Marketing & Communications Associate

Marketing & PR Associate

Chicago, IL — Hybrid (2 days/week in office, Wicker Park)

Full-time
· 0–5 years of experience

Start date:

on or before August 1, 2026

We are a growing Chicago insurtech company. We build software and services that help Americans make sense of health insurance — one of the largest and least understood financial decisions most people will make. It is a market of enormous scale that still runs largely on call centers and paper.

We are hiring one person to take responsibility for how the company communicates — to the press, to partners, and to the public. There is no marketing team today. You would be the first marketing hire, reporting directly to the COO.

The role suits someone who writes exceptionally well, is comfortable reaching out to people they don't yet know, and can produce polished visual work without waiting on a designer. Candidates who are strong in two of those three areas are encouraged to apply.

• Writing. Press releases, bylines, executive ghostwriting, landing page and product copy, email, decks, and scripts. Our voice is plain, warm, and precise. We write for a 68-year-old reader, not for other marketers.
• Earned media. Pitch and place stories in trade publications, Chicago business media, and national consumer and personal-finance outlets. Build the relationships if you don't have them, and use them if you do.
• Brand. Visual identity, social, video, landing pages, and presence at events and conferences. You will make the work, not just brief someone else to make it.
• Measurable marketing. Campaigns, content, and channels that generate leads we can count.
• Consistency. Keep the story, the message, and the voice coherent across every surface the company touches.

• Exceptional writing. Native-level fluency in English and real command of the language. You will be asked to submit writing samples and complete a paid writing exercise. This is the most demanding part of our process.
• 0–5 years of professional experience in marketing, communications, public relations, journalism, or a business of your own.
• Chicago-based
  , able to work from our Wicker Park office two days per week.
• Able to start on or before August 15, 2026.
• Self-direction. No one will hand you a brief. You will need to identify the work and do it.

• Existing relationships with journalists, editors, producers, or creators, and a track record of placing stories.
• Design ability — comfortable taking a page, asset, or campaign from a blank canvas to finished in Figma or Adobe Creative Suite.
• Comfort with short-form video and social.
• Published or public work of any kind: bylines, a portfolio, a newsletter, a podcast, a brand you built.
• Experience in a regulated industry such as healthcare, insurance, or financial services.

• Health, dental, and vision coverage.
• 401(k).
• Paid time off, with a required minimum.
• Hybrid schedule: two days per week in the Wicker Park office.
• Direct access to company leadership, and room to grow into leadership.