Product Owner

Product Owner - MyALEXHealth

Who we are

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. 

What’s the role?

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.

What you’ll do to be successful 

1.) Shape scope before work starts

• You’ll help define what we’re building before engineers ever pick it up.
• You’ll lead scoping and feature-shaping conversations, identify dependencies and risks early (technical, content, compliance), and help translate fuzzy ideas into clear, testable requirements.
• You’ll partner closely with Design and Engineering to define what “done” actually means.

Success looks like: work enters development with clarity, shared understanding, and no major “oh wait” moments.

2.) Own planning, estimation, and delivery accountability

• You’ll lead estimation with the team and turn it into delivery plans that are ambitious but believable.
• You’ll help the team understand capacity, make smart tradeoffs, and sequence work so progress is steady and intentional. 
• You’ll surface risks early, challenge assumptions when timelines get magical, and push for course correction before things go sideways.

Success looks like: we hit commitments because we planned well—not because we got lucky.

3.) Make decisions and priorities visible

• You’ll be the keeper of context.
• You’ll maintain decision logs, translate decisions into clear next steps, and keep Jira honest and up to date.
• You’ll reduce cognitive load for the team by making priorities, dependencies, and status obvious at all times.

Success looks like: anyone can quickly understand what we’re doing, why we’re doing it, and what’s coming next.

Experience & skills you’ll need

• 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
• Experience in regulated or highly complex industries is a plus

This job is not for you if…

• You’re looking for a well-oiled machine with fixed requirements, long roadmaps, and minimal ambiguity. This is a build-in-flight product, not a maintenance role.
• You prefer process for process’s sake. We use structure to move faster and think more clearly—not to create ceremony or hide behind Jira hygiene.
• You want to be handed fully baked specs and told what to ship. This role exists because the specs don’t exist yet—and someone needs to help create them.
• You’re uncomfortable pushing back on leadership, timelines, or assumptions. We value respectful challenge and clear-eyed realism over optimism theater.
• You like staying safely in your lane. Medicare, compliance, content, UX, engineering, and business realities all collide here. Curiosity and range matter.
• You want to manage work without owning outcomes. This role carries real accountability for delivery, clarity, and momentum.
• You’re allergic to regulated complexity. Medicare is nuanced, rule-bound, and occasionally absurd. If that sounds exhausting rather than interesting, this will be a long year.
  
  

Core Competencies

• Communicates Effectively
• Cultivates Innovation
• Drives Results
• Leads with Trust
• Mission Focus
• Strategic Mindset

The Details 

• Location: Remote, with a strong preference for Chicago-based candidates. The team is largely Chicago-based and likes to get together in the office from time to time.
• Starting Salary: $105,000 - $140,000 
• To Apply: please submit your resume as well as a cover letter detailing three reasons why you're right for the gig!

What Jellyvision will give you

Check out our benefits here!

Jellyvision is committed to continuous evolution and fostering a more diverse and inclusive workplace where everyone is welcomed, valued, and respected. It doesn’t matter your race, ethnicity, religion, age, disability, sexual orientation, gender, gender identity/expression, country of origin, genetic information, veteran status, marital status, pregnancy or related condition (including breastfeeding), criminal histories consistent with legal requirements or any other basis protected by law...we just want amazing people who are willing to grow along with us.

Although we have a Chicago-based HQ that employees are welcome to work out of whether they’re local or just visiting, this position is also eligible for work by a remote employee out of CA, CO, FL, GA, IL, IN, KY, MI, MN, NC, NY, OH, OR, PA, SC, TN, TX, UT, VA, WA or WI.