Director of Product

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: understand their goals, translate their needs into prioritized intake for our engineering teams, and ensure 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 knowledge.

• 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.

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.

• 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…