5×5 Trading helps Wheels Up complete fleet overhaul

Wheels Up said it continues to expand its Phenom and Challenger fleets.

Wheels Up has completed a major fleet modernisation programme 18 months ahead of its original timeline, with Boca Raton-based dealer and fleet advisory firm 5×5 Trading managing the acquisition and disposition of nearly 100 aircraft since 2024.

Acting as Wheels Up’s exclusive transaction partner, 5×5 helped the private aviation company simplify its controlled jet fleet from four aircraft types to two – the Embraer Phenom 300 and Bombardier Challenger 300/350.

“Modernising our controlled fleet was a defining step in the transformation of Wheels Up, and we set an aggressive timeline because the opportunity in front of us demanded it,” said Meaghan Wells, chief growth officer of Wheels Up. “Their transactional discipline helped us reach a simpler, more efficient fleet well ahead of schedule. That foundation now lets Wheels Up scale its Phenom and Challenger fleets behind our Signature Membership and deliver the experience our customers expect.”

“This is exactly the kind of engagement 5×5 was built for,” said John Odegard, 5×5 Co-founder and IADA Chair. “Fleet transitions of this scale require every acquisition and disposition to be managed in the context of the next.”

Founded in January 2024 by four industry veterans – Odegard, Seth Zlotkin, Chris Brenner and Jeremy Bogle – 5×5 Trading holds IADA accreditation and specialises in complex fleet transactions and corporate fleet strategy.

The founding team has collectively transacted more than $1bn in private aviation sales.

Wheels Up said it continues to expand its Phenom and Challenger fleets in response to strong demand for its Signature Membership and charter programmes.