Ventures & Investments
Where I'm building.
An operator-led venture platform across transportation, AI, hospitality, real estate, and operationally complex service businesses.
VP of Transportation, Founding Team
Flip
Voice AI and conversational automation for taxi, NEMT, paratransit, rideshare, and healthcare transportation — operating across North America, UK, Ireland, Australia, and New Zealand.
As a member of Flip's Executive Leadership Team, Will built and scaled the transportation vertical from early-stage growth through international expansion — defining go-to-market strategy, managing enterprise SaaS sales cycles, and negotiating commercial agreements with major transportation providers globally.
Key areas include enterprise sales, strategic partnerships with dispatch technology vendors, conversational workflow design, IVR optimization, and complex voice AI integrations across telephony and dispatch systems.
Represented Flip at major transportation conferences and trade associations, helping position the company as a recognized leader in voice AI for healthcare transportation and mobility.
Principle
Flywheel Technologies
Innovative dispatch, eHail, payments, and fleet management solutions for riders, drivers, and taxi companies worldwide.
Flywheel Technologies develops innovative technologies for riders, taxi drivers, and taxi companies around the world — from eHail and ride-tracking apps to full-service dispatch, metering, payments, and fleet management platforms.
The platform serves riders, drivers, businesses, and government clients with solutions spanning driver management, DirectPay rapid payments, prepaid card programs, food delivery, and paratransit services. Flywheel has partnered with Uber and been featured in The Verge and PR Newswire.
President
Old Dominion Transportation Group
Large-scale transportation operations — fleet consolidation, workforce management, and operational scaling across 1,000+ employees and contractors.
As President, Will led large-scale transportation operations and organizational consolidation — merging multiple transportation fleets and operational departments into unified structures.
Managed organizational growth and staffing across approximately 1,000 employees and contractors. Implemented operational efficiencies and scalable management systems across transportation logistics, workforce coordination, and operational planning.
Active Investor
Angel Investing
Investing in early-stage startups at the intersection of transportation, AI, and healthcare logistics.
Will is an active angel investor focused on early-stage companies building at the frontier of transportation technology, artificial intelligence, and operational infrastructure.
His investment thesis centers on founders who understand the operational realities of the industries they're building for — particularly in healthcare logistics, mobility, and automation.