About
A transportation operator who built technology — not a tech founder who discovered transportation.
Will van der Linde is an executive operator and entrepreneur with deep expertise spanning transportation operations, AI-powered enterprise software, hospitality, commercial real estate, and large-scale workforce management. Prior to helping scale Flip internationally as a member of its Executive Leadership Team, he led transportation and operational businesses with over 1,000 employees and contractors.
His work today focuses on transportation technology, operationally complex businesses, AI automation, and long-term venture development across North America, the United Kingdom, Ireland, Australia, and New Zealand. His leadership style combines operational pragmatism, relationship-driven growth, and hands-on execution in complex, rapidly evolving industries.
Philosophy
"The best technology doesn't replace operators. It empowers them. Real industries are built by people — technology works best when it supports them."
Career
Leadership Experience
Flip
ELT Member / VP of Transportation & Founding Team
Executive Leadership Team member. Built and scaled Flip's transportation vertical — leading enterprise sales, strategic partnerships, onboarding, customer success, and AI-powered automation across taxi, NEMT, paratransit, rideshare, and healthcare transportation globally.
Flywheel Technologies
Principle
Industry-leading taxi technology platform — developing innovative dispatch, eHail, payments, and fleet management solutions for riders, drivers, and taxi companies worldwide.
Old Dominion Transportation Group
President
Led large-scale transportation operations, merging multiple fleets into unified structures. Managed organizational growth across ~1,000 employees and contractors with focus on operational efficiencies and scalable systems.
Yellow Cab of Charlottesville
General Manager / Owner
Owned and operated a regional transportation company. Led technology modernization of dispatch operations, secured exclusive transportation contracts, and managed ~100 employees and contractors.
Main Street Arena
General Manager, Co-Founder
Oversaw operations for a large hospitality and entertainment venue — managing business operations, staffing, investor relationships, event operations, and customer experience across ~60 employees.
Media & Creative
Background in film production, video production, digital media, and event logistics — including work with the Virginia Film Festival and Kentucky Derby productions. This experience strengthened capabilities in storytelling, marketing alignment, and relationship-building.
Real Estate & Investment
Commercial real estate owner and operator with experience in property investment analysis, redevelopment planning, hospitality-oriented concepts, and operational property management.
Community & Industry
Executive Board Member of local business associations, Board Member of neighborhood organizations, and Steering Committee Member within the Transportation Alliance.
Education
University of Virginia · University of Mary Washington. Additional certifications including EMT-Basic and snow sports instruction.