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.  Position Summary: 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.  DUTIES AND RESPONSIBILITIES: Own the business relationship  * 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  Drive intake and prioritization  * 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  Work AI-first  * 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  Lead and develop your team  * 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 knowledge  Measure and communicate impact  * Define what “success” looks like for your BUs’ product investments and track it  * Own adoption metrics; understand whether what gets built is actually being used and driving value  * Communicate progress, blockers, and outcomes clearly to both business and technology leadership    DESIRED CREDENTIALS: Required  * 7+ years of product management experience, with at least 3 years in a senior or lead PM role  * Demonstrated experience using AI tools in your product work — not just awareness, but active, daily use; we want to see how AI has changed how you do your job  * Proven ability to build deep, trusted relationships with business stakeholders and become their go-to technology partner  * Track record of translating ambiguous, poorly-defined business needs into clear, prioritized product plans  * Strong written communication skills; able to write requirements and product documentation that engineers and AI agents can actually work from  * Experience managing at least one direct report  * Chicago-based; able to be in the office a minimum of 3 days per week  Strongly preferred  * Experience working in or alongside enterprise SaaS, B2B software, or complex multi-stakeholder technology environments  * Experience building or contributing to a spec-driven or AI-assisted delivery model  * Experience in a high-growth, transformation environment where the playbook was still being written  Not required  * Aviation or MRO (maintenance, repair, overhaul) domain experience — we will teach you the domain; you bring the product instincts, curiosity, and relationship skills to learn it quickly    WHO THRIVES IN THIS ROLE  This role is a great fit for someone who is energized by being the person a business unit actually relies on — not a ticket queue, not a project coordinator, but a real product partner. You are curious enough to learn a new domain quickly, structured enough to bring order to ambiguity, and confident enough to make prioritization calls that will disappoint someone. You see AI as a tool that makes you better at your job today, not a future trend to watch. And you are excited about the opportunity to help define what an AI-first product organization looks like, because we are building it right now.  At JSSI, we are committed to rewarding our team members with competitive and comprehensive compensation packages that reflect their contributions and talent. For this role, the annual base pay generally ranges from $160,000 to $230,000, with the final offer determined by variable factors including but not limited to market location, job-specific knowledge, skills, education, and experience. In addition, your total rewards package may include an annual discretionary bonus plan, incentive or sales bonus plan, or other form of additional compensation, based on your role. Additionally, for full-time employees based in the USA, Canada, or the Philippines, we are proud to offer a robust suite of benefits. This ranges from insurance offerings such as medical, dental, vision, retirement savings programs, among others, starting day one of employment. For a full overview of our offerings, visit the JSSI Benefits Page on our company website. JSSI is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status, or other characteristic protected by law. JSSI does not accept unsolicited resumes from individual recruiters or third-party recruiting agencies in response to job postings. No fee will be paid to third parties who submit unsolicited candidates directly to our hiring managers or Recruiting Team.