← The SaaS Podcast - Growing Profitable AI SaaS & AI Agents
The SaaS Podcast - Growing Profitable AI SaaS & AI Agents
448: Sigma: The Gutsy Rebuild That Took This SaaS from Zero to $100M - with Rob Woollen
00:53:30
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- [00:00]
Omar Khan
Foreign welcome to another episode of the SaaS podcast. I'm your host, Omar Khan, and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch, and grow your SaaS business. In this episode, I talk to Rob Woolen, the co founder and CTO of Sigma Computing, a data analytics platform that lets business users analyze cloud scale data without writing any SQL. In 2014, Rob left his role as a CTO at Salesforce to solve a problem he'd watched daily. The people making critical business decisions were stuck using spreadsheets because they couldn't access cloud data directly. So with a clear problem to solve, $8 million in funding, and a small team, Rob figured they'd nail the solution in about six months. They were wrong. Their first product automatically analyzed data patterns and told users what they should look at. People were polite, but nobody really wanted it. Eventually, two founding engineers quit, leaving just three of them on the team. Trying to keep their dream alive for the next three years, they built prototype after prototype, but nothing clicked. Then, in 2017, their VC set up a meeting with Snowflake's CEO, and they had 30 days to build something completely new. This time, they created a familiar spreadsheet interface that could handle massive amounts of cloud data from Snowflake, something that Excel couldn't do. And the CEO's reaction was like, I want this. When can I start using it? But the excitement didn't equal revenue. It took six months just to pass Snowflake's security requirements. And for the next two years, they built a small group of passionate users who gave constant feedback. And finally, in 2019, real customers started writing checks. And shortly after that, they hit the first million in ARR. Then, the very next quarter, their sales dropped to zero. Like, literally zero. The founders realized their product still wasn't good enough. And despite having hit seven figures, they were going down the wrong path. So they made the gutsy call to rebuild it from scratch. And that decision changed everything. Today, Sigma computing generates over $100 million in arrangement, serves over 1400 customers, employs around 600 people, and has raised more than $500 million in funding. In this episode, you'll learn why it took seven years to find product market fit, and how the founders stayed motivated through years of zero revenue. How rebuilding their product in 30 days for a crucial meeting with Snowflake's CEO became a turning point for the company. Why they made the risky decision to completely rebuild their product after hitting a million in ARR, and how it unlocked their growth why? We talk about how partnerships with cloud data platforms like Snowflake became their biggest growth drivers and what specific strategies Rob used to cultivate early champions who would evangelize their product within organizations. So I hope you enjoy. When was the last time you verified your app's emails actually reached users? Someone signs up, expects their welcome email nothing. They try password reset, silence. They assume your product's broken when really those emails are sitting in spam. Mailtrap is an email delivery platform built for product companies that send at scale, trusted by teams at Atlassian, Adobe and calendly get faster delivery, high inboxing rates and industry best analytics. And right now you'll get 20% off all plans with the code TheSassPodcastailtrapIO. That's Mailtrap IO. Rob, welcome to the show.
- [03:37]
Rob Woolen
Thank you.
- [03:38]
Omar Khan
Do you have a favorite quote? Something that inspires or motivates you?
- [03:41]
Rob Woolen
There's a quote. I think it's attributed to Alan Kay, who was an early computer scientist, and he said something like, make the simple things simple and the hard things possible. And that's been a guiding light to me in sort of interface design and really sort of product design.
- [03:57]
Omar Khan
Love it. So tell us about Sigma Computing. What does the product do, who's it for, and what's the main problem you're helping to solve?
- [04:05]
Rob Woolen
Sure. So Sigma is data analysis software. And the sort of key insight we had to found the company was that the underlying kind of cloud infrastructure had advanced pretty dramatically. So if you were a SQL programmer or a Python programmer, you got these cloud data systems where you could query billions of rows of data, you could effectively have almost infinite storage. The problem we saw was that if you weren't a SQL or a Python programmer, you were largely still sort of stuck with the same old BI tools or the same old sort of Excel spreadsheet. And we wanted to effectively enable anyone to leverage all this great enhancements. So we initially built something that looked largely like a spreadsheet. You could write formulas, things like that, but everything you did in that interface, it translated it to SQL and ran against these large cloud infrastructure. So you got sort of the power of the cloud systems, but an interface that anyone could understood. And we later extended that to you can now bring those types of interfaces into like any application. So like, Anyone building a SaaS application can embed Sigma within it and leverage that for all of their reporting and analytics, all the way to people building their own applications. They can do that now in our product as well.
- [05:23]
Omar Khan
Great. And give us a sense of the size of the business, where are you in terms of revenue, customers, size of team?
- [05:29]
Rob Woolen
Yeah, we crossed over 100 million in revenue this year. So we've been.
- [05:34]
Omar Khan
Congratulations.
- [05:35]
Rob Woolen
Thank you. I've. I always joke to people that we're sort of a tale of two companies because we founded the company 11 years ago and spent roughly seven years of little to no revenue and then have gone from 0 to 100 million in the last three and a half years. So that's been a fun growth path. And then as far as, you know, employees and customers, we're somewhere north of 600 employees. I.1 of the. One of the growth things I like is that you sort of lose count of exactly how many employees you have. And then from customers, I think somewhere north of 1,400.
- [06:09]
Omar Khan
And then I think you've raised like 580 million. Something like that.
- [06:15]
Rob Woolen
Something like that. We just did a series D last just about a year ago and then did a series C in 2021.
- [06:22]
Omar Khan
Cool. I mean, a lot of people listening to this are going to be like, oh, those numbers are just over my head. I'm still struggling trying to get to the first million in arrangement. And I think that's what I really love about your story is that on the face of it, people may not be able to relate, but when they hear the tale of two companies and the first seven years of almost zero revenue until you kind of had to overcome these challenges and just stay in the game long enough to be able to get to this point where things started to click, you got traction and then the business grew very fast. So I think a super interesting story. I want to start with where the idea sort of came from. And you explained that a little bit, but maybe just tell us a little bit about your background and what led to you getting to the point where you felt confident enough that, yeah, we're going to go and tackle the BI market.
- [07:16]
Rob Woolen
Yeah, in some ways we're a little bit unusual in our sort of founding story. So my personal background, I've spent now 25, almost 30 years in enterprise software. Prior to this whole adventure, I spent seven years@salesforce.com and was one of their CTOs and I led product management on their platform products. And one of the things that sort of struck me when I was at Salesforce was obviously they have all sorts of cloud data. Right. They have everyone's cloud sales data and obviously they're incredibly successful company. But I would watch how this company ran and you would see even though they had all of the cloud data in the world, it was generally still sort of run on spreadsheets and guesses on what we should do. And it struck me that the people that were knowledgeable about how to plan operations, how to plan how many salespeople we should hire, how to plan all this sort of financial side, they were Excel people and they were disconnected from sort of the enterprise and cloud data. And so the sort of fundamental epiphany we had, the fundamental idea was we had seen this big advancement in the infrastructure, just how could we make it so all these people that actually had the domain knowledge could actually directly leverage it. And that's what we set out to build now 11 years ago. And we've pivoted many times on how actually to solve it, but we interestingly have never pivoted on the problem we were trying to solve or the sort of aspiration of what we wanted to do.
- [08:48]
Omar Khan
Yeah, you said something to me earlier where you said, we've stayed focused on the problem we wanted to solve throughout this time, but the first seven years was almost just about figuring out what was the right product to build.
- [09:04]
Rob Woolen
Yeah. I've often told people, I can give you the explain people the problem. And they're like, yes, that makes sense to me. I can see why it's a big important problem. And then you say like, well, we're going to build the right interface to solve it. And I think there's, as entrepreneurs, you have to have the super amount of confidence. Right. So I remember we were very confident we left the VC firm and we were like, we're going to. Sure, within six months we'll have figured out the right interface to this. And we went off and built our first set of ideas. And as you can imagine from the seven year journey, our first set of ideas were not the right solution. And it took just many, many iterations of trying things and trying to get feedback and trying to interpret that feedback and then trying to figure out what is the right actual thing to go build. And that journey is painful and was very much what we spent a lot of that first set of years doing.
- [09:58]
Omar Khan
Yeah, now you guys were a bit unique in terms of you were able to raise money right out of the gate, weren't you?
- [10:03]
Rob Woolen
Yeah. So we're very fortunate. We had a long history in enterprise software, had a long standing relationship with venture capital firms, Sutter Hill Ventures, and my co founder and I were both entrepreneurs in residents there. So we had effectively developed the idea with the VC firm. So we had a big advantage out of the gate of yes, we Left with a Series A funding, that of $8 million, with honestly a big problem to go solve, but not yet a proven solution to it. And we largely just made the promise of we won't spend much money until we really know what we're doing.
- [10:41]
Omar Khan
And then at that point, were you crystal clear about the problem? Had you already spent time talking to potential customers, or was that something that you felt like we still needed to do more of in order to make sure we were crystal clear about the problem before we started building a solution?
- [11:00]
Rob Woolen
The problem we were always very clear on. It's funny, I found recently a document from early 2014 where we elucidated, here are the 10 things we think are wrong. And it was like, I would say nine of them. I would still write today. There was maybe one that I was like, oh, we're kind of off on that. So I think we were uniquely good at identifying something that was a big problem. And everyone we talked to resonated with, yes, this is a big problem. We were, I think, an odd situation in that how do you figure out actually solving it ended up being much, much harder and to this day continues to be something I feel like we're still, you know, still trying to fully solve this problem.
- [11:38]
Omar Khan
And what was the competitive landscape like at that point? I mean, 2014, I'm assuming there was a. It must have been a fairly crowded market even at that point.
- [11:47]
Rob Woolen
Oh, definitely. Business intelligence is one of these interesting markets where on one hand it's a massive market. It's, depending on your estimate, 25, 40 billion. It's somewhere where it's massive and supports many public companies. On the other hand, it tends to go through these generations where you had a generation of products like Cognos and SAP's business objects that all were kind of in the 2000s and then went through an acquisition phase where IBM bought Cognos and SAP bought Business Objects. You had people like Tableau and Click, and some of these players come onto the scene. Later on, you had people like Looker. And then there was a phase in, like, 2021, I believe, where a bunch of these acquisitions happened. Salesforce bought Tableau and Google bought Looker. And so it's an interesting market in that it's a very large market. There's. There's not a single vendor who just completely dominates it. And it continues to sort of evolve almost with generations. So what we saw early on was that these products had really focused on what we call sort of the data person, the person who's going to manage the data warehouse. And that was who they sold the product to and who they built the product for. And they largely sort of ignored everyone else. And that's really what we sort of was our kind of differentiation as far as like our strategy is we wanted to build a product that was really sort of embracing a larger audience.
- [13:15]
Omar Khan
Okay, so you've got 8 million in the bank, you've got a pretty clear idea of the problem you're going to go and solve. I want to talk about what that first version of the product look like and maybe why it wasn't the right product. But just kind of help me understand like how, how did you go about doing that in terms of building a team? Was it just, you know, the two of you, the founders, did you start hiring pretty quickly?
- [13:50]
Rob Woolen
We hired three people right out of the gate, so we had a team of five. Interestingly, the, the first employee we hired is still with us to this day. So he's been with us through every transition of every part of this adventure. And all five of us were technical, so we were all people that were going to build product. And we initially tried to build sort of, I think two or three prototypes. So even though a team of five, we actually were sort of building a couple things in parallel and we had some high level ideas. One of the big ones was that we tried. Our hypothesis was that we could build something where the intelligence of our system could actually figure out, like, based on your data. Here's the analysis you should be doing effectively. Here are the questions you should be asking about your data and we're going to present that to you. And this ended up being a colossal failure would be my description of it. And the missing bit in sort of our hypothesis was it sounded great to everyone. Everyone was like, yes, if you could do this, it would be amazing whenever we would show it to people. And this is one of the things I find is very hard. You have to sort of interpret what feedback people are giving you. People would sort of squint at it and they'd be like, yeah, that part's kind of interesting. This part is not interesting at all. And, and it took us a long time to digest an important lesson, which was we had assumed that we could just, a machine could just figure out all of the important things that say a marketing analyst or a financial analyst should know. And instead it's very hard to actually know, like what's in their head, what do they already know about? What do they not know about, what's actually interesting to them. And we had sort of discounted them as, like, being the driver of this whole thing. So we had to sort of pivot our mindset to say, what if we instead build a product where they were kind of in control as opposed to us servicing things to people? But I think, you know, people rarely look at your prototype and say, oh, you know, this is terrible, and not what I would want at all. They give you sort of more subtle feedback, and you have to sort of try to, you know, pull on those threads and interpret things.
- [16:07]
Omar Khan
So when you set out, you said, we're going to go and build the right product. It'll take us about six months to do that. And anybody sort of, you know, even if someone had told you back then, no, no, no, this is much harder. Even back then, if someone had told you this is much harder, it's going to take seven years, you would have, like, probably not believed them. Can you, like, maybe give another couple of examples of the types of iterations of the product you went through and why each time it still wasn't right? Because seven years is a long time.
- [16:45]
Rob Woolen
Indeed it is. We spent six months on sort of our first kind of idea, and it became clear that we couldn't just automatically figure everything out. And so we kept sort of saying, well, what if the human told us this? What if the human gave us a little more information? And at some point, it became. I think we got disillusioned with our idea. It was like, the human is really telling us a lot at this point. Like, at this point, the humans told us everything, and our system doesn't seem that amazing anymore. So at that point, we largely started over. And this is a point where we actually lost two of the founding engineers. I think they had. We were almost nine to ten months in, and I feel like they just. They felt like we were just swirling around, and they didn't get the feeling of like, oh, this is going to make it. And so they moved on. And we then went down to a team of three for about a year and a half. Yeah, and it's, you know, on one hand, it's obviously a little bit demoralizing because you've gone from a larger team to a smaller team. Three of you definitely is small enough that, like, you, you know, you spend every second with the same people. You go to lunch every day with the same people. I remember there was one day where the other two forgot to tell me that they had something going on and weren't coming into work that day. So I came into work. I just realized I'm the only person in this office by myself. There are funny things now, but at the time you're like, it's a little depressing to just show up there and be at an empty office.
- [18:17]
Omar Khan
And the signs like, it's like, you've raised a bunch of money, you're into this, into a year and a half, two years, you've lost people because they don't believe in this thing anymore. Someone looking at this externally wouldn't be thinking, oh yeah, this is the sign of a business that's going to do 100 million plus and whatever. So what kept you going at that point?
- [18:42]
Rob Woolen
I feel like as a founder you have to be entirely irrational. So if someone shows you the statistics and they're like, look, there's very little chance you could start a company and actually be successful. Here's all the headwinds against you. Here's all the big companies out there, their business intelligence. There's so many existing companies, there's so many reasons not to start a company. And there's so many people that I think are negative on any idea. You show them anything and they will figure out reasons to poke holes in it. So I feel like entrepreneurs. I often tell people, my number one advice to people is don't start a company. And the reason I say that to people is that if I can knock you off starting a company with just that, you should definitely not start a company again. I don't even know how to answer your question. It's just like I still believed we were absolutely going to build a huge company, that we were on this important problem. And so there was definitely periods where I was down and we were, I think, lucky that I felt like there was points where my co founder was down, there was points where I was down, but they happened to not be at the same time. And so just having a few other people would help sort of pick you up. But in general, we were just irrational.
- [19:55]
Omar Khan
Yeah. I think in many ways it's almost like you're irrational. But also it's funny that you're in the data business, but in many ways you were driven by your gut, by your intuition, and less about what the numbers were telling you about the business and the reality.
- [20:13]
Rob Woolen
Yeah, you can hear it, right? It's passion. I feel like this problem is so important to solve. I feel empathy for these people that are like, I just want to be able to do this work and I'm not a SQL programmer and that's not what I should become. And so I feel like, yes, you need passion. You need to really be super interested in the problem you're solving. And honestly, that's why it's interesting to still work on 10 plus years later is that I still have ideas every day of like, what if we could do X instead and make this better? I think you need that to go on that long of a road.
- [20:46]
Omar Khan
So let's talk about how eventually you got to that first million in ARR. What had you figured out about the product by then and how did you start finding the right customers?
- [21:03]
Rob Woolen
We went through several other, as you could probably guess from seven years, several other iterations of ideas on how to solve this problem. And about, I think it was the spring of 2017, so at this point we're, you know, three or four years into this whole adventure and our investors had invested in Snowflake, the data cloud and data warehousing company. They were doing very well even by this point. And they suggested to us, why don't you go down there and show them your latest prototype and you know, meet with their founders and CEO and see if they there's some sort of partnership you could set up here. And at the time, our product had nothing to do with Snowflake. We did our own sort of work and did our own basically entire stack. And I remember my co founder was like, we're going to go down there and meet with them and try to convince them that they should bring us to their customers, but then copy the data out of Snowflake and put it all on our product. It doesn't seem like a particularly successful pitch. And so, and I think that about 30 days between when we, you know, set the meeting when their CEO and founders could actually meet, we again started completely over rebuilt an interface. This time we integrated, we built, sort of focused on the interface part, but actually generated SQL and focused on we're going to leverage data that's in Snowflake and run on top of it. And even just over lunch, the reaction we got was so very different. I remember their CEO was like, yes, I want this. I personally want to go use this. When can I start using this versus Before, I would say we generally got sort of polite feedback to our ideas, but never the passion of like, yes, this solves a clear problem for me and I want it right now. How do I help you guys get this to me? And so that kicked off for us an early partnership with Snowflake and also just gave us a first set of users to give us feedback and kick the tires on the product.
- [23:04]
Omar Khan
What do you think you got right about the product at that point. I mean, obviously the fact that it integrated with Snowflake was a plus and at least table stakes. But what was it about the product after all of those iterations that you had gone through, that you feel like you nailed something? Right.
- [23:23]
Rob Woolen
I remember from this lunch, Snowflake's CEO at the time, Bob Mluglia, said something like, he's like, I'm the CEO. I can get someone to build whatever dashboard I want. And they had a problem. They had a classic BI product to build dashboards. So our insight was not people don't have dashboards. The problem that he spoke to was like, look, I don't know what I want until I actually can play with the data myself and see it. You see something, you're like, oh, this is interesting. Now I want to actually, like, monitor it and go deeper on this. And so for him, what we unlocked in that meeting was like, he could actually do all this stuff himself and then make sure he was actually making good use of his team's time when he asked them to go build some dashboard or build some set of reports. So I felt like early on, it was very focused on a particular user, but we would just change, almost like change their life. Right. They would go from, like, they would very dramatically change how they work. And that was kind of our first strategy, was to find people like this where we could just very dramatically change how they worked.
- [24:34]
Omar Khan
When did you say you had that meeting?
- [24:37]
Rob Woolen
It was in spring. I think it was in April of 2017. So we were three and a half years roughly since we had started the company.
- [24:45]
Omar Khan
Okay, so then that's only like halfway of the seven years of zero revenue. So I'm guessing they didn't sign some big contract and write a huge check for you at that point.
- [24:56]
Rob Woolen
Now, in fact, we were actually very focused at that point, not on the revenue side, but on a. Like, can we get passionate users? We had an additional challenge here, which is a positive side of our product, is we connect to the company's most important data. The negative side of that is there's a huge. Then security bar, even just out of the gate, you have to pass. So I remember even with CEO support at Snowflake, it took roughly six months for us to get all the security certifications we needed for them to be able to hook up to their real data. And so sometimes there's just barriers to entry to markets like that. That was one we faced. Another one we faced over sort of the next couple years was because business intelligence is such an established market, and there's a bunch of these established products. We'd often find people that would look at our product and be super interested in it. And then they would sort of, at the end of the meeting say, hey, you guys can do. And they would list off, like, 25 things, and we'd be like, no, we don't have any of those features yet. They're all things we were going to build. We don't have any of those yet. And so I feel like we definitely on the product side had, like, went through a bunch of iteration and trying to figure out, like, just how many of these things do we have to build out such we can get over that critical path of. Of getting people to the point where they can go from that looks promising to I want to actually sign a real check and use this product. And that took time.
- [26:27]
Omar Khan
Tell me about that salesperson you hired and how excitement turned into not so much excitement.
- [26:35]
Rob Woolen
Yeah, I mean, we. We started first on just trying to get people, I would say, to give us feedback. So we weren't even necessarily trying to close deals. And then after about a year and a half into it, I think it was in 2019, we started actually trying to have real, actual goals of quotas and things like that. And I remember we'd won an award at a Strava conference as the best new product. Um, we had a. One of our first salespeople, and at the end of the quarter, she closed deals three days in a row. And I was like, this is. You know, we just won this award. We're getting this recognition. We have this clear traction. Everything's gonna be up and to the right. And, you know, it's one of my things I like to occasionally show people on our. Even just company dashboards to this date, the next quarter, if you look at our sales, it went to literally zero. We spent three months after we quote, unquote, I felt like we were getting to product market fit. And we just struck out on every conversation that quarter. And it's, I think, an important reminder that it's still like, there's no light bulb that goes off. And it's like, oh, you magically have now achieved product market fit. It's hard sometimes to recognize it and figure out when exactly is it time to scale. And we had several points where it looked promising, but just it wasn't quite there yet.
- [27:59]
Omar Khan
So what do you think was wrong at that point? Was it a sales strategy? Was it a product? Was it a bunch of things that led to a quarter of zero sales.
- [28:14]
Rob Woolen
I think it was probably several different things. One is we certainly have some sales execution problems to get to zero, but I think those are probably the minor parts of it. I think for us the macro things were we were targeting. Our product only works if you have something like Snowflake or DataBricks or Google's BigQuery. You have to be in one of these cloud data systems. And so those products themselves were, that market was growing rapidly, but was still growing when we were in our early days. So even if we had built the product that we have now in 2014, we would have been selling into a tiny market at that point. So I think one of the sort of aspects of our growth curve is just the market we're dependent on was also just sort of going through its own maturity life cycle and having some realization of that as well. The other side, as we talked about before is I do think there is just a broad set of product features and getting the interface right that it took. And it took a lot, a lot, a lot of iteration on that. And we continue to iterate even after having that initial batch of customers.
- [29:20]
Omar Khan
One of the things that you, you did well, I think from what I understand is finding these champions in, in organizations like as you mentioned, like the people who are like really passionate about solving this problem and using your product. How did you, you know, how did you go about sort of building these types of relationships?
- [29:45]
Rob Woolen
Yeah, so our first strategy was, what we were looking for is we wanted people ideally within walking distance of our office. That was kind of a goal. It's one of the advantages of being in San Francisco where there's a lot of other tech startups. But we wanted basically a bunch of very, very high touch users who would be tolerant of an early stage product, but that they saw the sort of promise of it and really enjoyed kind of actively giving lots of feedback. And so we cultivated probably 10 of these types of relationships, people that we knew very well. And we would go to their office and we would sit next to them and they really enjoyed, I think, getting to give this level of feedback. And some of them, I remember we had one person who changed careers because they got so into data that they focused on, they decided actually they wanted to go do that based on their experience of using our early product. So there's a bunch of things like that that were, were very gratifying. I think the double edged sword that I took away from it was on the positive side. We had a bunch of people that were great for customer references when we did our early launch videos. They appeared in those videos. They were incredibly helpful for us as far as helping shape the early product. On the negative side, we were super dependent on these 10 people. And that's not a large number. Right. People change careers, they change jobs, they go on leaves, and all of a sudden you have two people on paternity leave or something. You've lost 20% of your champions is a huge problem. And so I felt like on one hand, we were probably overly focused on just the small set of people, and that held us back a little bit. It certainly hurt us if those people left the company. We had to almost sort of restart the relationship with those companies. So that was probably the lesson from that was while it was. Parts of it were really, really powerful, we probably went over in that regard.
- [31:42]
Omar Khan
Yeah, yeah. I mean, I think it's a great idea to build those champions in different companies, but if you have a huge dependency on them, you have some pretty significant points of failure if people do decide to move on. Right. So let's talk about, okay, so this, the end of this first chapter and the first company and getting to the end of these seven years. What eventually happened that got you from almost zero revenue to that first million?
- [32:16]
Rob Woolen
I think we started to get enough traction with partners, with customers that people went from like, oh, this is something that one person will play with to. We were starting to actually be like, how. How their company would do data analysis. We were starting to be like a critical part of kind of their real flow. And so you went from being able to sell like, hey, you know, would you just toss us $500 because someone's playing with it, to like, can we actually do a real deal here of, you know, even 15,000 or something like that, Something that was actually, you know, at least a decent entry point into a real company. And we also, as a company then started making some strategic positions, strategic goals on our kind of next steps. And that's. We made a transition from. I had been the CEO the first, roughly six and a half years of the company. And then we made the decision at that point, let's bring in someone who's a much more experienced leader and can help sort of scale the company. And so that's when we hired. Who remains our current CEO, Mike Palmer.
- [33:25]
Omar Khan
You've gone through this journey of seven years. You eventually get to the point point where it almost sounds like what you did was just go out there and ask for feedback, find those passionate people, get them using the product, then sort of test if they were willing to pay A few hundred bucks for the product and then just keep iterating and getting that feedback until you got to the point where you felt like there's real value being delivered here. Now is the time for us to be able to go and try to negotiate a real deal. And by that time I'm guessing, obviously any kind of sales, there's challenges to any kind of sale. But I'm guessing you got to a point where you had those relationships, you've demonstrated the value enough that finally all the hard work or just the persistence of staying in the game for seven years started to pay off.
- [34:33]
Rob Woolen
Yeah, I think that's a good summary and I think the, I remember one of the signs for me was early on I touched every deal. I knew every conversation we were having with a prospect and sort of where each deal was. I think the first time we closed a deal that was like of an equivalent size where I had no idea it was happening, I had no contact with these people. That was sort of like my first inkling of, ah, maybe we're at product market fit here. Like, I don't, you know, I don't need to be hand holding every one of these things because in the early days, right, you do all sorts of unscalable things. Right. I remember at one point we had a customer who was about to sign and they were like, how do I know that I can get 24. 7 support? And our answer was basically we gave a machine, my cell phone number, my co founder's cell phone number. Like we had to give those types of assurances to people in the very early days of just like, we will be here for you. And then sort of getting that transition to like, how do you make something repeatable? It needs to be like, it can't be that, right? Can't be all call Rob. And so that type of transition to me was really sort of where I started to see the spark.
- [35:42]
Omar Khan
When we were talking earlier, you said to me, okay, we spent the seven years trying to essentially figure out what was the right product to build. We then got to the first million in ARR and then we said we're going to rebuild the product. Like, why? What happened?
- [35:59]
Rob Woolen
Yeah, I think this is one of the more interesting decisions for us because when you're at zero revenue, it's not fun to pivot people. It's very hard to tell a team we're going to throw away everything that we've worked on and it's sometimes hard to convince people and you often lose people when you do that. But Even harder when you have some little first inkling of success. I think for us, when we looked at how those early users used the product, we still felt like it wasn't quite right. And it's hard to give you a better, crisper answer than that because I think at some level as founders, you have to have this vision of, here's the experience we want our customers to have, here's what we want out of our product. And this one was very much founder led. I think my co founder started the effort and then I joined it. And we had to convince the company what we were building was the right thing, that we had to shift a decent amount of our engineering resources onto it. And then we had to convince really the rest of the early go to market organization, you should stop selling the, the sort of previous interface and really focus on this new thing. And we were lucky enough that we had some people in the go to market organization who saw very early on the promise of this and believed, and they became sort of our internal advocates. And then we had one of our largest deals then that we initially sold. We convinced everyone to use the new interface and we closed that deal. I think from then it became sort of all right, now we're all on board. But it's a really hard decision to convince a company. Obviously if we were wrong, it would have been a very painful story to tell in hindsight.
- [37:42]
Omar Khan
So was this another intuitive gut decision from the founders where you don't have data that you can point to and say, here's why this isn't the right thing and we need to go and rebuild it. But you intuitively knew that. But then how do you articulate that to the rest of the team, like what to go and build?
- [38:08]
Rob Woolen
The short answer is yes. I think a lot of product decisions, for better or worse, come down to some idea, intuition, passion, some feeling you're trying to evoke in your users and you can see different data points that help support you. Like for instance, we were very focused on, we want to get a broader set of users using our product, not just technical data people. And so we could see in data like, we're not as successful yet as we wanted on that. Like, we look at the roles of our users, we can see they're still mostly sort of traditional, like, you know, data analyst roles. We want to see a broader set of roles so you can see data that will help support, you know, hey, maybe we should do something different. But there's still something, I think almost a responsibility of a founder to be willing to make some big bets and to make some almost passionate bets. And I think they're almost uniquely, sometimes qualified to do this because that is essentially what founding a company is. It is. I have some hypothesis I'm going to bet even just my own opportunity cost on making this happen. And I think those are often, even as companies scale and grow, those are often still. Who needs to sort of be involved in some of these kind of major turning points because they've lived this cycle and so sometimes maybe it's easier for them.
- [39:34]
Omar Khan
You get to the first million and then as you told us earlier, the company went from effectively 0 to 100 million in just a matter of a few years. And partnerships were one of the biggest drivers for you, like the snowflake relationship. Can you just tell me about like, how did you get that working? Because the snowflake conversation initially happened many years earlier, didn't lead to anything that moved the needle. What was different this time? That you've got that sort of hockey stick growth curve?
- [40:13]
Rob Woolen
Yeah, I think there's a number of things that sort of happened in kind of the markets and moved obviously in our favor and there's a number of things in our product that changed. But overall, from a strategy perspective, I think one of the interesting things about this market is each of the products by themselves are not actually useful. A data warehouse that has no data in it is not interesting. You, you need something that moves data into it. So there's a natural partnership between companies that move data and data warehouse companies and then being able to actually use the data, leverage it, build analysis. That's why there's a natural partnership between companies like ours and people like a Snowflake or a databricks or Amazon Redshift. And so on one hand, all these companies are sort of used to partner selling and used to working together with customers. And so that's a, that's sort of a positive, you know, entry ramp for us that this is not a new thing to any of these companies. But we had to sort of, I would call it sort of earn our stripes with them on actually getting a bunch of growth on our own, such that we were then much more attractive partner to them. I think everyone starts off envisioning a partner thing almost kind of one sided. Like it would be great if this big company brought me into every one of their deals. Of course it would be great. But if you're on the big company side, you're like, why would I want to do this? I think that's probably the biggest takeaway on partnership is sort of figuring out how do you actually think about it like a partnership, what is the important thing for them? And what we had demonstrated to a bunch of these companies was we had actually achieved this goal of we have people in almost every department using our product and so we could take these infrastructure products from just being sort of siloed into, hey, that, you know, fundamentally they only really have passionate users that are very technical to. We can make it so company wide you have people using your products and are knowledgeable with your products. And that became sort of a lever for us to get a lot more, I would say, strengthen the partnership and get things going. And then, yes, obviously once the flywheel goes and you have a partner who themselves is growing very aggressively, those are great sort of, you know, symbiotic things to get going.
- [42:25]
Omar Khan
So now that you look back and we talked about what kept you going, what drove you in that first seven years, you must have had a lot of skeptics, a lot of doubters. How did it feel when you actually got to the point where your relentlessness, your intuition, your drive actually finally proved you right after all those years?
- [42:52]
Rob Woolen
You know, it's kind of a funny thing because I feel like every step of the company there's some, you know, you take, like you're very appreciative of some level of success. Right. You know, even get. You sign your first customer. Like, we've, you know, we framed the first check we have still in our office and, you know, I feel like the first time I saw anyone just like mention Sigma that wasn't an employee. The first time I saw someone have a job description where they included Sigma as a required skill, there's all these sort of milestones that I think you can almost sort of come up with and they're good points to kind of almost reinforce yourself and reinforce the team on we're making progress. And I think those have each been sort of gratifying for me. Obviously, the, you know, the employees we've brought on, the relationships we've built with them, seeing, you know, those types of people grow, those, those have all been sort of very gratifying. I don't, I don't personally think that much about people that doubted us along the way because, you know, honestly, most people, you should doubt most startups.
- [43:57]
Omar Khan
Right, yeah.
- [43:59]
Rob Woolen
It's a logical thing, it's not a personal thing.
- [44:01]
Omar Khan
Yeah. All right, great. Well, on that note, let's, let's wrap up, let's go into the lightning round. I've got seven quick fire Questions for you. You ready?
- [44:11]
Rob Woolen
I'm ready.
- [44:11]
Omar Khan
Okay. What's one of the best pieces of business advice you've received?
- [44:15]
Rob Woolen
I think I would call it around alignment. So for me and for an entrepreneur, I think it's often like alignment with your investors and alignment with your employees. What type of company are we trying to build? How large of a company in our case? Part of our crazy story is we were committed from the start to building a public company. And so any idea that was not going to become a big public, independent company was not going to be the right idea. But everyone needs to be on, on the same page with that. And so I think that sort of focusing on alignment was a big thing for me.
- [44:45]
Omar Khan
What book would you recommend to our audience and why?
- [44:47]
Rob Woolen
So I'm a bit of a contrarian here. I don't read any books that are associated with anything associated with work. Books for me are my escape. So I get obsessed about these different topics and then I read about these topics for a while and then I switch to something else. So I was obsessed about World War II and especially the Eastern front for a while and read like 20 books about this. Wow. It got super depressing because this is not fun thing to learn about. And so then I found like I got really into Agatha Christie. I decided I was going to read every Agatha Christie book which she writes incredible mysteries and then there's a bunch that are terrible. And so I had to sort of figure out which ones were actually good. But I guess my overarching advice is not on a single book, but to find things like this that can be escapes. Because building a company is so stressful, you need some outlets. And for me, books are an outlet.
- [45:41]
Omar Khan
I think that's great advice. What's one attribute or characteristic in your mind of a successful founder?
- [45:47]
Rob Woolen
I'll go back to this sort of irrational exuberance. You have to so passionately believe in your idea that it doesn't matter how many people are going to poke holes in it, you're going to give it your all to try to make it happen. And it's still, I think, the one thing everyone needs.
- [46:05]
Omar Khan
What's your favorite personal productivity tool or habit?
- [46:09]
Rob Woolen
I purposely park about 15 to 20 minutes away from our office and even doesn't matter what the weather is. I do this and it's because I feel like this disconnect between coming to the office and leaving the office in both ways, something about just walking gives me somehow, it just unlocks creativity in my mind. I think about things somehow my mind just Sort of works in the background. And I feel like a lot of ideas that I wouldn't necessarily have sitting in the office or even sitting at home come out on this just sort of in a way, forced walk I do every day.
- [46:48]
Omar Khan
I've heard that from a lot of founders. It's amazing how some of the simplest things can have the most profound impact on, you know, you as a founder. What's a new or crazy business idea you'd love to pursue if you had the time?
- [47:01]
Rob Woolen
I don't think I have a specific idea, but I would like to do something very different as far as the type of technology I build. So I've always built kind of like Sigma, these sort of general platforms. Right. Sigma has customers in almost every industry, almost every job function. And I'd love to try something that was like, super specific, like, can we take someone who works specifically in industry X and has job Y and does Z every day? And could we make that dramatically better, like dramatically faster, dramatically easier? But something was just like laser focused. And for me, it's more just. I've never done anything like that. I've always been like, oh, how could we generalize this to any X and any Y and any Z? And so that, for me, I think, would be. I don't know. I have a specific one in mind. But there's something. Something about that focus that interests me.
- [47:50]
Omar Khan
What's an interesting or fun fact about you that most people don't know?
- [47:53]
Rob Woolen
I think that I'm in some ways this weird person in that I got my first computer about 40 years ago, and I think I knew at that point, just from tinkering around, this is what I want to do the rest of my life. And I feel like so many people, even my own kids, go through this journey of trying to figure out what do they want to do, and I'm this anomaly that I somehow knew I was lucky enough. It was a very, you know, it was very. It was something that was a very good thing to actually go do. And I've been doing that just ever since.
- [48:23]
Omar Khan
What was the computer?
- [48:24]
Rob Woolen
It was Apple iie.
- [48:26]
Omar Khan
Nice. Cool. And finally, what's one of your most important passions outside of your work, very much?
- [48:33]
Rob Woolen
Well, there's the usual ones are very much my family and my boys and my wife and puppy, but just my other sort of personal interests. They also haven't changed much in the last 40 years. I love soccer, so I follow the English Premier League. And I'm also a big Star wars fan. So every one of the shows that comes out. Doesn't matter if they're good or not. I have to watch every episode of them.
- [48:54]
Omar Khan
Awesome. Thanks, Rob. I really appreciate you taking the time. It was this really fun conversation. Great story and thank you for unpacking that for us. Hopefully it'll give other founders listening some some inspiration if they're going through some tough moments to keep going if they truly believe in their idea. And I love some of the things that you shared with us, maybe some of the things that you did. The tactics may not work today, but I think you shared a bunch of really useful principles that hopefully will help people who are listening. If people want to check out Sigma Computing, they can go to sigmacomputing.com and if folks want to get in touch with you, what's the best way for them to do that?
- [49:38]
Rob Woolen
I'm just robigmacomputing.com, so feel free to drop me a note or find me on LinkedIn.
- [49:43]
Omar Khan
Thank you. I appreciate you taking the time and I wish you and the team the best of success.
- [49:48]
Rob Woolen
All right. Thank you so much for having me.
- [49:50]
Omar Khan
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