How Revenue Leaders at Box, Calendly, and Lattice Scaled From $0 to $100M+ and Beyond

Hope everyone's had a great show. We have 3 esteemed CROs from the Stage 2 LP base, and we're going to talk about the pivotal moments in their current companies on what actually caused this to happen on revenue from 3 great companies. Before we do that, I'll let each, each individual give a quick introduction. Dini, you want to start?

Hi everybody, I'm Dini Mehta. I have spent majority of my career in startups just building and scaling different revenue orgs of all shapes and sizes. Most recently, I was the CRO at Lattice, which is a people management platform in the HR tech space. I joined the company when we were about $3 million in revenue and helped scale it past $100 million.

Good morning, everyone. I'm Kate Ollering. I'm currently Chief Revenue Officer at Calendly. Prior to Calendly, I had a good 8.5-year run at a company called Glassdoor, where we grew from about $10 million to into the hundreds of millions during that time. Career-making experience of a lifetime. And before that, I had a series of sales and go-to-market leadership positions at software and tech companies. And hard to believe I've been doing this for two decades now. It's good to be with you.

Hi everyone, I'm Mark Whalen. I'm the chief revenue officer at Box. I've been with the company for four years, and before that I was CRO at Tanium, an enterprise security company. And then before that, 10 years at Salesforce, a few years at Gartner. And started 30 years ago just across the highway selling hardware for Northern Telecom. Great to be here with you all. Thank you.

All right. Excited to dig in and learn. But Dini, starting out, Lattice, I know you came in really early. You want to paint that picture? And there was— that was your pivotal moment. You want to tell us what you did there?

Yeah, totally. That was one of the pivotal moments. So Taking it back, I joined, we were about $3 million in revenue, about 40 folks in the company. The go-to-market team was about 10 people. Sales was about 7 people. So really early days. And I was hired 'cause we were seeing a little bit of softening in our new business growth. Folks weren't hitting quota and was brought on to help diagnose what's going on and help us scale the business. I get there and I had seen the numbers in terms of the output, But what I couldn't connect the dots on was all the activity that was happening on the ground. Reps were taking 4 to 6 calls a day. They were doing lots of demo volume. So we had top of the funnel volume. That was one thing that was interesting. There's a lot of volume, but it's not— we're not seeing the output. Two, we were closing really small deals like $1,200 deals on one end, and we were also talking to really large companies like hundreds of thousands of employees. And both ends of the spectrum, we had interest, which was great for our product-market fit, but clearly from a go-to-market execution standpoint, we weren't focused where we were spending time closing $1,000 annual deals and also talking to these really large companies. And the third phenomena that I saw was we had a product-led growth flow on our website where you could go to the website, buy Lattice for your team and run with it. Awesome. But we also had a sales team that was out in market selling the full solution wall to organizations. And so there was a bunch of stuff happening. The good news was there was a lot of activity and we had a lot of initiatives in play. Bad news, it wasn't really driving the results we wanted. And so I came in and after looking at the data around churn, looking at the data around usage, talking to some customers, learning more about the persona, made a few key changes, which was nerve-wracking at the time because I was like one month in coming in here with all these, let's make all these changes. But it just felt right talking to folks and looking at the data. We said we're going to put a minimum in place. We're not going to sell to anyone under $4,000. So like, that was the first thing I did, which everyone's, what? In the sales team, like, how are we going to get to our numbers? Like, most of my deals and demos are coming from that early stage folks. And we knew that those people aren't getting the value out of Lattice. Today based on the numbers. So we said, all right, we're going to put a minimum in place. Two, we're going to pause on the full product-led growth motion, let people come in and experience the product. But we're going to sell through our sales team. We've got a sales team here. The best way a customer finds value on Lattice is by using the full product. And so we're going to focus in there. And then three, we defined our ICP. We said, here's the types of organizations that see value in Lattice. We've got limited resources, we've got a small team, and we really have to focus in because the opportunity cost— it's very tempting when you're a startup to do everything. In early days, you have to because you're testing a bunch of stuff. But at some point to drive operational excellence, you've really got to focus in. And so we said, we're going to focus in on— this is our ICP, put a minimum contract size in place. And put pause on PLG. And all of a sudden, people's calendars went from 6 calls to 2 calls a day. Still a lot for 2 new business calls a day. It's like very healthy volume, which is okay, we gotta add more capacity. And all of a sudden, even though the activity dropped, we started to see productivity go up.

Beautiful. Okay, I'm gonna come back to you with a quick one on like, how did you know from the close rate that it wasn't working, those 6 meetings? 'Cause I think a lot of founders are like, What should my funnel even look like? And then also how you actually define the ICP. Okay, but before I do that, I want to highlight a couple of points from Denny that we see a lot. First off, stopping PLG. Okay, that's always a question. It's like you're going to market. Should we do PLG or not? That's a tough question. If you ever have a question about that, it's a good idea to give it a shot. And because you could always kill it later and basically like The reason it probably didn't work is there needs to be a low time and effort to value use case. And Lattice is like an operating system. It's not something like a single person is going to download and start using it like a Dropbox or a Calendly. And so like intuitively there was probably a big question there. But regardless, they didn't waste their time by trying it. They found out that it wasn't working. And what did they end up with? They ended up with a really easy to use product Great.

Yep.

Let's switch to sales-led. Okay? The, the second point I wanna highlight that we see a lot at this stage that Denny did a great job on is the segmentation of the salespeople. It's totally cool to come outta the gate and sell to a lot of different people. You don't know what your vision's gonna stick with, but a year later you start to get a sense. And we, when we walk into organizations and you have 5 salespeople and all those salespeople are selling $3,000 ACV deals and $100,000 ACV deals, that's not going to work. Usually sellers are tuned for one way or the other. And so that was an obvious change that Denny did a great job on that we see at that particular stage. So let me come back to you with those two follow-ons. A lot of founders are like, how do I know what a good close rate is? And you said that they were doing 5 or 6 meetings a day, but you weren't seeing yield. What was the actual numbers?

Yeah, I think early on our close rates were like 20%, 15 to 20%.

Okay.

And then we changed, made the change, and it bumped up, doubled, went to 40%. Crazy.

Crazy. And do you remember the CAC? What was the old CAC and what was the new? Okay, that's okay.

Yeah. And I think what's really crazy is as we started adding capacity, everybody on the sales team is like, we can't add more capacity. My leads are gonna go to new folks. My calendar's gonna get emptier. And the win rate continued to creep up.

Nice.

Because they just had more time per op. And so you were going deeper with customers. These were quality customers. We were really optimizing for that op cost.

Cool. OK, and then so the other common thing we see is now is the time to refine your— I spoke about this yesterday— is a lot of founders try to sell a big product to everyone out of the gate because they raised venture capital and that's what the VCs want to see. But as VCs, we just want to see the vision toward it. We don't want to see you boil the ocean out of the gate. It's much better to find the best market to get to 5 or 10 million. So how did you go through that process of defining the ICP?

Yeah, we looked at our existing customers that were power users, so really high usage. They were renewing. These were raving fans. They loved the product. They were giving us feedback, really helping us build a better version of the product every month. And so we said, okay, who are these folks? And then we defined it off of that and said, We're just gonna focus in here. And yes, there's a lot of interest in a lot of different places, but if we do that, there's—

Boom, all-star. 'Cause most people when they do that, they look at the close rate and the CAC. No, you wanna look at where you're creating customer value to drive that decision, okay? Thank you so much, Denny. All right, so related to PLG, a lot of people are trying it, and at some point you get so big that's, hey, can we sell big deals now? And that's what really Kate did at Calendly. You want to talk us through that, Kate?

Yeah, absolutely. So when I joined Calendly, we had just completed our Series B. We took $300 million in venture and we were at about $100 million in ARR. So it was the point where we were thinking about kind of the next great growth horizon. And we had some data that showed that teams were interested in using the product. So if you're familiar with Calendly, it's scheduling automation. Our roots are in PLG, and predominantly in the beginning it was solopreneurs, prosumers, and small SMBs. B's that were coming through the funnel. What we identified as a pattern were there were some key use cases that emerged. So, it was quite a horizontal product, but these use cases began to show up prolifically. And so, the use cases make sense if you think about the folks in your organizations that do the most scheduling. It's sales, it's customer success, and it's recruiting. So, as we began to work with these customers, folks in those use cases started to ask us for deeper and richer solutions that were integrated into their workflows, making it easier for large teams at large organizations to stay in their stacks, but also use Calendly. And so from an R&D perspective, we made investments in what we call vertical solutions to support that. And what happened is the composition of our funnel began to change. We started to see IT administrators show up in the funnel. We started to see line of business leaders and RevOps leaders show up in the funnel. And in response to that, we had a small but mighty group of inbound sellers who could take a high-intent lead and convert it, but to take a high-intent lead from a large company and turn it into a large deal, we identified this was just going to simply be a, a different skillset. And we made the jump to invest in enterprise. And so what I'll share with you though, is it's not just about hiring enterprise salespeople. Yes, that's part of it. In my experience, both at Glassdoor and at Calendly, there's, an enterprise-ification that needs to happen across your org to really be ready for this. And I just have this simple framework in my head that goes product, people, process. So, from a product standpoint, you might think you have product market fit, but selling to large companies is different. You have to have the right security and administrative features and requirements. It's just far more intense to support a larger organization than it is, to support a mid-size organization. From a people standpoint, do you have the right profiles? At Calendly, we had to go out and hire a different profile, not just in sales, but in CS, in, in less intuitive parts of the company, like in marketing. As an example, in the early days, marketers just buy you leads, and as you progress into the enterprise, you need solutions marketers, you need collateral, you need selling tools to support the sales team, and that's a different skill set that's required in marketing. So just some examples of how the composition of the team and the folks that you need to bring in change too. And then from a process standpoint, you have to sincerely be ready to invest in enterprise sales and build infrastructure to make sure that these relatively expensive salespeople can be successful. So you have to build RevOps, add some enablement resources, deals desk, legal. In, in kind of the early days of exploring enterprise, getting an enterprise company to commit to investing in you is like literally less than half the battle. Getting through monstrous MSAs, getting through infosec questionnaires, and getting through the paper process at these organizations really becomes the challenge. And what's required is a whole bunch of infrastructure to support your sellers in completing those tasks. So if you think about across all of those things, you have to be really ready to enterprise your company, and it takes sincere investment, and you have to be prepared. And model the return that you think you're going to get from those things, which is what we did at Calendly, all driven by kind of this need from teams to have more vertical solutions.

All right, beautiful. A ton of stuff to recap there. My two follow-ons, so you can think about them, because I just— we're going to ad-lib this, right? So what do you look for in enterprise rep compared to mid-market? And then we're going to talk about the PLT— PLG trap, and I want to get your take on that. So just to recap Kate's experience, um, first off, A lot— this is a common, like, blueprint. You start SMB. It's not a good idea to start selling to the enterprise unless you have to. It's just a long slog. So it's good to start SMB mid-market. You hit $10, $15, $20 million. Lots of times going upstream is a great way to go. Now, do not come into the year and be like, okay, cool, we're going to go from $15 to $30, and oh man, our regular funnel only gets us from $15 to $25. I have an idea. Let's go upstream and tell the board we're going upstream and let's commit to $5 million. No, this is a long journey. We have to hire new reps. That's going to take 3 months. They have to onboard, 2 months, build pipeline, 6 months. So this is like a test that's being done and you want to be testing this before you need it. Okay. And so that's number 1. Number 2 is it is a test because you have to refine product market fit. Don't let your ego get in the way. This is not going to translate that easily upstream. It's almost like the beginning days again. So give yourself that time. The other thing I commonly see that happen with Kate and, and Calendly, I think to some degree is inbound is probably not gonna drive enterprise. Like it's really rare to get an inbound lead and be like, and then 3 months later, oh, we have a million dollar account. It's, it's cool. There's little triggers happening, but this is very much like account-based marketing, account-based selling. There's dozens of people who are gonna influence the sale. And some of them are coming inbound, and you're going outbound, and it's like really moving this boulder along, okay? So let's come back to first enterprise rep, 'cause that's key, is we gotta hire our first two. What's the difference between hiring a mid-market versus an enterprise rep?

Yeah, I think it starts with having the right ICP. So when we say enterprise, you immediately go to the 20,000-person company, and for us, enterprise was mid-market and the lower enterprise segment. And so you're looking for, reps who have done these deals, let's say $30,000 to $50,000 deal sizes, have a handful of years of experience doing that. And the big key that we needed to find and transition our org to was team members who had experienced value selling. Often you will inherit an org of very well-intentioned, smart, scrappy people who are selling features and functions because of your PLG roots. It's, hey, just show them the product, get them into the product, they'll convert. Selling to a different buyer, a line of business owner, a key business stakeholder in these larger organizations takes a completely different motion. You have to talk about business value and be able to make a business case for the value that your solution creates for their organization. Completely different skill set. So we really tested for that primarily in our hiring profile.

Another really cool work that happened that's relevant here by one of our other LPs, Oliver J. OJ was the one of the early reps at Dropbox to take them into the commercial world, and he was the founding CRO at Asana. And he has written a work called The PLG Trap, which is quite instructive for early-stage PLG companies, which says, like, your ability to sell an enterprise deal, like, you learn very little from your PLG experience, 'cause the PLG product was built for the end user, but an enterprise sale has to really hone in on the C-level decision maker. And rarely do those customer value props match up. So you have to have that sort of vision and strategic mindset from the beginning, is this going to create a stepping stone for us to have a customer value prop that also resonates with the C-suite? Did that happen at Calendly?

Yeah, and we're still in process of, I think that's a continuous improvement project for us. One of the things that I'll highlight is it's different for product too. It's not just your revenue organization and how they go and talk to customers. Your product teams have to think about a different customer too, because you're, as Mark said, your user is not your buyer. And so going out and meeting with different types of customers is really important for the product team. And I think as a CRO, you have to be able to influence your product team in that direction. Just as one example, our executive buyers want to see quantifiable Analytics and results. What productivity did you drive? How do you improve my revenue outcomes? And so part of what we did across Calendly was begin to invest in analytics so that we could tell a better story around the ROI of investing in scheduling automation. So it's like one of these examples of how the entire org has to go with you on the enterprise journey. Great.

Thank you, Kate. All right, let's finish up with Mark. So Mark's going to talk about being CRO and walking into a company that's having a little bit of a churn issue. And unfortunately, that's happened with a lot of companies right now. Whenever there's volatility in a macro environment, that typically leads to churn. And I can't think in my career of like 30 years, a time of like worse churn. Everyone's remote and we change our value prop. And then all of a sudden, the— it's a grow at all costs situation in tech and we're selling into that. And then that changes overnight and now it's all about efficiency. And that just leads to a lot of customers that signed up for something that is no longer relevant. In a very short period of time. So there's a lot of companies going through this, and Mark has come into Box and done a great job. Can you walk us through that story, Mark?

Yeah, sure. I joined the company 4 years ago. We were about $600 million in revenue, 4 or 5 years past the IPO. And as a subscription business, you're always growing, but the rate of growth was not where we wanted it to be. And generally, when a company's bringing in a new VP of Sales or a new CRO, they think they have a sales problem, and very often they do. And, and we did have sales problems. We, we still have sales problems. We're still working on them right now. But what I found after I arrived is that we had a churn problem that was, I would say, like on the unhealthy range. And I think the thing that we did as a team was really understanding why we had a churn problem. And when we went from the ocean to the bay to the rivers to the lakes to the streams up to the snowpack, when we got to the snowpack, we found that we had a product problem. And so we made some changes to the product. We made a number of acquisitions. We changed pricing and packaging. We changed messaging and positioning. And when we did that alongside all the improvements that we made in the sales organization, then the growth returned and we had dramatic improvements in churn. And it's much easier to sell to an installed customer than to a net new customer. And so when you churn a dollar, if you look at what your net retention rate is, if you're under 10%, if you're 120%, you didn't just lose a dollar, you lost $1.20 when you churn that installed customer. And if you have a leaky bucket, If you're a really high growth company, you might be able to outrun it. But if your growth is— we're Rule of 40 dynamics, we're more balanced in terms of growth and profitability. If you're not growing at 40% on new ARR, you just can't afford to have a leaky bucket. And so that's really the thing that we did as a company is get the whole team together. We would have these all hands meetings where when I, I would talk to reps and I'd ask them about a renewal and they would say, that's not my job. And that's a problem. And we do these all hands meetings that say, raise your hand if you're on the renewals team. And just the renewals team would raise their hand. And we did this thing like, get the whole company to raise your hands. It's the most important motion in SaaS, is your renewals motion. If you have a problem there, you can really put yourself into a death spiral.

Great. I have a couple follow-ups on like coming in as an executive to that and influencing it, and also how the process you guys, you all went through to diagnose that this was a product issue, and like the research you did to figure out what needed to be enhanced, if you can walk through that. But let's start with You're coming in, you're like the new guy on the block. You probably can't walk into the board meeting and be like, yeah, the sales issue is in product. That's gonna politically piss a lot of people off. Like, how did you handle that?

Yeah, so I left Salesforce 6 years ago, and I think that one of the things I've seen where my friends have left a place like Salesforce, and many of us maybe stumbled on our first role. I, I did after I came out, and I would take that job again. I would do some things differently. But I made some mistakes there. And the mistake that I made, that's the classic mistake that a lot of, I think, revenue leaders make when they leave a big successful company like Salesforce is what I refer to as the game and the game within the game. So the game that we are playing as revenue leaders is to deliver the number. It's real simple. It's a very binary job that we have. Either you're successful or you're not. But when I've seen people not do well in that first job after leaving a place like Salesforce, is generally what I call the game within the game, which is the way we show up as a part of the executive team, the way we interact with the board. And when you see challenges in the business that are maybe outside of your domain— my job is to lead the sales organization, but if we have challenges with product or with customer success or with marketing, the way that you drive consensus, the way that you get everyone on board with that is often where people move themselves out of a job where maybe they're winning in the game itself. You might be doing well against the target, but you're failing on the game within the game. And I think that's probably the biggest lesson I've learned in my 6 years since leaving the big company is like, how do you get everyone on board with what your vision is for the company and where you're seeing challenges? And I think the big thing that I did when I was at Tanium, I was vocal about some things that were outside of my domain within the first few months, and that didn't go very well for me. Because it makes it seem that you're taking your eye off the ball, and I was not. But if you have a quarter that's tough, then the board and the executive team has to wonder, is our sales leader on top of what we hired him to do? Uh, and so when I got to Box, a lot of these challenges I think presented themselves. Uh, but my thinking was coming off of the prior experiences, I'm really just gonna take notes on everything that I'm hearing about what's going on in the market. And then I'm going to validate it with first-party experience. I'm going to go meet with customers in all segments and all verticals all around the world. And I'm going to validate what the sales team is telling me because the sales team will tell you things that aren't always true. They'll tell you things that they want you to fix that maybe it's just one deal. Recency bias is a big problem. So after validating all of that and then hopefully building a good relationship with the executive team and the board, after a year I said, hey, here's, I think, some things that I think we need to focus on. And then I think by waiting, that was the right move because then we got the whole team on board. And to make that big of a shift as a company, and it was a pretty big strategic pivot for us, we needed everyone together. It couldn't be like one or two executives pushing it.

I'm going to squeeze in a, like a little sub-bullet question there too. Cause like it, and I'll let you think about it and make a point real quick, Mark. But if you were to, if a founder was to look at Salesforce for a leader, you probably could see some people over there that would be great at jumping into a startup and some that wouldn't be. And how should a founder look at that? Before you do that, to Mark's point, I watched some great coaching from an advisor that was coaching a team. And he explained the difference between a functional leader and a corporate executive. And that's an important transition. That you need to make when you get the C-level position. When you're like a director of sales and you're in the sales org, you're living sales all day, you're with the sales team, you're just thinking about sales. But once you become CRO, you're gonna get into trouble if you see your role on the senior leadership team to represent the needs of your people. You're gonna get into some trouble. You need to look at it as a corporate executive. Yes, when you are out with your team, you're leading your team, But when you're in the senior leadership team meeting, you're a corporate executive where you— everybody should remove their biases toward their function and operate as a single team toward a North Star. And I think we're hearing a great example of that, uh, from Mark. So Mark, like, for over a decade, so many VCs have come in and be like, okay, here's a Series B, now go find someone at Salesforce and hire them as your head of sales. So tell us, like, as you go through all your peers over there, what should a founder be looking for there to hire someone out of a big company that would work, and what should they look like as a red flag?

Yeah, it's a great question. So if you're thinking about hiring someone from a big company, and your target employer might be a Salesforce, it might be another great SaaS company out there, the common thing that founders, the common conversation that founders have is like, "Is she gonna be able to work in this environment?" Is he gonna be able to keep up with us or work in a startup? And there's almost this undertone of it's like work ethic or something, which I've always found really comical. My 10 years at Salesforce, I worked 365 days a year. The work was intense. Like, I didn't have a blood pressure problem before I went there, but when I came out, I sure did. And it's so like the idea of being able to keep up is, I always found funny. And when you work at a place like that, you're not like overloaded with resources. I was booking my own travel and managing my own calendar and doing my own expenses. It was work, like we were working. The thing that actually is, that people struggle with when they leave a place like that, is when you work for a company that's really well run, and you have first party experience of things being done right, and then you go to a startup where things are resource constrained, then what ends up happening is that some executives struggle with the resource constraint. So if you've seen a marketing event, maybe a customer event like this done the right way, or you've done a CIO dinner the right way, or you know how to do territory carving the right way, then when you go to an environment where it's not that things aren't being done right, but they're just not resourced, and if there's 10 things that you're used to doing the right way and you can only afford because of bandwidth to do 3 of them the right way, I think the thing that with some people when they leave a big company is that they have a fit when they can't have everything done the right way. It's not that they can't keep up and that they're not working hard and they're not willing to roll up their sleeves and get down and dirty. It's that they have sometimes not the right level of sort of patience and accepting that we're just not going to be able to do everything the way that I'm used to. And at Box, there's all sorts of things that I would like to be doing differently, but we're all living in a Rule of 40 world now, and we can't go fund every little thing that I think would make a difference. You have to choose what are the 3 things that we're going to do really well, and I'm just going to have to let go of these other 7 things.

Beautiful. All right, thank you so much. You have busy jobs out there, and we really appreciate you coming out and spending time to drop knowledge. Let's thank our panel.

Thank you.