Headway's total rewards package includes robust health and wellness benefits, retirement savings and equity ownership opportunities.
Source posting
Enterprise SaaS
Headway is hiring. 30 roles are open right now.
Browse the openings below to see requirements, locations, and pay where available. Scoutify can fill in and send your application to the ones that match your search.
HQSan Francisco, CA
Posted (90d)30
[01] HIRING NOW
See Headway's current openings.
We update these listings as we find new roles and learn that others have closed.
Open roles
30
Posted (90d)
30
Posted range
—
Roles with the most current openings
Marketing
8 roles
Operations
4 roles
Strategy & Operations
4 roles
Data Scientist
3 roles
Engineering Manager
3 roles
[02] OPEN ROLES
Apply to Headway now.
Live roles pulled from Headway's career page. Open one to see the full description, location, and pay, then let Scoutify apply for you, or apply on Headway's site yourself.
Work mode
The 20 most recent roles out of 30 open roles
Remote · full-time · $180k - 225k
Remote · full-time · $152k - 190k
Remote · full-time · $183k - 215k
Remote · full-time · $152k - 190k
Remote · full-time · $27k - 315k
Remote · full-time · $212k - 265k
New York, New York City, United States · full-time · $251k - 314k
Remote · full-time · $265k - 331k
New York, New York City, United States · full-time · $212k - 265k
Remote · full-time · $169k - 265k
[03] VISA SPONSORSHIP
U.S.-only hiring history.
Headway has no H-1B petition history we can find.
No H1B sponsorship history
Source: USCIS H-1B Employer Data Hub. Classifications: yes (5+ approvals), conditional (1-4), no (0).
[04] WHERE THEY'RE HIRING
Where Headway is hiring.
These are the cities named in current job listings. A role can appear in more than one city. Remote roles may also appear in these cities and can have location requirements.
Top cities by open roles
New York City, New York
7 roles
Remote: 24 positions
[05] OFFICES
Where Headway works.
© Mapbox © OpenStreetMap
We've mapped a Headway office at 497 S Hillview Dr, Milpitas, CA 95035-7702, so you know where you'd report before you apply.
Office data © OpenStreetMap contributors
[06] IN THE NEWS
Headway in the headlines.
Recent press coverage, pulled from Google News. Worth a scan before an interview or a cold email: funding rounds, launches, and leadership changes are the fastest way to sound current.
PCMag3 months agoUnofficial Networks3 months agoForest Park Review3 months agoBoing Boing3 months agoBehavioral Health Business5 months ago
Source: Google News. Last 12 months.
[07] FROM THE POSTINGS
What the job postings tell us.
These details come from the linked postings. Benefits and working arrangements can differ by role and location.
Headway is a Series D company with $325M+ in funding from investors including a16z, Accel and Spark Capital.
Source postingThe Senior Engineering Manager (Infrastructure) role owns cloud infrastructure, deployment pipelines, the database platform, observability and incident response.
Source postingSources reviewed 2026-10-19.
[08] ABOUT
What Headway does.
Headway is building a new mental healthcare system that makes therapy more accessible by addressing insurance barriers. Over 85,000 providers across all 50 states run their practice on its software, serving over 1 million patients.
[09] INTERVIEW PREP
Going through their loop?
Review the skills in Headway's job descriptions, practice relevant exercises, and explore any available candidate-reported questions.
[10] HOW TO APPLY
Your resume lands in Ashby.
Headway uses Ashby for applications. Follow the job link to complete the employer’s form and review its requirements.
Scoutify checks Headway's career page for new listings.
Applying to Headway? Sniper applies to new Headway roles minutes after they post, filling in the Ashby application with your resume and profile when a role passes your filters. Sniper sends one application per posting, and the employer's confirmation email for most applications lands in Scoutify Mail.
ATS identified from the application URLs on Headway's recent postings
[12] SIMILAR COMPANIES
People exploring Headway usually compare with these.
[13] FAQ
Questions people ask about Headway.
Not covered here? Email support@scoutify.com.
Is Headway hiring?
Scoutify currently lists 30 open roles at Headway. Follow the job links to check requirements and apply on the employer's career site.
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