Daniel Doubrovkine bio photo

Daniel Doubrovkine

aka dB., @awscloud, former CTO @artsy, +@vestris, NYC

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There’s much written about becoming an Engineering Manager, but little about going back to being an Individual Contributor. This is not surprising because it often feels like a demotion or giving up. This is my story and thoughts on leaving a CTO role and going back to being an individual contributor. I am six months into a Principal Engineer role.

About 15 years ago I began to see how every technical problem was a people problem, and naturally felt that the best way to solve technical issues, and to grow my career was to aim for active leadership positions. I also saw how much more value I could deliver with a team versus as a solo individual, and wanted to not only influence others, but to engage in active, team-wide ownership. I was told that I had all the key ingredients for being a successful manager - I easily defaulted to taking responsibility and blame for failures, and deferred entirely to my team, and their teams, for all successes. I also learned and saw my managerial job as enabling other people to do their best work. And so I became Dev Lead in 2003, Dev Manager in 2006, Director in 2008, Head of Engineering in 2011 and CTO in 2015.

In Summer 2019 I left that behind to join AWS in a Principal Engineer, IC role.

A Career Limiting Move

There are two kinds of comments that I encounter regularly coming from others. The first is that I stepped down from a very visible and important CTO role into irrelevance, therefore making a career limiting move and that I did an admirable thing by choosing to do what I love, despite making a career limiting move.

I do think perception is really important for my progress. Seems like many people think that going from manager to IC was a step down. Did I make a career limiting move?

I firmly believe that I did not. At 43, I have extended my technical relevance by a decade, working at an operational scale that is unparalleled. The combination of deep technical understanding, and my ability to demonstrably deliver results, has always been the enabling factor in my career growth. I am convinced that it will continue to be so, and in my last year as CTO I began to feel like I was dangerously hanging over the “organizationally important, but useless” line, where many very senior managers typically sit and vest. I don’t ever want to be that kind of ballast.

Finally, the New York CTO club has yet to throw me out ;)

Loss of Autonomy

One of the nice things about being CTO was that the only person that could tell me what to do was the CEO. And the CEO was so busy fund raising all the time, that they really didn’t bother, especially as Engineering kept cranking code, hiring people, etc. Did I lose my autonomy?

At Principal level I definitely did not. Working autonomously is literally in my job description. Specifically, my job is very much of a “choose your own adventure” kind, and as long as it benefits customers, I am given a tremendous amount of liberty to pursue anything. Typically this means attempting to solve thorny problems that affect a very large organization. I am tasked to identify challenges, gather data, understand limitations, and finally tell people how to do things, insisting on the highest standards. I am fully empowered to do so by nature of my level of seniority, and people surprisingly listen when I speak. Furthermore, as an interesting side effect of organizational structure and the fact that it’s highly unlikely I’d be promoted any further any time soon, I feel at ease raising controversial issues. I don’t need to optimize for promotion or likability, or to be excessively political.

Levels of Stress

I feel a lot less stress, but not because of the volume of work. I have different kinds of responsibilities and it’s liberating.

I work normal hours and I have more time to focus on tasks that require flow, and make me less stressed and happier. I never stopped writing code, but I can actually write code now, if I want to, as a primary, deliberate activity. And coding is like running, or writing and, simply put, makes me feel better. Once I get into flow I eventually hit a natural high. Time flies. I can choose not to take a meeting, cater to an investor or deal with an unhappy customer. I am not on call for catastrophic failures. I don’t have direct reports that routinely vent their personal life and frustrations with me. I deal with a lot less gossip and politics. I am nobody’s psychiatrist, and I am no longer the face of the organization.

Power

I did lose significant amounts of organizational power. I no longer know all the secrets. Many decisions that affect me are made by others, by design. As CTO I made all decisions for my team and for company-wide technology. I had access to detailed financial information, and knew when someone important was quitting or being fired. I had a word in hiring, firing and promoting at executive level. This is all gone, but so are the agonizing headaches, such as not being able to tell someone that they are about to get laid off.

In my individual contributor role I can only influence, but I cannot decide anything, except for technical aspects. This can be frustrating at times - I have to spend a lot of energy explaining a problem to a decision maker instead of just fixing it. But I now see how I made a lot of mistakes in the past assuming that I often knew the right answer. By going through the exercise of having to convince someone of anything with actual data and solid arguments I help them make the right decision. If they make the wrong decision I land on the losing side of disagree and commit, but I am learning to live with it, respect managers’ decisions, and work twice as hard on collecting harder evidence that helps them change their mind.

Money

AWS pays very competitively. And I am convinced that it is the best place to take advantage of a bright economic future. The opportunity for cloud computing is tremendous, migration to the cloud is accelerating, and growth within the cloud infrastructure is very substantial. We’re at the starting line.

Comparing apples to apples versus my CTO job is difficult and depends on how you value startup stock options. My Artsy stock options were valued as dollars within the compensation framework, but are currently a six figure liability with a huge tax bill, and an expiration date. My AWS RSUs are liquid and are the same as cash.

Given that experience, I think my IC role will be a net positive compared to another CTO role that I was offered when choosing my next adventure, as far as IRS is concerned.

That said, I did compare my IC job with the one of a Senior Development Manager in the same company. I am guessing that I am on the slightly lower end of that pay scale, although not by much. At the same time, my health is better and the stress level is lower. Some things money can’t buy.

One Way Door

A 1-way door is one you cannot take in the other direction.

Can I be a CTO of a startup again? The answer is clearly yes. My 5 years at Microsoft were critical in getting all my startup offers, but that experience is now dated. In some ways I’m refreshing my brand awareness. There’s no doubt in anyone’s mind that Amazon is a tremendous technology brand. AWS is a leader in cloud computing, the fastest growing IT enterprise in the world, the future. That opens doors, including the ones I’ve walked through.

Can I be a people manager again? The consensus is yes, too. In fact, it seems easier for me to go from Principal to Manager than from Manager to Principal. This makes sense: I already have over a decade of managerial experience, and I will hopefully have earned a lot of trust with Engineering teams by doing “real work” in the next few years. Most Engineers want to work for someone who understands what they are doing at a deeper level, and not for an organizational placeholder.

Conclusion

Did I make the right decision? Six months in, yes. And I am a big fan of Marie Condo. After weighing all the pros and the cons, going from manager to IC brought me a lot of joy. Maybe it will bring you joy, too?