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COMPANY HIRING GUIDE

How to apply to Headway

What Headway is hiring for and what its application asks, from the postings and application forms we checked. Newest posting added 2026-10-06.

  • 86 open roles across 40 job titles
  • 29 new open roles in the last 30 days
  • Applications on Ashby
  • Locations: Remote · US; New York, US; New York City, US; Remote; Remote · New York, US; Remote · San Francisco, US; New York City; Remote · New York City, US

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Remote roles at Headway

49 openings open to remote applicants in the US.

Headway Ashby careers site and sign-in

Headway posts the jobs listed here on Ashby, its applicant tracking system, at jobs.ashbyhq.com. To apply, open a posting below and follow its link to apply on Headway’s site. If that site asks you to sign in, use or create an account there: it is separate from your Applystead account.

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About Headway

Which applicant tracking system does Headway use?

The Headway postings listed here are hosted on Ashby (87 open postings), where you apply.

Hiring signals

  • Pay transparency: 43% of open postings list pay set by the employer (37 of 87 postings)
  • Postings list updated:

Open roles at Headway

Other openings at Headway

Headway hiring process: how to apply

From the Headway postings listed here and 10 application forms we checked.

  1. Choose a role above and open its posting.
  2. Apply on Headway’s Ashby application page (how to apply on Ashby).
  3. Fill in the form: it asks for contact details, resume or CV, cover letter, plus about 1 question specific to Headway.

What the Headway application asks

From 10 application forms we checked (2026-10-06).

QuestionAsked on
Resume or CV10 of 10 forms we checked
Cover letter10 of 10 forms we checked
Work authorization0 of 10 forms we checked
Visa sponsorship0 of 10 forms we checked
Salary expectations0 of 10 forms we checked
Voluntary self-identification (EEO)0 of 10 forms we checked
Questions specific to HeadwayAbout 1 question per form

Questions only Headway asks

  1. Who is your current or previous employer? asked on 10 of 10 forms

See Headway salaries

Employers in the same industry as Headway or on the same application system, hiring now.

Prepare your Headway application

Free tools for your Headway application

Guides

Questions about applying

What ATS does Headway use?

The Headway postings listed here are hosted on Ashby (87 open postings), where you apply. Headway has 86 open roles listed here.

Is Headway hiring right now?

Yes. Headway has 86 open roles listed as of 2026-10-06.

What does the Headway application ask?

The 10 application forms we checked ask for contact details, resume or CV and cover letter. Questions only Headway asks include “Who is your current or previous employer?”.

Does Headway ask for a cover letter?

10 of the 10 Headway application forms we checked ask for a cover letter.

Does the Headway application ask about work authorization?

None of the 10 Headway application forms we checked ask about work authorization.

Does the Headway application ask about visa sponsorship?

None of the 10 Headway application forms we checked ask about visa sponsorship.

Does Headway ask for salary expectations on its application?

None of the 10 Headway application forms we checked ask for salary expectations.

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