The Exchanges

Q Take me to that story. How did Ben bring you into Databricks?

A Yeah, so I met Ben Through VC networking and, and at the time, it was like, kind of late, 2015, so I was like looking at Mongo or Square or some of those companies and, and he was like, yeah, this company called Databricks, it's way earlier stage than anything you're looking at, but it's got the most upside of any company in my whole portfolio. There's seven PhD, super smart Berkeley computer guys, and they're just a bunch of Berkeley hippies and wanted to, you know, change the world, so they gave away their software for free and I need somebody to help them build a business. So, uh, I met the founders. They were just absolutely amazing. Ali and the whole crew.

AI assessment note: “I met Ben Through VC networking and... he was like, yeah, this company called Databricks”

Q How does AI change the sales process, do you think? Do you use any AI tools today in the sales team?

A Oh, we do. Yeah, we use Perplexity. We use Glean. We actually built some of our own AI, like a sales AI assistant. Our sales AI assistant, if we're like, hey, how do I get funding for an on-prem migration from Microsoft? You can just ask, and it'll tell you the process on that. We use perplexity. We'll do a lot of our upfront account research. Tell me, you know, how this customer uses data and AI. How would they get the most value out of Databricks? You can get a lot of information on that. And then our sales assistant We'll actually take that data or take that conversational stuff along with like our count data, right? Like it'll say, oh, they've been growing here. They've been spending on this product. They're working on this initiative. Oh, I also see in the press, they're interested in cybersecurity, stuff like that, right? So you can use AI to really accelerate all that research and get smarter. Cause again, the smarter you are on that customer, the more interesting questions you're going to be able to ask to try to find an area you can add value.

AI assessment note: “Oh, we do. Yeah, we use Perplexity. We use Glean.”

Q Okay, less than a million. Is it an art then? And how did you think about building the first playbook for Databricks?

A First, like, we didn't really have a set playbook or revenue model, right? Like, we were creating that. That was one of the things that really was exciting to me coming into Databricks was, hey, I get to help build the playbook, build the culture, all those kind of things. And honestly, first thing I did was like, hey, let's build out a team of people that I know know how to sell, and let's just go find out what customers will buy. So a lot of that first kind of stage of a company called product market fit from A million to ten million is, you know, we had all these Spark users, they're free, but let's just go talk to them and find out what would you pay for.

AI assessment note: “let's just go talk to them and find out what would you pay for”

Q What are the lessons on how to do it well for founders listening?

A Literally, we take the entire sales team. This is everyone, like, including me, like, I jump into the pit because we have a lot of, you know, younger salespeople too. But every Wednesday, all we did was prospecting. Because if you tell a salesperson, hey, go prospect four to eight hours a week, just not going to do it because it's painful. It's like hard. But you learn so much. And if you do it as a team and you make it interesting, we do it in San Francisco, you know, where the company was founded. I'd get breakfast in the morning. We talk about, okay, today, you know, you'd already have to show up with, okay, here are the three to five companies. I'm going to research for each salesperson. I'm going to try to get into these companies. He'd research their profiles and then, okay, here's how we want to pitch. At the time it was like managed spark. So here are the differentiators and we teach them how to pitch it. We'd go make phone calls, LinkedIn, emails, all that stuff. Then you break for lunch, like, all right, who got meetings? And then you'd share. Cause the collective learning, the faster you can iterate, that's your secret weapon as a small company is I can iterate super fast and pivot super fast versus a bigger company. That's how things change. But anyway, we'd say, okay, and it'd be like, well, I got this profile on LinkedIn and I got them with this message. And you t…

AI assessment note: “every Wednesday, all we did was prospecting. Because if you tell a salesperson”

Q What should all founders know before they go into enterprise? Cause it is a big decision.

A A couple of things. One, it's a conscious investment. It's a longer term investment. So you need some kind of sales expertise, their experience. Number one. Number two, they're also going to try to push their custom requirements on you, right? So you have to be a little bit careful. Like the security stuff is really important because again, if you want to be a mainstream tech provider, you got to know about security and governance and all those things. No enterprise is just going to let them use some tech that doesn't have security. The risk is too big. So you're going to get a lot of that, but you also need to be conscious. You don't want to build something that's just for one enterprise, right? You want to make sure whatever you're building, It's going to be applicable to 200 and, you know, you get some of these big customers, they can, they can wield a pretty big stick in terms of trying to do custom engineering.

AI assessment note: “A couple of things. One, it's a conscious investment. It's a longer term investment.”

Q I find people go too early into enterprise, um, often. And the hard thing I find with enterprise is the sales cycles mean it's tougher to determine success with reps, because they're just longer before you have closures. How do you think about measuring rep effectiveness? And what are your biggest lessons in what it takes to do it well? How do you know if I'm good?

A For enterprise or for any rep. Does it differ? I think it does slightly just based on the sales cycle, but I think upfront I'm looking at pipeline and activity. The number one thing I'm going to look at is this person getting the right meetings? Are they building the right pipeline? I got to make sure I'm inspecting that too. So, you know, early stage sales leader, you're going to want to go, Hey, I'm in your territory this month for this week, set up as many meetings as you have. And if you got one or two meetings, Probably don't have a great salesperson, right? So, and then you're going to see them in front of a customer. Do they ask good questions? Does the customer want to buy from them?

AI assessment note: “The number one thing I'm going to look at is this person getting the right meetings?”

Q So we're at like, I don't know, 500 K to two million in revenue, say, and we, we're going to hire that salesperson. What type of salesperson do you like to hire in that stage? And for founders listening, Do you recommend they hire? Is it the senior head of sales who's been there, done it? Is it the juniors? Who should we hire?

A I mean, if you're just hiring salespeople, find somebody who's smart, intellectually curious that you trust, you know, is going to work their tail off. In the technical field, you got to have technical salespeople, right? Again, I always say salespeople teach, they don't sell. They teach customers how to get value out of their technology, right? If you try to go for the senior Really senior folk. They're going to want to hire a bunch of people. So you got to make sure you got a bunch of funding to be able to do that. Otherwise get like a great first line manager, somebody you trust, spend a lot of time with them. Cause again, salespeople are good at selling. So they're really good at interviewing. You got to know what you're getting. Do a lot of back channels, all that kind of stuff, but get somebody that gets their hands dirty.

AI assessment note: “Otherwise get like a great first line manager, somebody you trust”

Q You mentioned 18 K ACVs and then the same month, two 50 K ACVs. So were you doing like SMB and enterprise at the same time? How do you think about whether you need to be in one camp or the other?

A Early days when I got there, they were all in selling to SMB startups, digital natives, Silicon Valley type folks, which again, like, we're like trying to convince someone to spend 25 grand and I'm like, it takes you two engineers. We made a big bet early on to invest in enterprise, and we did that early because, I mean, one, I thought that's where the money was, and two, long-term sustainable for a company, you have to have an enterprise business. I think there's very few businesses that can just scale based on startups and digital natives. They go up, down, all over the place, right? So you need to make that investment. It's going to take a little longer to pay off, The sales cycles are longer, but you're going to learn a ton too. You're going to learn about like when we entered enterprise, again, you could learn all kinds of new requirements about security, how to navigate the organization, even your legal process.

AI assessment note: “We made a big bet early on to invest in enterprise, and we did that early”

Q I've never had much patience, that's why I called it the 20 minute VC. Are you kidding me? I am, for this question, your, you know, adopted son, and I'm 23, I'm entering a sales org, first job. What's your biggest advice to me as a twenty-three-year-old entering sales for the first time, bright-eyed?

A Two things. One, go into an industry that's growing and you're passionate about it. Obviously, I think data and AI is where it's at today, but if you're going into tech, I'd say go into data and AI. So go into a market that's growing and gotta be passionate about it too. If you're like, ah, that's boring. Don't go into that. Number two is go where you're going to learn the most. A lot of people try to go, oh, I'm gonna get this amount of money instead of that amount of money. No, go to where you like the people, and they're gonna help mentor you, and you're gonna learn the most, because that's the whole thing about your first job or whatever is, how do I learn, and how do I grow as an adult, as a worker, as all those kind of things, right? Like, that's, that's what it's all about.

AI assessment note: “Two things. One, go into an industry that's growing and you're passionate about it.”

Q Yeah, you did. Brilliant. Um, when you look at the different stages of the company, what was the hardest? You can break it up into like, I don't know, 10, a hundred, a hundred, a 1,000,000,001, billion and beyond. Which was the hardest?

A They all have different challenges. The zero to 10, for me, was probably the most fun. It was tough, but I was like, I can sell ten million dollars or something to literally anyone. You know what I mean? Like, all I have to do is figure out what they want to buy. That 10 to a hundred million is pretty tough scale, because now you got a little bit of product market fit, but now you really have to get into like that enterprise motion, start getting referenceable customers, get them to speak about you. I really enjoyed that phase for sure. Then the hundred to a billion, now you're getting partners involved, distribution channels, you're scaling the sales organization. So now it's, you know, you're getting into the scaling function. You know, we just did three billion last year. You know, I think we'll be ten billion in a few years. So, you know, now you're in hyperscale and, ah, you know, a different set of challenges. So, each one I've enjoyed because they're different. I think the 10 to a hundred is one of the hardest things. Now, the hyperscalers in AI, they're like blowing through a hundred million, right? Like some of these companies, they're crushing it.

AI assessment note: “I think the 10 to a hundred is one of the hardest things.”

Q Should you discount to get them? Like, should you do anything to get those logos? How do you advise early stage companies on getting mega logos?

A I mean, first of all, like, enterprise sales is different than selling to digital natives and those kind of companies. You have to realize, like, just the sales process is different, who you sell to, how you sell, all that. But honestly, there's more money in enterprises, right? Because digital natives, they like building stuff. They're going to squeeze you for lower prices, right? Enterprises need expertise. They need help. You know, I don't know about just heavily discounting, but again, if you build a pricing model that scales, that it's base unit is based on your value, whatever that is, uh, as a tech provider, then you can scale it. So start with this one team or this one department, you can scale down the scope of it to get inside, like director has up to a hundred K. So, you know, find a champion that'll spend that amount of money, give the resources, Even if you just do a pilot, get that logo.

AI assessment note: “I don't know about just heavily discounting, but again, if you build a pricing model”

Q In the zero to five hundred billion range, which is a huge range, what did you not do that with the benefit of hindsight you wish you'd done?

A I started to invest in the partner channel much bigger. Partners are interesting, right? Like especially the big partners, big SI partners. At that point we had already done, Ali and I did the deal with Microsoft, right? Which became kind of pretty, uh, historical, I think in legend. Um, and it's still, you know, Microsoft's our, you know, biggest partner. It's a amazing partner for us. But like, you know, you got to start thinking through like channels and partner strategies and When you're so small, you're always thinking like, how do I get these partners involved? But you're too small and like, you know, go away. But once you start getting scale, you need to start investing early days in partners.

AI assessment note: “once you start getting scale, you need to start investing early days in partners.”

Q So going back to the 10 to 50, for you, what broke in that phase?

A Uh, when you're in this hyperscale phase, which I kind of see with some of the new AI companies, right? There's some great scaling AI companies is, You have to start thinking, like, traditional business might grow 20% year-over-year when you're doubling, tripling. My staffing and my leadership plan has to be what I need next year. So you can't be like, okay, I'm gonna incrementally add reps or leaders. You have to be thinking, we're gonna do fifty million, next year we're gonna do, you know, we did a hundred or two 50. Like, what does my org need to look at, at a 100,000,250 million? And I need to do that now. So I need to go get those leaders. I need to sell them personally. Why this is a once in a lifetime opportunity to get even bigger leaders than I need today. Because once I start building out the team and the leadership, now I can start scaling under them. You know, my biggest advice is, you know, you need to look at least 12 months out. Cause if you're just trying to iterate, you're not going to grow fast.

AI assessment note: “You can't be like, okay, I'm gonna incrementally add reps or leaders.”

Q Does it get harder to hire the hustlers as Databricks becomes an incumbent?

A I think Databricks is a once in a lifetime type company. It will be a trillion dollar company. Somebody in that data and AI space will become a trillion dollar company, and we're the innovation leaders. I think we can do it, right? And so part of that, when you think about getting talent at this level of scale, because we kind of skipped a couple stages now, is we have to become a destination company. People have to be like, I want to go to Databricks because I can build my career there. Because someday I want to be a CRO or a CEO or whatever, and they're going to teach me about how to do that in the right space better than anybody. I mean, think about like Microsoft early days or Google early days, like a big part of getting talent is you have to become a destination company. And, uh, I think Databricks is, is doing a pretty good job of that.

AI assessment note: “when you think about getting talent at this level of scale... become a destination company”