Head of AI-First Engineering

Jet Support Services, Inc. (JSSI); Chicago (IL); On-site; USD 180,000 - 280,000; Full time

Job summary

Jet Support Services, Inc. (JSSI) is seeking an AI First engineering leader in Chicago to guide the delivery of AI-enabled applications. You will own roadmaps, embed AI across the lifecycle, and maintain accountability for reliability and business impact of AI-powered features.

This role demands cross-functional collaboration and technical mentorship. You will drive standards, enablement, and a unified operating model for global delivery, balancing hands-on work with strategic direction and

Responsibilities

• Define and execute the team’s delivery roadmap for the applications in scope, using Claude Code Enterprise and agentic development as core capabilities, and partnering with Product and the business to prioritize and evolve those applications over time.
• Embed AI across the full delivery cycle: spec-driven intent, agent execution (plan, build, and test), automated verification quality gates, and production insight that feeds learnings back into the context store, while engineers remain accountable for intent, architecture, quality, and release decisions.
• Hold final accountability for the reliability, accuracy, and business impact of what the team ships, including the AI agents, LLM-powered features, and automation built into the applications in scope.
• Partner with peer engineering and architecture leaders to align on shared standards, roadmap, and reusable patterns, presenting clear options and recommendations to engineering leadership.
• Stay close enough to the work to prototype, review examples, challenge assumptions, and demonstrate credible hands‑on engineering judgment, using AI to the fullest in your own work and setting the standard the whole team is expected to meet.
• Drive responsible enterprise adoption of Claude Code (onboarding, usage patterns, repository context, guardrails, training, and)

Job description

Jet Support Services, Inc. (JSSI) is seeking an AI First engineering leader in Chicago to guide the delivery of AI-enabled applications. You will own roadmaps, embed AI across the lifecycle, and maintain accountability for reliability and business impact of AI-powered features.

This role demands cross-functional collaboration and technical mentorship. You will drive standards, enablement, and a unified operating model for global delivery, balancing hands-on work with strategic direction and