Director, AI-Driven Enterprise Engineering

Hirewell; Chicago (IL); Hybrid; USD 190,000 - 230,000; Full time

Benefits offered by this job

Full benefits from day 1

401(k) match 75% up to 6%

Flexible time off

Industry-leading benefits

Job summary

Hirewell is recruiting a Director, AI First Engineering in Chicago to lead a distributed team delivering enterprise AI-enabled software. The role drives the adoption of agentic AI tooling, ensures governance, and shapes engineering strategy across onshore and offshore members.

You will own hiring, coaching, performance management, and the operating cadence for a high‑impact delivery model. The ideal candidate has 10+ years in production software with 5+ years as a leader, strong MS stack skills,

Qualifications

• 10+ years delivering production software in enterprise or product-led environments.
• 5+ years leading engineering teams and distributed/global teams.
• Hands-on AI delivery with measurable outcomes.

Responsibilities

• Define and execute the team’s delivery roadmap with agentic development and AI tooling.
• Embed AI across the full delivery cycle and ensure credible hands-on engineering judgment.
• Directly manage a distributed team, including hiring, onboarding, and performance management.
• Establish governance for AI-driven development and secure coding standards.

Skills

AI delivery

Engineering leadership

C#/.NET

REST APIs

React/TypeScript

SQL Server/Azure SQL

Agentic AI tooling

Governance & security

Education

Bachelor's degree in CS/Engineering

Tools

Claude Code

GitHub Copilot

Codex

Job description

Hirewell is recruiting a Director, AI First Engineering in Chicago to lead a distributed team delivering enterprise AI-enabled software. The role drives the adoption of agentic AI tooling, ensures governance, and shapes engineering strategy across onshore and offshore members.

You will own hiring, coaching, performance management, and the operating cadence for a high‑impact delivery model. The ideal candidate has 10+ years in production software with 5+ years as a leader, strong MS stack skills,