Associate Creative Director

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Creative at Headway isn’t just about making things look good, it’s the strategic engine that shapes how we connect with our audiences and drive meaningful business growth. Our focused team of Art Directors, Brand Designers, Copywriters, and Creative Ops has built deep trust through consistent delivery of campaigns that both strengthen the brand and deliver results. As a senior leader of the Creative team, you’re equal parts visionary and doer. You collaborate across teams to develop innovative, emotionally resonant narratives that help more people access the mental health care they deserve. This role blends strategic leadership, oversight of both art and copy, and hands-on execution, ensuring that every creative decision amplifies our mission.

What you'll do:

• Lead and inspire a world-class brand creative team of art directors, writers, and designers to produce exceptional and craft driven work that moves the needle in the mental healthcare space.
• Own the brand foundation: champion the voice and visual identity, and guide how these systems evolve- from templates to brand campaigns.
• Shape the brand’s future: drive the full creative process from ideation through delivery, balancing bold creative thinking with strategic and business goals.
• Translate marketing priorities into actionable creative strategies and executions that land with clarity and emotional impact.
• Be the steward of the brand, providing direction and partnership to other creative leaders and cross-functional teams.
• Collaborate closely with Product Design to ensure brand cohesion across key touchpoints.
• Mentor and elevate junior creatives, fostering a culture rooted in craft, curiosity, and collaboration.
• Partner with ops to ensure ideas are executed at the highest level of quality and within the constraints.

What we're looking for:

• 8+ years of experience in creative roles (agency or in-house), with a track record of award winning work and demonstrated experience managing creatives.
• A portfolio that shows strong conceptual thinking, craft, and storytelling across mediums (digital, social, experiential, brand).
• Strong artistic vision and design taste with meticulous attention to detail, aesthetics, and brand consistency across all creative touchpoints.
• Skilled at shaping brand narratives and building integrated campaigns that drive measurable results.
• Confident presenter with the ability to articulate creative rationale to both creative and non-creative audiences.
• A collaborative and growth mindset— you enable others to do their best work.

Compensation & Benefits:

The expected base pay range for this position is $175,100 - $206,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

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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.

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