Kevin Boyle: Engineering Your Way to $30m ARR

Kevin shares some lessons learned in launching and building Gearset, a fast growing andself-funded SaaS company serving Salesforce developers.

Gearset was founded by an amazing team of product folks, with a heavy bias towards software engineers. Scaling from those engineering roots to a well-balanced company of sales, marketing, customer success and product development has been an amazing journey. It has required continuous personal growth and repeatedly embracing discomfort to keep up with what the business requires.

In this talk, Kevin discusses how his role has evolved over time as well as how he has addressed some of the challenges he’s faced leading a fast-growing self-funded SaaS company which recently took its first investment, a $55 million growth round from Silversmith Capital Partners.

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Transcript

Kevin Boyle 

Anyone want to shout out who that artist was going to go to pick them up like boosted it up some people might not know but it was either gonna be Bruce for that shot of post launch adrenaline, or else the greatest showmen but let’s do that on loop.

But I thought they’re trying to match Hugh Jackman’s energy metres set me up to field. So you got Bruce, the talk today is about starting gear set some of the story behind that, and how we grow it grew to the size that it is no, I want to go for lessons that I thought might be applicable. I went for things, there’s not much in the detail or trajectory or stuff about the company. But there were things that I wish I had known if I was doing gearset. Again, if I ever repeated this crazy endeavour. And hopefully, that means there’s gonna be some way transferable into your situation that is not just unique to us. I wanted to go for a talk with engineering in the title, because I think that’s sort of fundamentally who I am. So if I’m queuing at the airport, or from cooking dinner from loading the dishwasher, I’m probably overthinking that thing. I’m probably thinking about how I do it, probably watching to see how others do it and probably trying to optimise it, and possibly I’d resonates for some of you in the room. That trait of seeing the world as a system that can be you know, understood, modelled and optimised is pretty, pretty well rewarded as a software engineer. So that’s where I started my career.

And then as I started gear set with the brilliant team that we started with, we were kind of all software engineers, there was one outlier, who was like a PhD in human psychology. But he’s an engineer he just didn’t know didn’t know that he could do that thing, man. And so we we took that engineering mindset into pretty much everything the way the company runs, the seals. org is run like an engineering org. marketing’s are on like engineering and customer success, too. They’re all systems that can be modelled, that can be understood. There’s no black magic, there’s no seals, heroes, there’s there’s amazing colleagues that do amazing work, but they do it as part of a well understood system that’s methodical, cold and teachable and explainable. And then the reason I wanted to give this talk at BoS was I used to come to Boston as an attendee, and as a full time software engineer, and I was always in awe of the speakers that would come up and talk about their history of how they went about starting a company, they will talk about seals, they talk about recruitment, marketing, GTM, all these complex topics.

And I was just, I couldn’t see how to get from where I was, to where they were, you know, the sort of true entrepreneurs. And what I discovered was that a whole bunch of the stuff that I was doing in my day job was actually quite transferable, and to these other areas of the business, these other elements. And I also want to show what gearset went through going from zero to wherever we are now and sort of evolution along the way. It’s not to say it doesn’t require growth, it doesn’t require that you change your role all the time. It definitely does. But I think that’s natural for folks that are in product engineering anyway, so tech changes every five or 10 years, so often radically. So it’s a paradigm shifts and different languages and tools. So I think if you’re in this room, you’re probably very used to dealing with change you’re very used to dealing with with reinvention.

So about me, so I’m Kevin, I’m the CEO of gearset. We’re a software company that started here in Cambridge. That’s where most of us are based. There’s been 150, best here, including most of the leadership team. We’ve also got an office in London, mainly for that sort of depth of commercial talent. If you haven’t guessed my accent, I’m from Northern Ireland. And so we have an office in Belfast as well. I hired my brother to rot because he’s a real good software engineer. And then we opened an office in Chicago to almost all of our users are in the United States. So it was, it was useful to have folks on the ground in the country with the right accent and speaking to them.

We’ve also got remote hires all around the UK. And here’s how it helps teams. knuckle down can correct me and make sure I say this properly and have a real pdcp. But guess it helps teams manage their development on top of Salesforce and all those customizations. It allows them to adopt world class DevOps practices, and really just work the same way you’re working if you’re working in Python or JavaScript or rust. It makes Salesforce amenable to A modern software engineering and that sort of DevOps way of working. This is me in my staycation in Galway last summer. It’s a very beautiful place. But very, very variable weather. The I don’t think the the camera has been invented yet to capture the rain and the cold that was bothering me right then. But I liked it. I liked the photos. So the one I’m using, I’d like to keep this interactive. I think that’s more fun as a speaker on as listener. So I know there’s time for questions at the end. But if I’m saying something you’ve Emily disagree with or you just like me to expound upon and feel free to share it. The question is, if you don’t like asking questions in front of a big group of people, my contact info is over to the side there.

I’m not Kevin Martin on Twitter, and you just drop me an email, Kevin appears at the calm. David a background to me because I’ve influenced a built gear set and sort of why I want to do a startup at all. So from a pretty big family. I’m one of 10. And I’m one of the youngest. So lots of older siblings. They were into technology. So I grew up surrounded by technology, I grew up programming from a young age and things not meant I’m one of those very obnoxious people that from a young age can I knew what I wanted to do. I knew what I wanted to be. That was something working in software been a really great programmer. So I go about an acting job plan. I get my computer science degree. During that I did a couple of internships at Microsoft, you sort of forget it.

When you are living in Cambridge, or Boston, San Francisco, or indeed Raleigh, as I discovered. We’re surrounded by people that worked for Microsoft in the elk. But the hometown I grew up in. I didn’t know anyone that was working for Microsoft. That was not the that wasn’t the beaten path. That was to a nerd growing up in the 90s, early 2000s. You know, this was kind of where I wanted to be. This was where the best engineers were. They were writing the book, select readin, they were working on high impact projects like Windows and Xbox and office. Your family knew what you did you say you worked for Microsoft, people know what Microsoft is that’s got a bunch of recognition. So I love my internships there, I thought was a great, great company to spend some time at. But the challenges I saw Dan was, that was 2007. There was 80,000 people at Microsoft at that point. And it was sort of different difficult to understand how, as a grad, you could come in and make any impact on that.

How could you start to have anything and influence over something not big enough broad. So I wanted to try something smaller after college. And after graduation, I interviewed in Belfast sort of met these guys at a career fair, really connected with them. It’s really good company. And the very final stage of that interview process was the telly screen with the head of r&d here in Cambridge, the company had just been acquired by a Cambridge based company autonomy. Before I go on, has anyone here worked autonomy or in the leadership and autonomy?

And it totally worked for me. So Red Gate was an amazing company. It really cared about the products that built it cared about the way it built its products. So the engineering was great. It cared about its team and cared about its customers. This was entirely different, what I experienced that autonomy. And so I stayed there for about six years, there were three or four different jobs. And through all of that time, I was working in red gates core products, helping data professionals be successful with it with DevOps, all of the stuff that goes around that. Eventually, at Red, yet, I ended up running one of the r&d teams. And that’s where gear sets initially conceived and prototyped and comes out of.

So now I’m a gear set. It’s a incredibly high impact. It’s the most high impact thing that I’ve been a part of, I’ve got no colleagues just getting smaller and smaller if you graph the number of colleagues that I’m working with, and nobody knows what I’m doing. And I’ve just got no credibility and No, no kudos, but I’m loving it. So as I started to think about writing a talk, but how do you distil down seven years of sort of some of the most intense work that I’ve ever been part of, I started to think in terms of those years and stages of the company and the stages of the company went through, but also what that meant for us the growth that we had to go through myself and the team that that we’re running it. And it was an all consuming experience. And to be honest, it still feels that way.

So still very much feel in the middle of the whole thing middle of the maelstrom. It requires constant high energy, constant continuous challenges within us improvement. And myself and a couple of the others in the management team have used this phrase that from the very, very start, but it’s about six more months, six more months of this energy, and then we get to relax a little bit. But every six months, we’ve just claimed enough to see the next peak that’s over there. And because of the way our means are wired, we’ve forgotten the stuff that we achieve together, as this talk has been really interesting chance to reflect on the stages of growth of the company, and also the stages of growth that I went through as well.

So we break it down by years. So we started all as I suspect, as all startups do with a really healthy dose of naivety, we were unaware of the challenges that lay in front of us. I think if you knew the challenges, you probably wouldn’t get going. And repeat entrepreneurs serial, you know, folks that do it again. And again, like Bob was telling me, he’s not like seven times, I don’t understand that I don’t understand where you get the energy to do this more than once or twice. But we started, we didn’t really know what we’re doing. But we thought we’ll give this a go. The first phase was all product development. One of the benefits that we had of starting inside another larger organisation is we were actually shielded from a bunch of operational logistics, the real boring stuff, like meeting the bank manager to open a bank account, or negotiating leases, or working over your employee pension should be like, it’s just very, very boring. And we didn’t have to think of any of that, we got to spend all of our time understanding our users, and really making this thing work. We got that product development, really working and we felt like we had hit on something. And but along the way, we realise we’re just, it’s just too different to stay is inside of Red Dead. red gates r&d was all about building business units that could be inside red, get the next sort of business that could grow and develop and, and flourish within there.

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But we had ended up to different, the customer base was different, the buyer was different, the market, market personas were different. And our mode of operation had ended up different as well, we started to work really differently than a lot of other folks at Red did. So this thing was never going to it was never going to survive internally. We either had to spin it off and let it survive and thrive and grow or feel we had to let all that happen on its own merits. So we slid off from Red yet in 2017. Oh, no. Sorry, here, too. So I’m sleepy already. We split off from Red yet and 2017. I know. But my notes are here. So split off reget and 2017. We started with seven people zero revenue. But we got it all working, we got the commercial engine firing. And we started to scale the business. We’re now about 200x. Don’t know what we are, we’re about 200 and something people to 215 or to 20 or something, we have a really great culture that I love being a part of, it’s quite distinct from read yet lots of folks, especially in Cambridge think we’re real similar sort of two sides of the same coin, but very different and influenced by if you work anywhere for seven years, towards the end of that time, you’re probably going to start to get a bit frustrated with certain parts of it. And I was frustrated with certain parts of red yen.

And so I think gear sets quite different in some meaningful ways, as a more balanced organisation, which I’ll come on to in a bit. And finally, a position these things sequentially, this scale, and then no more AC, but you know, the gear set still in full scaling mode. It’s just I’ve noticed my role in that has changed significantly in the last couple of years. So before scaling and revenue, if you get a bunch of software engineers, and you ask them to go and start a company, the only thing they’ve got really is is there a capability to build product. So that’s where we started, we were going to identify a problem in the Salesforce ecosystem, and then build a product that we felt was worthy of fixing that problem worthy of those users. In our case, the ad actually came from within sight the house, read yet I suspect, like every other tech company full of Cambridge and Oxford graduates had a healthy dose of not invented here syndrome. If you’ve come across that phrase, this could exhibit itself in lots of different ways. It could exhibit itself in small ways, maybe of a cocky developer that just, you know, a built in list implementation that Microsoft have done, no good. I know they have done 1000s of hours of scale testing and load testing. But I can do better in an afternoon. And you would get custom list implementations. And then it could roll up to really big decisions. So red gear has its own custom CRM.

So if you wanted to sell to a customer or email them or something went through this custom bit of software that an internal team had built an internal product team and truth it was actually pretty good. It had telephony integration, Outlook Integration, it was it was actually fairly decent. But read yet just has no business being in the CRM business. It’s, you know, all this engineering resource going into building something that’s internal only. And so the inevitable happens. A VP of sales is hired. And he normally he says, Be gone with your bespoke gubbins. I don’t want any of this stuff anymore. I want Salesforce. I know how Salesforce works. I love Salesforce. I trust Salesforce. I can make it do the things that I want. Get me Salesforce And so a Salesforce implementation project is born at Red Gate worked with system integrator in London, they were pretty good at Salesforce, and put on a bunch of its own internal developers. And they were, they were pretty good at code. Unfortunately, they were very perplexed during this project, they were writing a really complex system, they knew what they were ripping out. They knew what the remodelling, they knew all the complexity of a 15 year old business, and what that would look like. But they didn’t have any of the tools that they were used to, that allow them to deal with complex problems. So they didn’t have source control. They didn’t have continuous integration, they didn’t have automated testing, their feedback cycle had just disappeared, this thing that they had had their entire lives. So they started looking around the market, they wanted something that was very akin to what red get offered database professionals, they wanted that for Salesforce.

And they couldn’t, they couldn’t find something that they thought was, was really great that developers would love to use. And so they came to us. We’re working in the r&d department, they come and they say, Kevin, Kevin, Kevin, there’s this mega opportunity. This market is huge, it’s underserved. We’ve got all these skills, we could go do something really, really great there. You know, put down your toys and your little innovation Playhouse and, and actually go and speak to some people. And we had heard this before, we’d heard lots of these sorts of stories. If anyone’s ever worked inside and innovation sell within a business or an r&d department is a really, really common story. There’s just everyone’s idea is the best idea ever. But this one actually was pretty good. And we started speaking to teams. And we just heard this really consistent thing. We heard that they all had this problem. They all have this problem with deployments, the problem was very similar. They talked about it in the same way. It was it was just, it felt different. The wrinkle was that added a few failures in a row would read good. And I was losing faith and was ready its ability to do innovation. And also faith in myself, I started to think like, I should pretty much stop playing at startups. And I should go and just be a really good software engineer. I see I was good at that thing. I’m not great at the startup thing. Maybe I should stop this. But you can put it down to arrogance, I felt more than my own lack of capability. It was the way Redgate was doing innovation, which at that point was modelled around the sort of bullets then cannonballs thing if you’ve come across that by Jim Collins, the idea that you’ve got plentiful of these late munitions, you know, you could plan to follow these bullets and the gunpowder that will fire them.

So rather than wasting your big cannon ball, do little bullet or mess, that’s fine. So I’ll do a bullet again. I’ll iterate, iterate, iterate, okay, that’s the sight line. That’s the path, put the put the cannonball in my limited resource. And but now we know we’re going in the right direction. The problem was I saw it was, I think the size of that initial munition really matters. So we weren’t firing bullets. We were firing little late BB pellets. And they were just blowing away in the wind. So we weren’t learning we weren’t. We didn’t actually know which way we should go. So I wanted to do gearset differently. I didn’t want to leave anything on the table. This time. I wanted to do things my way I wanted to be 100% control. And that way, if I feel there’s a totally personal selfish objective, if I feel then I could say that I feel because of me. There’s there’s no other reason for failure, other than my inability to do this thing. And so gearset did behave differently. It reported directly to Red Gate CEO at the time, broke lots of norms. Internally, he provided us air cover. And we ran essentially as an independent business with the perspective of glorious hindsight, and the job that I know how the CEO when the decisions that I know take, I think this was an absolutely bananas decision by them. I think it was one of the silliest decisions that Brexit has made, and Simon has made. I didn’t I wouldn’t trust it our team, we didn’t have the experience to do this thing. I definitely wouldn’t have trusted me like absolutely no knowing the journey of I had to go on. I don’t know why they did this. But it worked. And so now we can sit here with survivor bias and say this was a great idea. In hindsight, we assembled a superb team, the types of folks that really loved shipping software, because what I’ve learned is, you got a couple different types of people, you get people that love building stuff. And you get people that love shipping stuff. And those are often different pursuits. We write really good code, we build great products, be proud of what you build. But don’t build it for yourself. The act of creation isn’t the merit the act, the Get to your customers and them having value is the thing that’s, that’s good. And the team that we were, I was able to just pick the team that I wanted to really want to work with or folks that was high trust. It was it was just super.

So we had the team, we have the budget, what do we build? Well, let’s start doing some product management. We’re pretty good at product management. Unfortunately, this was product management in an area of where we had no credibility. For years, I’d been doing product management the conversations at Red Gate with red via email address and badge and stuff, if you’d speak to someone in the SQL Server or daily data tools market about red get, that’s pretty good. It’s got a lot of credibility. I’ve been doing it for five years. So I had a fair amount of credibility, like I could have a decent conversation with you and you, someone what I was talking about. With this, we didn’t we had no credibility. So we had to be really, really vulnerable and put ourselves out there. And we just started reaching out on LinkedIn to Salesforce teams, saying, Hey, would you have a conversation with us, and there was no more pretend she couldn’t, there was no bluffing like the, the asymmetric knowledge here was just, they knew stuff, and we knew absolutely nothing. So we had, we had to put ourselves out there and hope that folks were generous. And they were but 50 to 100 teams, they say, had conversations with us, we did jobs type interviews, and, and really spoke to them and tried to understand them. And over that time, we learned and we learned we learned and that whole experience of being vulnerable. putting ourselves out there, we sort of realised that was some of the best work that we were doing. And that became one of the first core values of gearset, this idea of embracing discomfort, you do your best work when you’re uncomfortable. And we actually codify that into the business. So we’re doing these research calls during the day, we’re doing collaborative designs with the team during the day. And then at night, we’re just coding away into the evenings, making really, really quick progress. And we get to prototype stage real fast. The amazing thing that I didn’t anticipate at the time, but as turned out to be true is that those original decisions, the way that we worked in just became the culture of the company. They weren’t decisions that we thought a lot about, we just thought they were a great way to build a product, having fast iteration cycles, speaking to your users a lot. This all worked really well for us.

And we just thought this is good. It’ll probably stop at some point, at some point, we’ll become a real company, and then these things will go away. And we’ll do software engineering, the real way you’re supposed to use in Scrum or something. But it’s lasted, as we’ve added another 70 software engineers on top of the seven that started it, we still do really small slices of product development actually made a note to read that ship up by the 37. Signals, folks. We use time constraints as a big thing as well, I think that was an excellent articulation of how gearset does engineering in a way that I haven’t been able to articulate. So I’m going to read that book and and hopefully we’ll be sharing around the time constraint that we were working to was sort of like 24 to 72 hours. That was the sort of the feedback cycles that we were operating on at that point. We had a rigorous focus on jobs to be done testing our assumptions, getting talking to our users, I guess our focus on jobs to be done was less rigorous.

And I anticipated given our website Teradyne a moment ago, but we tried, we still release updates two to three times a day, originally, it was easy. It was like one server and Dublin, you just copy over the stuff you’re good to go. Now it’s hundreds of servers around. I know like nine data centres or something. But it’s worked the same way. So we’ve had to adapt the actual mechanics of how we do that deployment. But we still do it, we still see a lot of value and getting that stuff out to our users all the time. And our engineers remain involved in making our customers successful and actually doing support. If you go on our website and do the intercom chat thing and speak to our speak to our support team, you’ll almost certainly end up speaking to an engineer pretty quickly, or they’ll get looped in. They’ll use that then as an opportunity to understand why he’s the product not working for you. What can they learn? How can they make sure this support ticket never happens again. And we hire engineers for that. So the engineers and the type that work at gear set, they have to like speak to customers, if you don’t like speaking to customers, if you’re, you know, only amazing at writing code, we’re probably not going to want to work together. Talking about jobs, we’ve done this with Kim, one of gearsets core values, as well as our website with the company values and focus on the jtbd is, is there. And when I wrote this talk, I didn’t know Bob was gonna be in the audience. I might I might have not included this slide. But Bob are two things to say thank you for making an excellent framework.

Yeah, I think it was this is truly changed how we we spoke we actually saw Bob do a thing at BoS and that was what made us go and research this stuff. And this, this this, this credit our company for us in lots of ways. So thank you for that give us a way to talk to users give us a way to talk internally about what we were doing. And then I also need to say sorry, because we don’t apply this maybe quite correctly. We don’t apply this rigorously and dogmatically perhaps as we should. So I’ve created an army of 200 people that go around saying focus on the jtbd jtbd without actually knowing what that means entirely. entirety correctly, but it works works for us. And I’m sending favour them tomorrow to the switch workshop. So they will learn and they will come back and be ambassadors and level us all up. The other book they loved during this time was the mom pass, this was a really, really impactful book on us. It gives you a way to conduct unbiased and effective customer interviews are very, very similar in lots of ways there lots of overlap. Certainly, some of the rules from that are, don’t ask for compliments. Don’t ask for hypotheticals talk about the past, rather than the future. It’s written by a software engineer, sort of for software engineers. It’s very, very short, which I, which I always love in the book. And the influence is so strong that if you were to join here sat and get our little starter pack thing with your computer, we include a copy of this book. My one problem with this book is the title, the Mom Test. So the title comes from the idea of, hey, I’ve come up with this new idea, this new business idea, I want to test it a little bit. So who can I go ask I’ll ask my mom. But your mom’s is relentless cheerleader in your life, she’s just telling you like, Oh, no matter what you say, it’s a great idea. Do that, do that do that.

And so the idea of the book is we need to get away to trick her into giving you your her her real opinion. It was definitely written by an American, because if you have an Irish mother, they are not the relentless cheerleader in your life. If you go to your mother and say, like, I’m thinking about quitting this job, but I’ve loved this been really, really good to me. And I’m gonna do this thing over here. It’s entirely unknown, I might feel they are not a relentless cheerleader. But the biggest, the biggest, good all the same. The only thing that we repeated a lot around this time was do things that don’t scale, we would just focus on making that one user successful. And this was quite a big deviation from how we worked at Red get, I’d read yet, you had to do like a lot of research. And it was all in aggregate and hypotheticals and market sizing and time and all this other stuff. And that was Ansible, for read good, because it was going to spin up and commit resources and all that sort of stuff. And there’s a million different things it needs to do. So which things there’s a prioritise. But for us, we could just focus on that one user, they had engaged with us. So by Christ, we were going to engage with them, we were going to talk to them as much as we could, we were going to iterate. And because we were fast iterating, we could do on a daily basis, we could just focus on making them successful. There’s been a little bit of loss of this as the company has grown. And I don’t entirely know why I think there’s a certain amount of human psychology kicks in. So if you joined gearset, today, it’s 200. And some people, it’s got nice offices, you’d look give out hoodies and stuff. And I think maybe people think it’s real stable, like it’s a dumb thing.

Whereas the way ice gear set is, you know, we are fighting for market opportunity, we are just trying to survive and grow. So we shouldn’t think too hard about what we’re gonna look like in five years and be blind to it. But let’s be successful today as well. So we encode this is one of the core values of the business as well, this idea of delivery over deliberation. It’s better to do something good No, than something perfect later. And particularly, I think, if you’re working with a bunch of high performers, if you’re working with high performers, and they’ve got an internal debate as like, as an Option A or Option B, Option A or Option B, should we get more data to help me understand what these options that is? The kinds of folks that I suspect you will get to work with? Both their options are good, you know, both their options are probably good enough. You know, one will be better than the other. Sure. And like bills thing yesterday, if you’ve got bills, reference to basil sustained yesterday about the one way doors and the two way doors, yeah, there’s some decisions that require you to do a little bit more deliberation.

But for I think, for guiding policy, delivery over deliberation has has stayed as well. And I think I would do this one, again. So these key lessons early in the company became company values, they became company values, the years later, none of the time, like they want me didn’t sit down and do things don’t scale, right and own company values. But we really thought like, how do we get successful? What were some of the things that we did that we liked, and definitely part of it was, you just count on specialisms, you know this, this idea of embracing discomfort, doing things doing your best work, when you’re doing something you don’t know how to do, I think it’s very valuable a startup, you’re going to need to do that, because you won’t have the specialist next to you. And you maybe you can hire in a specialist, they won’t understand it. So if you get a consultancy or something, they won’t understand that the way you do if you intrinsically do it. So bring them in, get them to help you get them to shortcut a bunch of the learning. But like, you’re gonna have to own this thing.

If you focus on helping users solve their problems, like life’s going to be pretty good. They’re going to engage with you, even if your product isn’t there yet. They’re going to trust you because you understand their problem. Especially when you’re not jtbd and get into the heart of things. And you’re very much on borrowed time. So our runway was really short. Your, your time is limited. So you’re going to have to see results quickly and, and all that to every over deliberation stuff. And yeah, don’t worry too much. It’s like all advice, right? It’s how you apply it. So it’s not that we’re doing is like randomly doing whatever we think is good that day. But you sort of always tried to get this balance of we don’t want to over engineer and we don’t want to under engineer. So this initial sort of hyper product focused phase of the company lasted about a year, year and a half, during which time we really confident that we’d find product market fit. Such was our competence, in fact that we went ahead and spun out of reget quitting our jobs and these things that we liked leaving behind all those, the comfort blanket that we’d had before we had any customers. So we had an absolutely amazing product. What else do we need? We’re good. So as the spin out paperwork is pinballing its way around HMRC.

The tax authorities here in the UK, lawyers, KPMG, Deloitte, more lawyers, more lawyers and more lawyers. We attended sales forces biggest conference in San Francisco Dreamforce, their trade show we brought we brought the product over there and had a booth dream has anyone been to Dreamforce? A few. Dreamforce is kind of hard to explain. I’ve done some of the big Microsoft conferences, both internal and external. Dreamforce is something different. I’ve heard it described as 1/3 tech conference, 1/3 sales conference and 1/3. rock concert. And all without candidate, you know, dollop razzmatazz and grandeur that only Salesforce have the q&a is to try and pull off. That’ll get redacted as well Kirk because I would never say Salesforce Haqqanis I’d say a more polite word.

The event was really successful. It boosted our confidence that way, as well as with any tradeshow could ever have gone for us. As folks are walking past the booth. We’re like, Hey, how’s it going? Have you heard of gear set? No. How have you not heard of this startup that doesn’t exist in the name came up with yesterday. Come on, come on, let’s show you a demo, we’ll show them a demo on the tablet. And the response every time was just it was just so good. It was it was just amazing. And we came back just buoyed even though the servers fell over. And we had to delete things. And thank Christ for infrastructure is code able to recreate AWS assets, the thing worked, and we had excited attendees. And we came back just with strong conviction that we’d head on something that was really going to resonate with a huge audience. We’re sitting on a winner, all we had to do was put stripe in to do some purchasing. And then like we were made, we didn’t really see the need for a sales team, just extra cost extra hassle. I mean, I don’t like speaking to salespeople, same as Ramadan earlier. And everyone’s like me, and everyone’s like him, right? So we just thought build it, and they will come.

But the money did not come rolling in. And much like Mr. Coyote, here we were, we were very much on our own, we’d left red get by this point, I’m doing payroll, I am our bank gay. As an aside, if any of you’ve ever done payroll for your company, or as if when you’re a consumer of payroll, you think this thing is like a well oiled system. And it’s all nicely integrated. And there’s no humans involved? Well, no, I was like logging into northwest and typing in my buddy’s account number and then typing a number to pay him. It was It was terrifying. What it was really good for was, I could see our bank balance going down just every month, every month, we just got closer to being dead. And I was gonna have to be the one that was gonna fire my friends, these guys who had talked into doing this thing with me, I was gonna have to let them go. And that was that was that was a nice moment of clarity, clarity, you know, that was created a point in the future of which I had to get things working by. And so we came this fork in the road. And we debated as a team.

We knew that there were features that we could build. We knew there were stuff that our product didn’t do. Obviously, it’s like a version point seven product, right? We know there’s stuff we can do. But we also knew that some folks were using it, they were using it to do their real job and they liked it. And they liked the product. And they liked the outcomes from it. But they weren’t buying it. So what should we do? So we decided to focus on understanding why customers weren’t buying. And so we took a bunch of computer scientists and a bunch of UX engineers, and we admitted the code and product wasn’t the thing that this embryonic business needed from us this point, we needed to start doing sales. So we got pretty ruthless of that we turned off all sound like we close Visual Studio, we started picking up the phones, we started calling our triallists and we started calling the event leads that were taken from from Dreamforce. And these weren’t nice prearranged calls. It was sad over LinkedIn about product management and sort of nice highfalutin thinking stuff. We were interrupting their day, you know, so we had a moment or two to the beat or to to pitch gear set, get to the heart of what was wrong that made them give us their details in the first place why they started the trial of this product. And we got good at that we get good at understanding and talking to them. And this was another case of having to embrace discomfort none of us had ever done any seals. Big big impostor syndrome here. We didn’t know what we were doing at all. Now to the interactive section. Somebody want to throw out any words for what you think of when you think of seals or salespeople. Hero to Always Be Closing classic Alec Baldwin. persuasive. Slimy sleazy, genuine, magnificent, interesting. So, Mark is that I actually wrote like two little bits of this, I wasn’t sure which way we go, because I will say a BoS audience, lots of people running businesses, they’ve got salespeople they’ve got. So how do you think about those things. But at the time, I wasn’t as smart as the average BoS audience, I thought sleazy and slimy, and the Wheeler Dealer trying to trick people into the preying on prospects to try and trick them into it. Or I also thought of them as credit card takers. I thought of them as people that mined phone lines, pick the credit card numbers, because their employer wasn’t smart enough to automate it away. You know, I just didn’t understand what this thing was. You can see a repeated theme of arrogance, you know, but that’s that’s what it is. But all that’s bullshit, right? That’s, that’s not. That’s not what sales is. I don’t know if it ever was it’s certainly isn’t. Now it’s, it’s not modern selling, modern selling. And the way that we do sales is the only way we knew how to do sales, we spoke to people, we understood their problem. And then we recommended where our product could fit where it didn’t fit. It was product management, but you asked for a credit card at the end. And I think that’s the value still that seals gives gearset today, and what great sales reps and our sales reps are amazing knots the value that they bring all the stuff around stakeholder management, creating urgency, creating desire, like there’s there is stuff to that, right.

But it’s only a little better. But I think the real value is being close to your customers and understanding where you fit and where you don’t fit. Ultimately, in the b2b world that we operate in, you’re not going to trick somebody into spending hundreds of 1000s of dollars, right, you’re not going to trick them into implementing a change management process and themselves or on their team, they’re only going to go through that level of disruption. If they’re confident that they find a vendor, a team that understands them that has a really strong diagnosis of what’s holding them back. And then outlines a great solution and a roadmap for helping them. So back to us. Or actually, before, I think I’ve got some more stuff to say and sales. Nope. So back to us, we’ve got a much tighter feedback loop, no. And it incorporates this additional heuristic that actually gets customers to sign up. So it helps us prioritise the customers that feel the pain the most, because it’s the ones that are actually going to pay us money, and helps us prioritise feature requests in like an economically effective way. It still requires discipline, it still requires us to do good product management and jtbd, it still requires us to, you know, want to build stuff people are asking for you end up with the foster horse and all that sort of stuff. But that played well to our core strengths. We were already we’re already pretty good product development organisation. So each of us now was this mix of software engineer, product, designer, salesperson, and owner of the business all in one head. And you had like seven of these people. And we all had the bank balance in our head. So we could take a very holistic and nuanced approach of what features we were building and what customers were helping which customers we leaned into helping and which customers were actually pretty sanguine about turning off us. If I started my career again, or if I was just given advice to a junior engineer or something in anyone’s Junior with sort of entrepreneurial ambition, I’d say do seals earlier. I think it’s an intellectually rewarding pursuit, it helps you understand your users. Product Management is great. I think product management dunwell get you to on the CMO calm. But I think cash is an ultimate compliment. If someone’s willing to part with their own money, or their internal credibility to unlock their company’s money. It just gives you an even tighter feedback cycle. It’s just the product management feedback cycle but even tighter, because now you’re having to get cash out of it. So as you scale the business, I’ve held this dual role of CRO and CEO, which I’m about to step down from because I’m a month away from having a child. So we’ve hired a CRO to take over from me. Seals also gave me a really deep understanding of our of our company in a way that I didn’t have it read yet. I’d read it I would look at the revenue graph revenue graph is real shiny looked real nice. Christmas time, snow would fall down on it.

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It had a bonus threshold lane when the lane went above that bonus threshold lane. I got to beat myself and you Kindle or something. It was fantastic. But I didn’t really understand read gates go to market not in detail. I could talk about it at high level I maybe even thought I knew. But I didn’t truly understand it. Not the way it did. Not the way I did after I did sales for gearset. Now I had a way to think about the business with customer acquisition cost, lifetime value, how to do segmented sales funnels. I had an X model and wasn’t just in my head, I could put it in a spreadsheet, and I could begin to forecast against it. So now we could say hey, if we invest the dollar here and the dollars we get out, and it all starts to just be nice and scientific. It allowed us to tweak and that allowed us to optimise real quick Like, you should read this book if you haven’t I suspect a lot of people have because obviously, he’s Dan Pink’s, so he’s quite well known. But it’s the idea that everyone’s selling all the time. If you define selling to be understanding and fitting and persuading, it’s not a sleazy exercise. I think it’s a great book. The other book I still love for this is the Mom Test when you apply it to sales, those same types of customer interviews, to get the customer to get to the root of their P and really feel it really emotive really articulated back to you, then you’re not really selling, they’re gonna tell you why they need to buy your product. So those are those are two great books in my opinion. 12 minutes shit.

So now we have our go to market, I think it’s like called product lead growth. But most people our sales team are only inbound opportunities are usually become aware of the problem and find gearsets see success and a free trial, and then engage with our sales team when the when the time is ready. We can make pretty good predictions about if we put $1 here, how much are we going to get out. And so that gives us levers to poll and 80 of payback timing. That allowed us to stay bootstrapped and still roughly double our headcount each year. So if you got to double your headcount each year, or something even close to that, at least, we found that very hard, that was very, very hard. And as it got bigger, it got harder, because now the numbers are getting bigger. So year, while it was sort of easy enough to find 10, if you’re fine, you know, but if you want to really get that growing not became harder and harder. So we started to spend a lot of time boosting awareness of our company, and also as an employer and what like, why are we different as an employer, like what, why should we come and work together all that sort of stuff that became as awareness, important as boosting the awareness of our product. Somebody mentioned recently that you can’t go to a pub in Cambridge, the minute without seeing one of our logos on the glass. That’s because we sponsored a beer festival about four years ago. And all those glasses ended up with pubs around Cambridge. It’s the single highest ROI piece of marketing we’ve ever done. And I got to drink loads of beer. We use things like glass door and entered competitions to see how we stacked up against their peers. And we want to do this in a very thoughtful way. It’s a very easy trap to fall into, like hiring heads or some sign of success or something. Because if you’re hiring heads like you, it’s easy to hire people like you just go ahead and hire them.

The hard thing is hiring the right people that are right for you, and then enabling them and setting them up to be successful. So that that was a thing we did thoughtfully, we did it first of all here in Cambridge, because we like being together, even when we’re hybrid or remote or whatever we like people to get together and spend time together. So we did that mostly in Cambridge until the culture got low, but a little bit more in nurture behind that. The other thing that surprised me, even though I don’t know why, because various folks had said to me that this would happen was I think you need to find ways to start supporting your staff at scale. When you have a lot of people working with you, sort of Murphy’s Law kicks in, and anything that will happen, sorry, anything that can happen will happen. At scale, it’s much harder to deeply know people and spot when things aren’t quite right. Especially in areas like mental health that are often silent and hidden. Like everybody, you know, I know a bunch of folks that have had mental health issues or have had in the past, I think it’s a really, really common thing. And people are very good at concealing it very often. So we started to find ways to be able to support people, we do things like you, the NHS is really good system. For Americans, it’s it’s real, real good. It’s not great for mental health, if you want to speak to a professional, you have to go through quite a few hops. So here’s that gets rid of all of those hops. And we keep a psychiatrist, the doctor on staff, therapist, and they you can just call them up, and they will invoice us their time. We don’t know who uses it. We don’t know what you’re using on the boat. But there’s somebody there that you can just call and lots of folks do. And I’m really glad that we did this, I’m glad we invested the people opposite skill that makes it all very open and transparent. We’re really working the problem together on the same side of the table is not OSFI them. And I’m really proud of where we’ve ended up. I was initially resistant to a bunch of this, I didn’t want us to policy, if I had it didn’t want to formalise it I thought that would you know, take the humanity away. But actually, as we scaled and people don’t know that you’re human, when you’re running a business, they think your your job title or whatever, doing things like this have been I’ve been really beneficial. And I’m proud of some of the good stuff gearsets done. The only thing that becomes real hard as communication. I think it probably becomes exponentially harder as businesses scale.

A few different reasons. There’s just more concurrent work happening. So the business is doing more stuff across more axes. And it’s impossible to stay on top of it. Even if you had perfect communication lines and perfect data. Smart driven. People are going to go off and they’re going to be busy doing what they consider to be the most important thing. And communication and data aren’t perfect. So you need to work really hard. Make sure that you’re checking in you clared communicating down what the strategy is using things like OKRs, whatever framework you want to use, you’re doing things to check. Are we all aligned? Are we all going the same way? are we all doing the right thing, what’s changed in our markets, what’s changed with us and our customers and businesses, what’s changed in macroeconomics, all those sorts of things. And you have to be mindful that for those of us have been around since the start, and they’ve been immersed in it, you’re, you’re sort of you have that curse of knowledge. So what’s obvious to us won’t be obvious to somebody new. So that communication challenge is just, I don’t think it gets ever bigger. And I don’t think it’s something we’ve cracked. But it’s something we should have Trey, Trey and Trey and Trey. And there’s so much going on, how do you keep it all in balance. Lots of the company’s leadership is drawn towards product development, like a moth to the flame.

I’m actually not too sad about this gearsets product company. So what we do, our viewpoint in the world is a problem should be solved with really great products. But we know that we know firsthand, we learned that product alone isn’t isn’t enough, it isn’t going to help us scale something to help us succeed. So we try and keep all the disciplines in the company imbalanced. And we do that through lots of different ways to break down silos and make sure that it’s a team culture rather than departmental culture. Some of the books that I would recommend they’ve been really useful to us, Richard Greenwald spoke on strategy is a super book, it gives you a way gives you a scientific way to think about strategy. I don’t know it may be a placebo, it may be, but it’s worked really well for us. And it’s given us a common internal language to discuss strategy in a slightly more objective way. And then the two from Lynn Cooney, I love The Five Dysfunctions of a Team really good. I’m sure a lot of people have come across that before. It’s a sort of the foundational how you build up a great team and what’s what’s important and creating high performing teams. And then the advantage is sort of the same, but for organisations. So it’s got these, like six questions you need people to answer as an organisation and have a tight answer on that if you want to create clarity and then over communicate that down. I’m not a natural born lover of business books. So I don’t recommend these terribly lately, I’d much rather read fiction either great fiction bill like June, amazing book, or airport fiction, like I just finished reading the James Patterson and Bill Clinton one, if you want to read a really good book about a fictional president, that goes off to defeat a cyber terrorist, a man is really good. But these are also fine. So with my sample size of one, I can confidently state that as part of a startup, you’re gonna have to constantly evolve your role. And even times that can be very radical, a radical shift. You may not notice it until you reach some inflection point. But if you stay adaptable and open, you know, it’s really crucial for being successful. I think it’s the reason we work at startups, right? Is the reason that you want, you want to be a part of something where you’re changing every couple of years. So if you embrace that discomfort and take the opportunity to grow, and it pays back dividends.

So what’s my job? No. Think it’s the same as it always was, keep us customer focus, keep us moving. Make sure that people are unblocked, make sure that we’re all moving in the right direction. Actors are public fierce. They think the inflection point for me over the last couple of years I think was Sally was talking to this yesterday about how if you’re doing work yourself, you shouldn’t be doing work yourself, you should be your team. Well, I’m I’m a very slow study. And that took me a long time to learn. But I know fully at that point where everything has to go through my exact management team. That’s those are the folks those are the leaders that are actually going to go and through their teams make work happen. And they have a hard job, you know, it’s no small feat, creating and keeping that team running. They’re running things that are much, much bigger than gearset. Well, it’s just a few years ago, in terms of headcount, complexity, ambition.

Kevin Boyle 

And I also think that I get sort of a unique perspective of anyone in the business, because I’m the only one that sits across everything. So I can kind of spot gaps that are ways that company can work together more effective ways. I don’t think I’m very good at this yet. I don’t think I’m very good at this managing through a group of execs, managing and managers that manage and stuff. So if this resonates in any way, or if you have tackled so you find techniques that work for you, I’d really love you to come and help me out and tell me what, how you can be a better at this thing. So that’s me, I think I said at the top, I’m fundamentally a software engineer, that’s gonna spend the majority of my time thinking about how to improve things. It’s a bit of a superpower and very useful, but it’s also a curse, because you’re, you’re always just so focused on what isn’t working, you know, what can you improve next? You don’t really spend any time thinking about what the team has achieved together. I was already in late 2021. And we sat down we started to think about what we both realised we not only built a valuable company, but that the opportunity that was in front of us was just way way bigger than we could have dreamed when we started this thing. So can we grow it from where we are now to be a multi billion dollar company that’s gone public or done any of these other things, I say we can, but it’s going to require that same level of growth that God has here, it’s going to require us to continuously reinvent, we’re going to find more great people to join us and teach us new things, helping our customers with ever more impactful things. And I hope that along the way, we can do that and become more successful, but never put that success ahead of building something that we’re truly proud of. Thank you.

Audience Member 

Kevin, really good talk. Thank you very much. I think one thing that stands out to me is your ability as an organisation to take feedback from customers from lots of different angles. I think that’s quite unique, especially your example of the engineers doing so how do you prioritise what you build when you have salespeople that are looking potentially at forward thinking initiatives? And you have engineers that are looking at now problems? How do you take all that data and focus on what’s a build question

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Kevin Boyle 

With a good product team that can take months out and and make a bunch of prioritisation. We’ve also, as Ryan was talking about yesterday, we’ve got separate teams that do sort of product initiatives that we know we’re gonna take a little bit longer. And then we free up engineering capacity to do reactive stuff, a b2b bug fixes, or it could be very small feature request, which we believe and we think it’d be good. But it’s not it’s not important enough to get scheduled or like preempt an engineering team. But we can put it to this team, and they’ll implement it. Yeah, next year, those techniques, but it’s hard. And it’s getting harder as we get bigger as well, like it’s noisier. But I think we’ve built a good organisation, a good culture of there, its feedback. And feedback is a gift. But I don’t need to act on it. I don’t need to, you know, I’m taking your feedback on somebody else’s. So our sales guys aren’t pushy. They’re not saying hey, do this to the customer, or, you know, we’re gonna lose this deal. And like, What the hell is the most important deal in the world, there’s a high degree of trust between those different those different elements, the organisation that understand, hey, we’re going to do some stuff, we’re not going to do all their stuff. Maybe we had for a couple of customers to build up a body of knowledge. And this thing gets like the heart of that what the jtbd is, you know, maybe we don’t solve it this way. We solve it some other way.

Audience Member 

Couple of couple of questions. Can you talk about the investment if you had any outside investment to help you grow? And what were the specific points that you took it on? And what does no more ice mean?

Kevin Boyle 

Yeah, so we took investment? Ach, sorry, I lost the second one last, no more I see, like, no more individual contributor, I’m not allowed to do any work myself at all has to be through the team is that sorry, we took investment in 2022. Yeah, last year, we didn’t actually need the cash, we had grown self funded. And we found investors actually really likes that model. So they’d like us to stay self funded. The reason we took investment was that sort of realisation that we haven’t just built a valuable company, but we’ve built a springboard from which we can go and do something much, much, much bigger. But we’re going to need some of the expertise, some of that external folks, we need to bring them in as advisors, or someone was saying earlier, like get their skin in the game. So we find the right investment partner for us. And those of sort of journey to take the management team on the board on they there’s a lot of people a lot of inertia behind that self funded model, weren’t keen to bring external investors in thought, it’s gonna disrupt this, they’re going to have short term goals and all this other stuff. But the folks that we find I’ve I’ve found incredibly helpful, and, and they’re, they’re very much aligned on what we’re going to do. So that was last year. That’s the only that’s the only folks that we have any intention to bring it in. And it was just to unlock that next. That next tranche of development growth for us.

Audience Member 

So that was really the second part of the question was, you know, do you have a functional board now having heard Allison this morning? Are you getting drive and insights from your board members that are helping you materially?

Kevin Boyle 

Yeah, I really enjoyed Allison’s talk earlier on boards. I actually loved this board. We had one prior to the investment. Again, one of the because of where we came from I have read yet read good Zocor, Freddie growing up company, it has grown up board and things. So when we started and spun off, lots of folks running ragged and same and ragged CEO said, We got to get a board for this thing. It’ll provide the right level of challenge and oversight and strategy and give you guys a sounding board. He was kind of doing the same thing as doing this talk. You know, he kind of wished he had him 20 years ago when he started the company. So when we’re starting our company, how does he help us shortcut some of the mistakes that he’s not sure I cut the mistakes, hopefully, avoid the mistakes entirely. Shortcut some of the learning and avoid some of those mistakes. So here’s just a good board from the start. And the investor gets a seat on that. And again, that’s what we wanted. We wanted them on the inside and It’s been great thank you amazing fabulous


Kevin Boyle
Kevin Boyle

Kevin Boyle

CEO & co-Founder, Gearset

Kevin is a software engineer that hasn’t written a line of code in the last 3 years. He studiedComputer Science in Belfast, before moving to Cambridge to work for Autonomy, Redgate and eventually starting Gearset.

Gearset is now 150 people with $30mm in ARR and has meant that Kevin’s spent the the last 6 years with an unhealthy work/life balance growing Gearset, but loved [nearly] every minute of it.

More from Kevin.


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