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. JSSI is backed by leading institutional investors GTCR, Genstar Capital, and Blackstone. Learn more at jetsupport.com.

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.

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.