jake weber

about

I am a writer, programmer, and senior manager at a high-growth startup. My work is focused on software, organization design, and collaboration, and can be connected by one recurring question: how can we thoughtfully design systems that produce better judgment, better work, and better cultures?


At Clutch I lead a 16-person implementation engineering team, where I spend my time hiring and cultivating exceptional teams, building AI-enabled workflows, designing resilient systems that anticipate change, and helping complex software become usable at scale.


I am currently thinking about the changing role of leadership in an AI-native world, making software and the broader internet feel more local and personal, cultivating curiosity in myself and others, and designing technology that protects attention rather than competing for it.

work

  • printernet
  • greenwich: an experiment in collaborative links
  • inventory-ing interview
  • taxis, busses, and subways: building anti-fragile tools and teams
  • whoa volume 2
  • why are computers so ugly now? an interview with Keegan McNamara
  • how top performers turn mistakes into opportunities
substack / writing / projects / twitter / people I'd follow

writing

  • be an idea expander
  • experiments and endeavors
  • street smart
  • polymathematics in one breath
  • what I ought to be doing: planting and growing
  • You Probably Haven’t Even Tried To Succeed
  • Be Prolific and Patient
  • Expanding Your Sense of What’s Possible
  • recommendations

recommendations

  • speed matters, james somers
  • willingness to look stupid, dan luu
  • what's going on here with this human? graham duncan
  • offscreen interview, craig mod
  • is it okay? robin sloan
  • my first year without an iphone, katie lowe

ways to support

  • subscribe to my substack
  • sign up for printernet
  • reach out to chat!