Does Headway ask for AI skills in its job ads?
Live dataFrom its Ashby job board · Last updated 29 October 2026
Above average
43%of Headway’s 90 open roles ask the candidate to use AI
- Rank
- #151 of 786
- Open roles
- 90
- Ask for AI
- 39
- As a requirement
- 10%
- Tool named most
Cursor
How many Headway job ads ask for AI
- 43% of Headway’s 90 open roles ask the candidate to use AI in the work: 39 job ads, 18 points above the 25% across 1,333 software companies.
- Headway ranks 151 of 786 companies with 10 or more open roles.
- It asks most in design ads: 5 of 5.
- The AI tool its ads name most is Cursor.
Which Headway roles ask for AI skills
Share of Headway’s open roles in each role that ask for AI. Roles with 3 or more open roles.Source: Lemonsignal
What Headway’s job ads say about AI
“Active practitioner with AI tools — you use them in your work today, not just in conversation.”
“We're using AI to automate clinical workflows, simplify complex insurance requirements, and give providers more time to do what they came here to do.”
“Operators are expected to use AI tools like Claude, Clay, Glean, and Attention to build, ship, and iterate workflows directly, staying involved through deployment and ongoing optimization.”
How we counted AI skills in Headway’s job ads
From the 90 open roles on Headway’s public Ashby job board on 29 October 2026. An ad counts when it asks the person to use AI in their own work. The full method. Work at Headway and see something wrong? Tell us.