Creative at Headway isn’t just about making things sound good. It’s the strategic engine that shapes how we communicate, build trust, and help people take meaningful steps toward care. Our team of Art Directors, Brand Designers, Writers, Content Leads, and Creative Ops partner closely to deliver work that strengthens the brand while driving real business impact.

As an Associate Creative Director, Copy, you are both a creative leader and a hands-on partner in the work. You’ll help define how Headway sounds across campaigns, growth initiatives, and key brand moments while overseeing our content efforts to ensure clarity, consistency, and craft at scale. This role blends big-idea thinking, people leadership, and day-to-day creative direction, ensuring every word reflects the care, credibility, and humanity at the core of our mission.

What you'll do:

• Lead copy direction across brand and growth campaigns, launches, and key initiatives.
• Shape and steward Headway’s brand voice, tone, and messaging across channels.
• Support our content and editorial team, ensuring alignment with brand standards and creative direction.
• Partner closely with senior creative leaders, Art Directors, and Designers to develop impactful and emotionally resonant ideas.
• Grasp the creative brief for the core insight, and translate marketing and business priorities into clear, compelling creative strategies and executions.
• Guide writers through concepting, iteration, and execution with thoughtful, actionable feedback.
• Act as a brand steward, collaborating with cross-functional partners to maintain clarity and consistency.
• Mentor and develop writers and creatives, fostering a culture rooted in craft, curiosity, and collaboration.
• Work closely with Creative Ops to ensure ideas are executed with quality, intention, and efficiency.

What we're looking for:

• 8+ years of experience copywriting and creative leadership, across brand and growth work (agency and/or in-house).
• A portfolio that demonstrates strong campaign thinking, voice development, and exceptional writing craft.
• A clear point of view on taste, storytelling, and what makes creative effective.
• Comfort balancing strategic leadership with hands-on creative direction.
• Experience overseeing or partnering closely with content and editorial teams is a strong plus.
• Confidence presenting and articulating creative rationale to both creative and non-creative audiences.
• A collaborative and growth mindset- you enable others to do their best work.

Compensation and Benefits:

The expected base pay range for this position is $169,000 - $212,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for 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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