Director of Product

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. Learn more at

JSSI is transforming into an AI‑first technology and product organization, and the Director of Product is central to that transformation. This is not a traditional product management role. You will sit within the product organization as the dedicated product leader for a few business units—the person that Finance, Sales, Tech Services, or another BU actually calls when they need technology to move their business forward.

You will own the entire product relationship for your business units: understanding their goals, translating their needs into prioritized intake for our engineering teams, and ensuring that what gets built actually solves the right problems. You will use AI as a core part of how you work—from generating first‑draft requirements, to analyzing feedback at scale, to tracking adoption—and you will be a visible example of what an AI‑first product leader looks like in practice.

You will manage 1–3 Product Managers. This is a high‑ownership, high‑visibility role on a team that is moving quickly and building something that did not exist before.

• Serve as the dedicated product leader for your assigned business units as the single point of contact for all product needs, escalations, and roadmap conversations
• Build deep relationships with business unit leaders and stakeholders; understand their goals, constraints, and workflows well enough to anticipate needs before they are articulated
• Represent your business units’ priorities clearly within the technology organization, and represent technology’s capabilities and constraints clearly back to the business
• Translate business needs into structured, prioritized intake for Solution Architects and engineering teams
• Own the “what” and the “why” not the “how”; partner closely with Solution Architects who own end‑to‑end delivery
• Maintain living spec libraries for your BUs: clear, up‑to‑date requirements that drive AI agents and replace traditional PRDs
• Make hard prioritization calls, communicate tradeoffs transparently, and protect the team from scope creep while keeping stakeholders bought in
• Use AI tools as a standard part of your daily workflow—synthesizing user interviews and support tickets, generating first‑draft requirements, analyzing adoption data, and accelerating every part of the discovery‑to‑delivery cycle
• Model what an AI‑first product leader looks like for the broader organization
• Stay current on AI tooling and capabilities relevant to your BU; proactively identify opportunities to apply AI to BU workflows and products
• Manage 1–3 Product Managers; provide direction, coaching, and clear expectations
• Run structured discovery and requirements processes that your PMs can learn from and replicate
• Develop your team’s product craft: stakeholder communication, prioritization discipline, AI‑assisted requirements, and domain…