“Hey, our fledgling startup is on path to being the next *INSERT BIG TECH COMPANY NAME HERE* and we think you’re a great fit for our CTO role”. Find me a technical leader who hasn’t been enticed by those words and you’ll have found a liar. So, what happens when one succumbs to the temptation and joins an early-stage startup? Well, if you have been wondering where I’ve been for the past couple of years, I was fighting the good fight at a small, early-stage NLP/Machine Learning based risk intelligence startup. And while I’m not retired or sailing around the world in my new 500-foot yacht, we were able to successfully exit the company with a net positive outcome for all involved. My hope with this post is that I can share some of my acquired wisdom, and perhaps steer the next willing victim down a similar path of success.
If I could sum up my key learnings in a few bullet points, it would boil down to this:
- If you don’t believe … don’t join
- Be prepared to contribute in any way possible
- Find the product and focus on building it
- Pick the race you have enough fuel for and win it
What I’d like to do in the rest of this post is break down each one of these items a little further.
If you don’t believe … don’t join
Maybe this goes without saying, but if you don’t believe in the vision, the people, and the product you shouldn’t join the startup approaching you. The CTO title is alluring, and it is easy to fool yourself into taking a job for the wrong reasons. But the startup experience is an emotional slog of ups and downs and it will be nearly impossible to weather the ride if you don’t wake up every day with an unyielding conviction for what you’re doing. As I’ll explain later in this post, you don’t need to believe you’re working for the next Facebook, but you do need to believe you are building a compelling product that has real value for you, your coworkers, your investors, and your customers.
Be prepared to contribute in any way possible
For the first few months on the job I used to go into our tiny office and empty all the trash bins because, if I didn’t, that small office with 5 engineers started to smell! It didn’t take long for someone to call out that I was appropriately titled, CTO (a.k.a. Chief Trash Officer). You might be asking why anybody would take a CTO job to wind up being the corporate custodian, but that is what was needed on some days.
While I have steadfastly maintained my technical chops throughout my career, I hadn’t really written a lick of production code for nearly two decades prior to this job. But with limited resources, it became clear I also needed to contribute to the code base and so I dusted off those deeply buried skills and contributed where I could. When you join a startup with that CTO title, it is easy to convince yourself that you’ll build a huge team, be swimming in resources, and have an opportunity to direct the band versus playing in it. But you’ll quickly find that in the early stages of a startup, the success of the company will depend on your willingness to drop your ego and contribute wherever you can.
Find the product and focus on building it
Great salespeople can sell you the Brooklyn Bridge. And if you’re just lucky enough, you might have a George C. Parker in your ranks. But the problem with great salespeople is they will do almost anything to close the sale and that comes with a real risk that they’ll sell custom work. If that happens over an extended period of time, you will be unable to focus on the core product offering and you’ll quickly find you’re the CTO of a work-for-hire / consulting company.
Startups face real financial pressures that often drive counterproductive behaviors. That often means doing anything necessary to drive growth in revenue, customers, or usage. But as illustrated in the graph below, high product variance will often ultimately lead to stagnant growth.
That’s because with every new feature comes a perpetual support cost. And if you keep building one-off features, and can’t fundraise fast enough, that cost will eventually come at the expense of delivering your true market-wide value proposition. If you allow this to happen, you’ll wind up with a company that generates some amount of revenue or usage but has no real value.
Companies that find true product/market fit should see product variance gradually decrease over time and this should allow the company to grow. Your growth trajectory may be linear when you need it to be exponential, but no per customer feature work will fix that problem and you may need to consider pivoting. If pivoting isn’t an option, it may be time to look for an exit.
As the CTO, a critical part of your job is to help the company find its product/market fit and then relentlessly focus on it. You need to hold the line against distractions and ensure the vast majority of resources are spent on features that align with the core value proposition. If you’ve truly found a product offering that is valued by a given market segment, and you can keep your resources focused on building it, growth will follow.
Pick the race you have enough fuel for and win it
I am an avid runner, and one of the great lessons of long-distance running is, that if you deplete your glycogen store, you’ll be unable to finish the race no matter how hard you trained. In other words, you can’t win the race if you have insufficient fuel. This is also very true of startups. If you’re SpaceX or Magic Leap, you’re running an ultra-marathon and you need a tremendous amount of capital in order to have sufficient time and resources to realize the value. But fundraising is hard, and even if you have an amazing product and top-notch talent, there can be significant barriers to acquiring sufficient capital.
The mistake some startups make is that they continue to run an ultra-marathon when they only have fuel for a 5k and that can lead to a premature or unnecessary failure. If funding becomes an issue, start looking for how your product might offer value to another firm. Start allocating resources towards making the product attractive for an acquisition. Aim to win a smaller race and seek more fuel on the next go around.
Taking on a CTO role at an early stage startup can be a great opportunity and lead to enormous success, but before you take the leap make sure you know what you’re getting into. Along the way don’t forget to stop and smell the roses. In the words of fellow Seattle native Macklemore, “Someday soon, your whole life’s gonna change. You’ll miss the magic of these good old days”.
Final Final Thoughts
No startup CTO is successful without support from an army of people. So I’d like to offer some gratitude to the following folks:
- Greg Adams, Christ Hurst: Thanks for giving me an opportunity and treating me like a cofounder from day one.
- Shane Walker, Cody Jones, Phil LiPari, Pavel Khlustikov, David Ulrich, Julie Bauer, Jason Scott, Carrie Birmingham, Rich Gridlestone, Bill Rick, Zach Pryde, Amy Well, David Debusk, Mikhail Zaydman, Jean-Roux, Bezuidenhout, Sergey Kurilkn (and others I may have forgotten): Thanks for being one the greatest teams I’ve ever worked with.
- Brandon Shelton, Linda Fingerle, Wayne Boulais, Armando Pauker, Matt Abrams, Matthew Mills: Thank you for being outstanding board members, mentors, and investors
- Ziad Ismail, Pete Christothoulou, Kirby Winfield: Thank you for the career advice during my first venture into the startup world.
*Note: You can read more about Stabilitas, OnSolve, and our acquisition at the links below: