# $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History

How Databricks Beat Snowflake · How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

20Sales · Aug 4, 2025 · 76 min · 15,147 words
Speakers: Harry Stebbings, Ron Gabrisko
Source: https://www.996.fm/episodes/20vc--ep-653fc8bc/

## Cold open

**Harry Stebbings** [0:00]:

You are listening to 20 sales with me, Harry Stebbings. Now today, we have an absolute unicorn from the sales world on the show. We have Ron Gabrisko, CRO at Databricks, which he joined in 2016. And check this out. Under his leadership, Databricks has scaled from zero to over $4,000,000,000 in ARR. He's grown the sales team from zero to over a thousand globally, leading expansion into the enterprise, government, and international markets. I do not know any other CRO or sales leader that has gone from 0 to $4,000,000,000 leading the charge. Incredible. And this is one of the best 20 sales shows we've ever done. But before we dive into the show today,

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## Conversation

**Harry Stebbings** [4:13]:

Ron, I am so excited for this, dude. I have heard so many great things. So thank you so much for joining me today. Yeah. Excited to be here. Thanks for having me. I've gotta start. You just mentioned before this how Ben Horowitz brought you into Databricks. Yeah. Take me to that story. How did Ben bring you into Databricks?

**Ron Gabrisko** [4:31]:

Yeah. So I met Ben through VC networking, and and at the time, was, like, kinda late two thousand fifteen. So I was like looking at Mongo or Square or some of those companies 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, I met the founders, they were just absolutely amazing, Ali and the whole crew.

**Harry Stebbings** [5:09]:

What was that like meeting Ali? Because I think I have a challenge doing this show where I meet Ali today, and I'm like, amazing leader of multibillion dollar company, and then I retrofit on seed founders. And I'm like, well, you're not as good as Ali. And I forget the slope that Ali's been on.

**Ron Gabrisko** [5:26]:

What was Ali like then? First of all, Ali's like one in a billion, you know. This is kind of my third founder, technical founder. He's a 100 x better than any of them because he can do the technical stuff, but he's also an inspirational leader and he he knows the business. Back then, he was like, when I joined the company, they were kinda transitioning to him as the CEO. He was actually the VP of engineering, and I was like, he was like recruiting me. I'm like, that's kinda, you know, different. Right? But no. The first thing when he took over as CEO, he was like, teach me sales. Like, I wanna learn sales. So, you know, we would sit down and talk about org charts and med pick and how organizations make decisions and Can you take me to that? So you sit

**Harry Stebbings** [6:08]:

down with Ali to teach him sales. Yeah. What did you teach him?

**Ron Gabrisko** [6:13]:

No. I mean, again, like enterprise sales is kind of a system. Like a lot of people think it's a black box, but it's not. It's it's a science. Especially complex organizations. When you're selling to enterprises, decisions are made not by one person usually, they're made by committees, right? So you gotta kinda know how to navigate organization, who are decision makers, who are influencers, things of that nature. You know, we talked about like med picks, some of the how do you build a playbook, what kind of reps do you hire. I mean, Ali's 10x smart, right? Like these all the founders are, like their brains work in a different way. So he gobbled it up. Now he's like an expert. Like, he'll we'll sit down. He knows exactly. Like, he's amazing salesperson now.

**Harry Stebbings** [6:56]:

So I love this in terms of the engine like characteristics, the science of it. But when you joined, it was zero, like, in revenue. No? Yeah. Less than 1,000,000. Okay. Less than 1,000,000. Yeah. Is it an art then? And how did you think about building the first playbook for Databricks?

**Ron Gabrisko** [7:14]:

First, like, we didn't really have a set playbook or revenue model. Right? Like, 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 10,000,000 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.

**Harry Stebbings** [7:51]:

I just wanna go back. You said about the playbook there and figuring it out. Founders are told today, the founder needs to be the one to create the playbook, and then you bring in the CRO head of sales to run the playbook for you. Yeah.

**Ron Gabrisko** [8:02]:

Do you disagree with that? Kinda depends. Right? Like, I think founder led sales is really important. No one can sell the vision and the passion of the company better than the founders. Like, Ali was really good at that. I'll tell you a story, like early days, like I was, I don't know, thirty, sixty days in and, I was like, hey, if we're gonna have a big business here, we gotta sell the financial services. And so I set up like 10 CIO meetings in Wall Street. You know, I brought Ali, Matei, Arsalan, I'm gonna go meet all these folks. And we went and met, JPMorgan Chase. This is back in like early two thousand sixteen. And, you know, we were, meeting with like the risk management. And first of all, we show up, I get all these meetings like immediately and I'm like, what's going on? And I'm like, why? The creators of Spark. We show up and there'd be like a 100 people and they just wanna take pictures with Matei. So it's hilarious. But anyway, they're like, we'll give you $10,000,000 to put this. And at the time, we're less than 1,000,000, like our whole first year targets like 10,000,000 to put it on prem. And Ali was like, no way, we're not doing anything on prem. He couldn't get out of the meeting fast enough. Right? Because his vision and the founder's vision was all around cloud, open source, and data and AI, which in retrospect was amazing insight on where the market was going. Anyway, so we just passed on it. And JPMorgan was like, we'll never be in the cloud. And, obviously, now they're like one of our biggest customers. So, they're massively in the cloud. We have Jamie Dimon talking at Data and AI Summit. But again, like that product market fit, I think building that playbook. If you can find the right salesperson as a startup, you know, to help you do that, you should. But again, I I believe in founder led sales, you gotta go meet with customers, you gotta understand what their needs are, how to develop the product. That product feedback loop of requirements and and what's valuable to customers is is incredibly important.

**Harry Stebbings** [9:52]:

So we're at, like, I don't know, 500 to 2,000,000 in revenue, say. And we're gonna 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?

**Ron Gabrisko** [10:11]:

I mean, if you're just hiring salespeople, find somebody who's smart, intellectually curious, that you trust, you know, is gonna work their tail off. In the technical field, you gotta 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 gonna wanna hire a bunch of people. So you gotta 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. Because again, salespeople are good at selling, so they're really good at interviewing. You gotta know what you're getting. Do a lot of back channels, all that kind of stuff. But get somebody that gets their hands dirty.

**Harry Stebbings** [10:53]:

Take me back to that. It's an amazing moment. You're at 500 k, whatever it is, and you join, and you start the sales process with Databricks. What were your biggest lessons from that one to 10,000,000 process with Databricks?

**Ron Gabrisko** [11:05]:

Go talk to as many customers as you possibly can. Like, we went and talked to hundreds of customers. Second, I, you know, I hired probably 40 people the first six months, some of the best salespeople from my network, and I was literally just go set up meetings and find out what what people will pay for and get the brand out there.

**Harry Stebbings** [11:25]:

Are you teaching them the

**Ron Gabrisko** [11:26]:

questions to ask, how to engage with customers? Yeah. We're learning the discovery. You know, eventually when you build the playbook, you wanna know, okay, as you start to scale, what's the discovery guide look like? What questions do I wanna ask? How do I position our solution? How do I position the value of it, the differentiators? But it's all about asking questions. Like, even when I when I interviewed for Databricks, they're like, hey, here's our pitch. Give us the pitch. Right? And I was like, okay. So I looked at it and it was like a lot of technical stuff, you know. I was like, well, you don't talk a lot about value, I talk more about time to value, innovation, all that kind of stuff. Like, okay, pitch us. And I said, what kind of company are you? And they said, okay, let's let's do that. I was like, okay, what are some of your challenges with data? Okay, you know, what are you trying to do in the future for your business? They're like, are you gonna pitch us? And I'm like, I am. You know, it's all about asking questions and trying to find where, you know, we can add value. And so then you build that into a system of repeatable plays and teach everyone. Teach them exactly what's the profile we're going after. At that time, I was like VP of analytics, you know, we run prospecting day every Wednesday just to get meetings. We're trying to get meetings and activity and all those kind of things, which is kind of a cultural thing, right? You need to know, I'm building pipeline all the time. And then here's our value and our differentiators, and you start to build up that customer base.

**Harry Stebbings** [12:46]:

Can you take me to prospecting day?

**Ron Gabrisko** [12:48]:

Yeah.

**Harry Stebbings** [12:49]:

How do you structure it? Yeah. What are the lessons on how to do it well for founders listening?

**Ron Gabrisko** [12:53]:

Literally, 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 gonna 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 gonna research for each salesperson. I'm gonna try to get into these companies. He'd research their profiles and then, okay, here's how we wanna pitch. At the time, it was like managed Spark. So here are the differentiators and and we teach them how to pitch it. We go make phone calls, LinkedIn, emails, all that stuff. And you break for lunch, like, alright, who got meetings? And then you'd share. Because 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 I got this profile on LinkedIn and I got them with this message and you teach that to everybody. Alright, everybody else starts trying. And so you start learning, okay, what are people interested in? How do I get meetings? All that kind of stuff. And eventually then, as you continue to scale that every Wednesday, it's just a muscle you're building. It's like going to the gym. And so I would have winter at the end, you know, we'd either do like a donation to their favorite charity or someone might get a cowboy hat today or a bottle of whiskey or something, you know what I mean? So just make it fun and have the team work together and eventually, like, they'll start doing it on their own, you measure the activity. What ACV's are you selling at that point? 18 to $20. I mean, I came grand. Yeah. When I came in, we're it was tiny. But the first, you know, say month I was there, we probably did a million bucks because, you know, as a more experienced salesperson, I could go in and say, okay. How are you using the technology? What's it worth to you? We found some customers that I was like, oh, that's 250 k opportunity. But at the time, all the deals were 18 k. I was like, no more deals, less than my Uber bill.

**Harry Stebbings** [15:09]:

Oh, dude. I like you. But okay. But there's a lot of founders who undersell, and they don't realize they're underselling. A thousand percent. How would you advise them to make sure that they're not underselling given the knowledge that you have?

**Ron Gabrisko** [15:22]:

We spent a lot of time, early days, debating how to do pricing. I actually think it was one of the smartest things we did at Databricks was we priced based on consumption. So you could start super small, but as you start to consume more, it could get super big. And then we expand it to multiple products, all that kind of thing. But if you think about data and AI, data is growing, the number of queries you're gonna do grows. So having a consumption based model is super smart. I see this mistake a lot, like people will be like, oh, I'm gonna price on users. Users. There's a cap on users. You know, if the economy goes down, then there's maybe less users. But if you can price based on, you know, what's your essence of value, then you can scale while we're sleeping. Right? Which is a big important part of I think, how Databricks built its pricing model is it's based on consumption. If you use it and you get value out of it, great. If not, you don't pay anything.

**Harry Stebbings** [16:14]:

Did you find in the early days that helped you to sell because people were like, oh, great. Removes the risk.

**Ron Gabrisko** [16:20]:

Yeah. Exactly. So we'll try it out. And actually, the one trigger that we did early on was traditional enterprise, you're always selling your services. We developed a thing we called strategic customer program where we'd be like, hey, if you spend a $100, we'll give you free resource. Because the biggest thing was like there was a gap in talent and expertise. Like our product was amazing but you had to know how to use it. And so we would add a resource. What's resource? A person? Yeah, a person. Like a smart technical person to be able to set it up, show you the first couple use cases, all that kind of thing. And then once they got enabled, they're like, oh, no. Get it. It's pretty cool. Right?

**Harry Stebbings** [16:57]:

At what level can you do that? Because I think we're in that stage again with a lot of AI tools where bunny enterprises are like, I know it's valuable. I can see that, but I don't know how to implement it. And the integration process is actually much harder for traditional enterprises. At what stage can you do in FTEs, fully deployed engineers? Yeah. It's like like a hot word. Thanks to Palantir. Yeah. At what

**Ron Gabrisko** [17:17]:

price point can you do

**Harry Stebbings** [17:18]:

that?

**Ron Gabrisko** [17:19]:

You know, again, early days, you just need logos. So it depends on your funding situation, but 50 or $100, say a $100. Okay. Give me a $100 a year. We'll do this pilot. I'll give you a resource to do it. But again, you're trying to get those big logos. Because now once I you know, the enterprise market's very much a FOMO. You see your competitors, they're doing this with this company. Oh, I better get on board, go fast to do that to compete. And so getting those big logos is so important early days, like, you need to buy them, and you need to put resources in them to make them successful.

**Harry Stebbings** [17:52]:

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?

**Ron Gabrisko** [18:00]:

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 gonna 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 its base unit is based on your value, whatever that is, as a tech provider, and 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 100 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.

**Harry Stebbings** [18:47]:

You

**Ron Gabrisko** [18:47]:

mentioned

**Harry Stebbings** [18:48]:

18 k ACVs, and then the same month, two fifty 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?

**Ron Gabrisko** [19:00]:

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, 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 gonna take a little longer to pay off, the sales cycles are longer, but you're gonna learn a ton too. You're gonna 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. What should all founders know before they go into Enterprise? Because it is a big decision. Couple 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 gonna 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 wanna be a mainstream tech provider, you gotta know about security and governance and all those things. No enterprise is just gonna let them use some tech that doesn't have security. The risk is too big. So you're gonna get a lot of that, but you also need to be conscious. You don't wanna build something that's just for one enterprise. Right? You wanna make sure whatever you're building is gonna 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. Should you ever do custom engineering? I wouldn't do it if it's just for one customer because, again, as a small company, your number one asset at tech company is your engineers. And you want them innovating on how you build the market and grow the market. If you build something custom just for one customer and nobody else is gonna buy it, you might distract your whole engineering team.

**Harry Stebbings** [21:05]:

You said you made a very conscious decision to invest in enterprise. Yeah. What does that actually mean in reality?

**Ron Gabrisko** [21:11]:

It's a decision that's the whole team. Right? It's Ali, the founders. Hey. We're gonna go after this segment. Does that mean you leave the SMB segment? We kept that going. We hired a first line leader that would just, you know in Arsalan at the time, he was running sales, one of the founders. Crazy smart, technical, gregarious, great leader too, like, one in a billion. And, you know, he was like, okay. I'm gonna keep the SMB DNBs going, which was generating money as we kinda built out the enterprise segment. So we personally did both. It's a handful, but, you know, I had done that before. Can you do both? You can do both. Because I

**Harry Stebbings** [21:48]:

really why when you see startups that are just going after enterprise Yep. And you have, like, big ACVs, but nine to twelve month sales cycles Yep. And then they slip. Yeah. And suddenly you've got nothing.

**Ron Gabrisko** [21:59]:

Well, I mean, it's hard. Like I said, it depends on what kind of funding you have. Right? Because eventually your business has to have enterprise. But the digital natives spend a lot of money, especially in the cloud, data, and AI. And they're also gonna be the canary in the coal

**Harry Stebbings** [22:12]:

enterprise before 10,000,000 in ARR stay?

**Ron Gabrisko** [22:15]:

We did in our first year, which I think we did 12 or 13,000,000 ARR, we did $2,000,000 I

**Harry Stebbings** [22:22]:

see you did $1,213,000,000 now.

**Ron Gabrisko** [22:24]:

Yeah. We did $2,000,000 deals with Enterprise. So again, you have to know what you're doing though. I think it is smart to do product market fit because those smaller customers will educate you on the requirements of the future market. So again, the canary in the coal mine, they're always gonna be the ones pressing the technology boundaries early days. Enterprises are gonna adopt that as the next phase. But again, you gotta remember, enterprises are gonna have another set of requirements that the digital natives might not have around security and all those things. You need to learn about that stuff too.

**Harry Stebbings** [22:57]:

12 to 13,000,000 in revenue. Yeah. Your sales cycles are not that long then if you're doing 12 to 13 in the first year.

**Ron Gabrisko** [23:05]:

I think early days, we had some pent up demand of just you know, it was probably three to six months because they were basically free users, and we just had to sell them on why they needed to get more of our premium stuff by paying for it, you know. Again, when I joined, we had hundreds of thousands of Spark free users. I was like, if I can't sell them something, suck at sales.

**Harry Stebbings** [23:27]:

Did you make mistakes in your hiring of your first sales team?

**Ron Gabrisko** [23:31]:

A lot of those early folks were people I knew. Like, they were known quantities. Like, I wanted smart, hungry, good at discovery, good at customer relationships, things of that nature. But of course, when you're

**Harry Stebbings** [23:43]:

What are the big fuck ups you see young founders or early stage companies making that one to 10 on building a sales team?

**Ron Gabrisko** [23:50]:

Probably the biggest thing is a lot of founders think, oh, I hired my a salesperson, now I don't need to do sales. Because a lot of technical founders, they don't really enjoy sales, right? So, I need a salesperson to, like, take this off my plate. I wanna focus more on the product and engineering. But ideally, you still need to be involved in sales because again, founder led sales requires you to hear about your product. No one's gonna be more passionate about selling your product. You have to still be involved until you can kinda get that, like I said, probably around five, ten million bucks where you have kind of a, okay, I know what people are buying, I can build a first playbook. That's the biggest mistake, is just don't delegate it to the salesperson because they could mess that up and that sets you back at least twelve months. So

**Harry Stebbings** [24:38]:

And also don't think sales is like a panacea for product market fit. Whereas like, oh, well, they didn't sell, so it's their fault. And it's like, well, maybe you just don't have PMF yet.

**Ron Gabrisko** [24:46]:

Yeah.

**Harry Stebbings** [24:46]:

That's not all the seller's fault.

**Ron Gabrisko** [24:48]:

Or maybe listen to your customers, you know, two ears, one mouth. And even today, good salespeople ask good questions, understand what the market wants from your product.

**Harry Stebbings** [24:59]:

I'm always struck by the dilemma between when you're in those early one to 10 phase. Do you do horizontal, see what resonates with different customer bases, be it financial services, be it logistics, be it healthcare, you name the different sectors that we can sell into? Or do you go, no, gonna sell to financial services with a verticalized sales team, very tight product marketing, and a really honed sales process for financial services? Do you go horizontal and broad or verticalized

**Ron Gabrisko** [25:29]:

and I mean, I think you have to start horizontal because you're, again, learning what's your applicability to the different verticals. I didn't go vertical at Databricks till we were probably 500,000,000 plus. Right? 500,000,000. Yeah. Because, like, again, like You skipped a few steps there.

**Unknown** [25:48]:

We

**Ron Gabrisko** [25:49]:

were at 13 a million. I know. I'm I'm just saying, like, I think when you verticalize your sales team, there's a whole another level of, like, resources and complexity that you're gonna add. Right? Because you're gonna add industry experts. You need to add that vernacular, add that to your training, to your enablement, your customer stories, all that kind of stuff. Early days, maybe financial services is the place to go. Like what I learned was financial services isn't in the cloud yet. If we're gonna be cloud, we're probably not gonna sell financial services early days. Let's go sell to the folks that are in the cloud already. Do you

**Harry Stebbings** [26:21]:

agree that you don't want to educate your customers on the problem? And so, like, for me, I don't want to tell LPs that they should be investing in venture because it's two steps. Then I need to convince them to invest in venture and then to invest in me. You want people who know that the cloud is where they should be and then, okay, Databricks, not educating them that the cloud is good.

**Ron Gabrisko** [26:45]:

It might be a little bit different now at the scale we're at, but, like, early days, if they weren't in the cloud, it was like bridge to door. Let the cloud folks convince them they need to be in the cloud because we need to generate customers and revenue. You spend a lot of time, time's your most precious commodity, right? Especially as a salesperson. So don't spend a bunch of time with people that aren't gonna buy anything, right? You need to go find so the whole world is our prospect at that point. Every customer is a potential new customer. One of our qualifying questions is, are you in the cloud? If you're not in the cloud, then you're not ready for Databricks. So let the cloud guys fight that out.

**Harry Stebbings** [27:21]:

So we're at 13,000,000 in revenue now. Yeah. Hold your horses on the 500. That's a shockingly late decision on verticalization. I was like,

**Ron Gabrisko** [27:31]:

very A lot of companies are still horizontal. They'll still be horizontal. Right? Like, I think AWS just moved to verticals, right, across the whole organization. They're a 100,000,000,000. So, like I mean, again, I think that's another choice you have to make on your strategy when you verticalize.

**Harry Stebbings** [27:47]:

So 13,000,000. Yeah. What starts to change when the sales team goes from one to 10 to now in that scaling to 50 10 to 50 mode?

**Ron Gabrisko** [27:56]:

Yeah. Now we have product market fit. Right? We have some references. We've seen how customers buy, why they buy. Now we're starting to get into the scale function. Now we can start to build a real playbook, start to train more and more salespeople.

**Harry Stebbings** [28:12]:

Don't laugh. When you say build a playbook, do you literally create a doc of questions that they should ask,

**Ron Gabrisko** [28:18]:

of FAQs? Totally. Discovery guide, here are the questions. You start with, here's the profile of the customer we're looking for. Here's the actual profile of the people in those customers. Then here are the questions we need to ask. Here's what how we position it during the first pitch deck. And then depending on your process, okay, are we gonna run POC or pilot forum depending on what what you're trying to sell as an intuitive how to get value out of it, demonstrate value and then try to, you know, close a customer. So you're building out that playbook, you're training everyone on it, They need to know how to do that so that you can rinse and repeat as fast as possible and gather customers.

**Harry Stebbings** [28:56]:

I mean this with the utmost of respect. If it's bluntly that codified, can we not just get some monkeys do this? I mean, it's like, here's the customer, here's the profile, here's the questions. Yeah. I mean, shit. Let's just get an AI avatar.

**Ron Gabrisko** [29:09]:

Yeah. Know. I mean, a lot of people say, like, hey, can we replace sales with AI? And I think there are parts of sales you can replace with AI, like maybe building a playbook, some of those things once you get those assets. But again, early days, you're creating that from scratch. It has to learn from something.

**Harry Stebbings** [29:24]:

Because if you think about, like, a playbook creator integrated into Gong, it could analyze tone, changes in voice Totally. Words, semantics, which work, and then say Yeah. What are

**Unknown** [29:36]:

the best questions

**Harry Stebbings** [29:36]:

to ask?

**Ron Gabrisko** [29:37]:

Yeah. Certainly should get should be able to use AI to get way better at that early days. But the one thing that will always require humans to sell are if humans are buying, because the buying process is an emotional process. You're trying to choose what problems do you wanna solve, what are the most important problems to solve, how do I solve them amongst many different options. And a lot of it gets down to if the technologies are okay, this one has some pros and cons, this one has some pros and cons, who do I trust the most, which organization do I think can get me there the fastest. If that's a person making the decision, it's not black or white. When bots are selling to bots, they don't need salespeople. But as long as as humans are actually solving problems and buying stuff, you need humans to sell it.

**Harry Stebbings** [30:24]:

So going back to the 10 to 50 Mhmm. For you, what broken that phase?

**Ron Gabrisko** [30:31]:

When you're in this hyperscale phase, which I kinda 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 50,000,000, next year we're gonna do, you know, we did a 100 or two fifty. Like what does my org need to look at at a 100,000,000, 250,000,000? 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 twelve months out. Because if you're just trying to iterate, you're not gonna grow fast.

**Harry Stebbings** [31:31]:

Is it ever dangerous to hire ahead of time? And what I mean by that is if you're hiring at 13,000,000 in ARR Yeah. And then you're bringing in people for like a year ahead of time, sometimes an org is not ready to digest talent. Is that ever the case, or is it actually just good to get them in earlier?

**Ron Gabrisko** [31:45]:

No. I think you have to think about that. Right? Like, what does it take for us? It's like we're gonna start to also have an impact on the culture of the company. Like, Databricks is very engineering even to this day, it's very engineering technical culture. When you start adding salespeople, they have kind of a different mindset, you know. So you have to think about how that culture fits into that. Do you think the sales reps are going to operate it? Not the best ones. I mean, listen, you go into sales because it has, you know, financial upside. The people I'm looking for, they don't ask, like, how much do I make early on? You gotta make sure they they love the mission. Like, the most important thing is you're building an army. They gotta love the mission. They gotta love the company first. Once they love the mission and the company

**Harry Stebbings** [32:29]:

Would you mind if I came and I just said, I am fucking hungry to make money and I will crush it and make sure I hit quota? I mean,

**Ron Gabrisko** [32:38]:

I love I love the grit and the energy, you know what I mean? But I also think in, like, okay, what happens when you don't? What happens when it gets tough? Are you gonna go to the next company and No. I blame you. Move around for poor leadership. So I I mean, I look on people's resumes, right, like if they have a bunch of one or two year stints, they're not long for Databricks. I need people like, when this get What do you like to see in a resume? Yeah. Again, I'm looking for grit, first of all, hard work and grit. Like, I want somebody to tell me like, hey, I had some challenges here but I worked through it, I worked my tail off and kicked some ass, right? I look for technical backgrounds too, like I'm looking for specific company profiles. Because I know if I get a salesperson that already has some data AI technical capabilities, they're gonna ramp way faster than somebody who's brand new. They gotta learn the entire technology space. Right?

**Harry Stebbings** [33:33]:

What's more important, someone has sold an ACV size before, a customer profile before Mhmm. Or they have the domain knowledge of the space.

**Ron Gabrisko** [33:41]:

Early days, it's the domain knowledge. That's more important. Yeah. I think so. Why is that? Because again, you're trying to teach customers how to get value out of your technology and if you don't add value, like especially in today's world, there's so many technical buyers, they don't really like salespeople. Like the last thing they wanna do is talk to somebody who's like, hey, you know, you wanna go golfing or whatever? Like, they actually want somebody that's gonna help them solve problems. Do you not just tie that in with a sales engineer? I mean, we had a great, we call it field engineering, but and Arsalan runs that team. It's a great team, right? But I think the salesperson themselves has to add value. In early days, it's technical. Now as you get bigger, like we have $100,000,000 accounts, you know, you need people that know the organization, can get access to the c level, all that stuff. But early days when you're just trying to get logos and early customers, you gotta be able to add value. You gotta be able to teach your customers.

**Harry Stebbings** [34:38]:

$100,000,000 accounts. Yeah. God, I I hope they got a customer success rep.

**Ron Gabrisko** [34:45]:

They have lots of people.

**Harry Stebbings** [34:46]:

I'm sure they do. Are you kidding me? That's insane.

**Ron Gabrisko** [34:48]:

$100,000,000 accounts. Yeah. We just did one for a 190,000,000 actually. No. So, yeah, it's pretty good. That must feel pretty great. Yeah. That's pretty great. Did you put a Slack message out? Especially when we're selling $18.

**Unknown** [35:01]:

Yeah.

**Harry Stebbings** [35:01]:

You know? Not too bad. Back and buy some Ubers. Yeah. Not too bad. Okay. So we're going 13. We have this process. Where are we at the end of year two?

**Ron Gabrisko** [35:09]:

50? Yeah. 30 to 40, something like that. We did a three to four x the next year. Yeah. Somewhere around that. So we might have got to 50. Did the leadership team put pressure on you to hit targets? I mean, Lee and I kinda built and the founders, you know, the early days of the company. Right? He basically built out the product and the engineering and, you know, helped me build out the go to market and stuff like that. And Ali's one of those guys, he wants to set the target as high as possible. And early days, I'm trying to make sure, well, let's make sure people can make some money too. Right? So there's always that tension.

**Harry Stebbings** [35:42]:

What are your

**Ron Gabrisko** [35:42]:

biggest

**Harry Stebbings** [35:42]:

lessons on setting comp plans effectively? Because it is important people make money and feel like they're winning. Thousand percent. What are your

**Ron Gabrisko** [35:49]:

big lessons? Early days, you gotta make sure that salespeople are crushing their numbers and making money, because that's gonna be your best recruiting engine. When you're trying to sell a company that has small revenue, you need people to take a leap of faith. They gotta hit the believe button. So I was like, who's gonna be my first million dollar earner? And I would make sure that that person does that because you know what? The best reps I would try to hire, they go, has anybody made a million bucks? And then they're like, can I meet them? And then they're gonna determine, is that possible to replicate? Early days, people have to be blowing out their numbers and making tons of money, and it's a great recruiting tool. Now So what does

**Harry Stebbings** [36:26]:

mean that do you set them deliberately low goals so they hit them and then they become Not low

**Ron Gabrisko** [36:31]:

goals, but I wanna make sure they're achievable goals. I want them to be stretched but achievable, and I'm gonna make the plans, like, pretty rich, you know what I mean?

**Harry Stebbings** [36:40]:

And their plans are like four x salary? Like, how do you think about setting it

**Ron Gabrisko** [36:44]:

effectively? Mean, a normal enterprise rep, you know, you're gonna pay 300, 350 k. So, you know, if they blow it out, you want them to make three x. In early days, we were doing big commit deals. I mean, like I said, I have one guy make a million bucks in the first year and then scale it and, you know, now we probably have 20 guys make a million bucks in, in the sales team. So you But you always have to have those big earners because it's part of the reason they're in sales, is because they want the big payday. Wow. Do I need make a million dollars plus? Yeah. Have you ever lost a million dollar plus person? I mean, eventually, people are like, hey, wanna go to the next startup and try to do that. Because we have great, retention, but as you scale, you have to be a little bit smarter too on how you spend your commissions.

**Harry Stebbings** [37:27]:

What

**Ron Gabrisko** [37:28]:

changes? You just get tighter? You know, we have 1,400 reps now, we have 5,000 people in sales, so like, you know, there's a certain budget we have to have on commission. So we'll schedule a plan. We know this many people are gonna make 200%, a 150, you know, you model it out. It's pretty sophisticated because now you have big numbers. It's not like you have 20 people. Do you ever look at it and go like, it's

**Harry Stebbings** [37:48]:

fucking nuts. Like, 5,000 people. I remember when it was me and Ali, he's like selling $18 deals. It's

**Ron Gabrisko** [37:54]:

funny. I know. Isn't it Yeah. It's fun.

**Harry Stebbings** [37:57]:

It's fun to think. World. Yeah. It's awesome. Okay. And so we have that. We have those million people. Great. When you look at them, say the 20, are there things where you're like, I see that nonconventional or unconventional trait in most of them slash all of them?

**Ron Gabrisko** [38:12]:

Yeah. Like I said, I talk a lot about grit and hard work. You know, my dad was a construction worker, my mom was a math teacher. They taught me, like, hard work overcomes talent every single day. So I'm looking for that's the special quality I'm looking for is, like, is this person gonna put in the extra hours, have the extra grit? When times get tough, are they just gonna stay in the office longer, make more phone calls, that kind of thing? Do you think

**Harry Stebbings** [38:37]:

there's many salespeople like that today? I am with dear friends with Jason Lampkin from SaaStr. I love the man, really. My my father and venture, probably hate that and say I'm his older brother, but you know, he's considerably older than me. And he's always like, no, Harry, sales reps don't want to work anymore. If they don't want to work, they want to dial it in and like go home. Do you find that the sales reps of this generation are not willing to work as hard as they used to?

**Ron Gabrisko** [39:03]:

I mean, that won't work on my team. Again, like, that's the kind of culture that I try to build. And again, I think if you're a good salesperson, you ask me like, did we lose any older breakers? Like eventually, like somebody's like, hey, I'm a startup person, I like to work at startups, I don't wanna work at a, you know, 9,000 person company or 10,000 person company, so they go to a startup again. But at the end of the day, like, I think that's what we have to teach that next generation of sellers, because it's gonna get even more competitive. Work your ass off. Out hustle everyone.

**Harry Stebbings** [39:34]:

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

**Ron Gabrisko** [39:39]:

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've kind of skipped a couple stages now, is we have to become a destination company. People have to be like, I want go to Databricks because I can build my career there, because someday I wanna be a CRO or a CEO or whatever, and they're gonna 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, I think Databricks is is doing a pretty good job of that.

**Harry Stebbings** [40:26]:

I love that in terms of being a destination company. How did the type of sales leader that you needed to be changed from 10 to a 100,000,000 an ARR?

**Ron Gabrisko** [40:35]:

Yeah. I mean, a 100,000,000, you know, now you got a lot more process, a lot more enablement. You know, I don't know everyone. I can't just reach out and make sure I get involved in the deals. And so a big part of it is how do you build that leadership team? Again, we talked a little bit about, like, what do you need in the next twelve to twenty four months? So you need to build leaders so that they can effectively develop talent. My rule is, like, if you have the best team on the planet and you inspire, motivate, mentor them, you get to win. I mean, we have a great product, which is also a massive advantage for us, but that's the number one thing you can do is if I put the best team on the field and they're well coached and inspired, I'm gonna win. What

**Harry Stebbings** [41:16]:

have been your biggest

**Ron Gabrisko** [41:16]:

lessons on

**Harry Stebbings** [41:17]:

building a

**Ron Gabrisko** [41:18]:

successful

**Harry Stebbings** [41:18]:

leadership team

**Ron Gabrisko** [41:19]:

with Databricks? Yeah. So I think a lot of it's like, again, the profile and cultural mix. Right? We talk a lot about first team. First team is the company. So sales leadership, the higher you go, the more it's gotta be about the company. You're not there to just make sure your people are successful or you know what I mean? It's gotta be, okay, here's our company mission, we're together, we're gonna do it. And so I think that camaraderie and how you build that team and how you build the culture is as important as anything else that you do in sales. People need to be feel like they're part of a a special mission. When was the culture at Databricks the worst and what went wrong? The worst. I thought we've always had a great culture, honestly. I I can't really say we have had bad culture. When was there a challenging time? As you scale bigger and bigger, one of the keys, I think, is probably how do you keep that early day culture. It's such a huge advantage when you're like a gritty, innovative startup. I think we've done a good job actually at Databricks keeping that, right? Like that's a big part of the founders is, like, we wanna be the innovators, the disruptors, the cool nerdy kids. You know what I mean? Like, that's what we wanna be. And so keeping that culture where you have grit and all that and not becoming a big company, that's a challenge. As you scale, how do you keep that and not become a big company where people are just it's bureaucratic, it's process, it's, you know, all the management team versus the the workers. So but I think we've done a pretty good job of that. I think our culture is second to none. It's a big part of why we're successful. In the 0 to

**Harry Stebbings** [42:58]:

500,000,000,000 range, which is a huge range, what did you not do with the benefit of hindsight

**Ron Gabrisko** [43:05]:

you wish you'd done? 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 kinda pretty, historical, I think, in legend. And it's still, you know, Microsoft's our, you know, biggest partner. It's amazing partner for us. But like, know, you gotta 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. And

**Harry Stebbings** [43:46]:

so you didn't do that early enough? Well, I think we could have done it earlier. Yeah. Absolutely. I think a lot of founders see channel partnerships as like the panacea. We're gonna have a partnership with Salesforce and it's gonna be like boom. Yeah.

**Ron Gabrisko** [43:58]:

Are the secret Early days, it's hard to do. Like like I would say if you're less than 50 or a 100,000,000, like you need to build a strong direct sales channel, and then you can build the partner channel. But at 500,000,000 now, we should be scaling moving stuff through channels, right? What does it take to do partner channels really well? Good question. Because sometimes, like partner leaders, they're like sales leaders that didn't make it sometimes. So I try to actually hire It's like VCs, which is founders that didn't make it. I like to hire, you know, people that have strong sales acumen, sales leadership, a lot of the same qualities that wanna build out channels because again, like, you know, me as a as a CRO, I'm a sales leader but I also spend, you know, 3040% of my time with partners because I wanna build that channel, right? And so it's a skill you need to learn when you're trying to build a massively scalable business. And so, you know, just getting a person that's always been in partnerships sometimes is a little bit dicey. I'd rather find somebody that's done some sales and done some partnerships. They've done it, you know, thoughtfully to build their career. So, I mean, I think that's important to do.

**Harry Stebbings** [45:07]:

Okay. That's a fantastic one. So that's what you maybe didn't do that you wish you'd done earlier. What did you do that you wish you hadn't done, and what are the reflections on that?

**Ron Gabrisko** [45:15]:

I think we did a lot of stuff right. Like, I think when we expanded internationally, I think we did it at kind of the right time. When did you do that? We probably started to do that to EMEA, maybe a 100,000,000 plus, 100 to 250,000,000, and then we were an APJ probably, you know, about 250,000,000 plus. You have to do that thoughtfully though.

**Harry Stebbings** [45:36]:

Any lessons on how to do internationally is much more?

**Ron Gabrisko** [45:38]:

It's hard. Yeah. It's hard because, you know, there's a lot of different things. Like you have to translate your culture, your playbook, you have to have leadership there that you trust. One of the big lessons I learned is you wanna transplant some of your talent. So I literally, like when we opened EMEA, took four or five of my, you know, best young hungry sellers and said, okay, you're gonna go to EMEA for a year, it's gonna be a great experience for you, you need to help them build the muscle over there and build the culture over there, right? And me personally too, you know, I'm doing multiple trips, one a quarter over there to get that going. Same thing with APJ, like transports some existing talent, talent, helps build the culture, all those kind of things. What do you think are the big mistakes you see people doing when they go international? I think some do it too early because, you know, again, it's gonna spread your focus of your sales leadership, but it's also gonna spread your focus for your product. Like, you're gonna see new requirements come up in Asia or new regulatory requirements depending on where you go. So I think the biggest mistake is people go early before they've really got that product market fit because they, you know, hey, they have a couple customers in EMEA, so let's go support them. And now now again, you gotta think about like, you know, I have limited team. You're constrained by your resources. Like, where do you want them focused? So I think that's probably the biggest mistake I see.

**Harry Stebbings** [46:59]:

I find people go too early into enterprise 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 closure. 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? For enterprise or for any rep? Does it differ?

**Ron Gabrisko** [47:24]:

I think it does slightly just based on the sales cycle, but How? Think upfront, I'm looking at pipeline and activity. The number one thing I'm gonna look at is this person getting the right meetings, are they building the right pipeline? I gotta make sure I'm inspecting that too. So, you know, early stage sales leader, you're gonna wanna 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 gonna see them in front of a customer. Do they ask good questions? Does the customer wanna buy from them?

**Harry Stebbings** [47:57]:

Is there a right amount of meetings? I know it's really granular, but, like, we mentioned Dagnum before. Dagnum was always like to me, when you get to my age, you know, the memory goes. But he said it's like six or eight, I can't remember what it is, but you can't do more than six or eight because you need to be researched, you need to be informed. Six or eight is the max.

**Ron Gabrisko** [48:15]:

Yeah. Do you agree with that? You know, we sit at the bar at, five a week is kind of the minimum. So, you know, five to ten is probably right, and that's six to eight. That's not a bad metric. But, again, you do wanna make sure you're prepared. It's just like any other sport.

**Harry Stebbings** [48:28]:

Okay. So you have five let's just roll with this. Have five a week, 20 a month.

**Ron Gabrisko** [48:32]:

Yeah. Do you have like an expected close rate? I'm building opportunities. Right? So at least 25% of those should turn into some kind of opportunity, and now I'm gonna work that opportunity. And, you know, they're gonna close at different rates depending on that organization, how can I get budget, things of that nature?

**Harry Stebbings** [48:49]:

Do you worry about setting goals that can be played? And what I mean by that is you're like, Harry, I want 20 meetings. I'm like, okay, 20 meetings. And my qualification process, shoot, goes down. How do you think about effective goal setting which can't be played?

**Ron Gabrisko** [49:04]:

Eventually, I'm gonna see pipeline and closures. But you're right. There's a delay. There's a six, twelve, maybe eighteen month delay on that. But that's why the first line manager and the sales leader is so important because I'm gonna go assess those meetings myself. Again, if you think about it, you need pitchers and batters. Right? So or catchers and batters. I don't know what, you know, I guess for cricket here you need. Bowlers and batsmen. Yeah. Bowlers and batters. So We didn't play rounders in this country. I know. I know. But I'm a baseball player. So if you think about it, the reps, like when I was first there, was like, just get me as many meetings as you can. Just put in there and be like, oh, we're working a deal with J and J. They're like, who do you wanna meet with? I was like, anyone with a J and J email address. Because I'll be able to assess, like, is that person got juice, you know, is there an opportunity, how do I navigate the organization? So again, go take as many meetings as a leader.

**Harry Stebbings** [49:56]:

I'm sorry. You will join that call and let them run it? Yep. Okay. So you are not running that call? Correct. And you sit in Yep. And you just listen?

**Ron Gabrisko** [50:04]:

Yeah. As long as it's going well. Okay. And if it's not going well, I'm gonna step in and try to help and Where does it not go well? Depends on the rep, their preparation, are they asking questions? You know, when you think about what's a successful sales meeting, we haven't even talked about that, like the basics of selling, It's like, have I generated some rapport? Do they trust me? Have I generated interest? Have I identified challenges? And have I driven to an objective? What was the objective of my meeting? Was it to get an x meeting? Was it get a POC? Was it get an introduction to somebody? So you need to have a game plan on all that. So you've had to research the company, the opportunity, the people you're talking to, their LinkedIn profiles. So a good meeting is somebody who really is prepared. Again, it's like, any sport, you practice 10 x more at least than you play. So if you have a one hour meeting, you should be preparing for it ten

**Harry Stebbings** [50:57]:

hours. So funny. There's a Usain Bolt interview, is amazing. Yeah. And he says, trained ten years for nine seconds. Yeah. There you go. Exactly. Sorry. Fuck me. That's a bad ratio. That's a really bad ratio. Yeah. I

**Ron Gabrisko** [51:10]:

mean, think about the Olympics. Right? Like, these people train their whole lives and it's over in a split second.

**Harry Stebbings** [51:15]:

Right? So Honestly, unbelievable. Going back to that, what it takes to do good meeting, I'm so glad you broke it down that way. Yeah. I know it's kind of facile of me to ask, but what do you find works in building rapport?

**Ron Gabrisko** [51:27]:

I mean, get to know somebody. Right? Like, be intellectually curious about their background

**Harry Stebbings** [51:32]:

and But I find a playbook. When I feel like someone's running a playbook on me, it doesn't build rapport. And so, like, for me, my job as an interviewer is to build rapport too, but to make someone feel safe. And, like, you know what? He's not here to get me, and he's open to and so I'll talk about my mother having MS or anything like that because you're like, oh, I feel like I'm getting to know this guy. Yeah. Be a little bit vulnerable. Yeah. Yeah. Exactly. Any lessons for you on, like, how you build rapport rather than, oh, whereabouts are you in the world? Oh, it's rainy in London. I'm

**Ron Gabrisko** [52:05]:

definitely not a weather talker. Normally, usually talk about, you know, where did you grow up? What are you interested in? What are your family? I mean, you gotta start small. You can't be like, oh, do you have any cancers we can talk about or anything? But like That's a savage stuff. No. But again, it's like, you know, how do you, how do you try to get to know somebody, right, get to know about them? I think a lot of people are influenced by where they grew up, their families. Like, I like to ask about that because I think a lot of people are like, you know, family's super important thing, so I wanna get to know about that.

**Harry Stebbings** [52:37]:

Do you find people lie about being a buyer? Because you wanna know if they have budget and if they're the buyer. Do you find that people overinflate their own status within companies?

**Ron Gabrisko** [52:45]:

I mean, listen. I'd never ask somebody, do have budget? I'm experienced enough to know what's gonna happen. I'm gonna get that information eventually. But, like, listen, everybody wants to be important. So like, let them be important. The reason they have in that position is because they have some decision authority. You know, I've done literally billions of dollars of software deals and thousands of deals, right? I kinda know how organizations work and I'm there to teach how to get value and I'll ask questions like, oh, do you have to do a value case for this? You know, how does that work? How does that process work? You know, who has to approve that? Who has buying authority? Like, you know, once you've established rapport, you can get, you know, a lot more deeper on that kind of information on how to navigate the organization. But you you can't really have that discussion until you've added value. How does

**Harry Stebbings** [53:33]:

AI change the sales process, you think? Do you use any AI tools today in the sense

**Ron Gabrisko** [53:38]:

of 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 know, lot of information on that. And then our sales assistant will actually take that data or take that conversational stuff along with like our account 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 cyber security, stuff like that, right? So you can use AI to really accelerate all that research and get smarter. Because, again, the smarter you are on that customer, the more interesting questions you're gonna be able to ask to try to find an area you can add value. So

**Harry Stebbings** [54:38]:

content preparation for the sales process. Yep. In terms of outbound, will we see outbound not die but be replaced by AI in terms of email outbound literally being done by AI?

**Ron Gabrisko** [54:50]:

I don't know if completely replace it, but certainly I think outbound stuff, the AI is actually better at it than humans, in my opinion, because it'll also learn what works faster. Right? Like that whole iteration process I did early on with, hey, everybody's gonna do prospecting day. If I start setting up a bot to try to ping people to get meetings, it's gonna learn what works and what doesn't work faster than I can get a team of humans together. Now, that being said, like, you wanna learn that, but it needs to be informed. Right? I don't think you can completely replace humans there.

**Harry Stebbings** [55:23]:

Also, a world of infinite outbound, does value of it not go down? If you know that you're being outreached by an AI, does the value of that not go down?

**Ron Gabrisko** [55:33]:

I don't know. I haven't thought about it. Still early days, but you're probably right. I mean, even now, like, I mean, how many emails and LinkedIn posts do you get? It's literally thousands. Right? Like, so which ones kinda go to the front of your box where you even take a meeting, right? A lot of it's gonna have to do with your brand and your message and, you know, what's happening in the market and how much you know about their company, right? Like, again, that's what I think AI can do is if I really know what's going on inside that person, inside that company, you're right. You might need a human to actually put a human touch to it, but it's probably gonna give you the content to get them potentially interested better. Right?

**Harry Stebbings** [56:12]:

Will you have more or less sales reps in five years time?

**Ron Gabrisko** [56:15]:

Again, as long as humans are buying software, I think you need humans to sell software. So we definitely use AI to become more efficient, but we're gonna hire quite a few folks because we're gonna go big.

**Harry Stebbings** [56:29]:

Did I answer that correctly? Yeah. You did. Brilliant. When you look at the different stages of the company, what was the hardest? You can break it up into, like, don't know, 10, a 100, a 100, a billion, billion and beyond. Which was the hardest?

**Ron Gabrisko** [56:43]:

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 $10,000,000 of something to literally anyone. You know what I mean? Like, all I have to do is figure out what they wanna buy. That 10 to 100,000,000 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 100 to 1,000,000,000, now you're getting partners involved, distribution channels, you're scaling the sales organization, so now it's, you know, you're getting to the scaling function. You know, we just did 3,000,000,000 last year, you know, I think we'll be 10,000,000,000 in a few years. So, you know, now you're in hyperscale and, you know, a different set of challenges. So each one I've enjoyed because they're different. I think the 10 to a 100 is one of the hardest things. Now the hyperscalers in AI, they're like blowing through a 100,000,000. Right? Like some of these companies, they're crushing it.

**Harry Stebbings** [57:43]:

Which one are you most impressed by?

**Ron Gabrisko** [57:45]:

I think Cursor's super impressive. I think they're growing crazy fast. Like I use AI for engineering and coding. They're doing really well. So, I mean, we'll see, you know, if they can sustain it. I hope they can, but, it's, you know, super impressive what they're doing for sure.

**Harry Stebbings** [58:00]:

You you know, you have been in a fight against Snowflake. Yeah. What are your biggest lessons on selling against competition? Everyone has competition today. It's one of the biggest things I've learned today investing Yeah. Is that before you used to have two or three competitors, Databricks and Snowflake, say. Now there's 15 competitors for everything. Yeah. What are your biggest lessons for founders on how to sell in competitive market?

**Ron Gabrisko** [58:21]:

So first of all, you need competition, otherwise, you don't have a market. Right? Especially early days. If nobody else is selling into your market, like, you know, what's the point? I don't think there's 15 companies that'll survive in it. You know, the traditional thing is there's three companies. There's three clouds. There'll be three AI players. You know, I think there'll only be one data and AI player, Databricks, but there'll probably be market, three. Mine, one. One. We'll win. We'll crush everyone. No. But I think listen. And the biggest player gets 80% of the market. Right? And the other ones, you know, get the rest.

**Harry Stebbings** [58:54]:

In consumer, that's the case. In enterprise, enterprise, it it tends tends to to be be the the opposite. Opposite. It tends to be much more distributed.

**Ron Gabrisko** [58:59]:

I haven't seen that. I mean, look at Salesforce. Look at ServiceNow. I mean, you look at Cloud and you're like AWS. Cloud's a little bit more even distributed, although GCP, you'd still say it's kind of a distant third, right? But AWS and Azure kinda neck and neck, that's a big battle. Getting back to the competition Snowflake question for us, like, it's kinda good to have somebody that's trying to make you better. And I'm ultra competitive, right? Like I'm an athlete, so like the reason I do sales is because I love competition, right?

**Harry Stebbings** [59:31]:

How far behind are they?

**Ron Gabrisko** [59:32]:

Five plus years in my opinion. You know, bet on the future early days. We bet on AI, we bet on the Lakehouse, we bet on Open Source, they're just dipping their toe into that. And if you look at it too, right, we're three times their growth rate, done '2 150, Snowflake the Databricks migrations, they're their top 10, like, you know, we're doing pretty well in that market. So I think we're the future and the founders made some really smart investments in technology bets in r and d to make sure we're well ahead of them. And so we'll continue to invest. It's great being private too, right? We get to, you know, overinvest in r and d, overinvest in sales. Do you think you've benefited from being private in a way that they haven't had the luxury of being private? It's massive. Right? We think it's early in the market. I say it's top of the second inning. And so if we can continue to pour money into innovation and r and d and, know, sales and distribution, you know, we're gonna grab, you know, more market share and, again, get further ahead of them.

**Harry Stebbings** [60:28]:

Have you not spent or have not spent as much that you would like to spend more of in the future?

**Ron Gabrisko** [60:33]:

Actually, our brand's gotten really good now. As we started to spend more on brand, I think we should have done more of that early. Marketing and brand. I wanna press even more on partners. You know, we'll fund 200,000,000 in projects to partners this year, but I would spend even more in partners and distribution training. We just started Databricks India Academy. You know, we'll train over a million people. India Academy? Yeah. Databricks India Academy. Oh, man. That's niche. Yeah. It's cool. Wow. Well, there's so many companies that, you know, have big IT and outsourcing in India, and so, we built a whole academy there to train all the, you know, Indian partners, Wipro's and the emphasis, and we trained a million people there. So

**Harry Stebbings** [61:15]:

What are your biggest lessons in what it takes to do president's club well? If I'm an early stage founder Yeah. Should I do president's club, and what do I need to do to make it good?

**Ron Gabrisko** [61:25]:

I mean, early day founders, what I've seen is they'll do the whole company an off-site, but it's not a President's Club. Right? What stage do you do President's Club? When you have enough of a sales team where because you know, President's Club is like ten, fifteen, maybe 20 of your people are going. But if that's only two people, it's not a President's Club. Right? So you gotta have at least, I don't know, 50 or a 100 people at least in sales before you join a President's Club because it's also like if you're an engineering company because we bring MVPs too, engineer side of it's gonna be like, what? Sales going on like a holiday for top performers? But if you think about the sales mentality, you're competitive, you wanna be one of the best, you wanna be one of the top ten, fifteen percent. So it's usually kind of a slightly later stage thing, would say you gotta be a 100,000,000 plus to do it. You have to be smart about how you invest in it. And the whole idea is create a special experience for the salesperson and their spouse. Get that spouse where they're like, wow, Databricks is an amazing company and you gotta make sure you go next year. I always say the power of pillow talk is so valuable. Yeah, totally. And my sales team cares more about who goes to club or as much as who goes to club as like, okay, what's the new commission plan, how does that work, all that kind of stuff. It's that important. Like people will be like trying to lobby for the people that are on the fence and you create that culture where, you know, everybody wants to get there and, it becomes a really fun thing. I'm making a way

**Unknown** [62:55]:

days, Databricks' sales go to shit. Well, it's over a weekend.

**Harry Stebbings** [62:59]:

Oh, it's over a weekend. Oh, it's fine. Oh, it's fine. Fine. But at Power of Pillow Talk, I think, is so valuable because when they come home and moan, I'm just not but remember, we did have a great time, and Ron was so lovely to us.

**Ron Gabrisko** [63:11]:

Well, listen, we're I ask for a lot. Right?

**Harry Stebbings** [63:14]:

They're traveling all the time. Does remote sales teams work? You said there about kind of, know, the pipeline building, the prospecting day, that being there in person.

**Ron Gabrisko** [63:21]:

Yeah. We have the saying, from one of my leaders, Michael Hartman, sell from your feet, not from your seat. If you have the opportunity to go meet a customer in person, go do it. If you have the opportunity to go do lunch or dinner, do it. Because, again, we talk about that rapport, talk about that relationship with the customer. They want that relationship where they trust you, where they know they can count on you to solve problems for them because a lot of times they're making a decision, it may affect their career. It could catapult them way into the future or not. And so they're gonna make a decision, like, the more time you can spend with them, spend with them in person, establish a rapport, create So the the expensive state dinner, not done. Because a lot of people are like, oh, that's so last year. It depends on the company. If you're going to sell to an enterprise company and you can get executives out for two hours to do a steak dinner, do it. It's worth it because now you'll have a relationship with those people that you wouldn't have had on thirty minutes over the phone. Right? Do you know what I miss? I miss golf days.

**Harry Stebbings** [64:25]:

I love golf

**Ron Gabrisko** [64:26]:

days. I don't get to golf

**Harry Stebbings** [64:27]:

with love it four hours on a course. Yeah. That's rare. That's rare. But can you imagine if you had four of your biggest Enterprise customers hanging out with each other, hanging out with you, shooting the shit, no phone?

**Ron Gabrisko** [64:40]:

Yeah. We try to do events like that. Recently, we did spring training events. We had, like, 30 customers there. Actually, I got to throw out the first pitch for the Texas Rangers and then It only cost you $5,000,000. It wasn't that expensive. But, you know, then we went golfing and dinner and, you know, you get to spend that kind of time. Now you have a different relationship with those customers. You gotta make sure they're the right customers. So

**Unknown** [65:02]:

Who who performed at your last president's club? We said we weren't gonna talk about this. Can we not let us talk

**Ron Gabrisko** [65:12]:

about that? Yeah. No. I don't know if that's public or not. So We don't have to. Maybe it is. I don't know. I mean, last year we had flow route. It was awesome. Yeah. Was fun. Was it was amazing.

**Unknown** [65:22]:

I heard that Ali did a breakdance to it. He did not. Oh, he did not? That was No. Fake He did not. He did not. He did not. That would be too good though. Although he is fun. Dude, I love that. Listen, I've so enjoyed this. Can I do a quick fire

**Harry Stebbings** [65:36]:

with you, Sean? Sure. Let's do it. Okay. There's so many places I could take this. Let's start with what's the biggest misconception people have

**Ron Gabrisko** [65:44]:

about CROs? The sales leader, most people think like, oh, you're in sales. Like, the only people in sales they've had a interaction with is like a used car salesman. They're like, oh, you have to be slick. Don't think being a sales leader, you have to be slick. Again, I think you have to be knowledgeable and trustworthy. You can be a mentor, right? You don't have to be tough. I'm a driver, but, you know, mentor people, inspire them. You have such a great voice as well.

**Unknown** [66:11]:

Oh,

**Harry Stebbings** [66:11]:

thanks. Yeah.

**Unknown** [66:12]:

You're like kind

**Harry Stebbings** [66:13]:

of like a a husky and Matthew McConaughey. I appreciate that. I think I look just like him. You know what? In ten years, I'm chasing my hero.

**Unknown** [66:23]:

I'm like, just talk to me, Ron.

**Harry Stebbings** [66:26]:

This could be a meditation app. Oh, that's awesome. Dude, where are you weakest as a sales leader today? Where do you think you need to spend time?

**Ron Gabrisko** [66:34]:

I mean, I'm all in on Databricks. Like, I spend a lot of time on Databricks. My kids are out of the house, so I travel all the time. Is that a hard or marriage? I have great marriage. My wife's like I mean, I wouldn't be able to do what I do without her. She takes care of everything while I'm here in London or Korea or Singapore or wherever, so

**Harry Stebbings** [66:52]:

What's your biggest Warren Buffett said the most important decision you make in life is the partner you choose to spend your life with. Going all the time. What's your biggest advice to me on partner selection? I told you at the beginning, you were like, how am I? This is hilarious. Get too off. You go.

**Ron Gabrisko** [67:08]:

Questions. That's funny. No. For sure. I mean, depending on what your life goals are, they have to be in line with your partner's goals, right? Like kids and, you know, what kind of work you're gonna do, all that kind of stuff. Like to me, when I look back at just life in general, like having kids is the best thing I ever did, getting married, best thing I ever did. If you do those things right, then it allows you to put your mind and everything into other things. I put it into Databricks. Like I had to make lots of sacrifices but my family was always there to make sure I was on the right track. So I think balance is probably the biggest thing for me. You you didn't really ask, but, you know, work wise, like, certainly, I'm sure there's a ton of stuff I can do better in terms of more patience and all that kind of stuff because I'm a hard driver. Yeah. That's my biggest thing is you gotta have a little bit of balance too, you know. I don't know how

**Harry Stebbings** [67:58]:

much patience. That's why I called it the twenty minute VC. Are you kidding me? I am for this question, your, you know, adopted son and I'm 23, and I'm entering a sales org. First job. What's your biggest advice to me as a 23 year old entering sales for the first time, bright eyed?

**Ron Gabrisko** [68:17]:

Two things. One, going into an industry that's growing and you're passionate about. Obviously, I think data in the eye is where it's at today. But if you're going into tech, I'd say going into data and AI. So go into a market that's growing and gotta be passionate about it too if you're like, oh, that's boring, don't go into that. Number two is go where you're gonna 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 what it's all about.

**Harry Stebbings** [68:58]:

Penultimate one, you can go back to any day in the Databricks journey. What day do you go back and relive? Relive? Oh, wow. That's a great question. Thank you. I'm a podcaster. Yeah. There you go. I've had some time on this. Yeah. They didn't even give me a heads up on this to you like, oh, that's great sales process. You're

**Unknown** [69:20]:

like,

**Harry Stebbings** [69:20]:

no.

**Unknown** [69:20]:

It's kind of my job.

**Ron Gabrisko** [69:24]:

One day you know what? I think when Ali and I got the first Microsoft deal signed was a pretty amazing day. So that was pretty game changing. Looking back Do you remember where you were? I remember when he told me, we were like on the 13th Floor, there's this like little conference room, we would like a couch in there, there was like video games in there or whatever, so In Databricks? Yeah. In the in the office. And they

**Harry Stebbings** [69:51]:

called you up and they're like, congratulations, you have a partnership?

**Ron Gabrisko** [69:54]:

Well, no no no. I mean, we've been working on it for months and months and months, but when when it finally got signed, we were like, you know, me and Ali were like, oh, great job. Good work. High five. Did Did you do a little victory dance? No. It

**Harry Stebbings** [70:06]:

was like back to work. Didn't put on any Taylor Swift No. Or Back to work. No.

**Unknown** [70:10]:

Yeah. So Taylor Swift. Shake it out. No. Yeah. No. Well, there's I'm more of a rap guy anyway. Listen, when you hear a trillian, Taylor can perform at presidents. Yeah. There you go. She's expensive though. She's pretty expensive, but a trillion's quite a lot of money. Totally. That's a goal for you. Totally. I thought that was a pretty good day though. Oh, that's pretty great day.

**Harry Stebbings** [70:29]:

Yeah. It's a cool day. Yeah. Yeah. Okay. Ten years time, final one, Where is Databricks stand in your mind? I think we're a

**Ron Gabrisko** [70:36]:

trillion dollar company then. In ten years? Yeah. It's an iconic company. I mean, how many trillion dollar software tech companies are there? There's only seven or eight, I think. It's funny. If you think back, like, people at Databricks today, it's like, you know, Microsoft people, what were they like back in 1985 or Google people back in 2000, you know, when they Is that started where you think you are in that journey? That's where we are. Yeah. We're early days, like, you know, we're obviously, doing well, but it's early days. So we got a lot of work to do, but we're excited about it. Like I said, I think market's amazing. I think we've made a lot of good bets. I think if we continue to invest and innovate, we can get there. So I think it'll be one of those iconic companies.

**Harry Stebbings** [71:19]:

Listen, Matthew McConaughey. It's been wonderful having you. Thanks for having me. Appreciate I wanna see shows like this are why I love doing what I do so much. So, seriously, thank you so much for being so open, and this has been amazing. Yeah. Thanks for having me. I loved it. Dude, you are I mean, are you kidding me? He has been the head of sales CRO from zero to 5,000,000,000 in revenue. What a hero. That was such a fantastic show to do. If you wanna see more, you can find it on Spotify. I'd so appreciate it. If you liked the episode and left a review, it'd make a huge difference. But before we leave you today,

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**Harry Stebbings** [71:54]:

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