Senior Product Manager in Toronto

Upwork Inc.'s family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work.

Upwork's Match Platform team sits at the heart of how clients and freelancers find each other. As Senior Product Manager for Match Platform, you will own the shared infrastructure that powers matching, personalization, embeddings, and evaluation across multiple product surfaces. This is a high-leverage role: the models, features, and frameworks you build become the foundation that other product and ML teams build on. You will partner closely with engineering, data science, machine learning, analytics, and marketplace operations to reduce duplication, increase reuse of shared capabilities, and drive measurable improvements in match quality and relevance.

Responsibilities

• Innovate: Drive the roadmap for next-generation AI-powered search, recommendation, and matching systems — including retrieval, ranking, personalization infrastructure, and the shared model and feature foundations that multiple product surfaces build on.
• Strategize: Own the AI/ML product strategy and roadmap, making deliberate tradeoffs between long-term platform investments and near-term surface-specific wins so teams build on a common foundation rather than duplicating work.
• Apply cutting-edge AI to solve high-impact customer problems, including but not limited to: NLP and intent understanding to better interpret what users are looking for; embedding-based and neural retrieval for deeper contextual matching; personalized ranking; real-time indexing for fresher, more relevant results.
• Own core models and evaluation systems: Set strategy for human labeling programs, offline evaluation frameworks, and online experimentation, and establish a unified data strategy for shared labels, features, and outcomes.
• Collaborate: Lead cross-functional alignment across product, engineering, ML, data science, analytics, design, and operations, moving work forward through clarity and trust rather than authority.
• Measure success: Define instrumentation, key metrics, and operating cadences that connect system-level insights to measurable product improvements.
• Stay on the cutting edge: Track emerging AI techniques and tools and bring them into your work early, keeping our search and recommendation capabilities ahead of the curve.

What it takes to catch our eye

• Proven experience as a product manager working directly on search, recommendation, ranking, or large-scale information retrieval systems, ideally in a marketplace or other two-sided context.
• Deep AI/ML fluency — able to partner effectively with engineering and data teams on retrieval methods, ranking signals, embeddings, model tuning, and evaluation, and to translate those concepts into clear product decisions.
• Demonstrated success leading experimentation and A/B testing programs and using results to inform roadmap and design decisions.
• Ability to translate ambiguous user and business needs into concrete, technically feasible requirements, and to make sound prioritization calls across systems, teams, and time horizons.
• Clear, inclusive communicator who drives cross-functional alignment in fast-paced, technically complex environments.

Come change how the world works. Upwork is establishing its first international operational hub in Toronto, Canada, and this role will require 3 days per week in office.

We’re proud to offer benefits that go beyond the basics, including healthcare coverage for you and your family, RRSP/DPSP retirement plans, mental health support, wellness reimbursement program, supplemental vacation, and an Employee Stock Purchase Plan.

Upwork is committed to building a diverse, inclusive, and equitable workforce. Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law.