Product Owner

Jellyvision•Chicago, IL

23d•$105,000 - $140,000•Remote

About The Position

Jellyvision makes ALEX® , the employee decision-support platform trusted by thousands of employers and millions of people to make smart benefits choices. We’ve done that profitably, at scale, for a long time—over $600M in lifetime sales, without losing our soul or our sense of humor. Now we’re taking on an even messier problem: Medicare. A small, senior team is building MyALEXHealth™ , a digital Medicare guide designed to help people move from employer coverage into Medicare with clarity, confidence, and dignity. Our goal is simple and ambitious: reduce decision stress, improve plan fit, and help people feel good—not overwhelmed—about one of the most important health and financial decisions they’ll ever make. This is an incubation-stage product. Translation: ambiguity is a feature, not a bug. We’re looking for a technical Product Owner to help shape how MyALEXHealth gets planned, built, and delivered. You’ll be a central force on a small, fast-moving team building a product that actually helps people—not just checks boxes. You’ll work closely with Leadership, Design, Engineering, and Marketing to shape features early, navigate complexity and compliance, and bring order to the chaos without slowing us down. You’ll have real influence over priorities and plans, and the trust to help define what “great” looks like here. For the right person, this role comes with meaningful ownership—and the satisfaction of putting structure and momentum behind a product that genuinely matters. We’re looking for people who are: Smart, scrappy, and comfortable figuring things out as they go Obsessed with users and the market—every interaction is a chance to learn Gritty enough to wrestle Medicare’s complexity without flinching Clear communicators who collaborate well and wear more than one hat Champions of progress over process This is how we show up. And our principles aren’t posters—they’re how decisions get made.

Requirements

A healthy amount of experience as a Product Owner, Product Manager, TPM, or similar role with real delivery accountability as well as a lifetime of being a tinkerer
A track record of shaping scope and plans for complex, interdependent systems
Strong technical fluency and comfort working close to engineers, with the ability to understand and discuss APIs, integrations, data flows, and system constraints
Experience using product and content development tools like the Atlassian Suite, Figma, Claude, ChatGPT, CMS platforms
The backbone to challenge timelines and assumptions when they don’t hold water
Highly organized, detail-oriented, and disciplined about follow-through
Willingness to do hands-on work—not just coordinate it
Pragmatic, direct, and focused on outcomes over ceremony
Strong written and verbal communication skills, with an instinct to advocate for users
Ability to thrive in fast-moving, evolving environments
Curious, humble, collaborative teammate