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. Weve done that profitably at scale for a long timeover $600M in lifetime sales without losing our soul or our sense of humor.

Now were 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 goodnot overwhelmedabout one of the most important health and financial decisions theyll ever make.

This is an incubation-stage product. Translation: ambiguity is a feature not a bug.

Whats the role

Were looking for a technical Product Owner to help shape how MyALEXHealth gets planned built and delivered. Youll be a central force on a small fast-moving team building a product that actually helps peoplenot just checks 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. Youll have real influence over priorities and plans and the trust to help define what great looks like the right person this role comes with meaningful ownershipand the satisfaction of putting structure and momentum behind a product that genuinely matters.

Were looking for people who are:

• Smart scrappy and comfortable figuring things out as they go
• Obsessed with users and the marketevery interaction is a chance to learn
• Gritty enough to wrestle Medicares 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 arent posterstheyre how decisions get made.

What youll do to be successful

1.) Shape scope before work starts

• Youll help define what were building before engineers ever pick it up.
• Youll lead scoping and feature-shaping conversations identify dependencies and risks early (technical content compliance) and help translate fuzzy ideas into clear testable requirements.
• Youll 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

• Youll lead estimation with the team and turn it into delivery plans that are ambitious but believable.
• Youll help the team understand capacity make smart tradeoffs and sequence work so progress is steady and intentional.
• Youll 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 wellnot because we got lucky.

3.) Make decisions and priorities visible

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

Success looks like: anyone can quickly understand what were doing why were doing it and whats coming next.

Experience & skills youll 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 dont hold water
• Highly organized detail-oriented and disciplined about follow-through
• Willingness to do hands-on worknot 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

• Youre 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 processs sake. We use structure to move faster and think more clearlynot 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 dont exist yetand someone needs to help create them.
• Youre 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.
• Youre 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: $105000 - $140000
• To Apply:please submit your resume as well as a cover letter detailing three reasons why youre 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 doesnt 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 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 theyre 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.