Director of AI-First Engineering

Jetsupport; Chicago (IL); On-site; USD 170,000 - 260,000; Full time

Job summary

Jet Support Services, Inc. (JSSI) is seeking an experienced leader to drive AI First engineering strategy across onshore and offshore teams in Chicago.

You will own hiring, governance, and the delivery roadmap for AI-enabled applications that impact engines, airframes, and enterprise platforms. The role combines hands-on leadership with architecture oversight, ensuring reliable, secure, and measurable AI-powered solutions integrated with Salesforce, Dynamics, and internal tools.

Qualifications

• 10+ years delivering production software in enterprise or product-led environments.
• 5+ years leading engineering teams and distributed or global teams.
• Hands-on AI delivery with Claude Code preferred.
• Strong governance, security, and SDLC modernization experience.

Responsibilities

• Define and execute AI First delivery roadmap with cross-functional partners.
• Embed AI across delivery lifecycle and ensure accountability.
• Lead engineering leadership and manage onshore/offshore teams.
• Establish governance for AI First development and secure coding standards.
• Translate progress and risks into executive-level narratives and manage dependencies.

Skills

AI First leadership

Engineering leadership

C#, .NET

REST APIs

React/TypeScript

Azure SQL

Education

Bachelor's degree in Computer Science, Engineering, or related field

Tools

Claude Code

GitHub Copilot

Codex

Azure DevOps

Job description

Jet Support Services, Inc. (JSSI) is seeking an experienced leader to drive AI First engineering strategy across onshore and offshore teams in Chicago.

You will own hiring, governance, and the delivery roadmap for AI-enabled applications that impact engines, airframes, and enterprise platforms. The role combines hands-on leadership with architecture oversight, ensuring reliable, secure, and measurable AI-powered solutions integrated with Salesforce, Dynamics, and internal tools.