E28: Interns to Enterprise: How Cresta's CRO Built a Category Leader

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

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Hello and welcome to the Revenue Leadership Podcast by Topline. I am your host, Kyle Norton, CRO at Owner.com, and every Wednesday we take a deep dive into the strategies and tactics that drive success for the very best revenue leaders in the world. So, join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your day-to-day with no fluff, no platitudes, and no sales pitches. And I am very excited for today. My guest is Alex Kramer, who is the CRO at Cresta. And Alex is a longtime enterprise sales leader, and he's interestingly spent his entire career in enterprise. Which is very unique. And Alex was the first, was first an enterprise rep for 6 years before making his way into leadership at Dynamic Signal, which is now known as FirstUp. Then he was the VP of Sales at Cresta, VP of Enterprise Sales at Gong, and is now back at Cresta as their CRO for the last 2 years. And today we are going to talk all about enterprise. How do you cold start in enterprise and win your first customers all the way through to how to scale enterprise teams? Can you playbook it? And if you can't playbook it, how do you scale enterprise with some predictability? So I'm fired up for this one and appreciate you joining, Alex.

Glad to be here. Thanks, Kyle.

So I gave people the quick career snapshot. What did I miss that's interesting for people to know about you?

Yeah, I've had a I have had a pretty unconventional, I think, career path. And like you said, always been in enterprise, always been interested in enterprise. But, you know, I got my first sales job when I was in high school. I worked at a car wash and learned how to wash cars and detail cars. And, you know, I was the guy that when you pull up, is trying to upsell you to do the hand wax or clay and wax.

Yeah, yeah.

And then had the brilliant idea that I was going to drop out of high school. So high school dropout and started my own car detailing business, auto detailing business. Did that for a few years, learned a ton, and then realized that I didn't like vacuuming cars every day. So ended up going back to school and went to UC Berkeley. And I think what really kicked off my career in sales was my girlfriend and I, senior year of college, unexpectedly had a child. And so I needed health insurance. And so, Got a job in a boiler room environment, you know, 150, 180 calls a day, hardcore one-call close, high-pressure sales, selling websites to real estate agents.

Oh yeah, a real hustle.

Yes. But realized that I love sales, that I was good at sales, and like gradually kept getting into more, strategic sales environments, got really into startups. I've been in venture-backed startups most of my career, and I think accidentally got into enterprise. I was hired at a company called Extol in 2008. And by the way, should I just run in, run into this story? Is this—

yeah, yeah, yeah.

Got into a company called Extol in 2008, venture-backed. B2B SaaS company. And we were so small, I was obviously extremely junior and was told to focus on SMB and mid-market accounts. But there were so few people covering the world, I asked my VP of sales at the time, like, do you mind if I go after a few of these bigger ones? And ended up closing a deal with Walmart. So just sort of accidentally worked my way into larger transactions. And then I think in the beginning, I was unconsciously competent and was figuring out how to do deals from, from the gut. And just over the years, yeah, I have been in more sophisticated enterprise environments.

So would you say you just had a knack for it quite early?

Yeah, just loved it. Love the complexity. Love figuring out the political landscape that you're having to navigate, love building relationships and understanding how the companies work. And so, I just always have been more stimulated focusing on large enterprise accounts.

Yeah. It's funny you say that you were stimulated by the politics of enterprise because this is the thing that I tell mid-market sellers were like, should I go enterprise? Should I go into management? Like, what should I do? And the thing I explained to them about enterprise, I'm like, let me tell you about how an enterprise deal works. There's 3 people that want to do it. There's 2 people that absolutely don't want to do it. And one of those, their job might be on the line. And if it sounds fun to you to like figure out this puzzle of how to, you know, Game of Thrones this other organization to get your deal done, you're going to love enterprise. And if that frustrates you and it's going to feel like it's some external force that you can't control and that's going to be anxiety-inducing, then definitely don't go in enterprise because—

I think that's great. Yeah, that's great advice. It's definitely part of the game that you need to understand the political dynamic in these deals.

Yeah. And it can be a blast. 2 companies ago when I was selling enterprise. It can be really fun. And you're like, okay, well, what board member knows a board member there? And how do we trickle down to this other person? And it's a cool puzzle, but it is definitely not for everybody, I say. So really uniquely, you didn't really do stints in SMB, mid-market commercial, then work your way to enterprise. You've been selling enterprise deals since 2008. And so you have seen this market, you've seen this market evolve a lot. Before we jump into this like cold start in the enterprise, what do you think is different about enterprise deals today than when you were selling them 10, 15 years ago?

I think 10, 15 years ago was the end of get really high up, take them out to a steak dinner, wine and dine, and they're going to make the decision on behalf of their company. And that's that. I've noticed that, you know, over the last 15 years, there's just more and more consensus that's needed, more collaboration that's needed. And so, um, I think that hasn't been great for a lot of sellers who are very enter or relationship focused only. Um, I've even seen situations where you start at the CEO level, um, you connect at that level really well, and you still can't get the deal done because the CEO is just not willing to steamroll the rest of the company and say, we are doing this, period. And so you need to win at all levels now. You need to win at the user buyer level. You need to win at the, at the mid-executive level. You need to win at the C-level simultaneously. I don't think that that was totally true 15 years ago. I think you could come in and have a C-level relationship and just That's it. Make the deal happen.

Yeah.

Yeah.

I don't know if this is my personal bias because I am a, you know, like a new school seller, but it feels like enterprise today is like way more sales craft than it was 10, 15 years ago. And you have to have, like, your game has to be so much better than a while back. I don't know if older sellers would disagree with me there, but it feels like just like in sports how an athlete from the '90s would get, uh, would have trouble in today's NBA. It feels like that, that's a dynamic, like everything is just more difficult in enterprise.

I think, um, you know, when I look at how our top sales reps in enterprise today are going about their accounts and their opportunities, there's definitely a much higher level of preparation and sophistication than I remember in earlier years.

Yeah.

Uh, especially there's more tools available to help you do that. Uh, but I think that the— there's more common knowledge of what great looks like. And I actually credit, um, for me being at Gong, uh, just you know, everybody now has game tape. They're studying their players. They're studying what works, what doesn't work. They know how a meeting looks if you don't prep well. They know how a meeting looks if you're not studying the company's key initiatives and mapping them back to your, to your solution before you walk in the door. So a lot of the tooling, I think, has helped. But I would agree with you that the— it seems that the quality of selling has gone up.

Yeah. And all of the Challenger research and everything you see would support that. You know, the number of buyers involved in a decision, the number of even like touchpoints needed to generate opportunities. It seems like the level of friction is just up. But I agree with you, like the ecosystem is so much more sophisticated and, you Speaking of Gong, I just did a course with Chris Orlob. And, you know, you look at the P-Club material and like, where was that when I was a, when I was a seller? Like, I'm reading Jeff Gitmer's like Little Red Book of Selling and like all these Zig Ziglar stuff, like all this funny old school sales stuff. And, you know, like LinkedIn influencers weren't a thing, like courses weren't a thing. It's just you can, you can get so good now with, with a bunch of—

He is so good, by the way. Chris Orlob. I mean, there is nobody that just has the magic touch at making sales content like that guy.

Yeah. Yeah. I get hit up to do courses constantly and it's just not really a priority for me, but I did a course with them because I really like and respect Chris and I wanted to get SMB sales content in front of a bunch of sellers so that they can be like, oh, I should go work for this guy. Yeah. That's I have no idea if I'm going to make any money on it. I don't even know the commercials. I signed an agreement. I didn't even look at it. I was like, I just want to do a course and see what it does for talent pipeline. But I really only considered doing it with him.

Yeah. Great.

For IC stuff. All right. So we're going to talk, we're going to break this conversation into two overlapping and related parts. One, which is cold start in the enterprise. Interestingly, Cresta started straight into the enterprise, which I'm going to ask you about, which is extremely challenging. Like, how do you win your first deal as a pre-revenue startup with a true enterprise? And then I want to talk about scaling enterprise. Okay, you've got a couple of reps, you're closing some deals, but a lot of the time that's founder plus VP sales magic with a couple of reps who are just good, but like, how can you scale these teams with some predictability? Um, and, uh, that'll be tons of really interesting content. So tell, just tell, give the background of like Cresta's first deals and sort of this cold start story.

Yeah. Well, first of all, um, Cresta is a contact center AI company focused exclusively in large companies, Fortune 500 companies like Verizon, CVS, UnitedHealthcare use Cresta to make their contact centers operate more efficiently or generate more revenue. And company was started in 2017 out of the Stanford AI Lab. And it was founded by 3 individuals, the guy running the Stanford AI Lab, Sebastian Thrun, who was the creator of Waymo self-driving cars, founder of Google X. So tremendous pedigree in AI. And then two of his top PhD students, Zed and Tim, together were the three co-founders of Cresta. So I think that they had an advantage that not a lot of entrepreneurs have, which is this pretty unbelievable pedigree. Especially with the connection to Sebastian Thrun. So, um, there's many ways to go about starting an enterprise. Uh, I think that there were certain conditions that they had that allowed them to start this way, but it is a really interesting story how they got started. So one of the first angel investors in Cresta was Scott Cook, the founder of Intuit. And, um, when he wrote that first check, just based on the idea and some of the early technology that they built, Zed, the CEO, tried to pitch him on, hey, why don't you guys be our first customer? And Scott's response was like, basically, there's no way in hell that I'm going to give two PhD dropouts access to my customer data. And there's really only one way that maybe you would get access to that is that if you became an intern at Intuit.

Yeah.

And so the way that the company started was the two, the CEO and the CTO became interns at Intuit.

Wow.

And they and about 7 or 8 of the founding engineering team rented an Airbnb in Arizona outside where the Intuit contact center is located. And every single day they showed up to work in the Intuit contact center as interns, studying what are the behaviors that are happening inside of the Intuit contact center that they believe could be automated or augmented with AI. What are the What are the areas of inefficiency or opportunity? And so that's how they got started. And they realized at Intuit, it was actually in their sales center, they had identified— Intuit's an unbelievable sales company, and they had identified in there the 7 key behaviors that must happen in every winning sales call.

And Intuit had identified that already?

Intuit had identified that.

Okay. Yeah.

And the way that they mandated it or managed to it is every seller inside of that call center had these 7 Post-it notes on their computer screen that reminded them like, okay, reassure their customer they've come to the right place, do discovery, assume the sale, whatever the behaviors are. I can't remember exactly. And so the, the first iteration was— of Cresta was, we're going to codify those behaviors into a language model, and then we're going to, in real time, make sure that in every conversation the 7 behaviors happen. And as a result, we're going to increase conversion rate. So anyway, That's how you get— that is one way you can get started in enterprise is you could become an intern and go into the company. The point being though is you need some social proof because they went and did that. They made that wildly successful because every day they're sitting there and they were just making sure and fine-tuning and writing code until it worked, until Intuit was happy. They left the internship, they signed a, uh, the first customer was Intuit for Cresta. And then you take Cresta, and then you take— then you've got something, right? You've got Intuit, it pays us money. And so then you go to, um, and by the way, when you're working on that, Intuit is telling you, you need to have these certifications, here's how you need to treat our data, to the API docs.

Yeah, exactly.

And so that was sort of a shortcut to figure out what do we need to go build, what do we need to go do, um, which probably if you're just on the outside, nobody's going to tell you. You're just not going to know. Um, and then though, you can go to customer number 2, who is Cox Cable for us, um, Cox Communications, and you say, look into it. They're a smart company. Look what we were able to do for them. We can bring the same to you. And, and they had a head start with some of the documentation. So, and then you just go from there. You have to really figure out how you just get one in the beginning. And it's not easy. So, but that's the, that's the Cresta way of how we started from zero to having an enterprise customer.

And so if we zoom out and we say, okay, I started an enterprise company. I didn't run the Stanford AI Lab and, uh, have a bunch of PhDs. What are the macro lessons there that people can take as to a bit of a, a bit of a map?

I think first of all, you're going to need to get somebody who trusts you, who can become a champion, and then, um, you're going to need to do a lot of work to get ready. I probably wouldn't start with Wells Fargo or JPMorgan, but maybe there's a mid-level company that's a little bit more willing to take a risk and move fast. You know, maybe it's, it's Chime or it's DoorDash that has some bigger company recognition. They're willing to take a risk in exchange for the newest, you know, getting access to the newest innovation.

More forward-looking, more innovative. Yeah.

And you just slowly build from there one at a time. And it's an incredible amount of hard work. I remember trying to navigate our way through some of these security reviews when we have, we don't really know what we're doing and we have one or two companies and on their side, they have a few security people. On our side, we have like 14. We have the entire company sitting on the Zoom trying to figure out what we need to do, what policies need to be created. Hang up the phone, you know, stay up all night creating the policy and then, you know, come back to them. So it's just, it's just a grind to, you know, but you start with one, then you get two and you build from there.

Yeah. And one of the really interesting things is like the cold start problem in enterprise is so much more difficult as I think people are clearly going to understand. And that is actually a feature, not a bug in my opinion. There's like a Seth Godin book that I like called The Dip. And one of the macro takeaways is like whatever monumental challenge you have to go through to find success on the other side, like that's what he calls the dip, like the really hard part to get to, get to your outcome. That dip actually becomes the moat because now everybody else trying to get into what you're doing has to go through that same dip. And maybe they didn't have that same CEO relationship at Intuit. They didn't have the same pedigree to let a company like that take a gamble because, oh, well, it's 3 PhDs from Stanford's leading lab and you've got a Waymo founder type of thing. It's a feature, not a bug, which I think people sometimes struggle to understand.

When you're trying to get through that cold start, there's definitely going to be moments where you feel like this will never work. I should just— this isn't going to work. This isn't happening. But you keep fighting, you keep fighting, you get through it, and then it does become a moat. Because I, you know, I remember in the first few years, we go from Intuit to Cox Communications to Adobe to, you know, to other big companies. And all the while, our competitors, they're closing 1-800-GARDENSUPPLIES.com, and they just can't they can't get there because they didn't do the hard work upfront. And so it was a huge advantage for us to go and secure our places winning the enterprise in our category.

Yeah. And I see this as a common pattern as well with enterprise companies. You basically have to do free consulting for the first year, maybe even 2 years of the company. And it's going to look like that and feel like Man, we're just like a dressed-up custom dev shop. Like, this isn't even a product. But I think that approach of just embedding so deeply in that company is a way to make it feel like, hey, I'm not taking a bet on this fly-by-night startup. I have a group of multiple PhDs and all these great engineers working bespoke on a problem that I have. One of the others.

Honestly, that— I mean, that was not— like you said, not everybody has an AI PhD in their founding team. But I think that's really why these companies wanted to buy Cresta in the beginning. It was not because they believed we could necessarily solve a huge, um, mission-critical business problem that they had, but it was we This is an insurance policy for us to make sure that we don't fall behind the competition because we now have some AI PhDs in the building with us.

Mm-hmm.

And we can call them and ask them about anything, and they can make sure that we know what the latest and greatest is. I think at the executive level, that's how they were thinking about it. They wanted that access. By the way, maybe we're going to solve a huge problem and it's going to have big ROI, but I think that was the thing that, that got us the deals.

Yeah. Do you think you can cold start into the enterprise without massive pedigree and credibility walking in the door?

Best enterprise sales reps who I know that know how to do a large enterprise deal teaming up with a founder that doesn't have a, a pedigree and fighting their way through to cold start enterprise. They would know, here's what we need to do, here's what documents we're going to need to have, here's the 6 conversations that need to happen before we can get a pilot. And, um, but I think if you don't have either one of those things, it's going to be very difficult.

Yeah, that makes a ton of sense. Or you're just doing a ton of free consulting for a long time until you can really, really crack it. But also helps when your board is Ben Horowitz, Doug Leone, former CEO of AT&T, Sam Ademati. Like, this is a pretty— I think that credibility, as I'm like, thinking it through, I think you got to have some unique credibility to cold start the enterprise, or else it might just like never really work.

Yeah, if you don't, I, like I said earlier, I would probably recommend go try to close a DoorDash first. Yeah, you know, that kind of upper mid, mid-market, and you work your way up from there. That's probably the easiest, fastest. But if there's a way, it's a moat. If there's a way to start an enterprise before the competition in an early category, it does become a moat.

Yeah, makes a lot of sense.

And going down becomes easier than going up. Going down.

Yeah, for sure. And so when did you start? Like how many customers did they have? And I wanna talk about like your early journey and all this.

I started and the Intuit deal was done. That was it. One customer.

Okay.

So I remember it was an incredibly risky move for me, right? Things were going well at Dynamic Signal. I love the CEO over there. CEO loves me. We were winning deals. I knew I wanted to get into the AI space and learn about it. And this company was just so exciting to me. Cresta. I was reading Hard Thing About Hard Things, happened to be reading Hard Thing About Hard Things, and I got reached out to to meet with the CEO, Zed, of Cresta. And part of the interview process was that I got to go meet Ben Horowitz and interview with Ben Horowitz. Cool. So it was just personally interesting, but I knew that joining A, at that time they hadn't even done Series A, pre-Series A startup working for a CEO who, this is his not just first time as CEO, but first job in a professional setting. I remember telling my friends, you know, 94% chance that this does not work out, but I'm going to do it anyway.

And it sort of didn't.

Like, it sort of didn't. That's right. Yeah. I ended up, not working out and leaving the company and going to Gong. But, and then, you know, had a great ride there and then coming back. But yeah, you're right. It sort of didn't.

Yeah. And then the, so, and then they, so new CEO came in, reached back out to you. How did that all come to be?

Yeah. So, well, first of all, Maybe even before we get there, I could just talk about the journey at Gong because I think that stint at Gong made me such a better leader. I saw what great leadership looked like. I learned so much in my time there. I learned a lot observing our CRO, Brian Longfield. I learned a lot observing our operational rhythm, you know, how we, how we do one-on-ones, how we do performance reviews. Having been at smaller startups, I had never really seen a really well-run company. I think Gong is very well run. So learned a ton at Gong. And then when I came back for the second time, I felt like I was, I was much more ready.

Yeah.

In 2020, end of 2022, 2023, I can't quite remember when ChatGPT happened.

End of '22, November.

Yeah. So ChatGPT happened. We all had that moment where we realized that the future is now. And I realized that contact center is gonna be the first place that gets disrupted.

100%.

So contact center is much bigger than I ever understood. It's $500 billion a year gets spent on human agents. Wow. And the work, you know, if you're, for most agents in the contact center, it's a stepping stone career. So you, it's their first job outta college. It's, you spend 6 months getting trained up, just about the time you're good, you're ready to go become a real estate agent, go do something else, get promoted, whatever it is. So the $500 billion is also incredibly inefficient in terms of the turnaround and manual conversations one-to-one and typing notes and putting them in a CRM and looking things up in a knowledge base when you don't know the answer and then coming back and, So it was clear to me when this ChatGPT moment happened, like, oh, Cresta, you know, best contact center AI engineering talent on planet Earth at a time when AI is having a revolution. And this is going to be their moment. So I was sort of, I was at Gong, but I was watching Cresta thinking about, man, that company is going to go gangbusters. And And then I got this random reach out from, from Ping Wu, CEO of Cresta. And he, he took an Uber from Palo Alto up to Mill Valley where I was living 2 days in a row to, to meet with me. And we just hit it off. His energy is so unbelievable and infectious and he's such a brilliant product and engineering thinker. So, I fell in love with the company again and he wanted me to come back, which by the way, there was some personal satisfaction in having that trust from him and from the board. And so, yeah, I decided to come back to Cresta.

Very cool. So then, I want to go back to early Cresta. And so you have this one Intuit deal, maybe it's like starting to get properly implemented. You— so talk to me about winning the next couple deals. Like what were the most important things to get those next few deals on the board?

Every single one was a knife fight to the death and the deals died 3, 4 times before they finally closed. And they, by the way, they're still like that. Every, every deal is incredibly hard. But I think the other thing that we did to compensate for how small we were and how inexperienced we were is we were very, very sharp with our ROI and our business case. So we would essentially go in there and we would say your top performing agents are 10 times as good as your average agent, whether that means from a care perspective, their efficiency, or a sales perspective, their conversion rate or the revenue contribution. And we're going to study what they do differently, codify it into AI, and then in real time, we're going to make everybody as good as your best. And in doing that, we're going to increase your revenue by 10%, and we will prove it to you for free. With an A/B test.

Hmm.

And so the value prop was hard to resist for companies, and we put our money where our mouth was. These were intense 30-day A/B tests. On our side, you got 14 engineers. On their side, they got their data science team. And, um, I think had we not had such a sharp ROI-centric value proposition, it'd be hard, but we would do that. We would win the A/B test and they would have but no choice to move forward with us. And so that's how we started in the beginning. Really, really focused with sharp ROI. Over time you realize—

You must have done crazy discovery and like qualification to know if you wanted to spend 14 engineers' time for 30 days.

We had narrowed the entire world down to 80 companies that we knew we were going to be able to make successful. Um, and then, you know, we couldn't get appointments with 72 of them.

Yeah, exactly.

So then there's 8, you know, but you didn't need many to get to the next level. Like, you know, at that price point, we're, you know, we need, we need 5, we need 5 or 6. Yeah. So that was the mission. Go get 5 or 6 of the right.

Because these are 7-figure lands and scaling to 8 figures plus, I would guess.

Yeah, that's right. Cool. But yeah, so that's sharp ROI. But by the way, that really sharp ROI becomes a problem later on because if they don't view you— if they— if you're so focused on only that ROI, you almost become like Google Affiliate Network where every single month they're like, how many sales did you deliver for us this month? And they forget about all of the software utility and the workflows that you're solving and the way that you're making the life, life better for agents. So slowly we've really had to broaden that ROI beyond just the return that we give to you. We also, you know, you're going to get better customer experience, better employee experience, and, um, And so that was an interesting learning. In the beginning, very sharp ROI, but now we don't run the play as hard in that way.

Yeah. And because as you get to a certain credibility and size, you don't need to do a 30-day crazy A/B test because you've got 10 of the biggest contact centers in the world with great examples.

Hey, talk, you know, we get the best results in the world, period. Talk to Verizon, talk to Cox, talk to CVS, talk to UnitedHealthcare, and they're pretty smart. So yeah, you can start to get away with more of that. We still do have to do pilots. We still do have to do tests, of course, but much less so than in the beginning.

Okay. And so, winning these first early deals, really sharp ROI, you clearly narrowed down your market to only people that you knew that were great fits and you could help. What else was key for you landing these like first handful of deals, would you say?

We're going to get back into traditional selling, but a very, very strong champion. Was essential and knowing their business cold was essential. So early on we would ask, can, will you, you know, we sign an NDA, will you let us go spend a day or two observing your operation, your call center operation? And we're gonna study what people are doing. We're gonna come back to you with a point of view on how we think we can help you save money, make money. So if we could build up enough of a champion that they trust to let us do that. So it's annoying for them to organize that.

Yeah.

And we can learn enough to build a sharp point of view and then put together a proposal that allows us to win a deal.

Yeah. Just the business acumen has to be off the charts.

Yeah.

In general in enterprise, but especially in early enterprise.

You have to know their business cold.

Yeah.

Who their competitors are, how they make money, what they're worried about, what the CEO's worried about, what the head of the contact center's worried about, what the agents are worried about. Yes, you definitely need to go there.

And how much of that is publicly available information? How much of that are you getting through discovery and through this audit process? Where were you going to stitch together that opinion?

A lot is available publicly. It's amazing how much you can figure out. I mean, especially now with, uh, with the AI tools.

Yeah.

Uh, but back then you actually had to read, uh, read the website, read the 10-K, read the news about the company, figure out a, a point of view, figure out what the CEO cared about and therefore what all the executives cared about. And, um, But you definitely needed to do that too, even before you get to the first meeting.

Yeah.

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The next time I'm in San Francisco, I want to hear about the stories. I'm sure there's some crazy stories of deals, deals dying, but I want to get into scaling enterprise and have enough time for it because this is something that I personally struggled with at League when we sold enterprise. I was personally involved in all of the biggest deals. It really didn't feel like we were doing a ton to build a lot of repeatability. And I don't know if that was because of our stage or, you know, the product market fit was very different than the crest of strength of PMF, but do you think you can playbook enterprise? Like, can you build structures and systems to say like, this is how we get deals done? I think that's the best question to start with.

It's a great question. So I'm in a hotel in Chicago right now. We just had our whole sales leadership team fly out and we're talking about our business and how we get better. This was a topic about, you know, one of the leaders was saying we need, we need a detailed playbook. And, you know, the consensus is that in the large enterprise that we, we don't think that we can do that. Um, we think that we can build— so we certainly have a sales process, and when I train the team, it's everybody follows this sales process, but but you do have the ability to deviate. If you deviate, you have to have a good reason why you deviated. Um, and I think that we have, we have plays that are proven, but I'm very hesitant to map out a very specific playbook. You need to hire smart people that come in and can assess the situation and be nimble. Um, otherwise you're going to have it— for us, you're going to have a playbook that's has 450 chapters and if this, then that, you know, if they have this incumbent, then you're going to run this play. And then if they have this other incumbent, but they're 2 years in, but it's on-prem, then you got to run this play. There's just too much variability, I think, in the deals that we didn't feel like we could write a playbook that just says, do these things, say these things, and then you're successful. So in that environment, what I've learned is I put most of my energy into making sure that I hire A players.

Mm-hmm.

And that's the most important thing. It relieves so much pressure on our enablement, on our operations team, on our frontline leaders, um, on the need to, to build very specific playbooks that tell you every single step, what to do or what not to do. And so I think over the course of my career, that's one thing that I've learned is spending much more time making sure you get A-players only in your business.

Yeah, I want to come back to that topic, especially as we talk about sort of the pillars of an enterprise team. I want to unpack. So talk to me about like how you define what's a sales process and like when does something become a playbook in your mind? Like how much structure is in this? Sales process? Like, what have you given to people as the outline, and where are they, where are they figuring things out on their own?

Yeah, like, for us, for us, a qualified opportunity is you've identified a problem that we know we can solve, you've got, um, a champion, and you know who the executive is that would need to say yes. That's it. And then they take a next step with us. So that's the beginning of our sales process. We have a couple of discovery meetings that focuses on both technical and business discovery, current state, business problems, how, you know, initiatives map to a contact center environment. We then have, you know, custom demos and probably 4 or 5 or 6 different custom demos for different types of buyers. And then from there, we split into a technical track and a business track. We have to go get the technical win, that's security reviews, that's IT, that's integrations. And then we have to win the business track. That's what's the plan? How do we roll out? What's the ROI proposal, time to value, all that kind of stuff. And so we, that, we give that to, um, our team and we enforce that, but it's not really a playbook where we say when you encounter this competitor, this is what you do or say. When you, um, uh, so it's more of kind of a loose framework for how to run your deal and how to push things forward. Yeah.

And how do you share best practices? Is so, because you've got a bunch of super smart sellers that are probably that are doing things that are unique to a deal that then you want to scale, what's the process for spreading that across the team?

So first, we're Gong users, so I'm all over that. Our leaders are all over that, listening to calls and trying to highlight what good looks like. Every week I have a loose agenda Alex's office hours where we just come in and talk about deals. We talk about objections that we're hearing. We're talking about successful meetings that we've had. And then it's the job of our frontline and second-line leaders to surface those things. Like I think a big part of their job is you need to be in the field, in the business, studying what's working, what's not working, what do customers care about, what are the objections? And then you have to bring that back to the rest of the company so that we can share it around. So I'm pushing my leaders to do that. I'm pushing the sellers to do the same, to feel comfortable, confident, even if they haven't put points on the board yet, that they're posting in Slack or sharing. And then lastly, I task the enablement team to be looking for these nuggets and to be resurfacing them and constantly doing enablement and highlighting, highlighting good, highlighting bad, doing win reviews, doing loss reviews. So, yeah, it's many things put together to identify the winning playbook.

Yeah. Are you using AI for any of that to try to pull out— I don't know if you maybe don't have the sample size, but can AI pull out any of these types of trends, do you find?

I mean, in a way, Gong is doing some of that for us.

That's true.

We're using AI and really very increasingly more interesting and useful ways, but I wouldn't say we have cracked using it for that yet. Yeah.

Mm-hmm. It's interesting in SMB because we get in any given week 400 to 500 calls run, like demos run. And so you can apply data science to that pool and really figure out like, you know, what makes one of the analyses we've done lately is like, what is the perfect amount of time to call a lead when they submit a form? Because, you know, your instinct would be like, call right away. As soon as they fill out the thing, like call immediately. But depending on the channel, actually calling right away led to lower win rates because maybe they've filled out a form, they're in the middle of reading something now. They filled out a form to get a piece of content. Or analysis and they're only like 30 seconds into it, they're not ready to book a meeting. So there's actually certain channels that we delay the BDR or the SDR calling for more than 5 to 10 minutes. And it's—

5 to 10 minutes is still pretty fast.

Oh, well, yeah. Yeah, we, my style of, revenue building is, is like very operationally centric. And so we're, we are like tightening the dials on every little piece of, of the machine. So like time to first touch, we're going to find that exact sweet spot. And for certain lead types, it's like as soon as that lead comes in, like we are, there's triggers firing in Slack to like push, push that lead to the person. We're trying to interrupt their workflow that so that they get it. but even like what is the optimal number of opportunities per month per account executive? So you take a fully ramped account executive, you know, you could give them 60 or 80 in our case, because these are one day, these are like one call closes much of the time. But at what point do they have so many opportunities that then the win rate starts to slip because they, they're just too busy. But, but, you know, like, and so whether it's Gen AI or ML, like, you know, all of these things work so well in this SMB environment, but definitely different in enterprise. I'm, I'm, I'm curious.

Yeah, I mean, for us, the way that, the way that we think about that, first of all, our data team has done a really good job of identifying what are the winnable accounts, what's our ICP. If you're, um, Most of our org is strat. We do have a, a new enterprise segment, which is just one step below. But for a strat seller, you're going to start here with 15 to 20 of those ICP accounts. Um, you're going to tier them into your top 5 or 10, and you're going to be laser focused on, in the first year, getting one of those to convert, 1 or 2 of those to convert. And the— once you do, typically what happens, let's say you come in and you close Wells Fargo in your first year. Now your job is changing a little bit. You're— now your job is to expand Wells Fargo. So we're going to trim your account book down from 15 or 20 to 8 or 10. Then you go after that, you go close Marriott. And now, now you have Wells Fargo, you have Marriott, you have 4 others, and pretty soon you work your way into a strategic account manager business. Some reps say not interested and we can move the account, but then we have best practices for once you have an account, what do we expect from you? You know, you need to understand the white space of the account. You need to understand the leaders over every every potential buying area, sub-brand, region, business unit. And you're, you're spending your time now much more on that account. So that's how we've scaled it. And you make room for more and more books as you have success. You're kind of, you know, you're taking some accounts away from people and making room for new reps to have full, full territories. Yeah.

Because even when you're selling into an existing account like Wells Fargo, it's still basically a new business sale. Like it's just as hard, but you've got an MSA and security done. So you're starting on, you know, maybe first base instead of in the dugout.

These accounts are shockingly large, especially in the contact center environment. There's just so much to go after. So you can't, And I think when you're new to Strat, getting accounts taken away from you, um, you're, you're typically not thrilled about that. But what I think the more experienced sellers have realized, that you make the most money when you're focused on just a few good ones.

Yeah, because you're not going to win a $10 million deal on the first contract.

Typically not. Yeah. Maybe if you're OpenAI, but for everybody else, likely not.

Yeah. But, you know, if you have a use case in the credibility and in legals and security done, you know, you can start to roll it up into something that's true enterprise. And that's the dream of an enterprise seller is like you do a bunch of years, you make really good money, you make $300,000, $400,000, like chipping away at your quota. But then you got that one year when you roast your number by 4x because you've got Wells Fargo that does something across every center in North America and all of a sudden you've cracked like that million-dollar year.

That's year 3. You know, typically it's year 3. Some reps can do it in year 2, but usually year 3 is the million-dollar W-2 year.

Yeah. So you've got some million-dollar sellers.

We do. Yeah.

That's cool. Hopefully some enterprise reps are listening. Yeah. It's for, because at League, a bunch of my team graduated out to now they're at Snowflake and Splunk and Salesforce in strat roles. And so, and I keep in touch with a bunch of them and the advice I give is like, look, like, You know, you have your baseline years where you just like, you got to hit your number, exceed by as much as you can. But like your main job is looking for your mega whale. Like that's the thing in your existing accounts. You're trying to figure out how you roll this thing up to the, like you're hunting for your 4x quota attainment year. And it's such a different mentality than even commercial or low enterprise.

Well, look, when I'm looking at resumes in the strat space, I can totally understand in a more SMB rep, you're moving, moving around to different companies every year and a half, 2 years. But if you're a strat rep, doing that doesn't make a lot of sense because it doesn't really get good until 18 or 24 months in. It doesn't get really good. So if you're leaving every 18 months, you're just— it's brutal. Your life is brutal.

Yeah, you're starting with a cold book, starting over and building.

Yeah, exactly.

Not knowing— like, you don't even know the— you can't even really sell sometimes. You're pretty useless in enterprise for the first 6 months. You don't know enough to have any credibility, or your solutions engineer plus your VP is doing most of the selling for you. Yeah, I very much agree. So let's, uh, before we get into the hiring topic, which I want to unpack, so back to this idea of like you can't really playbook enterprise, but you can definitely build a process in terms of building an enterprise machine or scaling enterprise, going from a small handful of reps to now multiple reps across multiple territories. What are the pillars that you need to build in terms of your foundations?

So I'm very lucky in that I have a partner, Russell Banzon, who I believe was the true secret sauce magic behind Gong's marketing. He was the VP of marketing at Gong, ran all their demand marketing and eventually ran the whole thing. And he came over to Cresta. He's our CMO. We have a lot of trust and respect for each other. So you need to have a partnership like that. You need to understand where your pipeline is coming from. So we know exactly, for Cresta, we know exactly where the pipeline is coming from. How much is coming from AE self-source? How much is coming from partners? How much is coming from events? How much is coming from inbound? How much is coming from SDRs? And then how much do we need to hit this quarter, next quarter, and the year? And so, you know, we're constantly looking at that. You do need that machine to be there to understand where you are. And I would say that's the first most important piece.

Can you generate pipe? Yeah.

Yeah.

And how much is AE self-source?

For us, it's 25%.

Oh, interesting. Okay, cool. So you need pipeline and the pipeline math, talent, which we're going to unpack even more. What are the other key things that if I've got, if I'm a $5, $10 million enterprise-oriented business that I'm like, okay, these are the units I need to build now to scale to 50 or 100?

If it's a very technical sale, you need sales engineering. So we have a sales engineering function. We have a few different types of roles. We have core sales engineers that get the technical win. We have strategy consultants who are helping you get the business win. Studying the company, building the plan. Here's the first 90 days. Here's the first 180 days. Here's the ROI. Here's, you know, how you're going to get people to adopt. We have solution architects. That's more complex integration design. Or sometimes we even have 4 deployed engineers who are going— they're, you know, fully capable engineers that get assigned to the account and they're going to build software with the customer. And so all, yeah, all of those pieces are part of the sales team.

Hmm. So sales engineering pipeline, you've got some, you've got your sales methodology would be like a, something that you need to get mapped.

Yep.

Anything else that you think people need to think about building if, if you, if they were a stage or two behind you? That they should be thinking about?

It depends on the business. Yeah, I guess, you know, you need customer stories, you need success. Um, that is a big, big part of our selling because in our environment it's incredibly competitive. The second that you come out with a winning feature, Salesforce announces it 10 days later.

Hmm.

Somebody might not be built yet, but it doesn't matter because the customers are too confused to know the difference anyway. Look, they said they had it, you said you had it, I saw videos, it all looks the same. Um, and so you don't really want to wallow around in the mud fighting about my AI model's faster or our transcription is 2% better, this or that. I like to sell pretending that we all have the same product, but we're going to outsell the competition. We're going to be better prepared, better relationship building, and sell with our customers. Tell, tell our prospects that we get the best results in the industry, period. And here's how we do it. And I'm going to introduce you to 3 customers that are going to tell you the story when you're ready. And to me, that's the most powerful thing. Without that, we'd be in big trouble.

Yeah, yeah, yeah. That's so much of an enterprise. So I want to come back to this talent topic. So, you know, you mentioned most of your energy goes into hiring A-players. What are you looking for in a great, like, true enterprise strat rep?

So we're making multiple bets in that area. We have a few reps who, you know, if you study our LinkedIn page, you'll see very seasoned, 20, 25 years in the industry. They know everybody, but maybe they don't know how to use ChatGPT really effectively to build an account plan, right? We have other reps that are more rising stars that are willing, they're still willing to break through walls or sneak into a conference, like whatever it takes to get it done. But they've never seen an 8-figure deal. And so those are ones where you go to the frontline manager and say, you're going to have to, you're going to have to really lean in here. You're going to get certain things that are magical and special, but you're going to have to lean in and co-run the deal probably on some of these. And so, yeah, we make multiple bets at the same time, all sorts of different profiles. It's not one type of seller. And I think it's Doug Leone at Sequoia. He always says there's many ways to heaven. I see that as true with who you hire and the profile of the person or the profile of the leader that we've been able to make successful.

And so then what are the common traits or skills that you're like, you're really zeroing in on? Or is that two different hiring scorecards for your seasoned reps?

No, look, look, you, you, This is, this is complicated, fast-moving, innovative, political selling. You better be smart. So I wanna see that you are generally intelligent, that you, you know, I wanna see how you write. Mm-hmm. And that's a base qualifier. I, I think that the job is too hard if you don't really wanna be here. So I like to test for, you know, why do you want to work at Cresta? What do you, what do you see in us that makes you believe that you want to be here? And are they thoughtful about that? I'm going to test their past performance. So at some point in the interview process, we will ask, walk me through your last 5 years of attainment. How'd you do? What was your quota? And then later we're going to ask them, now tell me the specific deals that you did that led to that attainment. And then we're going to dig into the deals and then we're probably going to backchannel to make sure that did they really do those deals? You know, um, and, uh, so that's one part of it. You have some experience, you've seen these deals before. Um, we'll make a few different bets, but I generally like people that are selling applications to business buyers rather than deep technical solutions to, to engineers. Just my own preference. Um, and then, uh, the last thing is we actually very rarely hire just through recruiters or cold outreach. We try to hit these pockets and we've been successful hitting these pockets where, you know, we get referred to one person. They were a top rep at this company. They came over in the first few months of their tenure. You know, they're not going to close a deal, but they still want to prove value. So we're pushing them to give us some references and we're pushing like, hey, who are the top 3 reps that you ever worked with? Who are the top 3 reps at your last company? And so we have been really successful hitting these pockets of like, you know, 4 reps at a time.

Yeah.

We had the Medallia pocket, we had the Qualtrics pocket, we had the Yext pocket, we had the Sprinklr pocket. And so that's been a huge shortcut for us. And then the other beautiful thing about doing it that way is everybody's sort of backchanneled. We know what we're getting, and then they come in with a buddy. They come in with a support system. So that's been something that we try to do. You can't always do that, but we push to do that. And then the final one is just grit, motor. How, how bad do they want it? If they get told no, do they fight through it? Are they okay? Missing their number or are they devastated by that? You try to test and see what's their motor and their level of competitive fire.

Hmm. Yeah.

Yeah.

And that can get hard to, it can get hard to find in enterprise because many of the most successful sellers have been in their current company 5, 10 years because they've got an awesome book. They're the guy or the girl. They get the inbounds and the bluebirds and the CEO specials. And so like finding people that are willing to go do something new and still have that drive, that's a tough one in enterprise.

When you find an all-star enterprise seller, it's in itself an enterprise deal.

Exactly.

There's reps who we've been keeping in touch with for years, um, and checking in on. And it's when you've done that and you have that bench that's warm, then you're right, if they're making a million dollars, it would be silly for them to start over and build. But, um, sometimes, you know, not every company, but a lot of companies it's just there's a moment when you can't make the million dollars anymore and things change and there's a new leader. And if you're top of mind in that moment, that's where you can find the A-player.

Yeah. I mean, you're an interesting example. You know, the ChatGPT moment happens. It's like, oh, this is great for Cresta and horrible for Gong. Like, you know, the call transcription being democratized overnight was like not great for that business, obviously. And Cresta ends up with you and your CMO who you gave a nice shout out to, Russell, you know, that's a winning strategy. Your pockets, it's funny because even in SMB, your pocket strategy is similar to what I've done. You know, I've got 4 or 5 reps now from Bench, well, like a director and a handful of reps from Bench, pocket from Touch Bistro, a pocket from Levelset because they got acquired. So, I pulled a bunch of people over and you and those folks have all done great because they're so low risk. You really know what you're getting. Okay. So, let's get into quickfire so I don't run out of time here. What do you think separates a good CRO from like a truly exceptional one?

I think there's many ways to do it. There's lots of different types of CROs that I've run into that inspire me. I think some of it is luck. I'll be honest, some of it is luck. You have the right CEO, you have the right company in the right moment because there are incredible CROs that I know that were at not great companies, but had they just been through luck, had they been at MongoDB at the right time, you know, they'd be known as the greatest. So some of it is luck. You get the right company, you get the right situation. Who knows?

Luck in company picking. I know a lot of CROs who are brutal pickers and it's, Too bad.

It's hard. It's hard to find a good one. But, you know, what makes Tom Brady better than Alex Smith, right, as a quarterback? There probably are some things about Tom that are unbelievable, but also he happened to be on the Patriots and he had the right coach, he had the right, you know, so some of it was luck. But I would say you got to have an unbelievable motor. It's a job that just never stops. And so to me, the best CROs have that motor, have that fire. They have a support system. I could not do my job if it weren't for my wife being supportive. I have 4 children, and if she wasn't very supportive of me and my career and being in this role, it wouldn't work. I'd be, you know, overconsumed with guilt and I just wouldn't be able to do the things that I need to do to be— to make, make things work.

Couldn't agree more with that one.

You need to have a, a great CEO who understands what it takes and is supportive of you. So it's not all just about the person, but look, the best CROs, it's just astonish me with, with the motor. Uh, they can take a million punches and they still are getting up at, uh, you know, a lot, a lot. I don't do this, but a lot of zeros, you know, 4:30 AM, they're biking 27 miles. Um, and they go to the gym and then they have the Power Smoothie. And like, you usually, you have just like a, um, superior, uh, you know, you have a lot of athletes because it is, um, grueling. So you got, you got to have that motor. You got to have the endurance.

Yeah.

I think also balance. Um, great CROs have balance and they aren't fluctuating between 10 and 0 in terms of their temper when hard things happen. They can weather them and control the weather for the company. And when great things happen, they're excited, but they're, you know, they act like they've been there a little bit, right? I think that's important.

Yeah.

So all of those things put together— some luck, some just, uh, biology, uh, motor intelligence, uh, yeah, hard job, definitely.

What's the most common advice you find yourself giving to emerging leaders, mentees of yours?

Be yourself. I think early when I was a leader, I would look at other leaders and struggle because, gosh, I don't know how to be like that. They give the great rah-rah speech every morning at 7:00 AM and getting everybody fired up. Fire your chair and start screaming. And I don't know how to do that. That's not me. But eventually I realized that you don't have to be like that. There's lots of different ways to inspire people and lots of different— and if you're trying to be somebody else, if you're trying to be the intellectual, but you don't have time to read 3 books a week, then you're gonna, you know, it's gonna show up as phony. So figure out what your style is and be that. Yeah, I think that's probably the number one thing for a new leader coming in is don't think that you got to look like your last CRO.

And people are allergic to inauthenticity and phoniness. Yes. So I look— that's why people don't like LeBron. You know, he's like, he should be this incredible, amazing thing.

I love LeBron, honestly.

Yeah. But he has a lot of haters for somebody who is so great and is a good family man and seems to like really have it all together. Like, why don't people, like, why, how could anybody not like him? Well, 'cause he's a phony.

Yeah.

That's, you know, he's pretending to read books and like, you know, pretending to be this thing and he's, you know, then does things outta character. I think that's a great lesson. He is a great lesson for CROs 'cause, you know, you can be trying to do all the right things, but if it's not you, people can see through it.

They smell it out.

What is the hardest lesson you've had to learn?

Um, there's many of them. As a dad of 4 kids, there's probably, probably something in there, but I'll keep it relevant to business. I think I've learned a lot of lessons over the years about being in startups, just about equity, about, you know, fundraising, about equity. And if you're, you know, I was at Gong If you're valued at $7.25 billion by— and you're fundraising, does that mean that the company is worth $7.25 billion actually? And understanding the difference between preferred stock and common stock and, um, exercise windows, I, I think that there are so many startup employees who will say that they're in it for the equity, but they don't understand how the game works. And there's a, there's a tragic hard lesson that's gonna be— that you're most likely going to learn at some point. And I've learned, yeah, um, playing in the startup game.

Yeah, taking money off the table, usually a good idea.

Usually a good idea.

Yeah, yeah, negotiating harder. Negotiating harder than anything else for equity terms. Honestly, the amount is irrelevant if your terms suck. Like, you know, if you're exiting a company and you're sitting on, you know, 10 or call it 50,000 options and they're a couple bucks a share and you have a 90-day exercise window, like, can you come up with $300,000 right now for—

And by the way, you don't have all the information to make that decision. And you're not gonna get it. You're not gonna figure out what are all, you know, every permutation of the cap table and the prep stack. And, um, so yeah, I think these are some of the things that, um, uh, there's a lot of education that needs to happen there. I've learned some hard lessons there.

That's a good one.

And, and also, if you're not a top executive, if you're not, you're probably not going to get a 10-year exercise window. You're not going to get all these things. You're not going to get the single triggers and all that stuff anyway. Um, so just, there is a very good strategy to go work at, um, a publicly traded company and just keep your head down, and that equity is real money that you can spend every quarter. Yeah, might, might not align with your, um, you know, with your values or your, what your soul wants, but Yeah. In terms of money-making, there's a lot of lessons to be learned there. Yeah.

Yeah. My Shopify equity was very real compared to my previous startup equity, even though you wouldn't think it. Last question before we wrap. What's the best thing you've read in the last 12 months?

Look, 4 kids, CRO job, don't have a lot of time to lay back and read, but I, uh, toward the end of last year, this is gonna sound funny, but I got COVID and it was the most relaxing thing that's happened to me in a long time. Like my kids weren't allowed to come in the room. I actually stopped working for a day or two and I, um, I read a book called Endurance, which was incredibly interesting book. About Ernest Shackleton.

Oh, I— this has been on my list.

Yeah.

Yeah.

So Ernest Shackleton was a British explorer. I don't know if he discovered Antarctica or if he was one of the first people to go to Antarctica. But anyway, this book is about one of the expeditions headed to Antarctica with his crew, and they get locked in sea ice.

Yeah. Yeah.

And when this happened, when you get locked in sea ice, like basically the boat explodes. And him and a group of 25 of them walk on sea ice for 18 months.

It's crazy.

Eating penguins and, and not one of them died. And they eventually got rescued 18 months later. So it just kind of, it was a good reminder that Q1 isn't that hard, actually. Yeah, it's not that bad. Yeah. So yeah, but I really— it's one of those books that you— I, I think I read it in 2 days. So yeah, definitely go read it.

That's a great note to end on. Well, this was great. I'm super, uh, excited that we dug into this topic. I learned a ton. Um, and so appreciate you joining, and everybody can go find you on LinkedIn and If you want to make $1 million as a seller and sell the best product in the category and learn from an absolute gangster, hit up, hit up Alex Acosta.

All right.

Appreciate it.

Thanks, Kyle Norton.

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