What Freestyle does
Ben and Jacob met in Calculus class in 10th grade, and tried founding a startup in high school — it didn’t go anywhere. During high school, Ben lead the frontend team for the World Health Organization’s COVID-19 App Team. After high school, Jacob went to Apple and Ben went to college. When there was an opening on his team, Jacob had Ben apply, and Ben left UChicago to go work at Apple. They spent about 2 years at Apple as Senior Engineers in the Conversational Engineering Department, before leaving to found Freestyle. Freestyle is directly inspired by what they saw as their failures of the tech they worked with at Apple.
Check the company’s own careers page — linked at the top — before a job board. A role appears there first, sometimes weeks before it is syndicated anywhere else.
Questions and experiences
Nobody has asked anything about Freestyle yet. If you have interviewed here, what you know is worth more to the next person than anything on the rest of this page.
Company facts compiled from public sources and last refreshed 9 September 2026. Details change; treat the company’s own site as the authority.