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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 · page 2 of 2

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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14,000+ US postings carry a listed salary for software engineering salary data across the industry.

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