I recently made the difficult decision to leave Amazon Web Services to run engineering for a later stage startup, Coalition. So many people have expressed curiosity about my decision that I felt it was worth exploring in a bit more depth. I hope that some of my own thought processes and ruminations might help others in their own personal journey.
Much of my decision is centered on the notion of impact. I have always carried an innate desire to have impact. Further, I am most motivated when I feel I am having a large impact. Impact comes at several levels, but several types stand out for me. I feel personal impact when I help employees to grow and develop. I feel customer impact when we deliver products and features that customers use and love. Finally, I feel business or financial impact based on the value we delivered to the organization.
I was fortunate to be in a position at AWS where my ability to realize all types of impacts was high and immensely satisfying. We grew a large team and I felt a significant role in the growth and development of the organization. We also grew Amazon CloudWatch and AWS X-Ray into large businesses with more than a million customers.
Where I started to feel things change more recently was in the relation of my impact to the impact on Amazon/AWS as a whole. Bear with me on this, but I think of it like this equation:
In my ideal, not only is the numerator large, but I want impact correlation to be close to 1. This is especially true considering that compensation tends to be most highly correlated to company performance. Whether real or perceived, I felt this ratio drifting further from 1 which in turn affected my motivation. That’s not to say that I ever discounted the numerator of this equation. My ability to drive impact was high. Running any AWS service, much less one with the number of users we had, is a special opportunity that doesn’t come around that often.
The desire for greater impact correlation led me to think again about startup opportunities. This was not going to be my first exposure to startups — I had joined one for the 2 years before joining AWS. Needless to say, it did not ‘start up’. In hindsight, I’m not sure how much of a chance we really had. There was an excellent engineering team, a good product, but not really enough traction to be considered product-market fit. It was a crowded columnar analytics space at a time when ‘big data’ was all the rage.
So this became the question…I knew that I wanted more Impact Correlation, but could I leave a role where I loved the team and knew that I was already having a lot of impact. Enter the regret minimization framework, credit Jeff Bezos. You can boil the regret minimization framework down to a single question: “in X years, will I regret not doing this”. Ironically, this was the same framework I used on the decision to accept the offer with AWS six years ago. I found myself with another regret minimization decision again, though. I knew that I wasn’t feeling the same motivation and believed that it was related to this notion of Impact Correlation. Further, I knew that if I didn’t try to do something about it I would regret it down the road.
This time around, I was much more selective in looking at opportunities. I knew that I could give up relatively guaranteed compensation at AWS for the chance to achieve impact correlation and associated equity opportunity, but there were limits. I was looking for a company with demonstrated product-market fit and a track record of revenue growth. Equally as important, I needed the mission of the company to resonate with my own sense of what ‘matters’. If I am going to pour heart and soul into something, I need to feel that there is a positive outcome for society. As an aside — AWS sets a very high bar for purpose and what ‘matters’ and this continued as a source of pride for me throughout my time there.
Enter Coalition. When the recruiter pitched an engineering leadership role to me, it was the cybersecurity aspect that drew me in initially. Cyber was on a short list of segments that had particular interest for me. It’s technically interesting and has clear tailwinds that almost certainly persist for the foreseeable future. I’ll be candid and say that at first, I wasn’t sure how I felt about the insurance aspect. Nonetheless, they seemed to be right in the zone I was looking for. The company clearly had product market fit and was growing rapidly. I started doing my own diligence on the company and set up time to talk with their founder/CEO Joshua Motta.
All of the pieces started to come together the first time I got to sit down with Joshua. For me, it was my most direct experience with founder-market fit. I’ve listened to founder stories before and felt that I had sensed founder-market fit listening to founders talk about their companies on podcasts (shout out to JCal, I’m an avid This Week in Startups listener and syndicate member!) but experiencing it 1:1 was pretty special. I challenge anyone to sit down with Joshua and not come away with a clear sense of just how much he was born to build this company.
Getting back to my comment about wanting to work on something that matters. Coalition certainly checked that box too. Helping businesses everywhere to solve the challenge of cyber risk is a laudable goal (and dang hard problem too!). It’s here that the lightbulb went on for me around the company’s approach to cyber risk and the interplay with insurance. The insight that led to the founding of Coalition is that Cybersecurity is a risk management problem, not a technology problem. Where there is technology, there is cyber risk, and no amount of technology can completely eradicate that risk because it’s fundamentally a human problem. What’s unique about Coalition is that they bring cyber tools, data, and deep security expertise wrapped in a business model that aligns all of the incentives with their customers to solve cyber risk. The result is a differentiated solution for a timely problem and the reason why they are growing so fast.
If you were paying attention to my LinkedIn feed, you already know how this story ends ☺. What I found in Coalition was a company where I felt my impact would be directly correlated to the outcome of the Company. We are tackling a problem that matters to the world and our customers. The company has demonstrated product market fit and revenue traction and a huge vision for the future. Last but not least, I feel a personal connection to the founders and team.
If any of this sounds exciting and motivating to you, we are hiring! We need all forms of software engineers (backend, frontend, full stack), SREs, software managers, security engineers and analysts, product managers, along with many other roles. Come help us solve the challenge of cyber risk and build the next great InsureTech company! Apply on our careers page or DM me if you would like to learn more.