📌 Core Information
🔹 Job Title: Head of Product Marketing and Brand
🔹 Company: Headway
🔹 Location: San Francisco, CA (Remote OK)
🔹 Job Type: Full-time
🔹 Category: Mental Health Care
🔹 Date Posted: July 9, 2025
🔹 Experience Level: 10+ years
🔹 Remote Status: Remote OK
🚀 Job Overview
Key aspects of this role include:
- Leading go-to-market initiatives across Providers, Patients, and Payers
- Building and leading a high-performing team of Product Marketers, Brand Strategists, and Comms professionals
- Defining and owning the overarching product marketing strategy
- Crafting and evolving compelling messaging and positioning
- Establishing and tracking KPIs to optimize brand reach, customer engagement, and business impact
ASSUMPTION: This role requires a strategic leader who can balance both strategic thinking and hands-on execution, with a strong focus on brand and product marketing.
📋 Key Responsibilities
✅ Build and lead a top-performing team, fostering a culture of collaboration, creativity, and accountability
✅ Define and own the overarching product marketing strategy, ensuring alignment with company goals, product roadmaps, and market opportunities
✅ Craft and evolve compelling messaging and positioning that clearly communicates Headway’s unique value to each target audience
✅ Own product launches end-to-end, introducing new capabilities to customers and reinforcing key value propositions
✅ Establish and track KPIs, continuously analyzing performance and optimizing strategies to improve brand reach, customer engagement, and business impact
✅ Shape and activate the Headway brand, building trust and recognition in the market
ASSUMPTION: This role involves a high degree of cross-functional collaboration, requiring strong influencing skills and the ability to work effectively with various stakeholders.
🎯 Required Qualifications
Education: Bachelor's degree in Marketing, Business, or a related field (or equivalent experience)
Experience: 12+ years of experience in integrated marketing, with a strong focus on brand and product marketing, including 7+ years leading high-performing teams
Required Skills:
- Proven track record of successfully leading both 0→1 GTM strategies and scaled product launches across multiple customer segments
- Strategic leadership and hands-on operational skills
- Strong cross-functional collaboration skills, with experience influencing stakeholders across product, marketing, sales, and operations
- Data-driven and results-oriented mindset, with experience developing KPIs, dashboards, and frameworks that connect marketing efforts to business outcomes
- Deep curiosity and customer-obsessed approach, constantly seeking to understand user needs and deliver meaningful value
Preferred Skills:
- Experience in the mental health or healthcare industry
- Familiarity with marketing automation tools and CRM systems
- Experience working with remote teams
ASSUMPTION: Given the remote nature of the role, strong communication skills and the ability to work independently are crucial for success.
💰 Compensation & Benefits
Salary Range: $280,500 - $330,000 per year (based on experience and location)
Benefits:
- 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
- Flexible PTO
- Employee Assistance Program (EAP)
- Training and professional development
Working Hours: Full-time (40 hours per week), with flexibility for remote work
ASSUMPTION: The salary range provided is an estimate based on market data for similar roles in the mental health care industry. Actual compensation may vary based on individual qualifications and experience.
📌 Applicant Insights
🔍 Company Context
Industry: Mental Health Care
Company Size: 501-1,000 employees (Mid-size)
Founded: 2019
Company Description:
- 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.
- The company aims to address the affordability issue in mental healthcare by connecting patients with therapists who accept insurance.
- Headway was founded in 2019 and has raised over $325 million in funding from prominent investors such as a16z, Accel, GV, and Thrive Capital.
Company Specialties:
- Mental Health Care
- Telehealth
- Insurance Acceptance
- Software for Mental Health Providers
Company Website: headway.co
ASSUMPTION: Headway is a rapidly growing company in the mental health care industry, with a strong focus on innovation and accessibility.
📊 Role Analysis
Career Level: Senior leadership role, reporting directly to the VP of Product
Reporting Structure: This role will lead a team of Product Marketers, Brand Strategists, and Comms professionals
Work Arrangement: Remote OK, with the option to work from offices in New York City, San Francisco, and Seattle
Growth Opportunities:
- Potential to shape the broader strategy of a rapidly scaling organization
- Opportunity to build and lead a high-performing team
- Chance to make a significant impact on a growing company in the mental health care industry
ASSUMPTION: This role offers a unique opportunity for a senior marketing leader to make a significant impact on a growing company in the mental health care industry.
🌍 Location & Work Environment
Office Type: Remote-friendly with offices in New York City, San Francisco, and Seattle
Office Location(s): New York, San Francisco, and Seattle
Geographic Context:
- Headway's headquarters are in New York, but the company has a strong presence in San Francisco and serves customers across the United States.
- The role is remote-friendly, allowing for flexibility in work location.
- The company offers a work-from-home stipend to support remote employees.
Work Schedule: Full-time (40 hours per week), with flexibility for remote work
ASSUMPTION: The remote-friendly work environment offers flexibility and the opportunity to work from various locations across the United States.
💼 Interview & Application Insights
Typical Process:
- Phone or video screen with a recruiter
- Behavioral and situational interview with the hiring manager
- Case study or project presentation
- Final interview with key stakeholders
Key Assessment Areas:
- Strategic thinking and problem-solving skills
- Leadership and team-building abilities
- Cross-functional collaboration and influencing skills
- Data-driven decision-making and analytical skills
- Cultural fit and alignment with Headway's mission and values
Application Tips:
- Tailor your resume and cover letter to highlight your relevant experience and skills for this role
- Prepare for behavioral and situational interview questions by reflecting on your past experiences and accomplishments
- Demonstrate your understanding of Headway's mission and values during the interview process
- Showcase your ability to think strategically and solve complex problems
ATS Keywords: Product Marketing, Brand Marketing, Go-to-Market Strategies, Cross-Functional Collaboration, Data-Driven Marketing, Mental Health Care, Telehealth, Insurtech
ASSUMPTION: The interview process for this role will focus on assessing the candidate's strategic thinking, leadership, and cultural fit, as well as their relevant experience and skills.
🛠️ Tools & Technologies
- Marketing automation tools (e.g., HubSpot, Marketo, or Pardot)
- CRM systems (e.g., Salesforce, HubSpot CRM, or Zoho CRM)
- Project management tools (e.g., Asana, Trello, or Jira)
- Data visualization tools (e.g., Tableau, Power BI, or Looker)
ASSUMPTION: The specific tools and technologies required for this role may vary depending on the company's tech stack and the candidate's expertise.
👔 Cultural Fit Considerations
Company Values:
- Patient-centric: We put patients first in everything we do
- Inclusive: We foster a diverse and inclusive environment where everyone feels valued and respected
- Collaborative: We work together to achieve our mission
- Innovative: We embrace change and continuously seek to improve
- Data-driven: We make decisions based on data and evidence
Work Style:
- Remote-friendly and flexible work arrangements
- Strong focus on collaboration and cross-functional teamwork
- Data-driven and results-oriented approach
- Fast-paced and dynamic work environment
Self-Assessment Questions:
- How do you embody Headway's patient-centric value in your work?
- Describe a time when you fostered a diverse and inclusive environment in a team setting
- Can you provide an example of a successful cross-functional collaboration project you've led?
- How do you stay organized and prioritize tasks in a fast-paced, dynamic work environment?
ASSUMPTION: Headway values candidates who align with their mission, values, and work style, and who can contribute to a positive, inclusive, and collaborative work environment.
⚠️ Potential Challenges
- Balancing strategic thinking and hands-on execution in a fast-paced, dynamic work environment
- Managing a remote team and fostering a collaborative culture across different time zones
- Navigating the complexities of the mental health care industry and insurance landscape
- Adapting to changes in the company's growth and prioritizing initiatives accordingly
ASSUMPTION: These challenges require strong leadership, adaptability, and a strategic mindset to overcome successfully.
📈 Similar Roles Comparison
- Unlike traditional product marketing roles, this position requires a strong focus on brand marketing and shaping the overall company narrative
- This role involves working with a diverse range of stakeholders, from therapists and patients to insurance providers and enterprise clients
- Career progression in this role could lead to senior leadership positions within the marketing function or broader business opportunities within the company
ASSUMPTION: This role offers a unique blend of product marketing, brand marketing, and corporate communications responsibilities, making it distinct from similar roles in other industries or companies.
📝 Sample Projects
- Developing and executing a go-to-market strategy for a new product feature targeting mental health providers
- Conducting market research and customer segmentation to inform brand positioning and messaging
- Collaborating with cross-functional teams to create and execute a marketing campaign for a national mental health awareness event
ASSUMPTION: These sample projects illustrate the strategic, collaborative, and hands-on nature of the role, highlighting the diverse range of responsibilities and initiatives the successful candidate will undertake.
❓ Key Questions to Ask During Interview
- Can you describe the current state of Headway's brand and how this role will contribute to its evolution?
- How does Headway approach collaboration and cross-functional teamwork, and how can I contribute to this dynamic?
- What are the most pressing challenges facing the mental health care industry, and how does Headway plan to address them?
- How does Headway support the professional development and growth of its employees?
- What are the key priorities for this role in the first 30, 60, and 90 days?
ASSUMPTION: These questions demonstrate the candidate's curiosity, strategic thinking, and commitment to understanding the role's context and requirements.
📌 Next Steps for Applicants
To apply for this position:
- Submit your application through this link
- Tailor your resume and cover letter to highlight your relevant experience and skills for this role
- Prepare for behavioral and situational interview questions by reflecting on your past experiences and accomplishments
- Demonstrate your understanding of Headway's mission and values during the interview process
- Showcase your ability to think strategically and solve complex problems
- Follow up with the hiring manager or recruiter after your interview to reiterate your interest in the role and ask any remaining questions
⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.
