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Lead Product Manager

Occupier

Occupier

Product
Toronto, ON, Canada · Remote
Posted on Mar 19, 2026

About the Role
We are looking for a product manager to own execution across our core product areas. The CPO sets direction — big-picture strategy, board and executive alignment, and our major product bets. Your job is to build and manage the engine to make it happen: run the sprint cycle, manage the product idea backlog, keep Sales and CS informed, and track what's actually working in the product. This role is critical in not just what we build, but in how we build at Occupier going forward. A key measure of success is how the product function operates at a fundamentally higher level because of the infrastructure you've built.
You'll share discovery, feedback, and release communication responsibilities with a peer PM, each owning a defined mandate. This is a tactical execution role. You should want to be in the details.

What You Will Own
Product Operation

Own the product development lifecycle from ideation to release, with clear owners and exit criteria at every stage
Create and drive the rhythm of the product org including sprint planning, roadmap reviews, and quarterly planning cycles
Manage Instrumentation to track adoption, feature usage, and outcomes against intended goals
Close the loop between customer feedback, support data, and the roadmap
Own tooling and process across the product and engineering interface backlog hygiene, documentation, and release communication

Stakeholder Management

Enable visibility for Sales and Customer Success on product questions, timelines, and feature status.
Capture and route customer and market signals into the backlog — structured, not ad hoc.
Create the process for continuous release communications, feature summaries, and change rationale for internal audiences.

Product Analytics & Discovery

Own product usage analytics; build and maintain the dashboards that tell you and the CPO what's actually happening.
Run ongoing discovery: customer interviews, in-app feedback, win/loss signals. Surface patterns to the CPO and share insights with your peer PM.
Manage the idea backlog: intake, triage, prioritization input — coordinated with a peer PM across the full product.

AI-Powered Execution

Design and implement AI-powered workflows across the full product function including discovery synthesis, spec generation, competitive monitoring, backlog analysis, release communication so that leverage is structural and repeatable, not dependent on individual fluency or the right prompt.
Build the systems and institutional knowledge that make AI a default part of how the team operates, not an occasional accelerant that a few people use when they remember to.
Maintain a forward-looking point of view on the AI landscape that goes beyond obvious tools, including what's entering the product development stack, what's changing about feasibility and build vs. buy decisions, and where the next wave of leverage is coming from.
Work fluently with AI coding assistants and understand what they change about engineering velocity, feasibility assessment, and build vs. buy decisions.
Bring the team along. Your fluency with AI should raise the floor for how the entire product function operates.

Product Ownership

Run the sprint cycle for your product areas — dependency tracking, escalation paths, and blockers cleared before they compound.
Partner with engineering on scope, sequencing, and pace.
Coordinate with design and data so discovery and validation are in-flight alongside delivery, not scheduled after.

What We're Looking For

5+ years in product management at a B2B SaaS company. You've been responsible for a high functioning product team area end-to-end, not just managed ceremonies.
You're a builder and an operator. Equally comfortable writing a spec, pulling a Metabase report, and running a customer call.
Strong enough with data to self-serve. You don't wait for an analyst to tell you what's going on.
You run experiments and make decisions on the results, including when the data is ambiguous.
Clear communicator in writing. Your updates don't generate follow-up questions.
You use AI tools daily as actual leverage, integrated into how you work, not something you try occasionally.
You want to be in the execution layer. You find the details interesting, not tedious.

Nice to Have

Experience at a B2B SaaS company with an enterprise or mid-market sales motion.
Familiarity with real estate, proptech, or operations and workflow software.
You've used AI to build something — a prototype, an internal tool, an automated workflow. You understand capability first hand.

What Success Looks Like at 90 Days

The product backlog is triaged and there's a prioritization framework the CPO trusts.
Release communications are going out consistently without CPO involvement.
Sales and CS are equipped with the information and context they need without relying on the CPO.
The product function's AI operating layer has a foundation. At least two workflows are live and embedded, the team has a shared standard for AI use, and you are already a thought partner to the CPO on AI product strategy.
You have at least one usage analytics dashboard in Metabase that the team is actually using.
You have introduced at least one AI tool or workflow the team has adopted.