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Careers at Headway
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Account Executive

$77,000/year
31 Oct 2025
Verified by Turrior

Content + Source + Freshness • 16 Dec 2025 • 95% confidence

78 / 100

Offer value

A compelling opportunity in a mission-driven organization focused on mental health, offering attractive benefits and the chance for significant impact.

  • Base salary: $61,600 - $77,000, plus commissions
  • Remote work available in a mission-driven organization
  • Opportunity to affect community health positively
Pros
  • Chance to work in a fast-growing startup in the mental health sector
  • Attractive compensation package including equity
  • Work-from-home flexibility
Cons
  • Startup environment may involve unpredictability
  • Sales processes could be challenging depending on market conditions
  • Potentially high workload due to scaling demands

Who it's for

Early to Mid-level • Remote

Good fit
  • Sales professionals with a passion for mental health
  • Individuals eager to work in fast-paced startup cultures
  • Candidates wanting to make a social impact
Not recommended for
  • Those resistant to sales roles
  • Individuals preferring established corporate environments
  • Candidates not interested in mental health topics

Motivation fit

Desire to help increase access to affordable mental health careInterest in developing sales skills in a high-impact environmentWillingness to embrace challenges in a startup setting

Key skills

Consultative salesNetworking and relationship managementAnalytical problem solving
Score: 78/100 AI verified analysis

About the job

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.

As a Provider Growth Associate (Account Executive), you’ll have an instrumental impact as we expand Headway across the country. You’ll be directly responsible for scaling our community of therapists and psychiatrists in order to increase access to quality care for those who need it.

As a sales expert in a rapidly scaling environment, you’ll be on the front line of expanding our therapist networks through a full-cycle sales motion. As the first point of contact for prospective providers, you’ll work cross-functionally to translate the insights you glean from your sales process into products and processes that help us execute on our mission.

You'd love this role if:

  • You have 1-3 years experience in consultative sales or consumer sales (bonus points if you’ve done this in a startup environment, or sold to small businesses before)
  • You know how to connect with people whether in person, over the phone, or over email
  • You have a deep work ethic and the desire to continuously improve
  • You like to be challenged and push yourself to get better every day and in every pitch
  • You have thick skin, and are comfortable thinking on your feet, trying new approaches, and bouncing back when things don’t go your way
  • You take a scientific approach to growth, experimenting with a variety of tactics to discover how to generate leads and sell you have the analytical ability to identify which channels warrant more investment, and which we should avoid
  • You want to learn and grow. You view this role as an opportunity to learn from a bright and talented team and are excited to take on more responsibility at Headway over time
  • You believe in our mission
  • You want to work for Headway because you believe in the importance of affordable and accessible mental health care, for everyone

Compensation and Benefits:

  • Salary information is based on a single salary target per role and is differentiated based on geographic location (Group A, B, or C)
    • Group A = NYC, SF/Bay Area, LA Area, Seattle, Boston, Austin, and San Diego
    • Group B = Chicago, Pittsburgh, Denver, Washington DC area, Philadelphia, Atlanta, Boulder, Nashville, Phoenix, and Portland
    • Group C = All remaining cities
    • Group A: $77,000
    • Group B: $69,300
    • Group C: $61,600
    • Examples of cities located in each Compensation Grouping:
  • Other compensation includes commission. Commission payments are monthly.
  • 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

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.

Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.

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