Role overview

Jobber is a platform that enables small home service businesses—plumbers, electricians, painters, landscapers—to quote, schedule, invoice, and get paid efficiently. This role offers the chance to lead product strategy for Teammate, an AI assistant designed to help service providers automate routine work and transform how they operate their businesses.

Key responsibilities

Own the complete Teammate growth model, spanning discovery, onboarding, first-value experiences, habit formation, and customer advocacy.
Build a deep understanding of how home service businesses operate and what drives them to adopt new ways of working.
Drive both new customer acquisition and activation of existing Jobber users as part of a unified strategy.
Design and iterate on AI onboarding and activation experiences directly with real customers.
Define and track metrics that demonstrate whether Teammate is genuinely changing how service providers run their operations.
Establish the business case for Teammate by building evidence of its value and charting a path to monetization.

Requirements

Five or more years of product management experience with a proven track record of shipping real AI products and seeing them through to sustained outcomes.
Demonstrated experience owning an AI adoption curve end to end, from acquisition through activation and retention, rather than executing isolated experiments.
A track record of moving AI products from early adopters to mainstream usage within existing customer bases.
Comfort designing for non-deterministic product behavior and making sound decisions when you cannot fully predict first impressions.
A growth mindset with the ability to thrive in ambiguity and evolving organizational conditions.
Experience with product-led growth covering both self-serve and sales-assisted approaches (bonus qualification).
Background in home services, field service, or SMB software (bonus qualification).

What makes this role worth considering

You’ll work within the AI Workflows product organization at a company recognized by Great Place to Work and Canada’s Most Admired Corporate Cultures. The role is based in one of four hub cities—Toronto, Edmonton, Vancouver, or Boston—and offers the opportunity to operate in a fast-moving space where technology, positioning, and scope continue to evolve as the team learns together.

Beyond the base salary range of $145,900 to $197,400, compensation includes equity rewards, health and wellness stipends, retirement savings matching, and fully paid extended health coverage. You’ll have access to a dedicated talent development program with career coaching and professional growth opportunities.