Senior User Experience Writer

Who you are

• 5+ years of experience in a writing-led, multi-disciplinary role spanning some combination of interactive content, UX writing, conversational design, content strategy, or digital storytelling
• You write like people talk, and you're funny without visibly trying
• You think in systems. Branching logic and messy data don't scare you; they kind of delight you
• You have an ear. You can hear when a VO line runs a beat too long or lands a shade too chipper
• You sweat the details. In compliance, "close enough" is how brands get in trouble, and you catch the thing everyone else skims
• You treat AI as a power tool, not a threat. You know where it speeds you up and where it makes slop, and you never ship the slop
• You have the portfolio to prove it: real work where you made something complicated feel simple and something dry feel alive. Interactive, editorial, advertising, or education backgrounds all fit
• We'll teach you the rest: Medicare's rulebook, our in-house tools (some with zero documentation), and the audio-mixing mechanics. Bring the instincts. We'll bring the manuals

What the job involves

• We need someone who can write the way people actually talk (warm, clever, human), about Medicare (a subject that fights back), inside strict federal compliance (poetry with your hands tied), while architecting the branching logic beneath the words, coaxing an AI voice into sounding like someone you'd trust, and steering the whole thing through carrier and CMS review without a single detail slipping
• If that list made you tired, we understand
• If it made you a little excited, keep reading
• You are, first and last, a great writer
• Everything else serves that
• Quick gut check on the voice we're after: someone decided the Part D coverage gap should be called "the donut hole," so a hole in your drug coverage would sound like a pastry
• That move, making the scary thing feel like an inside joke the two of you are in on, is the whole gig
• If you already have three better nicknames for Medicare's weirder corners, we should talk
• 1. Write like a human being
• Draft interactive, branching advisor conversations that feel like a smart friend, not a robot reading a policy. Write the linear stuff too: teaser and marketing videos, articles, and UX copy down to the button label and the error state
• Keep voice and tone consistent so product and marketing read as one brand
• The bar: people forget they're being walked through Medicare and just feel helped
• 2. Structure the branching and conditional logic so it's followable, buildable, and testable
• Hand engineers requirements, not riddles: here's the script, and here's what it needs the system to do
• Understand how data comes back from APIs and write so the words hold up against the real, messy data, not just the happy path
• The bar: fewer "wait, the logic doesn't work that way" moments after handoff
• 3. Direct the sound
• Generate and shape AI voiceover for our host so it sounds like a person, not a GPS
• Direct live VO talent when a project calls for it, and pick the takes that land
• Edit, mix, and caption to a clean, launch-ready standard. We'll train the technical mechanics; the ear is on you
• The bar: the voice sounds real, and audio never becomes the bottleneck
• 4. Get it live, and get it cleared
• Own content in our CMS from first draft to live URL, and QA it against your own script
• Prep scripts for compliance review so they're accurate to the Medicare program and true to the letter of federal rules
• Work with team leadership on carrier and CMS feedback: sorting what needs a real change from what needs a clarifying reply, and making the change without killing the writing
• The bar: content clears review in few rounds, with the charm intact
• And the part that ties it all together: you own the script, then you coach it to life. Designers, engineers, and collaborators build with you, not for you. The vision and the translation come from you, and you bring people along by making them want to nail it. Think showrunner, not assembly line

The application process

• We’re looking for writers so a resume alone won’t cut it for us. Skip the "why I'm a great fit" generic cover letter and submit this info instead to that section (in one document):
• A short sample of you. About 150 words, any format, that shows us your voice. Make us feel something, or make us laugh once
• Since you're attaching your portfolio, choose two of your favorite pieces from it and write one line each on what was actually hard about them

Benefits

• Medical, Dental, and Vision Insurance
• Majority of premiums covered for spouses/civil union partners/dependents
• Roth or Traditional 401(k) with match
• HSAs & FSAs with employer contributions
• Flexible-first PTO and work policies
• Self-care days to recharge
• Access to our Chicago office
• Gender-affirming support
• Generous parental leave, adoption, and surrogacy assistance
• Home office, gym, and wellness allowance
• Therapy stipend