jake weber

about

I am a writer, programmer, and senior manager at a high-growth startup. My work is focused on software, organizations, and collaboration, and is guided 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 days 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 interested in the changing role of leadership in an AI-native world, making software and the broader internet feel more local, cultivating curiosity, and designing technology that protects attention rather than competing for it.

work

  • printernet
  • greenwich: an experiment in collaborative links
  • inventory-ing interview
  • taxis, subways and busses: building antifragile 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!