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RevOps Journey: From Startup to Exit and Beyond

Featured Resources:

The GTM Growth Model

Mark Lerner:

All right, Anthony, welcome back to the Revamp podcast. I think this might be the first time we’ve had a guest on for a second time. You joined the podcast with my colleague, Gideon. I think I was looking at it just now, in August of 2020, which seems like several lifetimes ago. A lot’s

Happened since then. A

A lot’s happened, I’m sure, with you, with the world, a lot’s happened. So I guess we can, for the folks who are watching this or listening to this that hadn’t seen that episode, maybe we can get a little bit about your background, and then we can kind of talk about where we left off last time and where things are going now.

Anthony Enrico:

Yeah, yeah. Happy too. 

Well, I have a pretty eclectic background in B2B technology. Spent a lot of time in sales, marketing, and customer success, and then I found my way into Rev ops. So Rev ops is what I was doing in all the other roles. I just didn’t know it. And then finally somebody put a name on it, and then I raised my hand when there was an opportunity to move into that type of role, which is also how I got connected with DealHub, managing a tech stack and a fast growing startup.

So in my Rev Ops career, I was the head of Rev Ops for a really fast-growing company called Emailage, and they ended up getting acquired by LexisNexis, which it’s a massive Fortune 1000 company.

After that, I did another startup, and it was a really fortunate situation because it was a startup that was within the portfolio of the investors that were invested in Emailage.

So they were looking for a similar thing. They knew what I could bring to the table, and it was nice to see, okay, I tested my stuff in an email, let’s go test it out at another company called Boast ai. At Boast, my partner and I, my business partner, founding partner, and my current company Lean Scale, just realized that it’s really hard to pull Rev Ops off if you don’t have all the right skill sets on your team. And it’s really hard to get the right team. And if you do everything in-house, it’s very expensive. 

So we started a company called Lean Scale just two years ago, and we’re a rev ops as a service company. So we manage the planning and execution of growth for Venture-backed B2B  technology companies, and we manage all the systems, do the go-to-market reporting, and bring all of the best practice processes that we’ve seen from the companies that we’ve worked with and make sure we give people a headstart on their path to growth.

Mark Lerner:

And I look back at the previous episode, which I think had happened soon after the exit of your previous startups –  of the startup that was purchased by LexisNexis, and you had a very in-depth kind of model that you built where you kind were able to plug in numbers and just know exactly down to the decimal point you put X in, you get Y out. 

It sounds like those are some of the things that you’ve brought to the table in your current company, some of those best practices, maybe. I don’t know if you know what I’m referring to if you remember that conversation at all, but if you can, talk a little bit about it and maybe how you developed these kinds of best practices and these processes and how you have operationalized them.

Anthony Enrico:

Yeah. Well, we have a name for it now. We call it Growth Modeling, and if anybody’s listening, I’ll provide a link to a template that any of your listeners can download, and they can play with it on their own. 

But really, the concept of growth modeling is understanding, and all these companies really have this charter, but understanding where you’re at today typically in terms of annual recurring revenue, where you want to get to in the next 1, 2, 3 years, and then reverse engineering that into an operating plan.

So let’s say you want to double your annual recurring revenue. Let’s say you want to go from 10 million in ARR to 20 million in ARR. Well, how many new bookings are you going to need? How much pipeline are you going to have to build to feed the new bookings that you need? When does that pipeline need to be created?

How many leads do you need to generate to get the pipeline? And then, what does your brand awareness need to look at? And then also the customer success side. 

How are you going to drive your net retention up and just every component that drives your annual recurring revenue, what does it look like to go from point A to point B and then plug in all of the assumptions that you have and see what it takes? And usually the end output is just a budget number. It’s okay, are you willing to spend this amount of money to get to that amount of money?

And does it make sense?

Mark Lerner:

Yeah, I mean, that’s super interesting. I mean, not every company is able to plug in numbers. I mean, there are certain things you need to know, and it sounds like you had a pretty good system built in order to be able to have confidence in what you were plugging in when you started at a newer startup. You don’t have that kind of historical data to make assumptions with. Does that make it a lot more challenging?

Anthony Enrico:

Of course. It’s a lot more challenging. And so when we started at the new startup and what I’d say for any customer of lean scale right now, day one, we focus on laying the infrastructure and laying the groundwork to start measuring the things that need to be measured. 

So some of these things just take time. If you want to look at a pipeline conversion rate to understand your bookings goals, you need to make sure you’re the stage movement. So you’re actually able to measure that time and stage measuring your measuring your churn reasons. 

So if it’s something that’s market-related or something more related to your product or service, you can make some assumptions around that. So yeah, on day one, lay down the foundation so you can start measuring. But you’re right, you won’t have a lot of that data. So the next thing you can do is just start to make some assumptions and judgments, and probably the best way you can start with some benchmarks. So we do that with our customers. We say, okay, what’s a company in our portfolio of accounts, and how can we benchmark what their performance looks like? Or you can start to get a few leading indicators that you can try to extrapolate across other measurements as well.

But yeah, at the end of the day, you’re going to have to really just make sure you have the measurements in place and then see if your assumptions are holding true or not, and then make adjustments. But once you have a year of data under your belt, then you should be in a good place.

Mark Lerner:

Yeah, that was actually going to be my next question: what is the sample size that’s significant enough where you can have some level of faith to plug in those numbers and know that they’re kind of resilient? 

Anthony Enrico:

Yeah, sample size; well, I guess sample size and time, sample size, you just use what you have, and that’ll gauge your level of confidence in the plan.

 So you may need to bake in some buffers, but you’re going to have to use the best that you have. And as you get more, it should refine itself. But until then, it’s going to take a little bit of time and timing. So how long do you need to wait for some companies, it doesn’t have to be that long. If it’s a high-velocity type of sales cycle sales environment, you may be able to start getting some leading indicators in 30, or 60 days and enough data to at least gut-check if your plan is on track or not. 

For enterprise sales, it’s always the toughest one because it could take 3, 6, or 9 months to get something all the way to closed-won. You don’t know churn as well, because they’re typically locked in a longer contract. So are they not churning because they’re happy, or are they not churning because they’re just locked into a contract? 

So when you’re in that scenario where it’s a more enterprise environment, usually we just look at, okay, well what can we measure? Can we measure stage movement? Okay, how long has it taken to go from stage one to stage two to stage three, and can we start to make assumptions on how long the rest of the process is going to take?

Mark Lerner:

I want you to take a step back and kind of get a feel from you what the experience was like of being at a company that did this exit that I think all of us that work in startups in the tech space, that’s kind of the pie in the sky, the thing that we all kind of strive for in a lot of ways, whether it’s exit a private company or going public through IPO, I suspect with many things when it actually happens. It’s not exactly the way you imagined it, but I’d love to know what that experience was like for you leading up to it. What kind of pressure has it put on you as someone in your role, and then what was it like afterward?

Anthony Enrico:

Yeah, that’s a good question. And it is really unique.

 And first, I’ll say it’s the best thing that ever happened in my career by far. So that experience of going through, and I’ll walk you through, I entered when we were doing about three and a half million in annual recurring revenue, and then we were doing about 50 million in annual recurring revenue and then exited for half a billion. So I got a chance to see so much, which I could not be more grateful for, and not just the growth, but that company in particular, we were in the market in a lot of different regions. So we were in the market in Europe, South America, and APAC, we dealt with enterprise, we had velocity, we had some self-serve, we had multiple products. So all of these different go-to-market motions. I mean, I went to the best university to learn how to scale a startup I could have ever gone to.

You’re always thinking about it. I think maybe at least I am; you’re thinking, okay, if we were growing, if we keep doing this, we’ll get the next round of funding. If we get to this point, then maybe there’s an exit. 

But I don’t know if you ever actually believe it’s going to happen. You’re sitting, I don’t know if you’ve felt that. You’re like, you have these dreams, and you want them to happen, but I don’t know if you’re like, yes, this is going to happen for sure. 

So for me, the role I was in, I spent a lot of time with our exec team. I reported to our CRO and did a lot of the board reporting. I went to most of the board meetings, and I think I started to get suspicious when there were some meetings where I had to step out of, because that never had happened before. And I had been in fundraising board meetings, I had been in things, and I started to get a lot of reporting requests and a lot of weird things, a lot of urgency on reporting. So I don’t know, my senses were kind of something happening here.

And then I remember when I found out I was up really early, I just had, how old was Stella? She was two months old at the time. So I was up at 5:00 AM feeding her, and then my CRO called me at that time, which he never does; he doesn’t call at 5:00 AM. He might call me at 10:00 PM, but he is not calling at 5:00 AM. And he goes, this is going to be a really interesting day in email, just history. And I was like, oh, okay. It’s like today we’re announcing that we’re getting acquired, and I’m sitting there with a baby in my arms on the phone with him. 

I was like, what? And for us, it was an exciting thing. We knew we were growing. It wasn’t like, oh, we stopped growing, and we’re dumping the company off. It was like, okay, if we’re getting acquired, this is a good thing. 

So that’s how I heard the news and where I was when I found out. And then the next three months is just weird because that seemed to always be like the guiding mission, at least for somebody in rev ops, like, Hey, that’s what we’re working towards. And now that it happened, it’s like, what are we doing

North Star? Right?

Mark Lerner:


It’s like when if Elon Musk gets to Mars, what happens? Right? You don’t have a mission anymore.

Anthony Enrico:

We start building the settlement, or am I going to fly somewhere else? What do we do now?

Mark Lerner:

Yeah, I totally get that. There is something that drives you about a goal that is almost unattainable, that when you attain it, it’s like the dog catching the car, whatever that metaphor is like, okay, what now?

Anthony Enrico:

That’s the exact feeling. The exact feeling. 

And it is now, there’s a waiting period. They announce it, but the money hasn’t moved yet, and the transaction hasn’t happened yet, so you’re kind of just waiting. And then a lot of the team did pretty well too. So there is a day when you just refresh your bank account, and you’re a little bit happier, but those parts are kind of anticlimactic. 

You don’t even know when you just log in one day and, like, there it is. So a lot of hurry up and wait for stuff, and then it just does feel like, yeah, when the dog catches that car, what do you do now?

Mark Lerner:

So it sounds like you decided to go super early or moved on to another startup. And I assume, and maybe I’m wrong, I assume that you’re stepping into a very different world coming from a company that scaled from three and a half million ARR to 50 to a hundred million ARR and exiting for 5x that, what’s it like going from the end of the race back all the way to the beginning?

Anthony Enrico:

Well, I think something I didn’t have much of an appreciation for is, I mean when it happened, it was like, okay, let’s just go do it again.
You may have this incorrect perception of what it takes to grow a company. So many factors, I mean, it’s your product, it’s the value the product brings, its timing, and the current market conditions. 

I mean, there’s like a million things. I know I played a part in it, but you can’t rev ops your way to an exit. It’ll help, but that’s not the whole thing. 

So I think one, it was very nice to be able to go back to the beginning and lay the foundation. So from my Rev Ops perspective, I just had so much more knowledge and context going back and doing it again, and I felt like I could really help and lean in with the team more, or at the first company, I was more learning as I went and doing roles that I hadn’t done before.

But coming back and doing something that I have done before was just a nice experience to have, but it was just a different type of company and they’re doing really well. 

I think Boast is still a hyper growth company, and I didn’t leave by any means because Boast wasn’t doing well. I think I took that experience and that feeling of, wow, I can help. This isn’t just for me. I’m here helping the executive team. I’m coaching people, I’m setting up the whole company well, to be able to communicate to their investors, their board, I want to do this as much as I can. 

And that’s when Saka and I – my founding partner at LeanScale – are just like, wouldn’t it be cool to do this for hundreds of companies and then just get better and better and better at this art of rev ops and train people how to do it? 

And that just seemed like a really exciting opportunity for us. So that’s why we decided to open it up.

Mark Lerner:

And so, I mean, it puts you in a unique space. You’ve been to the Promised Land, so to speak, whereas you can step into a room and say, I can help you from this very start, build this thing to get to where you want to go.

I mean, I don’t know if you thought when you started at the previous company if it was going to end up where he did. I think for a lot of us, we have dreams, but being able to walk in the door at three and a half million and say, the things I’m going to do today are going to be the baseline for this company’s ability to 10, 20x, I imagine it’s really exciting. 

So today, working with your customers at Lean Scale, is that part of the offering? Is that what we do today is going to be the foundation that you can build on to get to an exit? You mentioned there were specific kinds of reports that the board wanted and all those things. Do you have an eye towards that when you’re starting even from scratch?

Anthony Enrico:

Yeah, I want everybody to have that experience, that experience that I was fortunate enough to go through. I want everybody to go through it. 

I mean, the amount of learning, personal development, and just value that you can create for the people at the company experience of integrating companies, you just get to learn so much. So that’s a big goal for any Lean Scale customer. 

And that’s how we frame what we do is we call it full stack rev ops, holistic rev ops, and we really always come back to that planning phase because if you can call your shot and grow from X to Y, then you can put yourself in a position to be able to do that, or you at least make the best bets possible that could put you in that position. 

And so when we’re doing things, I mean, a lot of the day-to-day work might not feel like that we’re doing, Hey, we’re fixing Salesforce over here, or we’re just pulling a sales report over there. 

But we’re always building things. With that in mind, can you gather the data you need to make really good decisions, and can you build a plan that is aligned with your strategic initiatives? As a company

Mark Lerner:

Working at LeanScale for the last two years, you got a very unique view of a role, Rev Ops, which I think several years ago was pretty not well-defined at all. Today is kind of the most sought after position for hiring. 

And as in all the conversations, so you’ve had the opportunity to watch that evolution happen. From your view, obviously, we’re in an economy and market that’s kind of in flux. What are some of the trends, some of the tea leaves that you’re seeing in terms of how the world of Rev ops is evolving and going forward, how that change is happening? What are some of the trends that you’re starting to see?

Anthony Enrico:

Yeah. Well, I’ll speak to some general trends, and then I’ll tie it to ops. These plans that we’re talking about and growing from X to Y, used to be done very differently. You could raise capital very easily. You could burn a lot of money on Betts that might not be that well thought out, and that actually were rewarded. So if you could figure out a way to burn your way into the next round, and a lot of companies were rewarded for doing that. 

So that is pretty much nonexistent anymore outside of a handful of true AI companies. So that’s really not how we’re doing things. There’s a huge focus on efficiency and being lean, and I also think there’s a much bigger focus on consistency rather than looking for the hockey stick.

So there are a lot more investors in this growth capital space rather than, Hey, I’m hoping for unicorns.

They’re saying, Hey, I’m hoping for a couple of first base hits, and if we can get into a business that has some good fundamentals, they’re consistently growing, and they can prove that they can consistently grow, those have become pretty attractive investments comparably in this environment at least. 

So given that, I think one of the things people in Rev Ops need to really be focused on is first being part of that strategic conversation, where I think Rev Ops before was more, Hey, take care of the systems, take care of the tools, run the reports that the VP of sales wants run, and then just be reactive to things that are going on where I see Rev Ops more being a leader and on the same level as your head of sales, head of marketing and needing to be strategic. So being the person who’s making the recommendations of where we should invest next.

Mark Lerner:

Yeah, I think over the last three years, I’ve had many conversations with Rev Oops leaders, and consistently that is the thing, this push for Rev Ops professionals and people in Rev Ops roles to advocate to be a strategic position rather than ACRM administrator or whatever. And it still seems like there’s that tension in some places where you’ll see a job title, a job listing for Rev Ops.

You realize it’s just a glorified Salesforce admin position and not really about the strategy behind the people, the process, and the technology to support the growth of the company.

So I think just wrapping things up as we kind of cover what we talked about, you had this, you have a pretty unique journey starting from a relatively early stage company all the way through exit, and then eventually being able to take that experience and help other companies build to scale. 

So for somebody in a Rev Ops role that’s listening to this right now and is dealing with some of the challenges that people in ops roles deal with, especially in this kind of climate, what do you think are some takeaways, let’s say, to advocate for themselves for quick wins that you think that they could walk away with?

Anthony Enrico:

Yeah. I think there are a couple of areas, and it depends on how ambitious the Rev ops person is. I would say if you start leaning in on planning and you start leaning in on this growth model process and providing recommendations, that’s probably going to get the attention of your executive team. A lot of the stuff Rev ops people will have an appreciation for. There’s a lot of firefighting, there’s a lot of things that go on behind the scenes. 

There’s a lot of work that goes into orchestrating these processes and systems. Unfortunately, a lot of that work is pretty thankless. So unless you’re in a closed room of ops, people who want to vent about how hard it is to do that, most people just won’t have an appreciation for it. But where I think you bridge the execution of ops into the strategy is leaning in on that planning process.

So I would find a way, if you can, to partner with your CRO partner, with your VP of sales, and start helping them put together their plans and making sure it’s integrated. I think that’s the best way or the best thing to focus on that can help move you into that strategic position within the company and also give yourself the license to do that.

You may not think that you’re best equipped, but I can’t think of anybody better who spends all day with the Go-to-market data all day with the Go-to-market teams and sees everything that’s happening to put together recommendations of what we should do next.

Mark Lerner:

Yeah, that’s a great place to put a pin in this, and hopefully, in another three years, we can touch base again and after LeanScale has IPO’d, and that’s it. 

Anthony Enrico:

Trying to

Trying to do it again, one wasn’t enough.

Mark Lerner:

Putting the band back together. 

Anthony, thank you so much for taking the time to chat with us today. Super interesting. I think there are some really great takeaways for our audience, and looking forward to hearing more success from you in the future.

Anthony Enrico:

Thank you, Mark. Appreciate it.