[12] Wheels Up's marketing strategy involves entertainment at major sports and cultural events for their VIP members throughout the year.

[14] Wheels Up also flies Beechcraft King Air 350i, which has good short field performance, cargo capacity and seats nine passengers.

[12] Wheels Up was a sponsor of American Pharoah at the 2015 Belmont Stakes, when the Thoroughbred won the racing Triple Crown,[15] and signed with the Miami Marlins as the team's Official Private Aviation Partner in 2018.

[27][28] In November 2024, Wheels Up announced the successful closure of a $332 million revolving equipment notes facility with Bank of America.

Alongside the aircraft, the deal encompassed associated maintenance assets and customer programs, marking a significant expansion of Wheels Up’s operational capabilities and service offerings.

The acquisition aligns with Wheels Up's strategy to enhance its fleet and maintain its position as a leading provider of private aviation solutions.

[29] In January 2018, CEO Kenny Dichter announced on CNBC Squawk Box that the company had retained Bank of America and Goldman Sachs to explore "strategic initiatives".

[35] On May 9, 2023 the founder and CEO, Kenny Dichter, resigned effective immediately, as the company faced mounting losses and potential bankruptcy.

Board member Ravi Thakran became the executive chairman and Chief Financial Officer Todd Smith the interim CEO.

[39] On Thursday, June 22, 2023 the company's stock lost half its value following a Wall Street Journal story that it had hired a law firm that specializes in financial distress restructuring.

A week earlier board member Ravi Thakran was given $648,000 annual compensation, plus 50 hours of flight time in Wheels Up Beech King Airs.

The next day Delta Air Lines purchased 95% of the company with a $500 million price, assuming ownership, after previously having held a 20% share.