About the Role

We are looking for our first Head of Communications to join Headway at a pivotal time for our company. In this role, you will lead a team responsible for defining, shaping and amplifying Headway’s story among a diverse set of audiences - patients, providers, payers, investors and employees -  establishing Headway as the trusted leader in the mental health category.  You will report to the Head of Brand, PMM & Communications and your team’s work will span corporate, product, consumer, financial and internal communications.  

As a masterful storyteller, you will be responsible for taking complex business initiatives and turning them into stories that are easy to understand, dynamic, memorable and influential in the market.  Given the nature of our industry, you’ll rely on your strong instincts and problem-solving skills to help us navigate highly regulated, sensitive dynamics. And as someone who loves the art & science of the job, you’ll leverage data, creativity and innovation to continue pushing the team forward, finding new ways to seize share of voice, drive key messages and foster positive sentiment in the market. 

You Will:

• Build our Communications Strategy:  Define our role & approach to communications at Headway, including the right channels and KPI’s that map back to our business objectives.  
• Craft Headway’s Most Important Stories: Demonstrating a deep understanding of our diverse audiences, business and industry dynamics, develop and steward core corporate, consumer, product, financial, and internal narratives that position us as a thought leader in mental health. Leverage data & AI to fuel an always-on machine of insights and creative storytelling.  In partnership with our executive team, help shape and amplify their voices as category experts.  
• Drive Share of Voice: Identify the channels, forums where our stakeholders are paying attention and then deliver outsized, positive attention for Headway in those channels
• Build & Protect Headway’s Reputation:  Working closely with cross-functional partners, anticipate and manage the communications implications of business and industry news. ​​Lead reputation and crisis planning, anticipating how issues may impact multiple sides of the marketplace and responding with clarity and care. 
• Turn Employees into Brand Advocates:  Ensure clear, consistent messaging that drives alignment, engagement, and trust across the organization during periods of growth and change.
• Attract & Retain a High-Performing Team:  Lead a team of communications professionals operating at the highest levels; consistently pushing them to grow and drive increasing impact in the org. 

You’d be a great fit if…

• You have 14+ years of experience and at least 7 years of management experience in communications, for healthcare, consumer or tech companies. 
• You’ve successfully led corporate, consumer and internal communications at high-growth, complex organizations that operate in highly-regulated environments.  
• Deep expertise in identifying, building & executing meaningful, enduring company narratives that result in positive reputation & trust for the organization. 
• You’re an excellent cross-functional collaborator; proven success translating your partner’s business challenges into communications strategies. 
• Strong customer-first instincts and the ability to influence without authority, especially during times of uncertainty. 
• Comfort operating in ambiguity in a fast paced environment with high visibility and impact
• You’re a force-multiplier, known for attracting and building high-performing teams and unlocking excellent work among all those around you. 

Compensation and Benefits:

The expected base pay range for this position is $251,200 - $314,000, 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

About This Role

Headway’s patient lifecycle function is a blank canvas. You will be the first dedicated lifecycle leader on the patient side: owning strategy, platform, programs, and team from day one. You will build the owned-channel relationship with every Headway patient from first contact through long-term care, using email, SMS, push, and in-app messaging to help people access and sustain mental health care.

This is a player-coach role. You will build and run campaigns yourself while hiring and developing a small team. You will work directly with Engineering to instrument events and ship notification infrastructure, and with Data Science to bring model-driven personalization to lifecycle at scale.

You Will

• Own the end-to-end patient lifecycle: from welcome and onboarding activation through appointment booking, session retention, and re-engagement.
• Select, implement, and operate our lifecycle stack: Iterable (email/SMS) and Knock (in-app/push) in a HIPAA-compliant architecture built on Freshpaint.
• Design and run a rigorous A/B testing program with incremental holdout measurement — not just click optimization.
• Partner directly with Engineering and Data to instrument events, build trigger logic, and deploy ML-informed segmentation and personalization.
• Build AI-assisted workflows for content generation, segmentation, and optimization. You use these tools yourself, today.
• Hire and develop a lifecycle team of 2–3 specialists in H2 2026.

Who You Are

• You have 5+ years in lifecycle/CRM marketing with hands-on experience in Iterable and/or Braze. You have personally built triggered journeys, not just approved them.
• You are fluent in Knock or eager to go deep on it: you understand the distinction between a CRM and a notification layer.
• You design A/B tests with pre-registered hypotheses and holdout groups. You can explain statistical significance to a non-technical stakeholder.
• You have shipped lifecycle programs in partnership with Engineering: you know what a webhook is, you can review a data schema, and you do not wait for tickets to be completed before thinking about logic.
• You are actively using AI tools in your work today: for content, segmentation, or workflow automation. You have a concrete answer to “what have you built with AI in the last 90 days?”
• You have worked in consumer health, consumer subscription, or a context where the user’s emotional journey matters. You understand what it means to send a message to someone managing their mental health.
• You are comfortable with HIPAA compliance considerations in marketing communications — or eager to get up to speed quickly.

Tools We Use

Iterable (evaluating), Knock (evaluating), Freshpaint, RudderStack, Snowflake, Statsig, LaunchDarkly, Braze (considering), Hightouch.

The expected base pay range for this position is $212,000 - $265,000, 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

About the role:

At Headway we are proud to have attracted the largest network of mental healthcare providers in the U.S. to our platform - but we have just scratched the surface of what’s possible. We are looking for an ambitious marketing leader to join Headway as our first Director of Provider Marketing, to help usher in a new era of growth for the organization, working to ensure every Provider in the U.S. knows and trusts Headway to help them grow a profitable, thriving practice. 

In this role, you will lead the provider go-to-market experience - from acquisition to activation, engagement, retention, and advocacy.  You’ll be responsible for deeply understanding the needs of the provider market and building break-through, meaningful work that connects, inspires and drives action.  

In this role you will: 

• Uplevel Our Provider Narrative: Reimagine how we communicate our product value to accelerate adoption of Headway’s full feature stack and maximize the potential of the Provider <> Headway relationship.  
• Support Growth & Sales objectives:  A critical cross-functional partner to Growth and Sales teams, you will deeply understand their objectives, and then structure and prioritize initiatives around equipping them to win: from owning the sales narrative and developing enablement tools to leveraging AI to rapidly accelerate channel acquisition messaging tests in the market.  
• Own the Provider Go-to-Market experience:  Lead the end-to-end provider marketing strategy and coordinated GTM efforts across the Provider org.  Develop differentiated positioning and messaging that clearly communicates the value of Headway’s feature stack in an increasingly competitive mental health platform landscape, and then execute best-in-class GTM campaigns that connect with Providers in a more meaningful way. 
• Strengthen the Provider Community: Evolve our community programs into a competitive moat that fosters connection and fuels loyalty, product adoption, and referrals.
• Lead a High-Performing Marketing Team: Build and lead a team that blends creative storytelling with analytical rigor. Instill a test-and-learn culture through structured experimentation, A/B testing, and continuous optimization; establish repeatable playbooks and processes, leveraging AI to maximize efficiency and impact.

You’d be a great fit if: 

• You have 10+ years of marketing experience, with at least 3 years in a leadership role owning go-to-market strategy end-to-end
• You bring a proven track record of building and executing multi-channel marketing programs that drive acquisition, engagement, and retention - ideally in a marketplace, SaaS, or platform business
• You have strong positioning and messaging chops - you can distill complex product value into clear, compelling narratives that resonate with a specific audience
• Experience partnering closely with Sales and Growth teams, including owning sales enablement materials and channel messaging
• You’re a data-driven marketer with hands-on experience running structured experiments, A/B tests, and using insights to optimize campaigns and build repeatable playbooks
• Experience building or scaling community programs as a growth and retention lever
• Demonstrated ability to hire, develop, and lead high-performing teams that balance creative excellence with analytical rigor
• Familiarity with AI tools and a track record of leveraging them to accelerate marketing workflows and testing velocity

Compensation and Benefits:

The expected base pay range for this position is $225,600  - $282,000, 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