Headway
What's the Company Culture Like at Headway?
Frequently Asked Questions
Headway has a mission-driven, collaborative culture built around ownership, strong relationships, open feedback and high standards. Employees work together to make mental healthcare more accessible while being encouraged to share ideas, solve problems and support one another. Five cultural principles guide how teams operate: Headway Owner: Go Where You Are Needed; Better, Faster, Fewer; Strong Belief, Weakly Held; Relationship-Obsessed; and Feedback Uplifts Every Level. These principles shape everything from daily decisions and communication to how employees work with patients, therapists and insurance partners.
- Employees share a strong commitment to the mission: Headway's culture centers on making mental healthcare easier to access and helping therapists spend more time caring for patients. Employees across engineering, product, sales and operations work toward that goal. One software engineer described coworkers as “incredibly empathetic, creative, and really passionate about what they do.” A chief technology officer also highlighted the team's combination of technical expertise and compassion, describing how their shared purpose brings people together to solve difficult problems.
- Ownership and teamwork are part of everyday expectations: Headway encourages employees to look beyond their individual responsibilities and help wherever they can make the biggest difference. Its Headway Owner principle asks employees to put shared goals ahead of departmental priorities and follow through on commitments. One business development employee described success at Headway as prioritizing the company's mission and working selflessly toward common goals. The Relationship-Obsessed principle reinforces this approach by encouraging employees to support coworkers as readily as they support customers.
- Employees are encouraged to speak openly and keep improving: Strong Belief, Weakly Held encourages employees to express their opinions, test their ideas and change course when new information points to a better solution. Feedback Uplifts Every Level, known as FUEL, makes constructive feedback part of everyday conversations, regardless of seniority. Headway also follows Better, Faster, Fewer, which encourages teams to concentrate on their most important priorities rather than trying to tackle everything at once. Together, these practices support open communication, thoughtful decision-making and continuous improvement.
- Team traditions help employees connect and celebrate achievements: Headway brings employees together through its annual HeadAway company offsite, team outings, virtual coffee chats and employee recognition programs. Teams participate in activities such as Yankees games, painting nights and happy hours, while Growth Awards and cultural shoutouts recognize contributions. Its sales organization also celebrates significant achievements through the Century Club, which recognizes employees with the greatest sales impact every six months. One senior provider growth associate described a workplace where colleagues celebrate small wins, coach one another and take pride in shared accomplishments.
- External signals:
- Employees rate the culture positively: Headway receives a 4.2/5 rating for culture and values, reflecting favorable employee perceptions of the workplace. (Glassdoor)
- Employees give favorable ratings for inclusion: Headway earns a 4.1/5 rating for diversity and inclusion. (Glassdoor)
- Employees recognize the collaborative environment: Workplace culture receives a 4.4/5 rating, with employees highlighting an inclusive environment and a clear sense of purpose. (Indeed)
Bottom line: Headway's culture combines a shared mission with personal accountability, teamwork and open communication. Employees are encouraged to take initiative, support their colleagues and find better ways of working, while team traditions and recognition programs help build relationships across the company.
Headway's Candidate Tradeoffs
If you’re weighing whether Headway is the right fit, these are the core tradeoffs to consider.
- Headway emphasizes real-world impact, but that comes with high-stakes work and increased accountability.
Headway Employee Perspectives
Describe your sales team culture in one word. Why did you choose that word?
Invigorating. Our team isn’t just focused on hitting goals — we’re helping reshape how mental health care is accessed and delivered in this country, one provider at a time. What makes the Headway sales team invigorating is our combination of drive, collaboration and shared purpose. As empathetic consultants, we support clinicians in building thriving practices that serve communities often left behind. With a product that’s free for providers and patients alike, every conversation is rooted in purpose. Each provider we bring on opens a new pathway for someone to get the mental health support they need — that’s the “why” behind every call we make. We win together by staying grounded in empathy, acting with context and always aiming for 10x impact. This isn’t just sales — it’s the frontline of change.
What are your team’s traditions or growth opportunities, and how do these traditions help team members connect, evolve and stay motivated?
We’re a close-knit team that holds ourselves to an Olympic performance standard — and we celebrate growth with just as much intensity as we pursue it. Our culture encourages us to act like Headway owners and go where we’re needed, which is a mindset that extends beyond role boundaries. Whether it’s earning a promotion in just eight months or stepping up to solve cross-functional challenges, we’re empowered to stretch our skills and follow our interests.
We stay connected through everything from attending Yankees games and happy hours to painting nights and virtual coffee chats. Our Growth Awards and cultural shoutouts highlight the way our values show up in real work. Our Century Club celebrates the individuals who had the largest sales impact every six months. And at HeadAway, our annual companywide offsite, we reflect on how our team’s daily actions shape the broader company’s success. These shared moments keep us energized, grounded and motivated to grow together.
How does a strong team culture make you feel more connected to your day-to-day work?
A strong team culture makes me feel like my work matters — not just to our goals but to the people around me and the customers we’re serving. I’m part of a team that sets a high bar, and that motivates me to meet it — not out of pressure, but pride. I’m trusted to take initiative, stretch beyond my role and contribute in ways that align with what I care about.
Culture shows up in our day-to-day: the way we celebrate small wins, share candid feedback and coach each other through challenges. Feedback isn’t just accepted — it’s baked into our cultural principles through FUEL (which stands for feedback uplifts every level), and it helps me grow faster. I feel supported, seen and energized knowing I’m surrounded by people who care just as much about doing excellent work as they do about each other.
Headway’s culture emphasizes shared responsibility, collaboration and a commitment to the company’s mission. Employees are encouraged to think beyond their individual roles, prioritize companywide goals and take ownership of outcomes that contribute to Headway’s success.
“Headway is extremely driven by our cultural principles, one being: 'Act like a Headway owner before a functional owner.' Success at Headway means prioritizing the success of our mission and acting selflessly to contribute to Headway's goals.”
Headway Employee Reviews
What People Are Saying About Headway
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Collaborative & Supportive Culture: Colleagues are frequently described as kind, talented, and eager to help one another succeed, with cultural principles that encourage constructive feedback and relationship‑building. This environment, paired with a mission many find meaningful, fosters day‑to‑day support and teamwork.
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Recognition, Pride & Shared Success: Company communications highlight programs such as cultural awards, shout‑outs, mentorship, and employee groups that recognize contributions and celebrate those who embody the values. These rituals and structures signal appreciation and help people feel proud of their impact.
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Empowering & Trusting Leadership: Employees describe trust and autonomy, including internal mobility and ownership over meaningful work. Onboarding is portrayed as welcoming and responsibility is granted early, reinforcing a sense of empowerment.
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
Has employee-led culture committees
Offers Employee Resource Groups
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.
