Product Manager

Jet Support Services, Inc.•Chicago, IL

1d•$110,000 - $160,000•Hybrid

About The Position

JSSI is transforming into an AI-first technology and product organization, and Product Managers are at the heart of how that transformation gets executed. Reporting to a Director of Product, you will work within a specific business unit as a trusted product partner — owning discovery, requirements, and delivery oversight for a portfolio of products and initiatives that matter to the business. This is not a coordination role. You will build your own relationships with business unit stakeholders, run structured discovery to understand what they actually need, and translate that into clear, prioritized specs that our engineering teams and AI agents can work from. You will use AI as a core part of how you work every day — writing requirements faster, synthesizing user feedback at scale, and continuously finding ways to do more with less time. You will partner closely with your Director of Product, who owns the overall BU relationship and team strategy. Within that partnership, you are expected to show up as a proactive, trusted presence with the business — not someone who waits to be pointed at a problem, but someone who finds them.

Requirements

2–4 years of product management experience in a business-facing, stakeholder-intensive environment
Demonstrated use of AI in your product work — at minimum, writing specs or requirements with AI assistance; we expect this to already be part of how you work, not something you’re planning to start
Proven ability to build trusted relationships with non-technical stakeholders and translate their needs into clear product requirements
Strong written communication skills; able to write requirements and documentation that engineers and AI agents can work from without interpretation
Comfortable with ambiguity — able to start with a vague problem and produce a structured, prioritized plan
Chicago-based; able to be in the office a minimum of 3 days per week

Nice To Haves

Experience working in complex multi-stakeholder environments
Experience contributing to a spec-driven or AI-assisted delivery model
Exposure to agile or iterative delivery processes — and the judgment to know when to follow the process and when to adapt it
Aviation or MRO domain experience — curiosity and the ability to learn a new domain quickly matters far more than knowing ours already

Responsibilities

Build and maintain business relationships: Develop strong working relationships with business unit stakeholders — understand their goals, workflows, and pain points well enough to represent them accurately to engineering. Serve as a responsive, reliable point of contact for your stakeholders; triage incoming requests and manage expectations clearly. Partner closely with the Director of Product to ensure alignment on priorities and communicate the full picture back to the business.
Run structured discovery and requirements: Lead discovery for assigned initiatives: ask the right questions, separate what stakeholders ask for from what they actually need, define the problem before proposing a solution, and break the ask into phases that deliver value quickly and allow for iteration. Own the spec library for your portfolio: write and maintain clear, AI-ready requirements that Solution Architects and engineering teams can work from directly. Use AI to accelerate the requirements process — generating first drafts, synthesizing input from multiple stakeholders, and maintaining living documentation as products evolve. Use AI to build mockups and prototypes that make the proposed solution tangible — pressure-testing ideas with stakeholders before engineering invests in the build. Define acceptance criteria and ensure solutions meet business intent before and after release.
Drive delivery and adoption: Partner with Solution Architects through the delivery cycle; stay close enough to the build to catch misalignment early. Own release communication to your business unit; ensure stakeholders know what’s coming, when, and how to use it. Track adoption metrics post-launch; understand whether what shipped is driving value and surface that information clearly. Identify and escalate blockers; keep delivery moving without creating pressure that compromises quality.
Prioritize and communicate tradeoffs: Maintain a clear, prioritized backlog for your portfolio; make visible what’s in, what’s out, and why. Communicate prioritization decisions to stakeholders transparently — including the ones that will disappoint someone. Protect the engineering team from scope creep while keeping stakeholders bought in to the plan.
Work AI-first: Use AI tools actively in your daily work — requirements drafting, research, stakeholder synthesis, backlog management. Continuously look for ways AI can make you a better, faster product manager. Stay current on AI tooling relevant to your domain; bring ideas proactively rather than waiting to be asked.