Lead Brand & Creative Strategist

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Mental healthcare is at a turning point — and Headway is at the center of it. We're building the infrastructure that makes mental healthcare work: for patients who need it, providers who deliver it, and a system that's been broken for too long. Now we need a brand that matches the scale of that ambition.

We're looking for a Lead Brand & Creative Strategist to join our Brand Marketing, Product Marketing & Communications team — someone who will help make Headway a household name and define what the future of mental healthcare looks like in culture.

This is a rare, early opportunity. You'll build Headway's first true brand strategy from the ground up — defining the unique role we play in the market, then translating that strategy into work that breaks through across products, campaigns, content, and experiences. You live at the intersection of customer obsession, cultural fluency, and brand craft. You know how to make a brand unforgettable.

You Will...

• Own brand strategy. Define and evolve Headway's brand positioning, narrative, voice, and visual identity — in close partnership with our brand and creative team. Ensure the brand flexes appropriately across our core audiences and objectives while staying consistently, unmistakably Headway.

• Lead creative strategy. Drive creative strategy for major campaigns, brand moments, and launches — spanning performance marketing, brand marketing, product launches, and corporate initiatives.
• Close the insight gaps. Partner with Customer Insights to map what we know, what we're missing, and what the market is telling us — so every brief is grounded in real human need.
• Drive cultural listening. Run listening sessions to surface what's being said — and not said — about mental healthcare, so our creative thinking stays ahead of the conversation.
• Stay competitively sharp. Keep a close eye on competitive positioning to ensure we're always distinctively differentiated.
• Get great work to the finish line. Lead feedback sessions with creative and product teams, delivering clear, actionable direction rooted in strategy and brand best practices.

• Build and steward brand systems. Develop brand guidelines and creative frameworks that keep Headway consistent and distinctive as we scale — and as more teams produce brand-facing work across the organization. This includes building AI agents and scalable tools that help teams self-serve on brand — so the guidelines don't just live in a doc, but are embedded into how work gets made

• Champion the brand internally. Be the internal voice and steward of the brand. Educate teams across Headway on how to use it well, and serve as a strategic advisor on brand-relevant decisions — from naming and product UI tone to partnerships and PR moments.

• Measure and iterate. Partner with Customer Insights to define how brand health and crea