Level

Headway careers & jobs

87 open roles · 1 at Level 4, 3 at Level 3, 4 at Level 2, 79 at Level 1 · 79 remote — page 1 of 2

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Headway salaries

Median salary
$230k
Middle half (p25 to p75)
$170k to $281k
Roles with a salary
76

Annual base pay in USD, measured on September 21, 2026. Method: calculated on the 76 open roles Headway currently publishes with an annual salary in USD, using the midpoint of each posted range. Hourly rates and amounts whose period is unclear are excluded. No figure is shown below 3 roles. How we measure.

Headway's largest hiring areas on Level are Software Engineering (20), Operations (11) and Product (10), out of 87 open roles. 79 of its roles (91%) are marked remote. Most listed in New York City; New York, NY; and San Francisco, CA. Most recent posting: September 17, 2026 (checked September 21, 2026).

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20 of Headway’s live roles are in software engineering — see every software engineering job tracked by Level (September 2026).

See how Headway compares across work around ai software engineering jobs sitewide.

7,124 US postings carry a listed salary for software engineering salary data across the industry, measured September 2026.

Headway careers: common questions

How many open roles does Headway have?

Headway has 87 open roles listed on Level on September 21, 2026.

Which teams is Headway hiring for?

The largest hiring areas on September 21, 2026 are Software Engineering (20), Operations (11) and Product (10), out of 87 open roles.

Does Headway hire remotely, and where?

79 of Headway's 87 open roles (91%) are marked remote on September 21, 2026. The most listed locations are New York City; New York, NY; and San Francisco, CA. Top countries: United States.

What does Headway pay?

The median advertised salary is $230k a year, across 76 open roles with annual pay in USD; the middle half runs from $170k to $281k (measured September 21, 2026).

When did Headway last post a job?

The most recent open role was posted on September 17, 2026 (checked September 21, 2026).

How do I apply to Headway?

Each listing on this page links to the application form on Headway's own hiring system (Ashby). Full list of openings: jobs.ashbyhq.com.

Method: live listings for Headway in Level's database, read on September 21, 2026. Listings come from the employer's Ashby job board. Teams are Level's job categories, assigned from the job title. Remote counts use the listing's remote flag; locations are split from the listing's location field. Pay uses listings with an annual salary in the most common currency, without conversion.