Director of AI Engineering

About JSSI

Founded in 1989 and headquartered in Chicago, Jet Support Services, Inc. (JSSI) is the largest independent provider of hourly cost maintenance programs for business aviation. JSSI delivers comprehensive coverage for engines, airframes, and auxiliary power units (APUs) across more than 300 different aircraft makes and models, helping owners and operators stabilize maintenance budgets, maximize aircraft availability, and protect asset value throughout the lifecycle of ownership.
JSSI has built a portfolio of complementary business lines designed to simplify the economic and technical complexity of business aviation; these include Maintenance teams , Traxxall maintenance tracking software, Parts & Engines , Conklin aircraft cost and performance data, and Aviation Capital asset-based financing solutions. Together, these offerings support owners, operators, and maintenance providers with integrated tools spanning ownership and maintenance planning, execution, and financial management.
With more than 6,500 aircraft supported through programs and software platforms, JSSI leverages its unique independence, unmatched scale, and data-driven insight to deliver customized solutions and support models aligned to the interests of each client — regardless of aircraft platform. JSSI is backed by leading institutional investors GTCR, Genstar Capital, and Blackstone. Learn more at jetsupport.com.

As Director, AI First Engineering, you drive the continued adoption of AI First engineering practices across JSSI’s software engineering organization, converting JSSI’s investment in Claude Code Enterprise and agentic development into repeatable, governed, and measurable engineering outcomes. This is a hands‑on engineering leadership role. Reporting to the SVP of Engineering, you will directly manage a distributed team of three to eight AI solution architects, engineers, and verification architects spanning both onshore and offshore operations. You will own hiring, coaching, performance, and the operating cadence that keeps an AI First, spec-driven delivery model moving in tight build‑measure‑learn cycles.

The successful candidate combines strong engineering fundamentals, modern Microsoft‑stack delivery, hands‑on agentic AI and multi‑agent systems experience, and proven change leadership. You will partner with Product and the business units to deliver high‑quality software through agentic, AI First practices while holding clear human accountability, secure development practices, and production reliability. You will build strong business relationships, developing a deep understanding of business practices and needs, then translating them into successful delivery. Success is measured by outcomes: what the team ships, its reliability and business impact, adoption maturity, and the trust the business places in JSSI’s engineering organization.

Responsibilities

AI First Engineering Strategy & Delivery

• 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.

Engineering Leadership & People Management

• Directly manage a high‑performing AI First engineering team, owning hiring, onboarding, performance management, and individual career development for your direct reports.
• Run a single operating model across onshore and offshore delivery capability, with time‑zone‑aware rituals and communication practices that make a global team operate as one.
• Coach your Solution Architects to set direction and mentor the rest of the team. Build the team’s collective AI First capability through a structured learning path, enablement sessions, champions, office hours, and communities of practice, all grounded in real JSSI codebases.
• Set direction collabor