, it's the best investment ever it took us, it took us time like there's been like starts and stops and all of that but we're in a really good place now especially with this this leader.

**[35:13]** I really really like the rebrand, because we've been talking a lot, we're interviewing CROs, heads of rev ops CMOs all the time, and rev ops has really been the team that people are leaning on to leverage AI I mean a lot of it is rather technical

**[35:33]** but you also need to know the context. So, that combination has been really really helpful in the go to market side of the house.

**[35:40]** What drove the change to say hey we need to rename this team from just rev ops to the AI team, and then what expanded on their plate that maybe wasn't there before.

**[35:55]** So, I think, about 18 months ago, we really started a whole company wide kind of like come to Jesus moment of, all right, the world is really changing here, and this is going to have to be one of the most intense kind of internal transformations

**[36:14]** that we ever make. And let's just like get ahead of this as much as we can let's like really push this top down as across the entire company.

**[36:22]** But at the same time, I think we also started having some honest conversations internally on our leadership team, kind of just, hey, what even is a rev ops.

**[36:34]** Now, in this new world, because 12 months ago, you know, we had somebody on our team.

## 36:36 — Renaming RevOps the internal AI team

**[36:42]** Top performers and she's excellent, who like she's setting up a bunch of different workflows and automations and doing a bunch of reports and, you know, things like that and we're like, now she's doing that, but she's doing that with a few prompts she's kind

**[37:01]** of in the terminal, she's doing it in one 10th of the time. And so, revenue operations manager like what even is that role because she's actually acting more like an agentic engineer or an engineer, or an AI agent manager, or I don't even know like what's the title

**[37:24]** like who knows like right we're trying to figure all that out, we have some options but and so we're just kind of like what this whole team, let's just address the elephant in the room, they are doing a different job now, we need some new skills but a lot

**[37:39]** of their skills are very transferable. And what if we just embrace it, and we call this team, what we think it actually is, and the reality was is like, as the company was making this transformation.

**[37:52]** We're all going to our full rev ops team and our data team. And we're asked, they're doing a lot of the work like they're the ones that are kind of helping us execute this and build the architecture like the infrastructure to be able to do a lot of this

**[38:05]** work. And so they had been doing it for the last 12 months are like, why don't we actually just fix this because it's not accurate right now to even maybe call you all revenue operations managers, if the scope of what you're doing feels very different like

**[38:24]** it's just not reflective of the same work anymore. And so we just wanted to get it right. We thought it was becoming confusing to call them revenue operations managers, which I think could be a little bit of a controversial take or and I think it's easy to disagree

**[38:39]** with that. And by the way, a lot of folks might be right. But they're just doing a completely different job, but also like the most valuable job in the company rev ops and data became like the star of the show.

**[38:52]** Whereas five years ago, it was always kind of like rev ops was was not one of the most glamorous jobs in the company. But now now it is.

**[39:02]** No, it tended to be a very thankless job. And if there's, you know, the best day you'd have is just no fires or nobody complaining. But now there's definitely an opportunity to take it to the next level.

**[39:16]** And I think one thing that's interesting is people who come up in rev ops, they're actually used to managing tons of systems, tons of different tools, picking up new ones all the time because the go to market tool landscape is exploding with new solutions every single day.

**[39:36]** And they're also used to working with some of the messiest data. You're dealing with just tons of unstructured data, tons of data incompleteness and being able to put guardrails and think about that.

**[39:50]** So I have seen some teams. It's not a massive trend, but I have seen a lot of teams say, hey, we're already doing 80% of the tech stack and data anyway.

**[40:00]** And it's the hardest part. Why don't we just also help with the product data, the finance data and the HR data? And then you can have it all under one house.

**[40:10]** And I've even seen a few heads of rev ops move into COO positions and kind of build their org that way.

**[40:18]** I know every company is a little different, but I am seeing that as a trend of broadening the scope and responsibility and then getting more influence in the organization.

**[40:30]** Yeah, that's exactly what what we did is, you know, rev ops for us started out as just a go to market function. And while it still does report into me, they are now just responsible for data for the whole company, whether it's product, also customer support or finance.

**[40:54]** It's just one whole team. Same thing with internal AI and the folks building like a genteck workflows and all of that that spans the full the full company.

**[41:08]** And it feels easier to do it. It always felt very natural to do it that way.

**[41:16]** What are some of the things that you have access to now that you just never had that teachable that allow you to operate and scale more than you've ever been able to before?

**[41:30]** So the other start with obvious, but like the data is accurate, like the underlying actual data is very accurate and there's high trust in the data. So when we have business conversations, we're not talking about all of the nuances to the data integrity and hygiene and all all of that.

**[41:53]** We're actually just able to have the business conversation because the data is accurate. I'll start there. But if you look at kind of the current infrastructure, the so that we have a weekly demand gen meeting.

**[42:06]** 12 months ago, six months ago, that meeting was in slide decks with some, like, okay reports that look, it has mostly like what we want. They don't look exactly like what we want all of that.

## 42:12 — What accurate data unlocks — and the tools they can't live without

**[42:18]** Now, it's exactly what I want. I created prompts. Our team has basically skills files, which can spin up the exact structure for this kind of meeting that we want for other functions.

**[42:33]** The data is automatically updated every single week. We press a button.

**[42:37]** Before we would have a slide deck with comments and stuff like that on it. Now it's a literally an application where we all assign and we can add our comments directly on it's like literally custom weekly revenue meeting application dashboard.

**[42:50]** Right. And so, then the work then kind of like all the follow up happens kicks off automatically, but it just saves so much time.

**[43:00]** And that's like one example where just like it would never have happened 12 months ago, let alone five years, six years ago.

**[43:10]** But then just to spin up a lot of these workflows like on, on our sales team as an example so like, think about this for a minute, you have inbound product flows lead flows lead routing flows where you kind of lead you route trials to maybe sales to drive beating bookings

**[43:34]** like that right. We now have a sales skill so when you sign up for circles product let's say you're kind of build us some type of digital business, you start having a conversation.

**[43:46]** We have kind of like lovable or replay, kind of like that, they help you build apps, we kind of help you build a digital business, let's say.

**[43:57]** There's a sales skill that our sales team technically who are like non technical right like they're in this sales skill the markdown files, and they're able to say, trigger a meeting offering.

**[44:10]** When these signals are true. And before this would take like a front end developer, our growth engineering team.

**[44:18]** It would be like two weeks of work if to get on the roadmap all that there's in there every single day making these like micro optimizations building off of reports that they just like vibe code in, you know, a few minutes with data that is actually accurate and it's just there's

**[44:32]** there's 100 version of that and I know you know that but it's just wild, how different it is.

**[44:38]** No, I, I think one of the things that you highlighted that never goes away is making sure you have the right data infrastructure, so you can build all this amazing stuff on.

**[44:51]** So and I think the biggest thing right now is can you implement a proper context graph to get things like your transcripts your CRM data your product data, all connected in a way to where you can then go build applications go build custom dashboards.

**[45:07]** Custom analysis and insights game plans, whatever it is that you're looking to build, but you still have to have that data infrastructure.

**[45:16]** Be bulletproof and you need to be able to trust it, or else you're going to build all these things and you'll be in a meeting and the CEO be like no that's not accurate there or we're not going to use this because that doesn't look right or it's hallucinating because it doesn't have the right data underneath it.

**[45:29]** So, and I think that gets really complicated to maintain, and you just need to invest a lot in maintaining that but to your point when you do it right.

**[45:38]** You can make really really good decisions, you can make $10 million decisions if you have the right data, but if not, it can be really really difficult to do.

**[45:48]** You know what, on that note, it's interesting a mistake that we made was as we initially set up our rev ops team.

**[45:59]** The, from a hiring profile perspective, we were focused on somebody who is much more, you know, if you think about kind of some of the some of the key criteria for what makes a great like rev ops data leader, a bunch of different things.

**[46:20]** And again, like, you probably know them better than I would, but a couple of things that came to mind are just like there's there's the data side of the things there's the kind of more like system side of things.

**[46:29]** And for us, we really in the beginning, and there's also like just like modeling forecasting business analysis kind of thing right and in the beginning we focused on the latter two systems and then a lot of the kind of like modeling forecasting analysis kind of business domain expertise stuff like that versus data.

**[46:49]** So then, when ultimately we're like hey we're growing really quickly we want to kind of scale up the function we want to hire a leader.

**[46:58]** We were feeling so much of the pain from not having a true kind of like data leader in the org that we over index and we actually hired a data leader who had almost no real like systems experience.

**[47:15]** And, and that worked out that guy's he's been in the role now for almost four years like he's, he's the one but he over index on data instead of the system side and we, you know, supplemented him with systems folks, but I think that was a little intentional, but not fully intentional

**[47:33]** and that's really paid off for us in the last year because he was over index on all the data stuff before kind of all of the AI applications became truly, truly necessary.

**[47:47]** Yeah and sometimes it, it takes the seemingly unsexy capabilities of managing a proper data warehouse managing proper data schemas so that way you can leverage the data and all the applications you need and when you're bringing on new tools because I'm sure you're bringing on new

**[48:03]** tools all the time.

**[48:05]** It just becomes increasingly more important. I'd love to know in your go to market tech stack what are some of the tools that you cannot live without ones that you're impressed by.

**[48:18]** Are there any categories that you're looking at that you think would be interesting to up level and enhance the stack you have today.

**[48:27]** Yeah, I'll share a couple that, that we use that are that we love, I'll share even maybe without naming names a couple that we've like tried and we like tried really hard we can make work like categories.

**[48:39]** Always take those two.

**[48:41]** The. So, so one that we've used, that's been key for us and it's kind of like our on ramp to using agents a lot more in our business. I don't know if we like we could use other tools today but we couldn't have a year ago they are really ahead of their time.

**[48:57]** They're relevant, relevance.ai, they let you essentially build agents have a lot of control over agents, we still use them all day every day today, in addition to a lot of the like custom agents that we built internally, that's been a really valuable one.

**[49:12]** Well, I, I think that's actually a huge. People are very good at making something that works well for them. But when you need to take this thing that you built and say hey, I need 200 people to now use it and have access to it and oh by the way there's like, you can't have access to certain

**[49:32]** data that I can have access to. I actually think scaling agents and scaling these things is a pretty difficult problem. Easy for me founder CEO I have God mode access to every single application we have and I can build whatever I want.

**[49:45]** But the second we need to start deploying it to the rest of the team, it becomes a real challenge.

**[49:52]** 100% man it's like on the one hand, we have some incredible new products that we've built like internal tools we've built, you know, for our org chart, it's called org 360.

**[50:06]** And it's incredibly complex and comprehensive and all that our customer success or they built their own tool internally. And it's called pickle super kind of like silly unintentionally doesn't sound professional at all, they both look completely different they're both completely

**[50:22]** different stacks and it's like, it's been fine for the last 12 months, but it's not going to be good for the next 12 months you know like we have to kind of start adding constraints and guardrails to kind of build.

**[50:34]** stuff. That's a great, great point.

**[50:39]** We have relevance is one hex, we use hex for a lot of our data visualization and it's just incredible it's like really a conversational UI, you start having conversations, ask questions, it builds all the reporting in front of you.

**[50:52]** Really, it's been my favorite data visualization tool ever.

**[50:59]** The other, something we've been trying that that hasn't really worked is for the lowest, I'll say like the least qualified leads that come in, where we can't have them talk to sales, but we want them to have more of a high touch experience we've been using, experimenting

**[51:19]** with some of the, like, AI avatars like the conversational like AI avatar tools, and some leads like they have long like really valuable seeming conversations but just not quite there yet where, from a brand perspective it's like, it puts up numbers like it,

**[51:41]** it does deliver value to these leads, and it moves them down the funnel and it converts them and it generates revenue but it's like, from a brand perspective it just feels a little off and not right and so we're, we were kind of one foot in one foot out kind of thing.

**[51:57]** So there's a couple of those we've been experimenting with.

**[52:01]** But there's a lot of tools right now. We all I mean a lot. Just to, you know, so, whole team, I think it's preventing my carpal tunnel. So I'm so happy that they invented that I'm just thinking like I used to type so much.

**[52:20]** Now I have a raspy voice instead because I'm talking all day, meetings and then when I'm not on meetings I'm still talking, but I think that's, it's huge and it just, it's so accurate, like it just works and it remembers all of your nuance things how you spell particular

**[52:34]** person's name, you know, all the esoteric internal language that you use, I think it's a fantastic tool.

**[52:43]** It's just mind blowing how much it improves your, you sound like one way, and then it comes down and I wish I sounded like that, you know, when it's all kind of typed down written.

**[52:56]** Yep, it makes my completely unstructured conversation look nice and pretty.

**[53:01]** Yeah.

**[53:03]** And he really appreciate everything you share to the podcast. I think there's so much to learn from. I am very impressed with the 1500 demos and learning from that before you brought in a VP of sales and also just like your sequence of hiring and looking

**[53:19]** for leadership first and then scaling I think kind of the nail it then scale it mentality that you've taken to this, and also the appreciation for rev ops I think once you've had a few journeys and go to market that's when you really appreciate the difference

**[53:36]** between having rev ops or not. And I think you're making the right move by getting them involved in leading the charge on AI for your organization, because it's the team that has the right transferable skill set and business context and knowledge.

**[53:52]** That's really in a position to do it. So, and I just can't thank you enough again for being on the podcast and I can't wait to see what you encircle do next.

**[54:03]** Thanks so much Anthony it was a lot of fun to just get the jam for a bit.