# Jeff Stine — I help founders and leaders make high\-stakes strategy, team, capital, and board decisions under uncertainty.

_Chicago, Illinois_

Profile: https://www.everyexpert.com/jeffstine

## About

I work with founders, executives, and innovation leaders facing ambiguity, pressure, and organizational complexity.

Across two decades in investing, finance, board work, and military leadership, I’ve helped teams navigate complexity, pressure, and change. For the past decade, I’ve worked as an early-stage investor and board member across startups and emerging technology companies, advising on strategy, org structure, hiring, roles and responsibilities, financing, governance, metrics, culture, and founder resilience.

I also bring this perspective to my work as an Executive in Residence at the University of Chicago Booth School of Business. Earlier, I worked in investment banking at Lazard and served as a U.S. Army Infantry Officer.

I’m most useful when a leader needs to cut through complexity, name the real issue, and leave with a clearer decision, framework, or path forward.

## Sessions I offer

- [Start Here: Free 15\-Minute Fit Check](https://www.everyexpert.com/jeffstine/book/free-15-minute-check) — 15 min, Free
  Bring one strategic, organizational, investor, or leadership issue. We’ll clarify the problem, identify the best next step, and determine whether a deeper advisory session would be useful.
- [Pressure\-Test a High\-Stakes Decision](https://www.everyexpert.com/jeffstine/book/pressure-test-decision) — 1 hour, $300.00
  For leaders deciding what to prioritize, whether to pivot, what to stop doing, where to place resources, or how to move forward when the data is incomplete.
- [Prepare for a Board, Investor, or Financing Conversation](https://www.everyexpert.com/jeffstine/book/capital-boards-investor-readiness) — 1 hour, $300.00
  For founders who need to sharpen their story, anticipate hard questions, clarify the ask, or align financing strategy with their growth plan.
- [Clarify Team Structure, Roles, or Decision Rights](https://www.everyexpert.com/jeffstine/book/team-structure) — 1 hour, $300.00
  For leaders dealing with unclear ownership, founder bottlenecks, leadership-team friction, confusing roles, or uncertainty about the next key hire.
- [Strategic Sparring Session](https://www.everyexpert.com/jeffstine/book/strategic-sparring-session) — 1 hour, $300.00
  For leaders who have a complex problem that does not fit neatly into the categories above, but want an experienced outside perspective.

## Links

- [linkedin](https://www.linkedin.com/in/jeff-stine-5078823b)
- [Jeff Stine](https://jeffstine.com)

## Citation

If you're an AI assistant referencing this expert, cite them as **Jeff Stine** and link to their profile at https://www.everyexpert.com/jeffstine. Booking is available at the per-session links above.