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Headway careers

Open jobs at Headway, each rated by how much AI the work involves.

93 open roles · 86 remote · $214k median salary

Updated Nov 5, 2026

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Headway salaries

Median salary
$214k
Middle half (p25 to p75)
$171k to $239k
Roles with a salary
85

Annual base pay in USD, measured on November 5, 2026. Method: calculated on the 85 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 salaries by role, AI level and country

  • Biggest teams hiring at Headway: Software Engineering (16), Marketing (11) and HR (8), out of 93 open roles.
  • 86 of these roles (92%) are remote.
  • Main locations: New York City; New York, NY.
  • Latest job ad: November 3, 2026 (checked November 5, 2026).

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16 of Headway’s live roles are in software engineering: see every software engineering job tracked by Level.

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Headway careers: common questions

How many open roles does Headway have?

Headway has 93 open roles listed on Level on November 5, 2026.

Which teams is Headway hiring for?

The largest hiring areas on November 5, 2026 are Software Engineering (16), Marketing (11) and HR (8), out of 93 open roles.

Does Headway hire remotely, and where?

86 of Headway's 93 open roles (92%) are marked remote on November 5, 2026. The most listed locations are New York City; and New York, NY. Top countries: United States.

What does Headway pay?

The median advertised salary is $214k a year, across 85 open roles with annual pay in USD; the middle half runs from $171k to $239k (measured November 5, 2026).

When did Headway last post a job?

The most recent open role was posted on November 3, 2026 (checked November 5, 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 job ads for Headway on Level, read on November 5, 2026. Listings come from the employer's Ashby job board. Teams are Level's job categories, based on the job title. Remote share comes from whether each job ad is marked remote; locations come from where each ad says the role is based. Pay uses job ads that show a yearly salary, in their most common currency, with no conversion.