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 on conversational and agentic access to Occupier's product, figuring out what customers should be able to do once the UI is no longer the limiting factor, and defining what "good" looks like when the answer comes back through an LLM instead of a screen.

• You will talk to customers directly and translate their real workflow pain into specific, testable use cases for conversational/agentic access.
• You will bring structure to a fast-moving space by turning ambiguous "customers want easier access to their data" signals into clear specs and measurable outcomes
• You will work closely with AI engineering to identify the highest-leverage workflows in lease administration and deal management that customers want to accomplish through natural language or agentic access.
• You will develop a rigorous point of view on output quality: how to judge whether an AI-generated answer is accurate enough to act on, and where the failure modes are likely to hide.
• You will think through the access-control dimension: ensuring the right people can take the right actions, and that customers can't see or trigger things they shouldn't.

About You

• You think in terms of customer workflows first i.e. if the UI wasn't a constraint, what would someone actually want to ask or do, and does the current product get them there.
• You have a sharp, testable instinct for judging AI output quality: you don't just trust a good demo, you look for where it breaks.
• You are a strong written and verbal communicator who is able to convey your thoughts succinctly with strong conviction grounded on clear rationale.
• You are opinionated about where AI creates real leverage and where it is noise. You can defend that point of view with sound justification.
• You are self-directed, enjoy tackling ambiguous problems and thrive in a scrappy, high-pace environment.

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 that users depend on in a B2B SaaS context.
• Experience defining evaluation frameworks and success criteria for AI features where outcomes are probabilistic.
• Strong bonus:
  • Working familiarity with the AI landscape (LLMs, agents, tool use)
  • Experience with workflow-heavy, data-intensive B2B products (lease management, ERP, legal tech, or similar a strong plus).

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.