In the summer of 2014, as the SVP of Engineering at Rent the Runway, I had a big challenge ahead of me. My CEO told me that she wanted to put me up for promotion to CTO at the next board meeting, but that as part of that promotion, I’d be asked to present the technology strategy to the board. She then returned every attempt I made at giving her this strategy until I finally created something that met her standards. And the rest, as they say, is history.
I suspect she didn’t have to put me through this exercise to promote me. The board was very happy with the fact that I had grown the team and developed the technology to a point of stability and high feature throughput. I’m incredibly grateful that she did push me through this exercise, however. During that process, I went from having only a vague idea of what setting strategy meant to having a concrete, forward-thinking strategy encompassing a way to think about both the technical architecture and the engineering team’s structure, which in turn ultimately influenced the way the company itself thought about its overall structure.
When I talk about senior leadership, I emphasize strategy as a critical element. Most people don’t even really know where to begin when it comes to setting strategy at the senior level. I know I didn’t. I had coaching, from the CEO and from an executive CTO coach that I was working with. I solicited input from my peers on the executive team. I posed theoretical questions to the senior members of the engineering team and used them to help me see some of the detailed problems. I certainly didn’t do it alone. So, with that in mind, what does setting technology strategy look like?