The Accountability Problem

Summary

This is a transcript of my keynote presentation at the Agile Cambridge conference in England on October 2nd, 2025. The topic was “The Accountability Problem.” How do we define software department accountability so our business partners don’t do it for us? Introduction The Accountability Problem Demonstrating Accountability Quantifying the Bet The First Two Years Conclusion Thanks for having me. I’m very happy to be here in Cambridge. This is my first time visiting, so I spent the afternoon Tuesday doing some sightseeing, including a lovely ride down the River Cam. I was delighted to learn yesterday that I had Simon Wardley to thank for chauffered punt rides, including the completely fictional story I was told about the mathematical bridge. One of the things I love about Cambridge is its rich history. Of course, lots of history is important when you have... ...this monster eating up every second. That’s the Chronophage outside of Corpus Christi college, if you aren’t familiar with it, and much more impressive in person than in my terrible vertical picture with window glare. Before we get going, I should explain my context. You’ll hear a lot of advice at this conference, and how much that advice is relevant to you has a lot to do with how much their context matches yours. I’m currently VP of Engineering at OpenSesame, and for the 23 years prior to that, I was a consultant. As VP, and as a consultant, I specialize in late-stage startups: entrepreneurial organizations that were successful enough that they were able to grow. These are companies with a product mindset that value entrepreneurial thinking, but they’re also trying to grow up and be “real companies,” and they’re trying to figure out how to do that without losing their entrepreneurial edge. So that’s the context of my material: entrepreneurial companies building software products that they sell. If you’re not in that situation, I encourage you to mine my talk for ideas, but don’t try to apply it blindly. And i...