Director of Product
Job Location:
Chicago, IL - USA
Monthly Salary:
Posted:
Application Deadline:
Vacancies:
Job Summary
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 willsit withintheproduct organization as thededicated product leaderfor a fewbusiness units the person that Finance Sales Tech Services or another BUactually callswhen 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 builtactually solvesthe 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 13 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.
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
Representyour business unitspriorities clearly within the technology organization and represent technologys 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
Maintainliving 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 13 Product Managers; provide direction coaching and clear expectations
Run structured discovery and requirements processes that your PMs can learn from and replicate
Develop your teams product craft: stakeholder communication prioritization discipline AI-assisted requirements and domain knowledge
Measure andcommunicateimpact
Define what success looks like for your BUsproduct investments and track it
Own adoption metrics; understand whether what gets built isactually beingused and driving value
Communicate progress blockers and outcomes clearly to both business and technology leadership
7 years of product management experience with at least3years 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 ambiguouspoorly-definedbusiness needs into clear prioritized product plans
Strong written communication skills; able to write requirements and product documentation that engineers and AI agents canactually workfrom
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 unitactually relieson 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 $160000 to $230000 with the final offer determined by variable factors including but not limited to market location job-specific knowledge skills education and 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.
Required Experience:
Director
About Company
Jet Support Services, Inc. (JSSI), is the leading independent provider of aircraft maintenance support and financial services in business aviation.
