Fry joined Ford Motor Company in 1977 as a graduate trainee from the University of Wales, where he had studied Economics. He worked initially in Sales and then Market Research before moving to Product Development in 1978 as a product planner. Over the following twelve years he contributed to a range of models including performance variants such as the Ford Escort Cosworth and the RS200.
In the early 1990s Fry spent a period at Aston Martin while the company was under Ford ownership, overseeing the development and launch of the DB7 model and managing the transition from handbuilt-only production at Newport Pagnell to higher-volume manufacturing at a new facility at Bloxham. He returned to Ford in 1995 as director of Service Engineering within the Customer Service Division.
Fry joined Prodrive as managing director in January 2001 at the persuasion of David Richards. Within four months Prodrive Automotive Technology had a full order book for the year, and the acquisition of Tickford Group expanded the company's engineering services. He also became involved with the Subaru World Rally Championship team during a poor start to the 2001 season; under his involvement the team improved sufficiently for Richard Burns to win the World Rally Drivers Championship that year. A Prodrive-prepared Ferrari 550 won the GTS class at Le Mans in 2003.
Early in 2002 Fry was appointed Managing Director of BAR F1 in addition to his Prodrive responsibilities. After significant reorganisation of the team, BAR finished as constructor runner-up to Ferrari in the 2004 FIA Formula One World Constructors Championship. Fry's first Formula One race victory as chief executive came when Jenson Button won the 2006 Hungarian Grand Prix — BAR's only race win as a team.
Under Honda's ownership from 2005 to 2008, Fry directed substantial investment into the team's headquarters at Brackley, Northamptonshire, including a new wind tunnel, new manufacturing facilities, and computational fluid dynamics infrastructure. These investments enabled him to attract Ross Brawn as technical director in late 2007. Together, Fry and Brawn designed the team's car and structures around the sweeping regulation changes planned for 2009. In late 2008, however, the global financial crisis prompted Honda to withdraw from Formula One at short notice.
Fry and Brawn persuaded Honda to continue supporting the team through the winter of 2008-09 while they sought alternative investors and completed preparations for the new season. When a global search for investment failed, Fry as CEO and Brawn as team principal took ownership of the team themselves, assuming all its liabilities, and renamed it Brawn GP. A deal was struck with Mercedes for engine supply.
The car for 2009 incorporated a controversial double diffuser aerodynamic design that generated significantly more downforce than rival configurations. Multiple teams challenged the legality of the device; the challenge failed, and competitors were ultimately forced to adopt similar features. The Brawn BGP 001 scored a one-two finish at the 2009 Australian Grand Prix and won eight races during the season, four of them as one-two finishes. Jenson Button won the Drivers Championship and Brawn GP took the Constructors Championship in the team's debut season. The story of the 2009 season is documented in the book Survive Drive Win, co-authored by Fry with former Times journalist Ed Gorman, and in the four-part Disney+ documentary Brawn: The Impossible Formula 1 Story hosted by Keanu Reeves, released in November 2023.
Mercedes Benz became majority owners of the Brawn team in 2010; Fry continued as CEO through the transition and left the renamed Mercedes AMG Petronas operation in 2013. In 2018 he joined professional esports organisation Fnatic as head of commercial strategy and chairman. In September 2021 Fry joined McLaren Applied as chairman at the request of owners Greybull Capital. In 2022 McLaren Applied were awarded a contract by the FIA to develop a new engine control system for the 2026 Formula One season, and in 2023 Fry facilitated McLaren Applied and Greybull's acquisition of Dutch e-bike manufacturer VanMoof and Italian solar inverter company Fimer.