Jellyvision needs a creative, scrappy Senior B2C Demand Generation Marketer who is looking for an opportunity to out-think, out-hustle, and out-care while building a mega-brand in the huge and broken market of Medicare.

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?

Jellyvision needs an entrepreneurial, scrappy B2C Demand Generation Marketer who is looking for an opportunity to out-think, out-hustle, and out-care while building a mega-brand in the huge and broken market of Medicare. You are the marketing leader for MyALEXHealth so think of yourself as a team of one backed with the support and resources of the larger Medicare team.

For absolute clarity, this is a senior individual contributor role. You won't manage a team (at least until we have real traction and are starting to scale), but you'll design and own the entire marketing function for a new product — setting strategy, picking lanes, managing the budget, building the playbook from scratch, and executing it yourself with the support from a cross functional team and a roster of freelancers and agencies as appropriate.

What you’ll do to be successful

1) Drive Business-to-Consumer Traffic

• Drive beneficiary engagement. Build the marketing engine that gets soon-to-be and current Medicare beneficiaries to discover, trust, and use MyALEXHealth. We're not naive - this market is noisy, predatory, and confusing. Breaking through will take creativity, tenacity, and a willingness to try things that haven't been done before.
• Own social media strategy. Pick the platforms where we can win (hint: not all of them). Build presence, generate leads, foster community. Befriend influencers who can amplify us. Create content that doesn't feel like "brand content."
• Become obsessed with our users. Understand how new-to-Medicare consumers think, what they fear, where they seek information, what language resonates. Build relationships through helpful, honest communication that doesn't talk down to them.
• Partnerships and visibility. Find organizations and influencers in the Medicare ecosystem who can help us build credibility and reach. Co-marketing, speaking gigs, media opportunities - whatever gets us in front of the right people.
• Own the website. Strategy, execution, optimization. Make it a place people actually want to visit.
• Keep tabs on competitors. Not to copy them - to know what's out there and where the gaps are

Success is measured by quantifiable growth in qualified traffic and user engagement - tracked through website visits, lead conversions, social media reach, and the percentage of visitors who complete key actions.

2) Build the Marketing Playbook

• Make a lot of stuff. Emails, posts, case studies, webinars, eBooks, direct mail, pitch decks, whatever it takes. You'll work with supporting players as needed that you get to hire and manage, but you're the strategist and quarterback. You know what to make, when to make it, and how to test whether it worked.
• Manage leads and customers through Hubspot. That’s our homebase and CRM.
• Track everything. Monitor performance, test relentlessly, report what's working and what isn't. We learn as much from failures as successes - maybe more.

Success is measured by a data-informed content strategy that consistently generates and nurtures leads through the funnel - measured by lead volume, conversion rates at each stage, campaign ROI, and documented learnings from A/B tests that inform future marketing decisions.

3) Navigate Complex Regulations Confidently

• Stay compliant. Medicare marketing has rules. Lots of them. You'll make sure we follow them while still being ourselves.

Success is measured by zero compliance violations while maintaining brand authenticity. Demonstrated through clean regulatory audits, approved marketing materials that still sound like "us," and a documented compliance process that doesn't slow down marketing velocity.

Experience & skills you’ll need

• 8+ years marketing experience. We’re going to prioritize people who have managed multiple aspects of marketing in a hands-on way but if you’re more junior in your career, no sweat- please just share how you’ve got a track record of diving in and figuring things out on your own.
• Exceptional and refreshing writing and communication skills. We mean it. Send us your best work.
• Proven social media track record, especially reaching older adults who don't want to be called "seniors."
• Data-driven decision making. You can analyze performance, spot trends, and adjust strategy accordingly.
• Creativity that solves problems. Not just "creative for creative's sake" - innovative solutions that resonate with real people.
• Collaboration and humility. You speak up, challenge ideas respectfully, take feedback gracefully, and care more about the team winning than being right.
• Scrappiness and business acumen. You're a Marketing MacGyver. You can mine the internet for insights, figure out what you don't know, and won't scale prematurely.
• A roll-up-your-sleeves mentality. No micromanaging. No posturing. No bureaucracy. Just smart people doing good work.

Experience & skills that would be oh-so-nice

• Familiarity with healthcare marketing, ideally to a 60+ demographic
• Time spent working with Carriers or FMOs
• Medicare knowledge (products, regulations, ecosystem)

The Details

• Location: Remote
• Starting Salary: $140,000 - $155,000

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.