How To Move Up-Market with Carta's Anil Kumar

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This is a podcast episode titled, How To Move Up-Market with Carta's Anil Kumar. The summary for this episode is: Hypergrowth companies are constantly reinventing themselves. At Drift, we often say, "what got us here isn’t going to be the thing that gets us to the next stage.” On this episode, we’re exploring one of those significant moments of transition: how companies move up-market and start to sell into larger, enterprise companies. Our guide through that transition is Anil Kumar. Anil is the VP of Go-to-Market Strategy & Operations at Carta, and prior to joining Carta, he successfully helped three other companies, Sift, Atlassian, and Quantcast, move up-market. In our conversation, we talk about the focus required to move upmarket, why the Enterprise sellers you’ll need in your organization should be Pioneers, not Settlers, and how your Post-Sale model likely needs to completely change to service these enterprise customers. Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @HYPERGROWTH_pod

Sean Lane: Welcome to Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. It's amazing how often inside of a hypergrowth company you have to reinvent yourself. We talk a lot at Drift about what got us here isn't going to be the thing that gets us to the next stage. And that's a hard thing to accept sometimes, especially when what got you here has been pretty successful. Today, we're going to explore one of those significant moments of transition, how companies move upmarket and start to sell into larger enterprise companies. And our guide through that transition is someone who has not only been there, done that, but he's actually done it three different times, and he's about to do it for the fourth time. Our guest today is Anil Kumar. Anil is the vice president of go- to- market strategy and operations at Carta, the equity management platform. Prior to joining Carta, Anil worked at Sift, Atlassian, and Quantcast, and helped all of them move upmarket. So he's seen this movie before. In our conversation, we talk about the focus that's required to move upmarket, we talk about why the enterprise sellers you'll need in your organization should be pioneers and not settlers, and we're going to cover how your post- sale customer success model likely needs to completely change in order to service these enterprise customers. Again, what got you here isn't going to get you there. As we started our conversation though, I thought it would be helpful to put a stake in the ground about what we mean when we say moving to the enterprise, how do you define enterprise? Can you even define enterprise? That's why Anil is here.

Anil Kumar: It's funny because you want a black and white but there is none. I've worked for companies in which enterprise is 2, 000 and above employee count, 5, 000 and above employee count, 10,000 and above employee count. I'm currently at a company in which it's 200- plus in employee count. And what's crazy about that is ultimately, the way I think about enterprise is the complexity of the sales motion. The complexity of the sales motion, and then from there, relatively, what's the ACV or the contract value, relative to other products or things that you're selling. But typically speaking, folks tend to cut it by either employee count, by the revenue of the company itself, or the revenue that you're bringing in. But ultimately, to me, it's about how complex is that sales motion relative to what you're used to doing?

Sean Lane: Perfect. So I think that regardless of the employee count, that complexity of sales motion is what anybody can relate to, relative to where they are at this moment in time. So one of the reasons that I wanted to talk to you about this is that, you've done this three different times, at three different companies, Quantcast, Atlassian, and Sift. So I'm curious, as you look back at the times where you went through this motion of, let's not call it moving to the enterprise, but let's call it moving upmarket or moving into a more complex sales motion, when you look back, are you able to now, in retrospect, pull out either commonalities or lessons that you learned and say," Oh, this is what it means to go through that process"?

Anil Kumar: It's a funny thing, but it all comes back to focus. All of us are going through 2021 planning right now. If you walk into your planning cycle and you say," Hey, I want to move upmarket, I want to start cross- selling a new product to folks, and I'm going to go into a new geo," you're going to fail. You're going to straight up fail. The probability of actually being able to do all three of those and put meat on the bone of actually executing on those growth initiatives, that's really, really difficult. But I put that out there because every one of us goes through that conversation, where we got bright eyes and we're thinking about next year's growth and we want to do all things at once. So to go back to your question, when you're thinking about moving upmarket, the best thing that you can possibly do, whether you're in operations, whether you're on the revenue side of the house, is just remember that extreme, extreme focus is the name of the game. And the more you do that, the better. Because at least in my experience, what I've realized across, when we did this at Quantcast and we did this at Atlassian and Sift, and now at Carta is, you're going to spend that first year or that first phase, just learning a ton about the new market, learning how to actually sell to them, how to market to them, what that all means. And you can't cheat that. I don't know how else to put it. You can't cheat that time of learning how to do that and do that well, which is why focus is so, so key.

Sean Lane: Anil's experience of doing this three different times is going to be our cheat sheet for this conversation. A lot of companies say they want to move upmarket, but how do you bring the level of focus and discipline that he's talking about into the process? First, he explained that you just simply need time. According to Anil, it takes a full year to just learn about the segment that you're trying to move into. Okay, so let's say that you've made that decision at your company and you want to move upmarket. Where do you even begin?

Anil Kumar: It's almost like starting a new business. That's kind of the way I think about it. It's starting a new business with the one difference being you've got money in the bank, you know you've been successful at this thing that's gotten you here, so you have that confidence. But if you don't treat it as a new business with the requisite failure or chance of failure involved, you're almost doing yourself a disservice. You and I were talking about Drift actually the other day, and what you're going through. And it was so exciting to hear that you were thinking about moving upmarket, but as you thought through, or as we kind of started really digging into it, there were questions around" Well, does our customer change? Does our customer base that we're targeting change? Do the competitors that we're selling against actually change? Is our differentiation, either our product, our services, all of it, does that change, or is it the same as what we're putting together?" Once you start answering those questions around," What does that competitive landscape look like? What is my actual product value? How do I differentiate myself, and who our customers are," then and only then can you get to the real meat of this thing, which is figuring out," All right, from there, realistically, who can I go after? What is the size of that market and who do I need to actually go after and successfully sell?" So specifically," How does our seller profile change? How does our actual go- to- market change?"

Sean Lane: Let's talk about each of those. So first, in terms of who do I need to go after, I would imagine, and through our experience of doing it, to your point, at Drift, the, let's call it firmographic qualities of the companies, I think, have to change a little bit. Yeah. So how have you gone about doing that? Because, what has gotten you to this point is not necessarily going to be the thing that gets you to the next level. So if you just try and copy and paste your scoring system and say," Okay, in this part of the market, I know that these three factors make an account in A," should I just copy and paste those into my upmarket? And say," Okay, we should look for these same criteria"? How do I know whether or not I'm going to fail doing it that way?

Anil Kumar: Absolutely. Well, if you do do it that way, you're likely going to fail. And it's crazy though, right, because we all do it. Like every one of my stops, we had done some version of that where we're like," Oh, all right. If I run a regression and I figure out these are the attributes, either by vertical or by product feature that have done really well for me," that historical precedent doesn't predict future success, particularly when it's a completely different customer. Almost always, it's always going to be different. What you got to do is go to the second, third, fourth, fifth level, and think through it and think about, if we use Drift or Sift as examples," What is the thing that really makes my product must- have? What is that pain point that we are solving that nobody else can solve as good as us?" Once you really, really get to," What is it that is that thing? What is that secret sauce?" then you then have to pair it to," All right. In a upmarket customer, what are the things that they are looking for?" And when I start to think about," What is must- have about me, and what makes me really, really special?" so strategic, differentiated, defensible, of those things, what are the ones that still make sense when you're going upmarket? Chances are, if there are like 10 things that are, in fact, strategic, differentiated, and defensible about you, only two or three are going to match when you look at the enterprise customer and their needs. And at the same time, their needs are going to be completely different. The security aspect of what you do has got to be so, so important, the ability to scale, to be robust in terms of actually supporting something at that grade. And then lastly, the service component. A lot of times, things that your customers tended to appreciate about you, but were nice- to- have, all of a sudden become must- haves in an enterprise or upmarket function. And things that customers didn't really care that much about, all of a sudden they care a ton about, or vice versa.

Sean Lane: The other thing that I think is interesting, too, is like you made a point before about focus. And I feel like, especially in the lower parts of the market, you can kind of get away with," Oh, our product does this and it does this, and it does this. And you can kind of choose your own adventure within this thing." But I think as you move further upmarket, the company that you're selling to is also probably going to have a much more narrow scope for what they're looking for you to do. Do you agree with that?

Anil Kumar: Totally, totally. I was just thinking through that. All of us always think, you get to product market fit, you're scaling, you've got this great, great growth, that is when this question becomes natural. That, in 2021," I'm going to go upmarket, I'm going to go to these new geos. I'm going to start cross- selling. I've got all this funding and these tailwinds.. I'm going to do it all." The reason why that never works is because of what you just said. If I go in and say," I'm going to go upmarket by providing 20 new features in 2021," you're a hundred percent going to fail. What you got to figure out is, what are the features that are must- have to that customer? And are they crazy robust that they're going to stand the test of time for that customer?

Sean Lane: It really just keeps coming back to focus. And to me, the first time I heard this, to be honest with you, it wasn't totally intuitive to me. I was thinking about cross- selling multiple products, across multiple lines of business inside of these huge companies. But Anil's point makes so much more sense. In his language, what are the small handful of things that are strategic, differentiated, and defensible about your product? And what about your product is going to be robust enough to hold up under the scrutiny and the complex use cases of a more mature company? And what about the people who represent your company as you move upmarket? Another thing that Anil taught me about was that it's a very different and specific profile of seller in the enterprise, as well.

Anil Kumar: One of my favorite AEs, Robbie Robbie Favish, enterprise seller at Sift, and he was the perfect, perfect profile for somebody like this, because he knew how to sell. He understood how to understand very clearly a customer's needs, and then translate them in the simplest terms, how he could provide a good service to them. And I'll never forget this, what he said to me. He's like, " Anil, you don't get it. It's not about our products. It's not about giving all these new products and features to our enterprise customers or prospects. It's just about educating them. It's just about like, the hardest thing is getting your foot in the door. And then from there, having a conversation with them in which they can have confidence in your product." That partnership, that education, that building awareness, that's actually more often than not the most important thing that you got to do when you're going upmarket. Because ultimately, it's the trusting. When you're going after big whale deals, for most of those companies, they've got really complicated procurement processes. There's 10 people who've got to check- off on something. Once I got a product, they're not in it with that product forever and ever because the product is the best in the market. They're in it because it's there. So our job as enterprise sellers then, or as folks that are then selling in the upmarket, is to build that awareness of what our product is, to build that trust with the potential customer. And then from there, build a longterm relationship. That's way, way, way more important than saying," I've got 20 cool new bells and whistles, and that's what makes me good in the market."

Sean Lane: The other thing that I think is super interesting about that, and you brought this up previously, you said," First and foremost, who are we going to sell to, and then what is the team that we need in order to sell to them?" I mean, the example you just gave of that rep and that true partnership and that true education, I would say, is probably one of the factors. But I would imagine that in your previous experience at some of those other companies, just the profile and the skillsets that you need on your team to successfully go upmarket are also totally different as well, correct?

Anil Kumar: Yeah. It ends up being almost completely different. Like the piece in which the DNA is the same, it goes back to, if you treat it as a startup. If you treat going upmarket as," I'm going to experiment, and I'm going to learn in that first year," then that's almost like your first 20 million at a startup, where the type of AE that you're getting, the type of solutions engineer, or customer success, or AM that you're getting, the number one thing that they've got to have in their DNA is, are they creative? Literally, can they take a playbook that doesn't exist, and can they create one in real time? What becomes part of that is, then can they flex? And then three, can they think about the customer and just run to that pain point, regardless of the structure that is or isn't there. Same example of Robbie. Robbie's partner in crime was a solutions engineer that was wickedly, wickedly good. We were prospecting into McDonald's at the time. This was a year- long sales cycle. And I kid you not, the SE ended up moving to Chicago. He was moving because I think his wife was doing a grad program there. But it ended up being probably one of the key reasons why we won that deal. Every day, he was basically in McDonald's office in Illinois, just building that relationship, understanding what the needs were, figuring out where the product parity was, where it wasn't parity, and what we needed to do to, again, establish that trust with everybody within the procurement side of the business. So if there's anything I could say, it's find pioneers. You don't want settlers. You want pioneers, because you're effectively starting a new business and you need people who can be flexible, who can be creative, who can survive in an environment that doesn't have a lot of structure. What we don't want to do, and I've done this almost every single time, and we end up learning from it, what you don't want to do is say," Hey, this is my goal in 2021, I'm going to throw all my marketing dollars at it, all my demand gen folks at it, my entire SDR team, my entire AE team, my entire account management team at this one problem, because that's what I think focuses." That's actually patently false. If you do all of that, you're wasting a ton of resources in a really inefficient manner, with folks that more than likely aren't actually ready for that step.

Sean Lane: As Anil describes the profiles of these first handful of enterprise sellers for your company, I couldn't help but think about two of those enterprise pioneers that I've been working with at Drift. Their names are Miles Kane and Evan Cassidy. I started at Drift on the same day, actually, as Miles and Evan. And for the past three years, they've been tasked with exploring that upmarket frontier. And they have some, if not, all of the traits that Anil is talking about. They're educators, first and foremost, they bring a level of creativity to their role, and they are the ultimate partners to their customers. Another thing I observed about Miles and Evan in watching them work is that they are incredibly adept at making connections throughout an organization and working their way into different parts of a company. And so I was curious if that was a skill that made Anil list, as well.

Anil Kumar: It for sure is part of the criteria. If you look at old school killers who are enterprise sellers from Oracle, they're actually all trained how to multi- thread, and multi- thread properly. So that DNA, that's got to be part of the DNA. The difference is, if you throw somebody with that profile from a big company enterprise, come in with a big Rolodex and a huge salary, they're likely not going to be your pioneer. But the DNA behind them of knowing how to multi- thread, knowing how to really understand the business and get to know the customers and build that trust over time with one, two, three, four, five folks, so that you really know who your champion is, who your decision- maker is, and who the other five influencers are, that piece has got to be there. And if you go back to Drift, you can go to Sift, Quantcast, any one of these companies, that's not something that is must- have when you're an SMB or mid- market, because the faster the sales cycle, the less the sales strategy or the multi- threading is the essential part. What makes you click when you have a ultra- fast sales cycle is, you got a compelling event, and your customer's interested in you. And chances are, if you're at a good company, you're in the game as one of the top three, top four things that somebody can pay. That's basically the game for us in the admin market. For enterprise, it's totally different. More than likely, you're beating out somebody whose product is actually inferior to yours, but it's about ripping and replacing.

Sean Lane: Yeah, I feel like if you bring in those true, seasoned enterprise reps too early in that pioneer process, they're going to fail, and your pioneering process is going to fail. But if you've already gone through that year that you talked about, and built some of that foundational work, and figured out some of the creative methods that work for your product inside of these companies, and then you can add those folks in as accelerants to your enterprise sales team, that's where they're probably are going to be the most valuable, and also level up those pioneers who were there in the first place, who might not have that skillset. But if you've tried to bring them in first, then you might fail and not really understand why

Anil Kumar: And I'm typecasting a little bit, you can find folks who've got traditional big company, big Rolodex, big salary enterprise experience that can be nimble. That being nimble, that's actually the must- have. That's way, way more important than the Rolodex. The Rolodex is nice, because as you said, it's accelerant.

Sean Lane: So we've talked a lot about selling to the enterprise, how you pick these accounts out, the team that you need to put together in order to move upmarket. The other thing that comes next is servicing these upmarket accounts. Again, from my experience at Drift, that is also a massively different animal in terms of expectations, and then how you build out things like capacity models for how many people you need to service these accounts, and how many accounts they can work at a given time. All of those dynamics change. So I'm curious, as you think about everything that happens post- sale, and you look back at your experiences, what would be the biggest ingredients for you, if you were building out an enterprise customer success team or services team, as you're taking Cart upmarket?

Anil Kumar: Empathy, actually. It's empathy and maturity. You don't necessarily have to have had the enterprise customer success experience before. But if you have strong empathy towards your customer, if you know how to really, again, build that relationship, understand their needs, be able to take noes, and understand the why behind a no, generally speaking, you're going to be fine. If you treat it as, customer success as a machine, and capacity planning is all about ratios and seeing how many people I can load up an account with, or how many accounts I can load a person up with, again, that works when you're in SMB and mid- market. That pretty much always fails when you go to enterprise. The strategy component and the relationship component of the CS team function, or person, becomes way more important when you're going upmarket. Y. I'll give you an example from Quantcast. Any time we serviced or supported really, really big companies, they treated us as partners and our kick- ass, really, really great CSMs or account managers, they thought about it as partnerships, as well. They were effectively the thought partner to the customer. It wasn't just about selling advertising to them, it was understanding what was their media strategy? What was the portfolio of products that Quantcast was a part of? What were their customers that they were trying to sell to, and how could we actually be better about that? Everything about what I just said, that takes a ton of time and investment to really understand your customer's business and your customer's customer, and then think through how you can help them. It takes a lot of time. It takes a lot of effort, which is why making it so that they can actually be set up for success, aka they have small portfolios, that ends up being really important.

Sean Lane: It was really funny, we had an example this week, I think, of something similar to what you're talking about, where the partnership just becomes so evident, better than any CSAT score or anything could possibly be. We had two customers, actually, who named their Drift Bot after the person on the implementation team. We have this amazing woman on our implementation team, her name is Robin, and two different customers named their bot Robin. And so like, if that is not a phenomenal signal that that thing is going well, and they are completely bought in, and bought into that person, not just Drift... Because also, the other thing too is, for that partnership to exist, I feel like it's just as much about the person on the other side as it is about the product. If something does go wrong with the product in one of those scenarios, guaranteed they're going to have a hell of a lot more patience, and give a lot more leeway to someone like Robin than they would in a scenario where they didn't feel that same level of partnership.

Anil Kumar: Totally, totally. Because by the way, things are definitely going to go wrong. That's the beauty of enterprise. It's so complicated. You're going to have fires, and more than likely when you're going upmarket, you're actually not ready for it. You're selling a little bit of a dream. So that empathy upfront and in that investment in the relationship and empathy, it just pays dividends. I'm thinking through this because you and I both, we're on the customer side a lot, right? I bet you we know the same people. And you know, from stops before Drift, who are the people who were just insanely good as partners for you, who thought at a level that was, legitimately and authentic, what your needs were and how you could be better at what you do. Ben Chen at Clari, he's an awesome example. I've worked with him now three times, where this is a guy who, the night before Thanksgiving, will get on a call with you to scope a demo, to help you sell it to your boss. That's the level of empathy and commitment that you expect and want when you're playing at that level. What's funny is, it goes both ways. Because when you build those partnerships, they don't go away. When those folks win, you then celebrate their wins with you, because they effectively are part of your team.

Sean Lane: You know you have a true partner when Anil is rattling off Ben Chen from Clari's name off the top of his head. So shout out to you, Ben, and also shout out to Robin on the Drift team. True partnership is really tough to find, and it takes a lot of time invested on both sides. I particularly liked Anil's advice to understand your customer's customers. And what he has found is that, a lot of those partnerships, and a lot of that understanding, can start with a single dedicated champion. I was curious how Anil had leveraged partnerships like this in the past, to grow use cases inside of an organization from just one geo or one line of business to many, many more.

Anil Kumar: It's a really, really good point that you mentioned, because when you talk to really killer enterprise sales execs or AAEs, almost always to a T, they're going to tell you that what you just said, that's like eight out of 10 times what your enterprise deals are about. They're toehold strategies, where you start with a business line or a geo that effectively allows you to de- risk your product or service with the prospect or customer. You prove your worth there, and then over time, you build and you grow. In every one of those cases, whether it was that Atlassian, when we looked at our enterprise segment and selling the stack to them, Quantcast, when we were going at top- paid retailers, it was the same thing over and over again, which is, find somebody who will be your champion, who quite frankly, is going to be willing to take a risk on you. Make it worthwhile for them. Deliver that value. Make them your champion by them succeeding because they've got you as part of their game. And then over time, build that relationship. And it's almost organic. Naturally, that becomes where there are other opportunities for us. The relationship piece is so, so key. The little things like, and it's not just QVR, it's like, this is where us, on the ops side, we can structure these things with QVRs and check- ins and all that other good stuff. You got to be authentic about it. You've got to really, really care about your customer. And thus your communication becomes," How do I make my customer successful?"

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?

Anil Kumar: Pass. Let me think on that one.

Sean Lane: All right, I'll come back. Favorite part about working in Ops?

Anil Kumar: You get to build.

Sean Lane: Least favorite part about working in Ops?

Anil Kumar: Oh my God. It's under- appreciated. Always, always, always, always, there's always one more thing.

Sean Lane: Always. Better, better, never done. Someone who impacted you getting the job you have today?

Anil Kumar: Al Chesser, the godfather at Carta.

Sean Lane: All right. Any good story behind that?

Anil Kumar: He's literally the godfather. I prospected into him for months and months and months. He wouldn't return any of my calls. Finally, I get ahold of him, and it's a 20- minute conversation. And it's one of those things where, when you know, you know, for him and for me.

Sean Lane: That's awesome.

Anil Kumar: And my book, by the way, Win Forever, Pete Carroll.

Sean Lane: Oh, interesting.

Anil Kumar: I hated Pete Carroll when he was a college coach, and now that I'm in a capacity where you're coaching and leading and managing, I actually love his philosophy, which is... I mean, his philosophy is win forever, but it's, translate for me, it's do the best work of your life together.

Sean Lane: Yeah, and also just, I mean, the guy's what, like 69 years old, something like that? And just brings unbelievable energy to what he does with a bunch of 20 year olds, every single day. It's very inspiring.

Anil Kumar: If you love what you do, it's not work. I think above all else, that's the thing you just see with him. And I know for me, that's what I love about Ops. We get to build, but quite genuinely for me, I love building, and I love creating, and I love actually scaling things. And our roles in Ops are so instrumental to that.

Sean Lane: I'll have to pick that one up. All right, last one for you. One piece of advice for people who want to have your job someday?

Anil Kumar: Have a growth mindset, more than anything. Walk into every, every, every situation thinking about," What can I learn from the people around me? How can I push myself? What don't I know?" And then from there, good things happen. Don't be afraid to ask those questions. If it's in front of the CEO or CFO, or an SDR, it doesn't matter. You can always learn from the people around you. If you've got that growth mindset, if you stay curious, good things happen

Sean Lane: Thanks so much to Anil for joining us on this week's episode of Operations, and shout out to Jason Phillips, another member of our enterprise team at Drift for helping to make the connection. Thanks so much, Jason. If you liked what you heard on today's episode, make sure that you have subscribed to the show. A new episode comes out every other Friday, and it'll show up in your feed automatically. And if you really liked what you heard, please leave us a six star review on Apple Podcasts, six star reviews only. Quick scheduling thing for everybody, because two weeks from today is going to be the day after Thanksgiving, we will not have an episode on the 27th. So we'll be back with a new episode on December 11th. Thanks so much for listening. That's going to do it for me. We'll see you next time.


Hypergrowth companies are constantly reinventing themselves. At Drift, we often say, "what got us here isn’t going to be the thing that gets us to the next stage.” On this episode, we’re exploring one of those significant moments of transition: how companies move up-market and start to sell into larger, enterprise companies. Our guide through that transition is Anil Kumar. Anil is the VP of Go-to-Market Strategy & Operations at Carta, and prior to joining Carta, he successfully helped three other companies, Sift, Atlassian, and Quantcast, move up-market. In our conversation, we talk about the focus required to move upmarket, why the Enterprise sellers you’ll need in your organization should be Pioneers, not Settlers, and how your Post-Sale model likely needs to completely change to service these enterprise customers. Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @HYPERGROWTH_pod