Headway
What's It Like to Work at Headway?
Frequently Asked Questions
Headway supports employee job satisfaction through meaningful responsibilities, professional development, regular feedback, flexible work and benefits that help employees care for themselves and their families. Its five cultural principles — Headway Owner: Go Where You Are Needed; Better, Faster, Fewer; Strong Belief, Weakly Held; Relationship-Obsessed; and Feedback Uplifts Every Level — encourage employees to take initiative, work together and continue learning. Headway developed these principles with input from hundreds of employees and focus groups involving more than 70 people across departments and seniority levels.
- Employees are encouraged to take ownership of their work: Headway gives employees opportunities to make decisions, solve problems and contribute outside their immediate responsibilities. Its Headway Owner principle encourages people to help wherever they are needed, while Strong Belief, Weakly Held encourages employees to share their opinions and remain open to better ideas. These expectations give employees room to take initiative while working closely with colleagues across the company.
- Professional development includes regular feedback and learning opportunities: Headway's Feedback Uplifts Every Level principle, known as FUEL, encourages employees and managers to share feedback that helps people improve. Managers are expected to understand employees' long-term career goals and support their development. Full-time employees can also receive a $500 annual professional-development stipend, and internal advancement provides opportunities to take on new responsibilities. One senior provider growth associate described feeling that their work matters and having the support to stretch beyond their immediate role.
- Benefits help employees care for their mental health and families: Headway reimburses eligible mental-health copays and therapy expenses through a health reimbursement arrangement of up to $2,100 annually and provides an employee assistance program. Employees can choose among four Cigna medical plans, three dental plans and two vision plans. Headway also offers company equity and up to 16 weeks of paid parental leave alongside fertility and family-forming support through Carrot. These benefits give employees support for their healthcare needs, financial future and family responsibilities.
- Remote work and company events help employees balance flexibility with connection: Headway supports remote work across the United States, with offices in New York City, San Francisco and Seattle. Employees can build relationships through the companywide HeadAway offsite, team gatherings, virtual coffee chats and employee recognition programs such as Growth Awards. Its Relationship-Obsessed principle encourages employees to support one another and build strong working relationships, even when they work in different locations.
- External signals:
- Employees rate the workplace culture positively: Employees give Headway 4.2/5 for culture and values and 4.1/5 for diversity and inclusion. (Glassdoor)
- Career development receives favorable feedback: Employees rate career opportunities 4.0/5, reflecting positive sentiment around opportunities to learn and advance within the company. (Glassdoor)
Bottom line: Headway supports employee satisfaction by giving people meaningful responsibilities, opportunities to develop their careers and benefits that address their personal and family needs. Flexible work, regular feedback and opportunities to connect with colleagues help create a workplace where employees can feel supported while doing work that matters.
Yes. Headway employees generally recommend the company as a place to work, particularly for its mission, talented colleagues and opportunities to make a difference. Employees appreciate working with people who care about improving access to mental healthcare and contributing to projects that help patients find therapists covered by their insurance. Positive employee reviews, favorable leadership ratings and confidence in the company's direction reflect an overall positive workplace experience.
- Most employees would recommend working at Headway: Employee feedback shows that 78% would recommend the company to a friend, while 83% approve of CEO Andrew Adams and 81% have a positive outlook on the business. Employees frequently mention the company's mission, knowledgeable colleagues and opportunities to take on meaningful responsibilities when describing what they enjoy about working there.
- Employees find the work personally rewarding: Headway helps patients find mental healthcare providers who accept their insurance while making it easier for therapists to navigate insurance requirements. Employees across product, engineering and operations contribute to work that makes a difference in people's lives. One product manager described how rewarding it is to simplify the healthcare system and see the results for patients. A chief technology officer also discussed the satisfaction of developing technology that gives therapists more time to focus on patient care.
- Employees enjoy working with talented and supportive colleagues: Headway brings together people with experience in healthcare, technology, finance and operations who work closely to solve problems. One software engineer described colleagues as “incredibly empathetic, creative, and really passionate about what they do.” An employee in business operations also highlighted the relationships formed with coworkers and the opportunity to learn from experienced teammates as reasons they enjoy working at Headway.
- Employees have opportunities to contribute beyond their immediate responsibilities: Collaboration across departments gives employees a broader understanding of the business and how their work affects patients and providers. Product and engineering teams regularly work with growth and operations colleagues to understand everyday challenges and develop solutions. Projects include improving insurance processes, helping patients connect with therapists and building technology that reduces administrative work for providers. Employees can see how their contributions support the company's mission while gaining experience across different areas of the business.
- External signals:
- A majority of employees recommend Headway: 78% would recommend the company to a friend, and employees give it an overall rating of 4.0/5. (Glassdoor)
- Employees express confidence in leadership and the company's direction: 83% approve of the CEO, while 81% have a positive outlook on the business. (Glassdoor)
- Workplace ratings are positive across several areas: Employees rate culture and values 4.2/5, career opportunities 4.0/5 and senior management 3.9/5. (Glassdoor)
Bottom line: Headway is recommended by a majority of employees, who appreciate the company's mission, their coworkers and the opportunity to contribute to improving mental healthcare. Positive employee ratings, confidence in leadership and opportunities to do meaningful work make Headway an appealing place to build a career.
Headway's Candidate Tradeoffs
If you’re weighing whether Headway is the right fit, these are the core tradeoffs to consider.
- Headway emphasizes accessible, engaged managers who provide regular support and alignment, though that often includes more frequent check-ins and active collaboration.
Headway Employee Perspectives
What is your role, and what attracted you to Headway? Describe the moment when you knew you’d found the right fit.
As chief technology officer at Headway, I lead our engineering organization and shape our technology strategy. What drew me to Headway was personal; my own experience with therapy showed me how life-changing mental health care can be but also how difficult it can be to access.
I knew this was the right fit during my conversations with the team about their vision. Mental health care runs on outdated, disconnected tech stacks that make life harder for both therapists and patients. At Headway, we’re fixing that. We’re building the infrastructure to connect these broken systems and using AI — especially large language models — to save therapists time and help people find the right provider faster. The team’s mix of technical excellence and real compassion for this problem made it clear to me that this is where I wanted to be.
What's your favorite part about working at Headway?
My favorite part about Headway is the direct impact our work has on people’s lives. When we improve our platform, we’re not just increasing metrics; we’re helping someone find a therapist who might change their life, or helping a provider spend less time on paperwork and more time with patients.
I also love the technical challenges we’re solving. Building infrastructure that connects patients, providers and insurance companies has us work on both extremes of technical complexity. We build optical character recognition for faxes coming from doctors, but we also work on LLMs for patient to therapist matching. It’s interesting technical work that also happens to serve a meaningful purpose.
The team culture is something special, too. Everyone here truly believes in the mission of expanding access to mental health care. That shared purpose creates a lovely environment where people are motivated to solve hard problems together rather than just advance their careers.
What advice would you give to job seekers looking to join your growing team?
Headway is aggressively growing the engineering team by investing in a substantial number of new software engineers. We are solving a generational problem and need the best talent to help us achieve it. If you’re interested in joining us, show us how you think about solving problems, not just your technical skills. We’re building systems that haven’t existed before, so we need people who can navigate ambiguity and find creative solutions.
Also, connect with the mission. Mental health care access is a problem that affects virtually everyone, either directly or through someone they care about. The most successful people on our team are those who understand why this work matters. Finally, be ready to grow. We’re scaling rapidly, which means there are constantly new challenges to tackle and opportunities to expand your impact. The best engineers on our team are those who see problems as opportunities to learn something new.
Headway is building a new mental healthcare system. One patient, one provider, and one insurance partner at a time.
Everyone has had an experience with the U.S. healthcare system where it's really complicated. There's hundreds of insurance plans, there's lots of complicated terms like deductible and co-pay and co-insurance. And I think it's really fulfilling to be able to simplify all of that complexity down, and that feeling of seeing my work directly affect the mission of making people's lives better is really what motivates me to bring my whole self to work every day.
Our mission is to make mental healthcare more accessible, and the group of people that work here really actually reflect that. So everybody here is incredibly empathetic, creative, and really passionate about what they do.
Headway Employee Reviews
What People Are Saying About Headway
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Mission & Purpose: The mission to make mental-health care more accessible is described as meaningful and energizing, giving day-to-day work a clear sense of purpose. Feedback suggests employees see tangible impact through enabling insurance acceptance and reducing administrative burden for providers.
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Team Support: Colleagues are often seen as smart, kind, and collaborative, creating a supportive environment aligned to a shared goal. Feedback suggests cross-functional work among product, engineering, operations, and customer-facing teams is a strong cultural norm.
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Autonomy: Employees are said to have high ownership, with encouragement to operate beyond narrow job descriptions and act quickly. Feedback suggests this autonomy enables visible impact and rapid learning in a fast-growing setting.
Headway's Awards
Headway's Benefits
Company or teams have recognition rituals for individual work
Employee feedback used to shape policies and strategy
Encourages autonomy and ownership from employees
Established employee awards to honor work and contributions
Managers give public shoutouts and celebrate employee milestones
Managers offer consistent feedback loops
Provides modern technology across teams
Provides resources to build team camaraderie
Quarterly engagement surveys to gauge employee satisfaction
Documented career progression frameworks
Documented path to leadership development
Encourages lateral mobility to expand skills and impact
Promote from within
Defined values and mission statements
Documented operating principles
Hosts in-person all-hands meetings
Implements team-based strategic planning
Leadership encourages open, transparent debate
Open office floor plan to encourage communication and collaboration
Policies promote a low-ego, team-driven culture
Prioritizes mission-driven work in decision-making processes
Prioritizes real-world impact of work in decision-making processes
Promotes a people-first, social culture
Uses an OKR operational model to clearly define goals and priorities
Offers a remote work program
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco, and Seattle.
