Osterman began his career working with Dan Buettner on the Blue Zones project and helped him found the Quest Network.

[4][5] Osterman's next feature film project, 400 Days, starred Brandon Routh, Caity Lotz, Ben Feldman, and Dane Cook, and was inspired by MARS-500, a psychosocial isolation experiment designed to prepare for the first crewed mission to Mars.

[7] He then went on to direct another feature with Syfy Films, Hover (2018), a near-future Sci-Fi picture starring Cleopatra Coleman (also written by), Shane Coffey, Beth Grant, and muMs da Schemer.

[8] His most recent feature film, The Fence and the Fox, a crime drama revolving around cryptocurrency, is set to air in the fall of 2024 and stars Noah Anderson, Ella Ma, Jeremy Davies, Frank Whaley, Tom Cavanagh and Bruce Bohne.

[9] In addition to filmmaking, Osterman has worked extensively in the creative/branding industries, helping create over 25 brands that can be seen in Target, Best Buy, Circuit City and Dick's Sporting Goods.