About Occupier

Occupier is the modern lease management platform that real estate and finance teams at high-growth brands rely on every day. We help corporate tenants centralize their lease data, automate compliance, stay ahead of every deadline, and maintain visibility across their entire portfolio. We are a hands-on team that takes pride in what we build. AI is core to everything we do, from the product our customers rely on to how we work internally. We hold ourselves to a high bar and are always working to raise it. The opportunity in front of us is real. The way tenants manage their leases has not changed much in the last few years, and we are leading the shift. Trusted by brands like [solidcore], Vuori, Van Leeuwen, and Seismic, across over 100,000 leases, the market opportunity is significant and the timing has never been better.

About The Job

This is an individual contributor (IC) role focused specifically on AI product – standing up the MCP layer across Occupier and defining what AI-native lease management actually looks like in practice. You will be paired directly with an AI engineer, operating as a two-person team responsible for the full arc of this work: from identifying high-leverage use cases to shipping production-grade AI features our customers rely on.

You will have a near-term focus on building out the MCP layer that connects our platform to the broader AI ecosystem. You will work closely with a dedicated AI engineer to move fast – defining what to build, why, and how to measure whether it's working. You will identify the highest-leverage places in our lease administration and deal management workflows where AI changes the game for users. You will define what "production-grade" means for AI at Occupier — reliability, accuracy thresholds, evaluation frameworks, fallback behavior. You will talk to customers and translate their real workflow pain into AI use cases that are specific, testable, and shippable. You will bring structure to a fast-moving space – turning ambiguous opportunities into clear specs and measurable outcomes.

About You

You have shipped production AI features – not prototypes, but things real users depend on – and you understand what it takes to get there. You think natively in AI. You reach for it first when solving problems, and you use it heavily in your own day-to-day work. You are comfortable with ambiguity at the frontier. You don't need a playbook — you help write it. You are a strong written communicator — your specs are clear and grounded even when the underlying technology is not fully settled. You work well in a tight two-person team. You and your engineering partner move as a unit, not as separate functions. You are opinionated about where AI creates real leverage and where it is noise. You can defend that point of view with evidence. You are self-directed and thrive without heavy management overhead.

Requirements

5+ years of product management experience, with at least 2 years owning an AI or ML product in production. Demonstrated track record shipping production-grade AI features – not just experiments – that users depend on in a B2B SaaS context. Working knowledge of the AI tooling landscape: LLMs, agents, MCP, tool use, embeddings, evals, and how they fit together in a product. Experience defining evaluation frameworks and success criteria for AI features where outcomes are probabilistic. Ability to work closely with an AI engineer as a peer – you don't need to write the code, but you need to understand the tradeoffs. Experience with workflow-heavy, data-intensive B2B products (lease management, ERP, legal tech, or similar a strong plus). Comfortable being the PM on a greenfield surface area where the right answer is not yet known.

Why Occupier

Competitive compensation packages. Excellent medical, vision, and dental plans – we contribute. Generous family leave policies. Unlimited time off and half-day Summer Fridays. Remote-first culture, with offices in Toronto and Boston if you'd like to be in an office environment.