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 creative effectiveness are measured (awareness, perception, campaign performance) — and use that data to continuously sharpen strategy.

You’d be a great fit if…

You have 10+ years in brand strategy, brand management, or brand marketing — and a track record of building brands that earn lasting reputation and trust.

You've navigated complex, regulated industries and know how to make bold brand work land in environments where stakes are high.

You're an exceptional cross-functional collaborator — skilled at translating business challenges into brand and communications strategies that stick.

You have strong customer-first instincts and can influence without authority, especially in ambiguous, high-stakes moments.

You're energized by fast-moving environments — comfortable with complexity, undeterred by uncertainty.

You're a force multiplier: the kind of leader who makes everyone around you better and inspires excellent work at every level.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.