Corporate culture: A lesson in unintended consequences

It's been a little more than six months since I left finance to join Rent the Runway. Upon hearing that I moved from a big investment bank to a small startup, many people comment on how different it must be. And it is, but in ways than you might not expect.

The day-to-day aspects of the job are not that different. On the technical front, I'm designing SOA-structured systems, thinking about building a messaging-based data bus, worrying about how to model business workflow into software and making sure we can process everything we need to process in time. I have more freedom to choose the technologies I want to use but I'm also more constrained by limited resources to manage the complexity of additional systems. The giant internal infrastructural support organization I had for hardware and level one support is replaced by a giant cloud vendor that does pretty much the same thing but with crappier hardware and faster turnaround. The people-related work is mostly unchanged. I still use the skills I learned for building consensus across teams, coaching people in their careers, and managing up, down, and laterally. I run plenty of meetings, make plenty of schedules, and continue my struggle balancing management and organization with architecture and coding. My schedule starts and ends slightly later in the day, but even my hours are not much different.

Unlike some that have left finance, I don't hold any major grudges against it. I learned a lot in my six plus years working there, about technology, leadership, and working with people. So given that the work is similar, why leave the better paycheck and general stability for the uncertainty of startup life? I'm much happier now than I was in my last years in finance, and the reason for that is not technical, but cultural. When I started in finance, the culture was surprisingly startup-like. It was more formal, but each team was dedicated to the business they served and we were able to work fairly autonomously in support of that business. Over time, though, the culture changed to become more centralized and thus bureaucratic. Instead of picking the right thing for your business area, you had to get approval from people that had nothing but a vested interest in seeing their pet technology promoted in order to get themselves promoted. That of course led to politically-driven technology which is an absolute nightmare for a person that cares deeply about building great systems.

Ironically, I believe this happened at least partly because the company was concerned with building a formal technical career path in order to promote and retain technical talent. At first, this resulted in senior technical people getting much-deserved recognition and it was great. I wanted nothing more than to reach that highest level myself. But soon the highest-level title ("technology fellow") had been awarded to the backlog of people that truly deserved it, and it became something that was expected to be awarded to more people every year; each group needed to have one, and it was a cheap way to recognize and retain people in years when salaries were stagnant since it didn't necessarily confer any increase in compensation. This growing group of people, many qualified by deep work in one small area, were now expected to help guide the technology decisions of the whole company. And so a bureaucracy was born. Decisions that would have been made via influence within a group and business area started to be dictated by committees far away from that group. The fellows started, unintentionally, to squash creativity of those below them on that same technical track they were supposed to be growing.

As bad as that was, in my opinion the biggest problem with this role was that it was not equivalent to the same level title for managers, "Managing Director". Because the role of fellow became more of an honorary recognition than an actual promotion, it came to pass that the savviest fellows would also get themselves promoted to Managing Director (MD), and thus become first among equals. No longer did the mere tech fellow have the strongest voice in the technical decision making; everyone started striving to become more than just a fellow, and in order to get that MD promotion they needed the backing of the other tech fellows that were also Managing Directors. As we all know, the best technologists are not necessarily the best politicians and decisions started being guided more and more by those better at politics than technology. In this way, an effort to promote and retain technologists ended up building a technical culture of decision making driven by politics and bureaucracy.

At the end of the day, finance is an industry that cares first about money (duh), and secondly about power, and that is true for every successful person that works there in any capacity. Technical qualifications will only ever be rewarded as they make or save money. If you don't find finance fascinating, or care about money above all other things, this cultural friction may grind you down. I've discovered the truth in the wisdom that you enjoy your job more when you're working on a product that you use and enjoy. Rent the Runway has a different goal than my old investment bank; yes, we want to make money, but we want to make it by delivering a great experience to our customer, an experience that I participate in and really love. And that is a goal that I know I can build a great technical culture around.