Head of Engineering jobs in Chicago — demand, required skills, and comparable metros (2026)
As of 2026-08-08, Skillenai has indexed 4 Head of Engineering postings located in Chicago over the past 90 days. The skill mentioned most often is data science, with demand up 200% vs the prior 4 weeks.
Last updated · 90d ending 2026-08-08
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Frequently asked questions about Head of Engineering jobs in Chicago
+Are Head of Engineering jobs being posted in Chicago right now?
Yes. Skillenai has indexed 4 Head of Engineering postings located in Chicago over the 90 days ending 2026-08-08, with demand up 200% vs the prior 4 weeks.
+What skills do Head of Engineering jobs in Chicago require?
Across Head of Engineering postings in Chicago indexed by Skillenai over the 90 days ending 2026-08-08, the skills mentioned most often are data science, agentic AI systems, microservices architecture, data pipelines, carrier networks.
+Which other cities are hiring Head of Engineering?
As of 2026-08-08, the metro areas posting the most Head of Engineering jobs outside Chicago are San Francisco, Berlin, Malta, New York City, Amsterdam, based on the Skillenai jobs index.
+How can I get notified about new Head of Engineering jobs in Chicago?
Skillenai sends a daily email digest of new Head of Engineering postings as they're indexed across the open web. Set up a saved search filtered to Chicago from your account dashboard after creating a free Skillenai account.
Weekly Head of Engineering postings in Chicago — last 90 days
Skills most often required for Head of Engineering in Chicago
| Name | Postings | Share |
|---|---|---|
| data science | 3 | 75.0% |
| agentic AI systems | 3 | 75.0% |
| microservices architecture | 3 | 75.0% |
| data pipelines | 3 | 75.0% |
| carrier networks | 3 | 75.0% |
| data graph | 3 | 75.0% |
| Agents | 3 | 75.0% |
| API | 2 | 50.0% |
| Clickhouse | 1 | 25.0% |
| Card acquiring | 1 | 25.0% |
| enterprise relationships | 1 | 25.0% |
| ML-driven product capabilities | 1 | 25.0% |
Other top cities hiring Head of Engineering
| Name | Postings | Share |
|---|---|---|
| San Francisco | 14 | 350.0% |
| Berlin | 4 | 100.0% |
| Malta | 3 | 75.0% |
| New York City | 3 | 75.0% |
| Amsterdam | 2 | 50.0% |
| Ann Arbor | 2 | 50.0% |
| Bengaluru | 2 | 50.0% |
| Brasil Novo | 2 | 50.0% |
| Lima | 2 | 50.0% |
| London | 2 | 50.0% |
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How this was computed
Counts derive from the Skillenai jobs index over the 90 days ending 2026-08-08, filtered to postings whose canonical role is “Head of Engineering” and whose locationCity is “Chicago”.
- city
- Chicago
- role
- Head of Engineering
- source
- Skillenai jobs index, deduplicated daily
- data_as_of
- 2026-08-08
- window_days
- 90
The demand, skills, and geo numbers on this page come from the same Skillenai labor market index that powers our API. Use it for compensation benchmarking, hiring-competition analysis, and skill-adoption tracking.
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