Our roots are in the military.

Ten years ago, Transition Overwatch founder Sean Ofeldt was in an all-too-familiar position faced by every military member at transition – uncertainty. Leaving the military was like jumping out of an airplane and leaving everything he knew behind. Trying to navigate a new world in the total absence of resources and a team was extremely difficult. Sean didn’t want to continue doing what he did in the military, and had no mechanism to discover career paths that were optimized for his experience and skillset. That journey set Sean on a path to discover a better way to approach military transition.

Through the lens of experience, and years of ideation, the Team at Transition Overwatch has created the Unconventional Apprenticeship. It’s the optimal way for military members to successfully transition into a civilian career and launch into a path with unlimited growth. We believe that even though transition is hard, you shouldn’t have to “embrace the suck.” 

Meet the Team

sean ofeldt
founder & chief executive officer

Crystal Shelton
Customer Success Manager

Emily Bose
Managing Director, Sales & Operations

Mick McGilloway
Managing Director, Partner Operations

Stephanie Gamulin
Marketing & Community Manager

Rory Wilcox
Training & Development Manager

Adam Marx
Partner Success

Lynlee Grubb
Partner Success

David Zacharias CAPT USN (RET)
Senior Managing Director, Military Internships

Fiona Nelson-Lafuse
Partner Success

Aly Aguilar
Customer Success

Marideth Espliguera
Customer Success


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