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Founder / Operator·Freight & 3PL

Drew Wilkerson

Chairman and Chief Executive Officer at RXO Inc.

Charlotte, North Carolina, USA

DW
Why they matter

Built RXO from a 2022 spin-off into a top-3 North American freight brokerage via the $1B Coyote deal — a first call for anyone diligencing freight brokerage or 3PL consolidation.

Background

Drew Wilkerson is Chairman and CEO of RXO, Inc., a $4.5+ billion asset-light freight brokerage he has led since XPO Logistics spun it off as an independent public company in November 2022. He joined XPO's predecessor brokerage business in 2012 and rose through regional VP and P&L leadership roles to president of North American Transportation before being named CEO of the spin-off; he previously spent six years at C.H. Robinson. He holds a B.S. in public relations from the University of South Carolina.

Notable deals

  • 2024
    Led RXO's $1.025 billion acquisition of Coyote Logistics from UPS, making RXO the third-largest freight brokerage in North America
  • 2022
    Named CEO to lead XPO Logistics' spin-off of its tech-enabled brokerage platform into RXO
  • 2025
    Named Chairman of the RXO Board of Directors in addition to CEO role
  • 2026
    Named a 2026 "Rainmaker" by DC Velocity for leadership in logistics and supply chain

Call-prep brief

Background

  • Chairman & CEO of RXO since its November 2022 spin-off from XPO Logistics; named Chairman in May 2025.
  • 19-year brokerage veteran — joined XPO's predecessor in 2012, rose through regional VP and P&L roles; prior 6 years at C.H. Robinson.

Current Focus

  • Scaling RXO's brokerage volume and technology platform (RXO Connect) post-Coyote integration.
  • Managing leverage taken on to fund the $1.025B Coyote Logistics acquisition (equity from MFN Partners and Orbis Investments plus debt).
  • Expanding managed transportation, last-mile, and global forwarding as complementary brokered services.

What They Care About

  • Technology-enabled brokerage differentiation (dynamic pricing, load-matching automation).
  • Freight market cyclicality — positioning RXO to capture share when spot/contract rates recover.
  • Integration execution: realizing the ~$25M in targeted Coyote synergies without customer/carrier churn.

Recent Moves

  • Closed the Coyote Logistics acquisition from UPS in September 2024, roughly doubling brokerage scale.
  • Expanded RXO's Charlotte (Ballantyne) headquarters, adding 216 jobs (announced November 2024).
  • Named a DC Velocity "Rainmaker" for 2026.

Potential Sensitivities

  • Freight recession/soft market conditions have pressured brokerage margins industry-wide — approach growth claims with data.
  • Integration risk and debt load from the Coyote deal are a live topic for investors.

Questions to Ask

  1. How is the Coyote Logistics integration tracking against the targeted $25M in annualized synergies, and where are the remaining risks?
  2. What inning is the freight cycle in from RXO's vantage point, and how is that shaping capital allocation for further M&A?
  3. How is RXO's technology stack (RXO Connect) differentiating win rates against larger brokers like C.H. Robinson and Uber Freight?

Outreach draft

Subject
Freight brokerage diligence — RXO's Coyote integration
Hi Drew, I'm working with a private equity team evaluating opportunities in the freight brokerage and 3PL space, and your work building RXO into a top-3 North American brokerage — culminating in the Coyote Logistics acquisition — stood out as directly relevant. We'd value 20-30 minutes of your perspective on where the freight brokerage market is headed, how technology is reshaping competitive dynamics, and what you've learned integrating a deal of Coyote's scale. Happy to work around your schedule, in person or by phone. Would you be open to a short call in the next couple of weeks? Best, [Placeholder Name]

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