Tag: Product Management


  • Reproducibility Matters More Than Scalability

    For the past two years, the loudest debates inside our company have used the same vocabulary: scale, productivity, AI. Every quarter delivered a fresh version of the same conversation. How do we scale sales? How do we make customer success more productive? Which AI tool takes which workload off whose desk? The vocabulary came from…

  • Losing an Enterprise Deal: How to Tell Your Team

    An enterprise customer we had built toward for months backed out, late and without warning. The gut punch lasted twenty minutes. What mattered was the next few hours: what we told a team of forty, and in what order. Here is the playbook, and where we went off script.

  • Encoding Judgment Is Not a Writing Problem

    Turning how your best people work into an AI Skill sounds like a documentation job. It isn’t. The hard part is judgment, and the moment you try to write it down you hit a forty-year-old problem that AI has quietly moved rather than solved: the work is no longer getting the knowledge out, it is…

  • Two Patterns of Great Product People

    Over the past couple of years, I have had a few product people on my team, received coaching myself, and picked up a lot from conversations with other PMs, founders, and people who think deeply about building products. The contexts are always different. Different industries, team sizes, stages. But two patterns keep coming up with…

  • Product Team Collaboration

    In my last blog post, “The Framework Trap,” I talked about all the problems we ran into when engineers, designers, and product team members were working together. I’ve come to see that Scrum, with its strong emphasis on the right processes, has actually been more of a hindrance than a help to our team. While…

  • The Framework Trap

    When we started working on our products, especially our software, we had a pretty inexperienced team. Some of us had already worked on software projects at other companies or participated in research projects at universities or research institutions. The team’s most experienced member, in terms of years of professional experience, was a software engineer with…

  • Let business and product Outcomes guide you

    Over the past 12-18 months, we have established the initial structures for a middle management level within our company. The reason for this was that the number of employees had increased significantly from just under 10 to over 30, which would have resulted in a management depth of around 15 people with only two founders.…