How teams at Oscar left one of the world’s most complex Jira instances
Oscar Health is a technology-driven health insurer that serves hundreds of thousands of members across the United States. Founded in 2012, the company builds and maintains the systems responsible for enrollment, claims processing, care coordination, and member support. Oscar migrated over 600 people across engineering, product, data science, IT, and security from Jira to Linear in a month.
Pete Zalewski had seen this story before. Earlier in his career he was a Jira admin for a software company. Not his primary role, but one he felt obliged to step into. There he witnessed firsthand the temptation of endless customization, and the havoc it can wreak on a company’s ability to move quickly.
“If you’re offered custom fields you’re going to have the urge to use them,” he said. “They coagulate as a workflow that doesn’t suit anyone.”
Fast-forward to his current role as a staff engineer at Oscar Health, a large technology-driven insurer operating in one of the most regulated environments in the country. Oscar’s Jira instance had grown into exactly the kind of system Pete remembered: hundreds of custom fields and years of accumulated process layered on top of one another. Atlassian once told them it was among the three most complex Jira instances in the world.
Then they hit a ceiling, literally. Oscar maxed out Jira’s custom field limit.
When that happened, teams had no choice but to re-use custom fields from other workflows, giving each field different meanings across different parts of the company. “Provider Specialty Details,” for example, was a custom field for incoming corrections to the provider network, but served double duty for the engineering team to track expected behavior in bug reports.
The switch happened fast
Given the scale and complexity of their Jira instance, the thought of switching to Linear might have seemed daunting. But Oscar was motivated to become faster and more innovative so they went for it.
The rip-and-replace fear is overblown, it was a breeze to move everyone over to Linear.
The entire migration took just over a month for 600+ people. Several factors made Oscar’s move to Linear faster than anyone expected.
Linear’s import tooling made it easy to bring over the information that mattered. Exporting projects and backlog history and pulling them into Linear was straightforward, even with the size of their instance.
But what Oscar chose not to migrate was just as important. They left behind all those custom fields and workflows that had accumulated over years. As teams looked closely at their old setup, they recognized how much of it they didn’t really need for daily work. “It just turns out people haven’t missed all those custom fields and workflows,” said Zalewski.
Once engineers started using Linear, the rest of the migration unfolded organically. The adoption rate was fast. “We didn't need to corral people onto it. People don’t need to be prodded into using Linear,” said Zalewski.
Engineers felt the change right away
Linear changed the rhythm of day-to-day work at Oscar almost immediately.
Work that used to disappear is now visible
Infrastructure and platform teams were fielding constant one-off requests through chat threads that were impossible to track or prioritize. Linear Asks turned that invisible work into something they could actually manage.
Leadership can finally see what’s happening
Greg Chagnon, Vice President of Engineering, used to spend hours each week piecing together project status from spreadsheets and Google Docs. Now he opens a Custom View in Linear and has what he needs for Monday morning team meetings.
Everybody here seems happier with Linear.