Jake manages the 3,000-acre (600ha) in-hand farming operations for Penelope Bossom, trading as Overbury Enterprises, located on the Gloucestershire/Worcestershire border. A LEAF Demonstration Farm since 2012, Overbury has been a pioneer in regenerative agriculture since 2015, integrating arable cropping with a flock of 1,000 outdoor lambing ewes. The farm operates a diverse Higher Tier Stewardship scheme (since 2021) alongside a 2023 Sustainable Farming Incentive (SFI) agreement.