About

Caleb Weaver

Caleb Weaver

I've spent 25 years where new ideas meet old rules — the first decade helping transformative elected officials inside government and politics, and the 15 years since on the business side of the same dynamic.

Working for Barack Obama, Elizabeth Warren, Tom Vilsack, and the Governors of Missouri and Illinois early in my career, I saw firsthand both the opportunities and challenges of upending the status quo. Great ideas don't succeed on their own, but require careful, long-term strategic engagement to accumulate support, neutralize opposition, and change hearts, minds, and policy. I also learned how government actually works, and, equally important, what business looks like from the other side of the table.

Since leaving government in 2011, I've prioritized working with interesting people inside interesting organizations doing interesting things — first helping big companies prepare for and respond to acute challenges, then going in-house to companies trying to upend an industry by bringing a new idea to market: Uber, Ridwell, and Mill, running government affairs, public affairs, and the adjacent functions that come with them.

The industries I've worked in have had little to do with one another: transportation, healthcare, consumer products, recycling and organics management. The underlying challenge has been the same nearly every time — a company was doing something the existing system wasn't built to accommodate, and business growth required a senior leader to build a strategy that effectively managed the regulatory, policy, stakeholder, labor, and political dynamics at play.

Initially hailing from the Midwest, I settled with my family in Seattle over a decade ago, laying down roots across the region's business and political communities — relationships and institutional knowledge that take an outside advisor years to develop. Much of my work has been with companies in Seattle and the Bay Area, two of the places doing the most to build ideas that outpace the existing rules.

I serve on the boards of the Seattle Metropolitan Chamber of Commerce, the Alliance for Gun Responsibility, and Transportation Choices Coalition. I hold a J.D. from Harvard Law School and a B.A. in history from Yale.

In their words

“I've worked with dozens of leaders in the policy world, and what sets Caleb apart is more than his political and legal expertise. He understands the business end to end and sees clearly how it connects to policy. He's collaborative, sharp, and proactive, and he has a deep grasp of local, state, and national politics and how they affect the business, its workers, and the communities it serves.”

Brooke Steger — former General Manager, Pacific Northwest, Uber
Recommendation on LinkedIn

“We wanted to move fast, Caleb helped us do that intentionally. We wanted to launch everywhere, Caleb made sure we could launch in the important places while reducing our risk. … His personal integrity, sharp and strategic thinking, and human-first approach make him one of the best people I've worked with.”

Aliya Marder — Co-Founder, Ridwell
Recommendation on LinkedIn

“He has extremely good judgement under pressure and is able to context shift quickly which is critical in a fast moving start-up environment.”

Suzy Sammons — Communications, Public Affairs and People, Mill
Recommendation on LinkedIn

Track record

Uber

  • Favorably resolved Uber's operating status across multiple states
  • Negotiated an innovative resolution to labor-classification issues in Washington State

Ridwell

  • Enabled Ridwell to launch and operate across dozens of cities nationwide
  • Maintained labor peace through an active union organizing drive

Mill

  • Built a strategy to move from local jurisdiction pilots to municipal program integration
  • Negotiated a favorable resolution to a major international supplier dispute

I take on a handful of engagements at a time, and work directly and hands-on as part of each team.

Get in touch