10 amazing years building great teams and great software

Test Double’s mission is to improve how the world builds software, and we also believe that building great software and building great teams are intrinsically linked. Co-founders Todd Kaufman and Justin Searls had a conversation reflecting on the first 10 years of the company, and thinking ahead to Test Double’s future impact. Much of that conversation revolved around how helping people find joy in meaningful software development work is at the heart of what we do.

Why did you start Test Double?

Todd: So Justin and I were working at another consultancy at the time, and I always think of the scene from Jaws, where they were all sitting around a table comparing scars from other encounters. That was Justin and I on a 5-hour drive back from a client, talking about all of the current issues with that engagement. The more we tried to pull on the thread and get to the root cause of these issues, the more it started seeming like the company that we were working at was the problem. And it mirrored a lot of the issues we saw with other consulting companies that we had worked at in the past. So we had the right blend of, I think, ignorance and courage to say, “Hey, we could start something that would be different, and that would address a lot of these issues.”

Justin: A particular top of mind issue at the time was that a lot of large software companies had developed a pessimistic stance towards not only software development but the competence of software developers. An idea had taken hold that maintaining high-quality software at scale required a company to constrain software developers with strict rules about how to do their jobs—when and where to work, what tools to use, how to review & audit code. It all came from a place of wanting to protect the software from the worst programmers, but had the effect of stifling the capabilities of the best developers. With that mindset, a company’s best-case outcome is mediocrity, not greatness.

I think the thesis Todd and I shared—and that Test Double has proven to be right—is that if you take great software developers who are highly skilled and motivated and you make it management’s job to remove obstacles from their path, then they will run circles around teams encumbered by management-imposed constraints. The fact that we might be able to start our own company and honor people’s autonomy at work in that way was really, really exciting.

What was the spark that convinced you all to take the leap?

Todd: So, I can remember the setting. It was definitely at that coffee shop in Worthington. I think the timing to me that was interesting was that Steve Jobs passed right around the time we were contemplating this. It got us both watching a lot of the old Steve Jobs talks, and him talking about putting a small dent in the universe as his goal and that purpose really resonated with me. And that made it feel almost like I was like wasting my career if we didn’t at least give it a shot.

Justin: Steve Jobs’ death hit me really hard for some reason. Of course, partly because he was so young, which reminded me that life was short. But a particular line from his 2005 Stanford commencement speech when he said that, “for the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been “No” for too many days in a row, I know I need to change something.”

If you have this opportunity to do something potentially significant, and the downside risk would be needing to find a job just like the one I held previously—especially given that the prospects of finding work as a programmer are always pretty good—it just seemed like it’d be a waste of something precious to not take the chance.

What was most important to you as you started?

Todd: I don’t know that I have a great answer for this. I would say probably knowing it wasn’t going to be just Justin and me then made it important to try to codify in our minds what it meant for someone to be highly capable to do the work that we were going to seek out. So I think in many ways, if you ask anyone to describe our consultants, you’ll hear empathy, drive, continuously improving, good communicators. And I think we tried to stumble upon what that recipe was pretty early on. And honestly I don’t think it’s wavered a lot since then. I would say that’s probably been the biggest factor looking back on our success.

Justin: My first priority starting the company was to prove to ourselves that we could build a resilient, fault tolerant, financially secure business model of staffing developers, working on client teams, invoicing them, getting paid, and then saving as much money as possible to build what we called runway: to bank as many months of payroll as we could in case sales dried up. I think that was the firmament, that was the foundation for being able to accomplish what Todd’s talking about in terms of bringing other people into the organization and growing it confidently.

And the thing Todd always successfully used on me in the early days— whenever I was resistant to growth or afraid of not being able to successfully maintain that financial security for the sake of our next hire—was to put the image in my head that Test Double was a sort of developer rescue. We could help developers who are driven, smart, and capable from employers that didn’t appreciate and value all of those strengths. And we could give them more autonomy and flexibility, all while working fewer hours and using the technologies they want to work with. It was ultimately about helping others find joy in their work. Why wouldn’t we want to give that to people? And so we made it our job to create the business as a system that could offer people a healthier relationship with work.

Over the past 10 years, has what’s most important for you changed?

Todd: I mean I think what has changed since then is we’re no longer just a cadre of software developers and consultants. What I’ve really come to appreciate is people coming in with a depth of expertise in areas that we don’t have, and seeing the impact they can have on the organization. To me, the recipe has broadened for what this company needs.

I was talking a little bit earlier about what the characteristics are for a consultant in the software space. Now we don’t just need that, we need to have recruiting, sales, and marketing. And we need consistent healthy operations and effective communication from leadership. And I’m not good at any of those things depending on the day, so it’s not enough for us to just continue bringing in great consultants and say, hey, we’ll figure out sales, we’ll figure out marketing. It doesn’t scale to this level. So, we have to keep focusing on and finding those puzzle pieces that are missing and fit them in to help the organization.

Justin: Todd’s describing what the company needs to continue operating with excellence in the next stage in our evolution. What we’re working to accomplish in the industry hasn’t changed as much as what the company needs to do the same work on a larger scale.

Ten years ago we had to start with clients who had never heard of us and didn’t have a reason to think that we had anything special to say. We had to keep our heads down, do what we were asked, and do such a great job that they eventually became interested in hearing our opinions. Proving ourselves at each new client would typically take months over multiple projects.

We’ve built a bit of credibility now based on our track record. Don’t get me wrong, I’m still in disbelief that we get to call some of the best engineering teams in the world clients: companies like GitHub and Zendesk and Gusto and Betterment. If we deploy that social capital wisely, we can have a bigger strategic impact on new clients within minutes, not months, of starting an engagement. Todd’s comment about making a dent in the universe, you know I used to be kind of cynical about that. But now it’s becoming true: the degree to which we are having a material impact on the organizations we work with has become really profound. It’s our responsibility now to make the most of this opportunity that we’ve been given.

Why did you all choose to shift to a 100% employee owned ESOP?

Todd: I think this week’s been a pretty good reminder for us about one of the biggest mistakes we saw in the consulting companies we used to work at was the level of inequity based on contribution, and being on the short end of that inequity. I think we both had some pretty deep scars from feeling like we were taken advantage of. A small number of people were standing on our backs to make a lot of money while we were doing a lot of the excessive work.

Jason Karns actually pinged me after one of our ESOP talks a while back. He remembered a lunch we had early on with him, Andy, Justin and I as full-time employees. One of them asked what it looks like for shareholders in the future. We said it will look like equity is delivered based on value delivered. We didn’t know at the time exactly what that meant, but we discovered it along the way as we started the ESOP process. That’s probably the biggest thing. Our focus has always been on making sure that people are rewarded for their contributions, and that no one is making a disproportionate amount of income or value based on just a role or whether or not they started the company.

Justin: For me I think it’s a shame that the financially optimal tech career virtually requires people to switch jobs every couple years as they play the startup lottery to try to get early stock in a SaaS product that—if it achieves unicorn status—may pay off some unknown amount based on later valuations, share dilution, exit strategy, and so on. And if you end up at a startup that doesn’t reach an astronomical valuation (as most don’t), then you just spent years of your life working overtime under high pressure and often corrosive team environments, only to walk away before rolling the dice again. In software, your financial destiny is almost entirely outside your control. The cycle is fundamentally unhealthy, and there should be other ways to make a career for yourself in tech that don’t require you to be constantly looking over your shoulder at other opportunities.

So, what I think the ESOP will do for our people is to enable them to view Test Double as the last job that they’ll ever need. They can come here to do great work, keep doing great work, and be rewarded not just in terms of their salary compensation, but in having a real equity stake in the company that they’re helping to build. You know, if you look at how the company has grown over time, I don’t think it’s an exaggeration to say that somebody who works at Test Double for 10-15 years could be well on the way to being able to fund their retirement.

How have you seen the mission and values evolve over that first decade?

Todd: I don’t think our mission changed. I don’t think in the early years Justin or I could clarify what it was, but we both complained a lot about software. We knew it was broken, and I think we spent the vast majority of our time either trying to address it or to build up teams around us that could address it. So, I think we got clarity on the mission when we started using some leadership coaching early on, that our industry’s broken, and that was what got us out of the bed in the morning. We wanted to have a positive impact on this industry no matter what the size.

I think the values have maybe changed a little bit. We’ve gone through two rounds of codifying them. Both times we’ve polled the audience to try and see what people feel our values are. Those are really a list of things that we think are important behaviors. They help define culture, but they’re not all-inclusive. The things we had identified early on as being really important to our business are still really important to our business.

Justin: The first leadership coach that we worked with tried to get us to articulate the company’s mission. And Todd within 30 seconds answered: “to improve how the world writes software.” Final answer, full stop, complete comfort in that. And, for me, as someone who’s generically uncomfortable with mission statements as things that bad leaders hang on the wall to try to cynically motivate people, I think that over the years since I’ve changed more than the company has. I started out jaded by painful experiences I’d had working at big companies and skeptical about the prospects that we could really have an impact on the industry. But over the years, Test Double’s mission has really won me over because I can see it working.

We strive for excellence and we insist on doing right by everyone. And now we’ve got dozens and dozens of great clients as evidence of the positive impact that we’ve had. The more time goes on, the more stories we hear about people that we’ve never even met who have been positively impacted by our agents’ work. Ten-years-ago-me would be shocked to learn that I now genuinely believe that, for all of its problems, our industry can be materially improved. It can be fixed.

What are the biggest things you learned along the way?

Todd: How much time do we have? Justin once described it as like walking a tiered version of a pyramid, because you can only see to the next level. Then when you get up to that level, “Welp, not there yet.” I feel like the learning is kind of incessant. You will always be figuring things out. I think the biggest thing I am realizing now is how much, at the size that we’re at, communication becomes more important to my role than actual action. So in the early years, if we want to stand up a website or even want to start work in a new state, Justin and I will just do the work. If we wanted to hire somebody to take on client services, we’d just go hire someone. The thing now, you have to spend almost as much time focusing on communicating to the team—the why, the how, the what—as you are actually doing the thing. That’s probably not my strength, so that one’s really front of mind for me.

Justin: When you’re starting a company, it has all sorts of needs: somebody needs to make a quick website or we need some place to store documents or we need an accountant or somebody to help us draft a contract. When the stakes are low, these are competencies that we were able to get by doing on our own, or get a bit of outside help to handle them. But as the company grew, the stakes kept rising—things like securing the right liability insurance policies, meeting the regulatory requirements of each new state and province we entered, or negotiating increasingly complex contracts with massive corporations. Todd and I increasingly got put into roles and jobs that were too far afield from our comfort zones and our expertise.

I’m so grateful that the experience forced me to step out of my comfort zone and into whatever roles needed to be filled. No one gave me permission to show up at community events and start giving conference talks, to take sales calls with world-renowned companies, or to hire people smarter and more experienced than me. Too many people’s growth is inhibited by being made to feel they need to stick to what’s listed on their job description, to stay in their lane, or to wait to be told what to do. One thing we’re working to foster at the company is the space and safety for others to step outside their comfort zones into new roles that give them just as much of an opportunity to grow as we had.

What do you envision as the future for Test Double for the next 10 years?

Todd: I think what I have really valued as we’ve grown is just being surrounded by so many awesome humans. It’s a small dent in the universe, each project that we work on, each client interaction that we have. And if you start adding those up it really can be pretty significant. That’s kind of a snowball rolling at the top of the mountain. I think what I’m excited about in the future is figuring out how to scale what we have—an awesome culture that supports the growth and fulfillment and the joy of these people doing this kind of meaningful work at our clients alongside each other. I want to see that expand, and see the number of great people who get to experience ownership and what I think is pretty special.

Justin: If I had to pick just one thing to be excited about Test Double’s future it’s the opportunity for us to form deep and trusting partnerships with our best customers, with engagements that are interdisciplinary and strategic, and accomplish ambitious things by more fully tapping into the diversity of skills and experiences that our growing roster of consultants possess. That may look like helping a business realize a vision they couldn’t achieve on their own. Or to equip engineering leaders to successfully transform how their companies organize around and execute on building great software. We’ve been careful to avoid defining a monolithic and prescriptive “Test Double Way” up to this point, but as we observe common patterns across so many software communities and client organizations, maybe we’ll someday have the opportunity to contribute a repeatable process or framework to the zeitgeist that will help heal one of the countless sources of pain in this industry.

What is important to you as the company continues to grow?

Todd: I think that probably the biggest challenge is maintaining connectedness with the team. And I think invariably in a stage of growth that we’re approaching you can’t have the same kind of deep relationships you used to have with everyone. So, I think we’re in this phase of figuring out what it looks like to have deeper relationships with a smaller portion of the people at Test Double, and maybe more shallow relationships with the broader group as well. Figuring out how to maintain that level of connectedness—even if it’s with a smaller portion of the team—will be critical to making sure people want to stay here and be a part of this.

Justin: The people at Test Double are here because they believe the road to improving software is challenging, counterintuitive, and often messy—but that the work is important. And the focus is on the end goal of making software that is comprehensible, reliable, and does right by everyone impacted by it. The thing I continue to think about in terms of risk that we need to continue to stay focused on is our commitment to excellence and improvement. As companies grow there’s always a risk that they commoditize and dilute what made them great in the first place. I think a lot about Jerry Weinberg’s old maxim, the Law of Raspberry Jam: “the wider you spread it, the thinner it gets.” As an organization scales up, we have to continue to invest in making more jam, so that what we have to offer never loses its potency.

What’s something that you’ve been thinking about in software development, and why?

Todd: This may reflect me getting a lot more distant from actually writing software as the years have gone on. But I am increasingly of the opinion that there are no software issues. They’re all people issues. They’re all communication issues. The more we can figure out how to address those things, the bigger impact we’ll have as teams. To me that seems like the ultimate root cause of all of our issues, whether it’s communication through the code or whether it’s communication outside of the code, to me that seems to be the area of the biggest need in our industry. And it still feels like an area where a lot of people struggle. So, trying to help people improve with that is at the forefront of my mind.

Justin: Years ago, I had a conversation with Sandi Metz and was describing our goals with the company. She replied, “Happy chickens lay better eggs,” meaning to say that developers who are well taken care of, and treated with respect and love, will dramatically outperform developers who don’t have safety at work. And in the last ten years we’ve been striving to answer “how can we create a system to help people find joy at work?” But as soon as we started seeing the fruits of that effort, it became clear that a lot of people are uncomfortable with expressions of positive feelings about work.

So this has become the next frontier in my mind: how do we address the fact that knowledge workers in the Western world seem bound by a cultural expectation to be miserable at work. Maybe it’s because our jobs don’t require as much physical exertion as manual labor that we search for other ways to signal that we are nevertheless exerting significant effort. It manifests itself almost as if people are incentivized to signal the value they create with expressions of performative misery. Of course, maybe it’s genuine and you truly are miserable in your job. But even if you have a pretty plum gig and nothing to complain about, I continue to meet people who are reluctant to admit it. Sometimes they fear their joy will be perceived as selfishness relative to their less engaged colleagues. Or they worry they’ll miss out on a promotion if they’re seen as too satisfied with their current station. What can we do to reframe people’s relationship with work, not only so they find joy in the work, but they feel like sharing that happiness openly and perhaps cultivating positivity at work?