Headway

0. Company Stats

Industry: HealthTech

Founded: 2019

Size: 800+

Location: New York, NY

Stage: Growth Stage

Stock Symbol: N/A

Work Style: Multi

1. Company Snapshot

Headway is a New York-based healthtech company building the infrastructure to make mental healthcare affordable and accessible across the United States. Founded in 2019 by Andrew Adams, the company has built the first software-enabled national network of therapists who accept health insurance, solving a problem that blocks millions of Americans from getting care: 70% of therapists do not accept insurance, leaving patients to pay out-of-pocket rates most cannot afford. Headway handles all the billing, credentialing, and administrative work so therapists can focus on patients, and so patients can actually find and afford care. The platform now supports over 65,000 mental health providers across all 50 states, covering more than 600,000 appointments per month, and has served over one million patients. Headway has raised $325+ million in Series D funding from Andreessen Horowitz, Accel, Thrive Capital, Spark Capital, GV (formerly Google Ventures), and Health Care Service Corporation, with a valuation of $2.3 billion as of its July 2024 round. The internal team of 800+ employees works fully remote across the US, with optional office access in New York City, San Francisco, and Seattle.

2. Culture & Gen Z Alignment

Mission You Can Actually Feel

Headway's mission to make mental healthcare accessible to everyone is one that lands differently than most startup pitches, particularly for Gen Z, a generation that experiences higher rates of anxiety and depression than any prior cohort and has more openly grappled with the broken state of mental healthcare in America. Employees across every function consistently describe feeling personally connected to the work in a way that is hard to manufacture. Reviews repeatedly note that the mission functions as a genuine daily motivator, not a poster on a wall. For workers who want their day job to mean something beyond the next quarterly target, Headway provides a rare combination of scale (millions of real patients) and urgency (a healthcare crisis that is very much ongoing).

Remote-First, Nationwide Hiring

Headway is fully remote by design, not as a COVID-era holdover. Employees can work from anywhere in the US, with optional in-person hub space in NYC, San Francisco, and Seattle. This is a meaningful structural advantage for Gen Z workers who want to live where they choose rather than where the headquarters happens to be, and it removes the geographic gatekeeping that keeps many early-career opportunities concentrated in a handful of expensive cities.

Diverse Roles Beyond Engineering

While Headway is a tech company, a substantial portion of its workforce sits in operations, sales, customer experience, provider support, and strategy functions. Roles like Provider Growth Associate, Operations Associate, and Customer Experience Associate are genuine entry points that do not require a computer science degree, and several Glassdoor reviewers in these roles describe getting promoted within two years. Six active employee resource groups and a flat-ish structure give early-career employees unusual visibility and access across the organization.

3. What Employees Say

Company Ratings

Glassdoor: 3.3/5

Indeed: 4.0/5

Pros:

- Mission and People: Reviewers across roles consistently highlight the quality of their colleagues and the strength of the mission as the most compelling reasons to stay. The phrase "smartest people I've worked with" appears frequently, and most reviewers describe a genuinely warm team dynamic even in a remote environment.

- Remote Flexibility: Fully remote with no mandatory office days for most roles is called out as a real and valued benefit, not just a talking point.

- Career Exposure: The pace of growth means early-career employees are often handed more responsibility than they would get at a larger, more bureaucratic company. Multiple reviewers in ops and sales roles describe rapid promotions within two to three years.

- Meaningful Day-to-Day Work: Employees describe seeing their work reflected in real outcomes, whether that means a therapist successfully credentialed and seeing patients, or a patient finally connected to affordable care.

Cons:

- Below-Market Compensation: This is the most consistent theme in critical reviews. Multiple reviewers describe pay as below tech-industry benchmarks, particularly for those not in Group A cities like NYC and San Francisco. The no-negotiation compensation philosophy, while framed as equitable, is cited as a source of frustration by experienced hires who feel their market value is not reflected.

- No 401(k) Match: The company offers a 401(k) and Roth plan but no employer match, which several reviewers flag as a meaningful gap versus peer companies.

- Pace and Work-Life Balance: Reviewers frequently describe the pace as intense. Sales and Provider Growth roles in particular carry high quotas, and several reviews note that falling below quota for even one month can trigger a performance improvement plan. Working beyond 40 hours per week is described as common.

- Quiet Layoffs and Headcount Instability: Several recent Glassdoor reviews (late 2024 to early 2026) reference patterns of full-time roles being quietly replaced by contractors, and a general instability in headcount planning. This is worth watching for anyone evaluating job security.

4. Compensation & Benefits Snapshot

- Customer Experience Associate and entry-level Operations roles start around $41,000 to $55,000 per year; Provider Growth Associates (inside sales) typically earn $54,000 to $77,000 base with commission, per Glassdoor data as of 2025 to 2026.

- Senior individual contributor and management roles range from $90,000 to $145,000+; senior software engineers average around $144,000.

- Equity (stock options) is included in all offers, which is unusual for non-engineering roles; the company frames every employee as an owner.

- Medical, dental, and vision insurance through Cigna with four medical plan options; benefits begin on day one of employment.

- 401(k) and Roth plans available; no employer match as of early 2026.

- Up to 16 weeks fully paid parental leave for all parents, including adoptive and foster parents.

- Carrot Fertility benefit for inclusive family-forming and fertility support.

- Therapy reimbursement HRA up to $2,100 per year for out-of-pocket mental healthcare costs, directly aligned with the company mission.

- Flexible unlimited PTO, plus seven days guaranteed sick time; annual winter holiday break.

- Annual home office setup stipend and monthly telecommunications reimbursement for remote workers.

- Annual professional development stipend.

- $30 weekly commuter reimbursement for NYC and SF office users; office lunch provided Tuesday through Thursday at hub locations.

- Life insurance at 100% of annual salary up to $500,000, employer-paid.

- Six employee resource groups (ERGs).

5. Why Gen Z Might Thrive Here

- Mission That Hits Different: Mental health access is not an abstract policy issue for Gen Z. It is personal. Working at a company actively expanding access to affordable therapy, at scale, is a rare opportunity to connect professional work to something that directly affects your generation.

- Remote From Day One, Everywhere in the US: No need to relocate to New York or San Francisco. Headway's remote-first structure means you can build a career at a $2.3 billion company from wherever you actually want to live.

- Equity Access Across All Roles: Stock options are not just for engineers at Headway. Every employee receives equity as part of their compensation, which gives early-career workers a stake in a company that is still in high-growth mode with a clear path toward a future liquidity event.

- Early Ownership in a Fast-Growing Company: Series D with $325M raised but still scaling fast means there is genuine opportunity to own meaningful work early. Reviewers in operations and sales consistently describe being handed significant responsibility within their first year.

- Built-In Therapy Benefit: Headway reimburses up to $2,100 per year in therapy costs for employees, and actively encourages staff to block calendar time for therapy sessions during the workday. For Gen Z workers who prioritize mental health support as part of their employment equation, this is unusually genuine.

6. What Gen Z Should Ask Or Consider

- Ask specifically about the compensation philosophy: Headway uses a no-negotiation, leveling-based pay model. Before accepting an offer, confirm the level you are being placed at and what the pay band looks like for that level, and ask what the typical timeline is to reach the next level.

- Ask about the 401(k) match situation and whether that is expected to change, given that multiple reviews have flagged its absence as a pain point. This matters meaningfully for long-term financial health.

- For sales and Provider Growth roles specifically, ask what the quota ramp looks like in your first three months, and what happens if you fall below quota during ramp. Several reviews describe PIPs being issued quickly, which is a real consideration when evaluating the role.

- Ask directly about the current headcount and whether the team you would be joining has experienced any recent restructuring. The quiet layoff references in recent reviews are worth raising openly.

- Consider where you want to live relative to the city bonus structure: pay bands appear to be meaningfully higher for employees in Group A cities (NYC, SF). If you are remote in a lower cost-of-living area, understand your actual band before comparing offers.

7. Locations & Where Headway Hires

- Fully remote across all 50 US states; no relocation required for any role

- Optional office hubs in New York City (85 Delancey Street), San Francisco, and Seattle

- Company-wide annual offsite called HeadAway brings the remote team together in person once per year

- No international hiring noted in public sources; US-based roles only at this stage

8. How Headway Works

Work Style

Available: Remote, Hybrid

Work Environment

Available: Office, Remote

Benefits

Headway offers medical, dental, and vision coverage through Cigna starting on day one, with four medical plan options and majority-covered premiums, alongside life insurance at 100% of salary up to $500,000, short and long-term disability, a Healthcare FSA, and a Dependent Care FSA. Employees receive up to 16 weeks fully paid parental leave, Carrot Fertility support, and a therapy reimbursement program covering up to $2,100 per year in out-of-pocket mental health costs. Flexible unlimited PTO, seven days guaranteed sick time, an annual home office setup stipend, monthly telecommunications reimbursement, an annual professional development stipend, equity in every offer, and a 401(k) and Roth plan round out the package; there is no 401(k) employer match as of early 2026.

9. Awards & Recognition

- <a href="https://rankings.newsweek.com/americas-best-online-platforms-2025">Newsweek America's Best Online Platforms 2025</a>

- <a href="https://www.greatplacetowork.com/certified-company/7083261">Great Place To Work Certified</a>

11. Sources

Last Updated: March 13, 2026

- Company Website: https://headway.co

- About Us Page: https://headway.co/about-us

- Careers Page: https://headway.co/careers

- Built In Benefits Page: https://builtin.com/company/headway/benefits

- Built In Workplace Profile: https://builtin.com/company/headway

- Glassdoor Salary Data: https://www.glassdoor.com/Salary/Headway-NY-Salaries-E3019578.htm