Clarity Over Chaos: A CRO's Playbook for Category-Defining Companies

0:00 Josh Heller is the chief revenue officer at Coactive AI, a Forbes AI 50 company backed by A16Z and Bessemer. But what makes Josh different from most CROs you'll meet isn't on his LinkedIn. Before Coactive, he started his career in finance, earning his CFA, and says one of the best things that actually ever happened to him was getting laid off by Goldman Sachs. He then pivoted to tech sales, rode the responses rocket through the Oracle acquisition, spent eight years at Imperity taking them from zero to 80 million in revenue, joining when, as he puts it, the website just said the future of marketing and the product

0:38 was literally Google Sheets in the backend. Before that, here's what really caught my attention in our prep call. Josh is also the former president of Bats in Prov in San Francisco, which has helped in every aspect of his career. And he said recently he made a decision about his mental health that he says has made him feel better than he ever has in his entire life. We're going to talk about all of it, the anxiety of being a CRO, the clarity that comes from unexpected places, and what it really takes to build something category defining. Josh, thank you so much for being here. Really excited to dive in. You told me in our prep

1:15 call that you've never felt better in your entire life. For a CRO at a high growth startup with three kids under 10, I've got three kids too, so I know how stressful that can be. That's not what most people would expect. What changed? Yeah, thanks, Anthony. And again, just so excited to be here. I consider myself one of the luckiest people on the planet. I have a wonderful family. I get the luxury of working for an ad back startup in Silicon Valley, doing something that I love. And I grew up in an environment where mental health was discussed quite a bit. My father dealt with

1:52 and still struggles with severe depression his whole life. His father dealt with it, and so it became a topic of conversation fairly often. He actually eventually became a facilitator in Chicago for depression and bipolar support, and really helped a lot of different people in that area. And for me, I looked at my father and the level of mental health issues that he faced with. And for myself, I don't have depression. It's not something that I've experienced. But I have, at times, often, I should say, felt anxiety in a lot of different situations. But because I'm generally an optimistic person, I'm generally a happy person, and anxiety

2:40 is something that I always thought looked at as a tool. It's something that helped me really focus, allowed me to work on a lot of different things at once. It propelled me to work harder and work more. I thought it was this thing that was energizing. But over time, I started to realize that maybe it was getting in the way. So the first thing I decided to do was stop drinking. And again, I was only socially drinking with friends at this point. I've got kids at home. I don't drink at home. But when I go out in sales, it's something that happens often. And so I actually, ironically, was going to meet

3:13 up with some old colleagues of mine. And I was going to cab on the way there. And I was using the Calm Meditation app. And I only had five minutes to get there. So I had five minutes to meditate. And I'm like, you know, I'm just going to go do this. I'm going to meditate before I go in there, because I was feeling stressed. And so I started to meditate. The funny thing was, the first thing that the meditation said was take a deep breath. And unfortunately, the cab I was in had a particular odor to it, which was not very pleasant. But I took this deep breath. And I still kept with the meditation. And five

3:47 minutes later, I arrived in my destination. I felt calmer. And when I got there, all of my former colleagues started ordering drinks. And I instead of ordering, you know, a drink of alcohol, I ordered a mocktail. I just wanted to see if I could show up in a way that was good. Could I have fun, but also importantly, could I be entertaining? And in sales, like you really want to be the one who is able to entertain a group. And I found that I was I found that I was able to actually listen better and focus and be kind of, you know, as hopefully as charismatic as ever. And then the next morning, importantly, when I woke

4:19 up, I didn't have the hangover that I normally did. And I didn't feel as anxious that day, as I normally would have if I did that. So I, you know, I stopped drinking those December in 2024. And have excuse 2025. No, 2024. So it's been about 1415 months. And then in November, another family member of mine who was who was trying to treat anxiety started taking Zoloft for that and as kind of our process to help this family member with their mental health issues, I started exploring that for me and decided that I would try it. So I started taking Zoloft a couple months ago to deal with my mental health and found

5:01 that it's created a level of clarity and focus and kind of the freedom that I that I didn't realize was possible to now access these other tools that I've been deploying to deal with my mental health as well. Something I think a lot of people will have a difficult time differentiating and and I do too, is normal level of stress from having the role the season of life that you're in with young kids. How How did you differentiate between, hey, this isn't just me wanting to do a good job me having a sense of urgency or me feeling like something is important. And where you started to become aware where, hey, these are actually limiting emotions

5:50 I'm having. And this is actually holding me back from being the best version of myself. Were there specific examples, thought processes or things where you really started to be able to differentiate the two? Yeah, I think it was a few things. You know, one, when I when I would work, you know, I have my endless to do list and felt compelled to try to tackle as much of it as possible, even to you know, when you're kind of working and it's like, you know, late at night, or it's things and you realize you're not producing as quickly as you normally do. You're not thinking clearly.

6:26 That was starting to happen more and more with all of the different responsibilities that I have as a CRO of collective. I have leadership responsibilities, I've got my team responsibilities, and then I'm still an individual contributor in what you do. Like you're very much just on the ground and doing all this. So to take on all that at once is just a massive amount of responsibility, and it was starting to be almost overwhelming in terms of the ability to tackle each of these things. And I had, because I've used other techniques like meditation at times, where I've taken the time to stop, pause and feel that clarity,

7:06 I realized that I can work more quickly and work through problems faster. What the medicine has allowed me to do is have more of that more often in just kind of my natural state. And so when I'm working now, I'm tackling the most priority important problems. If something comes in that's stressful, I'm not dwelling on the thought that it's stressful. The feeling of stress exists, but you don't over index on it and spend time. It's kind of like meetings about meetings, right? Like we don't need the meeting about the meeting, you just have to tackle it. And that's what allowed me to do here. So when I'm working, I'm focusing

7:42 on work instead of like thinking about, hey, I should be with my family and all these other things. And then when I'm with my family, I spend time with them and I'm not focusing on all the work stuff I need to get done. So it's allowing me to compartmentalize better, which has actually seemed like it's created time. And that's been magical. So I'm accomplishing more in less time. And that obviously gives this great feeling of success and accomplishment, which would alleviate stress as well. So it's been this kind of wonderful virtuous, virtuous cycle. Yeah, I absolutely know what you're talking about when you're in that doom loop of stress

8:17 where as you put it, you're stressing about the stress or feeling guilty about whichever you know, area you're investing time into. And I think when you're earlier in your career and you're younger, maybe you're just physically able to do this more, you always compensate with just more hours invested into work. So you could always work through the night, work over the weekend. And I think when you have a family that starts to break up where you don't have that option anymore. You actually have other responsibilities too that you can't just ignore unless you want your family to fall apart, which I don't think anybody does.

8:49 So then you have to get really strategic and intentional about your time and then making sure, okay, during this window in which I have to work, I have to be in the top shape possible. And I love that you bring up not drinking as well, because yes, maybe you're entertaining that night. And I think you can do it without the alcohol. But also, the next day, you need to get back back in shape and back to battle. So if you start compensating on that night and then you have the hangover, it really, really reduces your ability to be effective. And I think it's really important to know, like, hey, you don't have to just put in more

9:28 hours, you can get your mental and physical health in a good spot to be more productive during the work time. Sure. And if you fly out on a Monday, you know, you go to New York on a Monday, you drink Tuesday, Wednesday, Thursday, you fly back Friday, you get in at, you know, 10 or 11 o'clock at night, and then you want to show up for your wife who's been managing three kids on her own for an entire week and your kids want to play with you early in the morning. It's, you know, if you've been drinking all week, it's a lot harder than if you have that mental clarity, where you can show up and be present for them.

9:59 And then it's really, I mean, that my family energizes me, you can see, you know, the things behind me, it's my family is everything to me. And so I want to be there and be as present for them as possible. And I felt I, I owed that back to my family, which again, you talk about removing friction. If I'm gone and I'm out having these fancy dinners and all this, I think a lot of people, you know, I get advice from other, you know, sales leaders, it often is men that say, well, make sure you don't tell your wife about the fancy dinners or don't tell them about that, because they have stress and they have guilt and, and you get to live

10:28 a lifestyle that not everybody at home gets to, gets to live. You know, and I, and I, for me, I don't want to have that stress. I want to be a, you know, I'm out there to work and get my job done and then come back and be the best I can be at home as well. Anytime I'm traveling, my wife and kids have a term for it. They call it work vacations. So it's where I get to go on a vacation, but it just happens to be working in Puerto Rico, Miami and can, you know, set up for the next, you know, a couple of months. So you better believe that you think of it as work vacations as well. So 100%. Um, talk to me a little

11:07 bit about your trajectory starting off in finance, then moving into tech, moving into an SDR role, which I think is probably the hardest job on the planet. Um, and then the rise to being a chief revenue officer. And I know a lot of people who, who listen to this podcast are there in sales, they're in rev ops, they're aspiring to be a CRO. That's, that's kind of the pinnacle of the GTM career. Um, what does it actually mean to be a CRO and what weight do you carry in that role? Sure. Um, yeah, I started my career in finance. Um, the reason I did it was I was good at math and I liked money. I understand it just

11:51 made sense. Um, uh, ironically, uh, I had taken a semester off in college sophomore year because I didn't know what I wanted to do. And I was thinking about like all these different things. I ended up, um, actually selling cashless ATMs, which might be a different story for another day. Uh, I would go door to door and, and, you know, trying to convince people that they needed to put in the machine. Um, it was almost like, uh, at the time it was almost like a Venmo where you had a box, you swipe your credit card and it would, or debit card and money would transfer from one person to the other and print out a little

12:23 receipt, give it to the, to the cashier and they would like, uh, use that as if it was cash. Uh, and then you pay a little fee for it. It was, it was kind of genius at the time. And so I, I did a bunch of different things, trying to sales and I wasn't successful. And so I said, I better go get a degree and went back to college, uh, to do that where I entered the business school and said, okay, what is the thing I'm good at? And that's, and that's a, uh, you know, um, uh, graduated with a degree in, in, uh, finance and venture management, uh, joined a finance, financial rotation program. So I get to see, you know, corporate accounting,

12:55 cost accounting, um, audit, these different kinds of elements within, within finance. Um, and then convinced the program that they should send me to Palo Alto to join Siemens venture capital, where we invested both in, in startups, as well as in, um, uh, venture capital funds. We had a fund to fund business on behalf of the Siemens pension trust. So I really liked it. Um, but I, I kind of wanted to do something else and I had a recruiter reached out, uh, and ended up, uh, moving over to wealth management and was in that for a couple of years. And then Goldman Sachs reached out and, uh, you sort of don't say

13:31 no to Goldman after going to be good for the resume, it'd be good to try it out. Um, and so I joined the wealth management team in San Francisco, which was one of the largest wealth management teams at Goldman, um, and got to work for some, you know, uh, you know, very, very wealthy people. And we actually managed their money as well. Uh, plus, you know, money of, of a lot of different people. Um, you know, they're, um, very well-known folks, uh, that, that you can imagine, uh, that Goldman, uh, managed. So in that process, I was getting what's called a CFA. It's a chartered financial analyst. It's, it's essentially

14:01 a master's in finance. I was working all the time. I was studying for this and I, well, I liked it. I didn't love it. And Goldman Sachs did the best thing they could have done for me, which was they, they laid me off and it was a part of a massive, you know, restructuring that they had done. I was one of many people that, that lost their jobs and it really did two things for me. One, it solidified my relationship with my wife who actually wrote a list of the hundred reasons she loves me. Uh, when this is when we were dating and I said, this is, you know, this is someone who's really special, you know, they're, that she really

14:33 cares about me even in the hardest of times. And then two, um, I took, you know, I was able to think about what were the things that I, that I loved. And I thought about, you know, the experience of, um, you know, selling cashless ATMs. I thought about the experience of being, you know, a little kid who would show up at school with a peanut butter and jelly sandwich and come home with a watch and explains to my mom all the transactions I made in between to go from, you know, A to B and, um, or when I was interviewing for the role at Siemens and the finance program and the woman in HR asking me, I'm sure you

15:04 don't want to be in sales. And I was like, well, no, finance is the thing I'm good at. And so I kind of put all that together. And, um, I, I, I ironically was able to reach out to the same recruiter who recruited me into Goldman. She had left that company and was now recruiting for startups and talk to her about, you know, what, what I could do, how do I get into sales? How do I get into technology? How do I kind of take advantage of the resource around me? And she connected me with an SDR leader, a guy named Andrew Reasonfeld, who's a fantastic SDR leader, um, and has since gone on to be a fantastic sales leader. Um,

15:39 and he had a background in finance. And so when he saw my resume, he was really interested in having that conversation because he thought we were good at research, we were good at analytics, and, and would, would he like people that were a little more seasoned in their career for the role? Um, so I stepped into the role and I loved it. I mean, it was, it felt natural to be in that situation, but I was also able to use financial skills from a research perspective, from an ROI perspective to talk to customers in a different way. Um, and then I really leaned into it. So I was the one, I was actually doing demos for my

16:10 AEs and I would learn the product, you know, deeply enough that I could be in that situation. And then the other thing I did, uh, I used to, I used to transcribe meeting notes verbatim for my AEs. And then I would go and I would summarize it at the end and I sent out the notes. And what that did was it created value for my AE who wanted me to be in meetings. Um, I was, I was fireflies. I was gone, right? I was just going to say, yeah. If only I had the, you know, the wherewithal to realize that it was an actual idea and the value of what I was doing, but, but it was, Hey, Josh

16:48 has to be in the meeting because he's going to add value, whether it's from a demo or from this, he could be there. Um, so with that, I was able to quickly advance and join the mid market sales team within, within responses. And I was, you know, one of, one of the, the comments I got from the people I was selling to, which I thought was the biggest compliment I could have, could have had. I had a book of 75 accounts and this company thred up, asked me if I had any other like prospects or customers that I worked with. And I took that as such a side of like how responsive I was, how much I cared about their business,

17:20 how much I leaned in with them. It was also, I was working all the time. So it was, I was able to, you know, to, to do that for a lot of different people. Um, but I really leaned in and that allowed me to, to, to sell even for accounts that were seemingly not going to be sellable, was able to, to be very successful with those different accounts. Um, and so with that, I was able to move into, to enterprise sales. I was able to convince the team to, to give me a seat, uh, particularly as there was some, uh, folks that moved around. I ironically got to pick up the same territory I had as an SDR. So I knew it well, right? That helps.

17:53 Exactly. And so I had the relationships. I had people in there. I was able to, to kind of work with that. Um, and one of the, uh, relationships I had was with a woman named Jeannie Jones who was running guest experiences for Alaska airlines. And I used my finance experience with, with spreadsheets and numbers. And she actually sent me her marketing budget in the spreadsheet and asked her if I'd like clean it up for her. Um, so I was able to, to get a window into her world of all the things she was spending money on and built sort of an untrusted relationship, uh, with, with Jeannie at the time to the point where

18:29 she then sent me a list of, uh, her goals for the year. She had 30 different goals, things from improving the customer experience, better marketing, acquiring new customers. And next to the goal, she put a company where she thought, uh, could, could help them. And by this time we'd been acquired by Oracle and we had a whole suite of products we could sell. So Jeannie, um, uh, you know, I would look at one of them was like the Oracle DMP. And I was like, sure, we could talk about that. But then eight of them were this company called Emperity, which I had never heard of. Uh, so I went to the Emperity website and

18:59 sure enough, all I said was the future on marketing. I had a little email capture on the bottom as if people were going to just come, you know, well, I want to know about the future of marketing and get all this information. Uh, but I, I, she introduced me to the founding team there and I, you know, I fell in love with the company and just the environment of being surrounded by, by brilliant people. Um, so I joined there as an IC, um, and eight years later I left as the head of sales, um, having been responsible for the majority of the enterprise business, uh, within that, within that company, uh, prior to coming to, to Coactive.

19:32 I, I think that's a special moment. Um, when, when you move from being an IC to leading the team, being responsible for a team quota, um, it sounds like the company's overall quota at that time. What changed? So as you made that transition for people who are about to make that transition or aspiring to make that transition, what was different? How did you change your day to day? How did you change your approach to your work? What you felt responsible for? Um, and what made you successful in that role? Yeah. Um, you know, it took me some time and I think if you go back to the anxiety, we

20:07 did, you know, hit on that in a bit. Like it, I think it impacted my sort of emotional intelligence at the time. And I kind of like my recognition of where I was in terms of my own maturity, um, in there. And I, I, cause early on when I joined, I wanted to be a, a leader within and parody. And I was told a few times in, uh, not so uncertain terms that you'll never be a leader here. And, uh, they kept hiring sales leaders to, to manage me and I kept outlasting them. I kept selling and they kept leaving and not being successful. I kept selling and I remember, um, I was in a board meeting one time and the, the, my

20:44 job was to explain kind of our pitch to the board, like what we were doing. And I felt so honored. I'd never been in a board meeting before and I got the chance to go and present the sales perspective. And at the end of it, one of the board members said, how do we put Josh in a box? And I remember thinking to myself, like, this is crazy. Like, why can't Josh figure out how to put Josh in a box? And yet they keep bringing in new sales leaders for it. Um, and, and so it took me some, you know, emotional maturity to, to recognize, you know, why I was being told I wouldn't be a leader there and, and got a lot of feedback

21:17 from different people on, on, on things like that and started to really work with the team about the way I was showing up to my colleagues and how I could be more effective as a, as a contributor. And I, I think I started to do that within my, within my deals themselves. I managed it more like a CEO to the point where, um, people on the team wanted to be on my deals because they knew we were, one, they knew we were going to win, right? They knew we were going to be successful, but also I was going to celebrate them in every way. I was going to help, you know, support them. I was going to be in the trenches with them.

21:46 Um, we go out for big dinners after we get the win. Um, we would do all of these things and I would really recognize and be a partner to, to my colleagues in it. And it was going to be hard, like you're going to come, if you're going to work on one of the deals, like you're going to work probably harder than you've worked before because I was doing that too. And I think in, in those people started to recognize that there was an opportunity. So then I got a chance to be a, um, a regional leader, um, and actually build out a set of strategic accounts. One of the things that I was really good at was, was recognizing

22:17 that this capability we had could, could, could be used horizontally. So we had done a lot within retail, but I was able to see, Hey, this actually applies to telco. It applies to QSR and applies to automotive. And so I built out the strategic accounts and kind of had the chance to kind of build that within, um, the, the team. And then there's restructuring and whatnot ended up leading an entire team, uh, as one of the managers went out. And then, um, there was a, uh, our, uh, we had a new CEO, uh, he transitioned on our, our head of sales at the time. And he asked me if I can, if I would take that, that role at that

22:50 point. Um, and it was, you know, sort of, um, it was kind of, kind of mind, mind blowing at that, at that time to be able to get the opportunity, but it was from being successful again and again, and kind of each of those levels and focusing less on kind of that ambition, but instead of being, you know, proving I can be successful and bringing a group of people along with me. Yeah. And it's, it's a very hard thing to do. You see it time and time again where, Hey, you take your top rep, you put them in the management role and they have a very tough time making that transition. Um, and at the same time, you know, nobody's going

23:27 to feel confident moving someone in that role unless they are a top rep, because I think a big part of being head of sales, being a CRO, like you're there to win and you're there to do what it takes to make it happen. So you have to have a breadth of skill sets that sometimes don't always go together, but I think your diversity of experience to probably played a big role in that being able to take in finance, like a analytical mindset, thinking of, Hey, this thing is a system. Um, which of course you're at lean scale. That's how we think of things as well. Like GTM ops, the whole thing, we just think of it like

24:03 a money factory and how can we get the most throughput? Um, but I think your diversity of experience really tee you up really well. And I think it's very hard for people to make that transition. Yeah. One of the things that, that I found, and this kind of goes back, you know, we've talked about what kind of improv and whatnot before, but is putting yourself in uncomfortable situations and the growth that comes from that. And I think a lot of people are afraid to, to do that. And I, I love it. I thrive on it. So the opportunity to take on a new challenge and, and, and feel like you're there's imposter syndrome. I mean,

24:42 I feel that all the time I've, I've been at places in time and collective where I've told our leadership or I've told my CEO, I'm not sure I'm the person for this. I'm not sure I can help and, and, and navigate us through these challenges. I don't, I don't feel that way currently. I feel with my mental health under control and all of these things that we're doing, I know that I can do it. And it's, it's taken time to get there, but I think that's the other part. It's time. It literally takes effort to, to, to put in and, and feel the lows so that you can recognize what they are and, and, and find where your

25:15 weak spots are. And I think, you know, related to that, you mentioned, you know, I do have a breadth of experiences, which is true, but I also recognize that I have more, more gaps than I do capabilities. And so go to market operations. You know, I wanted to hire somebody who, who loves go to market operations, who like, for me, I love being in front of customers and solving hard problems and motivating a team and, and kind of working in shaping an organization and a vision. I don't also have time to obsess about our go to market operations, even though I'm obsessed with the importance of operations. So I brought in somebody who,

25:52 who knows it, who lives it, who breathes it. And, and, you know, that's his passion and then try to take blockers out of his way. So he feels empowered to, to, to bring those systems into coactive so that we can, we can scale. You know, similarly, there was, and I found there were gaps on how do we do partnerships where I think I was pretty good to understand the go to market partnership. But one of the things are my CEO said, he was, you're not very good at partnerships right now because you're not understanding the importance of the product side. And so recognizing that the partnership leader needs to think about

26:26 that, that technical integration. We're design partners with Amazon Nova that has both product implications in engineering and also has implications that go to market. And they need to be brought together those threads in order to have a truly successful, you know, a partnership with, within, within the company. So it's, again, it's, it's not just like, I, you surround yourself by people who are, you know, experts to you, and then you listen to the feedback and you take it and you grow from it. I think knowing and understanding your gaps might be even more important than knowing where your skill sets are, especially in a leadership

27:01 role. So you can build the team around you that you need to win and talk about doing something uncomfortable. I think the move to coactive as chief revenue officer, that's really, really putting yourself in a new situation, a brand new market category defining type of product. Tell me about that experience and what helped you make the decision to move to coactive and know that it was the right fit for you. And what have you learned from the experience so far? Yeah, I appreciate the question, Anthony. Moving to, to coactive was a hard decision for a lot of reasons and in other, other ways it was, it was easy.

27:53 I had a recruiter reach out and, you know, when you're in sales, you get recruiters that reach out all the time. This opportunity happened to be 15 minutes from my house, which is unique to have an AI startup in San Jose, as opposed to, you know, downtown San Francisco or in Palo Alto. And I did a little bit of research on the company and I saw the CEO and the CEO Cody Coleman, you know, there's a bunch of information and podcasts on them. And it turns out it was actually in a book called Grit by Angela Duckworth, where she wrote about his background and Cody's story is phenomenal. He was, he was literally born in prison. His

28:29 mom was incarcerated when Cody was, was born. He never met his father and he ended up moving in with his grandmother, his maternal mother's mom. And then after a few years his mother was released from prison and eventually moved back into the house with them. And so she wanted to start a, it's either like a pet store or a veterinary store and she, she ended up buying 13 cats and 13 dogs and bring them into the house. Well, Cody's allergic to cats and dogs. And so he described going to high school as a literal breath of fresh air, as, you know, it is his experience. And I think by the time he went to the, went to high school,

29:13 the police had been called on the house 65 different times for disturbances and other things. So his upbringing was about as challenging as they get. And fast forward, he ended up being the first, you know, African-American to get a PhD from Stanford in 20 years. He was under Matei Zaharia who founded Databricks as his PhD advisor. And he started to coactive, you know, the Monday after he got his PhD. So the reason he's in Angela Duckworth's book is because she has since referred to him as the grittiest person that she knows. And for me during the, during the interview process, you meet Cody and he's charming and he's,

29:48 he's wonderful. And it's, it's hard to believe that he's had the background that he is because he's all of these wonderful things. But through the process I was sitting and I was leading sales at Emperity. I had gone from zero to 80 million in ARR. You know, I, I loved Emperity and it was, I bled the company that I worked for. And I told Cody, I said, I can't actually, like I'm not, I'm not able to do this. I can't join. And so Cody said to me, he goes, do me a favor. He goes, just come to the office, meet the team. That's kind of all I ask of you in this process. And I said, you know, sure enough. I said, sure. I also liked that

30:23 the CEO, even though his technical was able to kind of sell me on the idea of coming in. And so I went and I met the team and I got to meet our head of engineering who grew up in a small village in India, didn't have any clothes, ended up, didn't learn English until he was in eighth grade. His, his, he ended up moving to the United States. He took a flight to Kansas. It was the first time he'd ever been on a plane where he had nothing more than a suitcase, landed in a blizzard. And fast forward, you know, him, he actually built the first infrastructure for Tesla to under, under, underneath the autopilot capability.

31:01 So the computer vision models and whatnot. And so for his story to me, it was just as miraculous or, you know, you know, Cody's co-founder Will, who grew up in Columbia and his family had to flee in order to escape kind of the violence in Columbia. And where there he grew up, you know, middle class. And then he moved to the States and they had nothing and his dad's occupation didn't transfer his mom's occupation in transfer. So they had, they had nothing. And he ended up being, you know, a PhD in neuromorphic computing from Northwestern. He and Cody had met an undergrad. And so you start to see this and our head

31:35 of customer success, Suzanne, who was one of the warmest, most lovely people I'd ever met. You get that feeling of, of, of what this is. And you just, you don't care what they're going to do anymore. You just have to be a part of, of that magic. And so I said, you know what, I want to go do this and I want to be a part of this, a part of this journey with them. And so they were, I was fortunate enough that they, they gave me a shot as well. That is so cool. And, and I think when I reflect on my own experiences, I think it has, it's definitely not the destination. Sometimes it's the journey, but every time it's who you're

32:09 on the journey with and, you know, I think surrounding yourself with people that really inspire you and you get to work alongside them every day. I don't think there's anything better than doing that a hundred percent. And you kind of ask me, what's the, what's the role of a CRO at an early stage startup? And for me, it's, it's been a couple of things. I think of it as we talk a lot about product market fit and trying to find how your product meets existing demand in the market. For, for me, one of our, one of our investors, Martine Cassado coined a term called market annealing. I think that the CRO is responsible

32:56 for product market strategy and market annealing differs from product market fit in that you're trying to not only shape the product, but also trying to shape the market and trying to understand what the demand is and educate your buyers. And so we've hit on a real problem in our space of content understanding. Like anybody we talked to says, yes, I have that problem that you're trying to solve, but the, the, the how you solve it in the, in the face of AI and is, is incredibly complex for most people and they're not sure. And, and, you know, Cody and Will were some of the earliest minds in bringing, you know, big data and

33:34 AI and these systems, you know, to, to gather Cody actually founded something called Dawn Bench, which became ML Perf, which is the first, um, machine learned benchmark for system performance that, you know, Nvidia, so it was a hundred engineers working on it today. Um, and, and so these problems are, are, are hard to solve and you have to help people understand that the impossible is now possible with AI and it, you know, you still need systems though to turn possible into something that is practical and production ready and, and able to use at scale. And we work with image and video data that is wildly different from,

34:11 from structured data sets. Like what Chet TBT does is phenomenal, but taking in a, you know, 9 million minute, uh, uh, you know, valid or video on demand archive from, from NBC's peacock library, doing that at scale, like being able to ingest that content, much less to be able to, you know, tag it and understand it and search through it in an efficient way is a really, really hard infrastructure problem combined with AI problem. Um, and then being able to like, again, make, make AI sort of usable in this sense. Like there's just so many things that come together, but you have to go convince people that this thing is possible

34:44 and that there's a better way. And then now what are all the use cases you can go and do with it? So, um, what I've really focused on is, is kind of hoping to guide coactive through this, our own market and kneeling journey, going from sort of multiple verticals with multiple offers into a focus and medium entertainment into, um, Hey, we're a platform company into, you know, we need this, this search for a killer app. And I, and I say it almost as if, as if I'm, you know, alone on that, but it's really working with the team to understand where we are. Like our, our head of product and engineering was very

35:16 set on what our killer app should be had this whole idea for, um, uh, what we call context studio. And it, you know, it came from him. It wasn't, it wasn't, it wasn't my idea, but being able to understand what those people are and navigating that and bringing that and making sure that we're all communicating and getting on the same page is something very much that I feel responsible for. And to the fact where when I joined, I stood up something called pizza and planning. Uh, and the goal is like, Hey, every, you know, every Monday with the leadership team is going to get in a room where we're going to have hard

35:45 problems to solve as opposed to meeting with the set agenda or with, you know, set times, it's really about tackling problems. And we just go until we finish the set of things that we have to accomplish. Uh, we order some pizzas or whatever else, uh, we decide for the day. And, and, but the goal is to align, go to market and product and engineering together, um, so that we're constantly in communication and sharing feedback and pushing one another. To me, and I've worked with probably hundreds of CRS at this point, I think that's the biggest differentiator is leaning in on that product side, leaning in on the engineering side,

36:25 not just saying, Hey, I own the quote, I own the number, you know, give me all the things I need in order to go do it, but saying, Hey, I actually need to bring that market feedback in, influence the product roadmap, influence how we're engineering something, and then bring that back to market. To me, that's always the biggest part where, you know, individual contributor to head of sales, you need to start empowering through people. You need to start owning a team, inspiring people to win on their own. And then from head of sales to CRO, you really need to take accountability for the whole company. I, I mean, especially

37:02 in startups, CRO is usually right next to the CEO, especially if you're doing anything like fundraising, if there's an exit, you're on stage and you're right there with them. So you need to be intimately tied to the mission, the vision, the strategy, and then taking that market feedback into it. Sounds like that's what you're taking on as, Hey, in this new role, this new mission, I'm really taking on more accountability on that side of the business. Um, I would, um, yes. And we're just going back to my improv days. Um, uh, when I think about it again, I, for me, I don't, I don't want to take credit for all

37:47 of that's happened there. I think our, when you look at the different teams and the people to me, it's more how do we piece it together to recognize that, you know, Cody, it's kind of funny. We laugh sometimes because we have a lot of these aha moments, which is traced back to like, yeah, I've been saying that for 18 months, that, that thing that like our long-term vision and whatever it is that we want to go and do, but, but it's one thing to have a vision. It's another thing to systematically think about all the steps that are required to go and achieve that. And I think, you know, we have too much of this, this gap between

38:17 the two of like where we are today and where we want to get and how do we go systematically? And so I think I've, I've, I've helped the team to communicate the, the kind of their, their parts in it and pull out what we need from, from each of them in order to, to do that so that each person can, can fulfill their best role within them. And it's, it's been hard and it's really been, I think where I struggled and I think a lot of stuff that created a lot of angst early on was, was not necessarily playing the right role myself or not understanding multiple people in the room. And, and now, you know, with this mental

38:52 clarity, it's been kind of funny because I was, we were in our leadership team meeting and often, you know, I had been the one who was sort of fighting a point and like wouldn't let go of a point in order to, because I thought it was right. And I wasn't necessarily hearing the other side. And sometimes it's like, no, you think you hear the other side and you just can't. But with the, with the clarity now and being able to focus, I found myself that I'm more often now the person that's hearing both sides and bridging them together. And it's, it's been kind of a really transformational sort of, sort of growth that is, that has

39:24 happened in the last couple of months that, that has really been empowering for me. Well, and where things are going, especially the market you're in, like infrastructure level AI, everything is changing so much. I mean, even LeanScale, when we started, so I, I was a head of RevOps for companies before starting LeanScale. I started in 2021. At the time, RevOps really meant like, hey, you're implementing Salesforce, HubSpot, and maybe outreach or something like that. That was kind of the crux of it. And now we're implementing cloud code and open AI codecs. And we're doing pilots right now where we're doing open cloud

40:08 implementations and like managing full blown AI systems. So as you're going through, you need to be able to keep that plasticity so you can evolve and update along the way. Or else you're going to be left behind. So I think, I think it's important that you have that mindset. You can hear both sides and then synthesize it into action and doing something with it. Yeah, for sure. And I, I, you know, kudos to you and the, the work your team has done on that. I mentioned to you the, the research you sent over on me and my background and my profile, like I would love to have it for my prospect meetings heading, heading into

40:45 it because you guys really put together something, something thoughtful. And I loved, you know, you followed up with the, with the storyboard and other ideas and the way that you've incorporated AI into your work. You can, you can tell that you scale in a way that you wanted to be able to do previously. So if you can get an extra podcast in or, you know, one, maybe 10 podcasts more because of the work that you're doing, you're using Riverside. Riverside is probably going to send me video clips after this that I can promote on LinkedIn. And, you know, their video understanding, right? Like the, the world is changing. The way that we understand

41:14 and view content is there going to be, you know, if you don't embrace it, you're in some, some trouble right now. So yeah, but I'm really, really impressed with how you've, how you've taken that on, Anthony. Yeah, I appreciate that. And it has been helpful, not just on, I think a lot of people think about the efficiency gains, but also I think even more important, it's helped with quality. So yes, I have an agent that does the guest research helps with the storyboard and that process comes up with details about their background. I never would have been able to

41:44 investigate on my own, putting together some really thoughtful ways to guide the conversation. That would be really difficult to do on your own too. So efficiency and quality. I wanted to go back to something for just a minute, if you don't mind, because, because when we were, when we were prepping for this and you were talking about the concept of, of market annealing, that was a new concept for me. And I, I think, I think at a high level the way explained it, like maybe some of the listeners will get it, but I would love maybe practically, in your own words, defining this is what market annealing is. This is when you know you need

42:26 to be doing this. Like, is this important for your business or not? And then what are some strategies and pillars that you have to shape the market? Like, okay, we, we know we have to do this. We know it's a problem, but then how do you actually do it? Yeah, it's so funny. I, um, uh, my, uh, Will, who I mentioned that the co-founder at Coactive yesterday, he goes, Oh, I have something for me. He came over at the end of our meeting and he, he gave me this, which it's a, it's a Yu-Gi-Oh! card, um, which I had a full, I played Pokemon, but not Yu-Gi-Oh! It is Josh's kitchen analogy. Um, so anytime you

43:01 need a good analogy, it says like, Josh will be there for you. So I feel like I failed in my, in my role the first time they asked me about marketing a new link. Cause the way that I think about kind of the process that we were in is, is we built this platform company and you can think of the platform almost as a, as a kitchen where we're really great at preparing foods of all kinds, right? We can take it any type of image or video data and extract value from that, right? We can extract signal from it, turn it into, into structured data. The, the, the challenges is that, you know, our, um, sales team, you don't even

43:37 think of it as like, as like waiters, we're out there talking to hungry people and these hungry people, you don't want different things. Some people want spaghetti and some people want sushi and some people want, uh, you know, steak and some people want lobster, et cetera, et cetera. And we would go back to the kitchen or, or chefs, the engineers and ask them if they could make these different types of meals. And sure enough, they would say, yes, like we've got the best kitchen in the world. We can make any of those meals. And so we'd go and we try to, you know, bring it back. But the thing is with the spaghetti, they want

44:08 garlic bread and with steak, they want mashed potatoes and with the hamburger, they want French fries. And even though that all sounds really similar, there, there's some differences in there. And so, so in order to like truly get value for them to be, you know, for the customer to be satiated, um, we weren't able to kind of fully hit that on each of those different buckets. Um, and so what we decided is we got our leadership team together and we thought about what do we, what do we grade at? Um, and what are the things that are there? We did double on the fact that, Hey, we've got a world-class kitchen. Um, and one of

44:37 the things, um, Satya, our head of engineering and head of product said was we need a killer application. Like if you take, if you take Databricks as an example, even though it's a great platform for, for streaming structured data and bringing that building analytics on top of it, it wasn't until they created notebooks that people could get instant value from it. So we were starting to think, Oh, what are all these different killer app ideas that we could do? And the, the where we landed was on this idea of context studio, um, uh, which allows direct sales teams for, for publishers to package their content and be able to, uh,

45:10 bundle it up for, for advertising use cases. Um, for me, that's our, that's our hamburger stand. So we said from a go to market perspective, instead of being waiters going out there, that we are going to be outbound 100% focused on this idea and talking. So, so that means from sales and marketing and how we face the, the, the world, we're going to go there to prove the concept that you can build a restaurant on top of our kitchen, which is ultimately what we want people to do. And so we've set up this hamburger stand. And now what we're doing is we're looking for people who are hungry, but they want hamburgers. And so we're

45:42 going to places where people like from an event perspective, like where do people hang out that want hamburgers? And it's more easy to find them. And it turns back and we bring back the orders. It's okay if somebody wants a square hamburger and somebody wants it with lettuce or tomatoes, whatever those things are, it makes it easier. And it turns out our kitchen is getting stronger as we do that. So it's going to be more likely we can go stand at the next restaurant. But our, but our chefs are really focused and we're delivering and our customers are able to get this thing. And, and it's been this really, really transformational

46:09 process as a company. It's, it's taken a lot of friction out. So you think about, again, the organizational clarity that it's created around how we qualify opportunities, how we preserve, you know, our time, which is truly the thing that's most important to us has gotten significantly better because we're out there selling hamburgers. And now if somebody wants to buy hamburgers, that's great. We can build the greatest hamburger chain that's ever lived. And we can get value or, you know, we can start to stand up these other restaurants, you know, on top or have our teach our customers how to, how to stand up their own. And it's

46:42 been, it's been really kind of eyeopening for us as a, as a business for kind of the approach that we take here. Is this mainly a defining your ICP and shifting your solution for that ICP a little bit, or is there something deeper going on with this whole process? Yeah. To me, I think it's a little bit more we're in the, in what we're doing, we're educating our customers. We still work with a lot of product teams that want to build their own application. And so we're showing them how easy it is to build this application. So it's a demonstration of what we do when you think about the long-term vision. If we're a platform

47:19 where people can build, you know, for product and data teams to create intelligent apps on top of their own structured content, to be able to show kind of prove the art of the possible in the, like, so we integrate with third party apps and people see some value and they get that, but being able to highlight that how easy it was, like we've, we're going to go from concept to application in something like six or eight weeks. I mean, it's, it's phenomenal. And that's the speed of what AI can do. Cause AI from like a UI perspective is easy. The stuff that we created around the platform, the infrastructure to be able

47:48 to process 9 million minutes of content, you know, before the end of the end of the year, like, uh, is really, really hard. So we built the hard thing and now it's about, you know, putting these things on top of it. I think we're going to be able to, to go to market. So yes, it's the ICP where we have clarity and we have that, but it also allows us to, to, um, to get to showcase this thing that we've, that we've created, um, which is you get, you get competitors looking at us. There's competitors that are like, Oh, maybe I'm going to buy that hamburger stand and just take that whole thing from it. And there's, it's,

48:21 it's really created, um, more optionality for us in terms of how we, how we advance in the future. Um, and, and allowed us to kind of systematically think through this end vision of, of being a, being a content platform. That makes sense. So it's not just the ICP part, but the, I think the big difference is inspiring the art of the possible, as you put it, um, because I think that can bridge the biggest gap. I don't know if you've seen open AI's like mass market commercials. They had some during the Superbowl. Um, I think their latest one shows somebody building a workout plan. And like, obviously like you don't use chat GPT just for a workout plan,

49:01 but that might inspire somebody to say, Oh, didn't realize I could do that. That's an interesting use case. Now I'll use it for all these other things too. Um, and I think, and when you're building something so infrastructural and like you are, then I think that makes a ton of sense to be able to show, Hey, here's some inspiration for what you can build if you work with our technology. Right. And part of it, what's, what's, what's been great about this process is it's also have this re rethink the commercial models. We've had some friction where, you know, if you look at the hyperscalers, if we're building

49:34 the, you know, the infrastructure here, it is a competitive tool. But if we make that more of a pass-through cost and then focus on usage based or value based, our customers get excited because they can come in at a lower kind of cost point. They can get value immediately. And then from our, we're, we're no longer sort of taking margin from our potential margin from the, from the hyperscalers. It's really a true partnership. So we're design partners with Amazon Nova. If you want to use Amazon Nova, we want it to be the same price, whether you use us or you use AWS directly for it. And so that removes some friction

50:04 in that process as well. And instead like where we should charge is the value you get on top of it. Right. And so we, that's where we've kind of focused that and it's been been really, really helpful. So I think one of the things like having the commercial model to map to what you're trying to accomplish that long-term vision has been a, has been a really key, key point. And again, I can't take credit for that. It's been through other people have on the team have suggested those ideas and it's, it's, you know, doubling down on it and recognizing and then going out and testing and validating it in the market has

50:33 been been really, you know, game changing. Well, there's a lot of annealing to be done in the market right now. And I'm definitely taking this back to my team as we move into, you know, lean scale is very well known for GTM ops, but as we move into more of the AI ops for, for companies that are scaling quickly, a lot of people don't know what that means. So I think I, we have a lot of that work to do on our own as well. And I appreciate you sharing the framework for it. Yeah. Thank you, Anthony. I'm sure you guys are gonna be wildly successful in your, in your pivot as well. I hope so. Josh, this has been really

51:08 great. I really appreciate you sharing everything. One, you've had a phenomenal career arc. Just such a diverse background, taking chances every step of the way. Even if you had some doubts just stepping in and leaning in any way. And I also really appreciate you sharing all of the personal side of the story. Cause I think that's something a lot of people have a tough time opening up about, but it's so important to the role that you have as a husband, as a father, as a leader in the organization that you're in right now. There's a lot of responsibility when you're in that position in life. And I appreciate you sharing all

51:46 of the ways in which you've helped get yourself in the best state possible to be your best for others. Josh, again, I just appreciate it. And, and thank you for taking all the time and just want to kick it to you if there's anything you want to leave the listeners with before we close up. Yeah. Thanks, Anthony. Well, I'd be remiss if I didn't plug a transparency sale by my buddy, Tom Caponi and his, so my, my, my view on being, you know, forward and transparent is really important to me in terms of the way that we communicate, including with things like mental health. And it's interesting how often like now, if I tell somebody, hey,

52:27 that I'm feeling well, they asked why. And I explained kind of the journey I'm on every single person I talked to relates to it. Every single person has some version of mental health that they're either struggling with or have just overcome or whatever it is. And even though it's a taboo subject, everybody can talk about it in a really easy way. So hopefully it becomes less, less taboo. But I guess if I had to leave on anything, I would say to me, there's a lot of parallels between kind of your individual clarity and how you think and how the organization

52:55 operates. And if you can help your, your teams to remove sort of any barriers that are stopping them from, from thinking clearly on their day to day, I think has, has tremendous benefit. I like to think of it as like a lot of people talk about technical debt. But the reality is you can build partner debt and customer debt and employee debt, sort of just the same by taking on too many things at the same time and not fulfilling those promises. So if you can, you know, restructure and, you know, help both the individuals and the organization to pare down the number of things that they're focused on, so that they can gain clarity, you know,

53:29 the whole system will operate better. And then you can layer in other things as you're kind of mentally prepared or organizationally prepared to take on those new challenges. I think in a world where we're filled with unlimited possibilities, unlimited information, the biggest competitive advantage you could have is clarity. And I think you've given us a lot of practical ways to achieve that. Josh, thank you so much. I appreciate you for being here. And I can't wait to follow your career and see what you do next. Thanks, Anthony. And likewise on your journey to the AI ops, I think I'll be quickly following

54:10 and learning from you as well. So thank you so much for the time today. Of course.