Published on September 20, 2026. management (221)

One of the interesting challenges of the AI ecosystem in 2026 is that new, effective patterns emerge faster than I can adopt them. I’ll find a handful, get back to work, and realize a month later that I’d missed four or five more. The adoption cycle for Imprint this year has been something like:

  • January: get every engineer onto Claude Code every single day
  • March: ok, let’s also get everyone else onto Claude Code or Claude Cowork every single day

  • April: local development is bottlenecked on checkout and worktree model,

    instead create ~10 local workspaces which each have an independent checkout of every repository, and operate at the workspace level, not at the repository level, so it can generate cross-repository pull requests across frontend, backend, infrastructure and data monorepos

  • June: oh boy, agent-driven development is heavily constrained by lack of a common task management

    system with higher visibility and less permission complexity than Jira, so let’s migrate the entire company over to Linear and hard stop on Jira

  • July: yikes, now we have visibility into all these tickets, many of them are trivial

    but managing them through local development isn’t scaling, let’s roll out an orchestrated harness which internally we call “Agent Fleet”, along the lines of Stripe’s Minions