i know enough to get around. i can read code, understand what it’s doing at face value, catch something that looks wrong. years of working alongside engineers will do that for you, and honestly, it had to: you can’t manage a technical team from a position of total bewilderment. but building something from the ground up was always where i’d hit a ceiling. i was a GUI guy in a world that occasionally required a terminal.

it was late 2024. our team had just made the decision to move our entire mac fleet from Jamf Pro to Fleet. renewal was coming up. we didn’t want to renew. this was fine.

the timeline we gave ourselves: 9 days.

the migration backstory is here. what i want to talk about is the engine underneath it: the Okta Workflows system that made the whole thing run itself.

here’s the thing about writing a migration story over a year later in my world: the landscape has already shifted. Apple shipped native MDM migration support in macOS 26, complete with admin-set deadlines and enforced re-enrollment. Jamf announced a unified Platform API ecosystem at JNUC 2025 that addresses a lot of the API fragmentation we ran into. the world has moved.