Creative Strategy Lead

Sailor has exceptional product market fit

• Exponential growth: We serve tens of thousands of patients and cover 37 million Medicare lives across all 50 states, with organic demand making Sailor one of the fastest growing companies in healthcare.
• AI powered, deeply human care: We harness the power of AI while keeping human connection at the center of care, creating an experience that feels personal, continuous, and deeply human.
• Talent dense team: We are a 25 person team in our NYC office and are backed by the founders of Ramp, Nourish, and Headway.

About the Role

Location: New York City, in office, 5 days a week.

We’re hiring a Creative Strategy Lead to build the creative engine powering Sailor’s B2C engine. You’ll own creative strategy and production end to end across an eight figure annual budget that’s scaling fast. You’ll report to the Head of Growth and work closely with paid media, analytics, patient ops, clinical, and our brand and design team.

The role has two parts.

• Own the creative-to-performance loop: Creative is the biggest lever we have on Meta, Google, and YouTube. You'll set the creative roadmap, decide what we test and why, and read results against cost per acquired patient, not cost per click.
• Build the team and the machine. Today creative runs on a small team, freelancers, and agency support. You’ll build the team and operating model (designers, editors, copywriters, creators) that ships high volume, compliant creative every week, and use AI to make it faster with every cycle.

Your Key Responsibilities

• Set the creative strategy. Own the creative vision and roadmap across every channel, grounded in performance data and patient insight.
• Run the creative testing engine. Set KPIs, keep a steady test and refresh cadence, and scale what works.
• Make creative that works for adults 65+. Master what earns older adults’ trust, and lead our patient story and testimonial program.
• Build and lead the team. Hire and develop staff, freelancers, creators, and agencies, and set the bar for craft and speed.
• Build scalable creative systems. Stand up the briefs, pipeline, asset library, and AI tools that let us produce at volume.
• Protect the brand and stay compliant. Own how the brand shows up in performance creative, with every claim meeting HIPAA and healthcare marketing standards.
• Be the internal creative voice. Serve as the authority on brand expression and patient perspective, partnering with the founders on how Sailor shows up in market.

What We’re Looking for

• 4+ years in creative strategy or performance marketing, ideally at a high growth DTC or digital health company or a performance creative agency.
• Strong instincts for paid creative. You know what stops the scroll and what converts, and you can explain why from first principles, before launch and after.
• Data driven storyteller. Fluent in hook rate, hold rate, CTR, CVR, and CAC, and you connect the numbers to the story so data drives decisions rather than defends them.
• Systems builder, AI native. You’ve built a creative pipeline from scratch, kept quality high as volume grew, and already use AI to make it faster.
• Deep empathy for the people we serve. Our patients are 65 and older, and many are seeking mental health care for the first time. Everything we make has to speak to them with respect.

Our Offer to You

• Competitive salary and equity
• Comprehensive benefits, including medical, dental & vision insurance
• Flexible PTO and sick days
• Lunch and dinner in our beautiful Soho office covered by Sailor
• Team building events
• Additional: One Medical Membership for US employees, HSA, Talkspace, HealthAdvocate, Teladoc Health