Senior Product Manager, Match Platform (AI)

Location: Toronto, Ontario, Canada; the role will require 3 days in the office once the Toronto hub opens.

Annual base compensation: $167,500–$209,000 USD, plus eligibility for an annual bonus or sales incentive plan and long-term equity incentives.

Company

Upwork connects businesses with global talent and AI-enabled work solutions through its marketplace and enterprise services.

What you will do

• Own the roadmap for AI-powered search, recommendation, and matching systems, including retrieval, ranking, personalization, and shared model foundations.
• Define AI/ML product strategy and balance long-term platform investments with near-term product-surface improvements.
• Apply NLP, intent understanding, embeddings, neural retrieval, personalized ranking, and real-time indexing to improve matching quality and relevance.
• Set strategy for human labeling programs, offline evaluation frameworks, online experimentation, shared features, labels, and outcomes.
• Align product, engineering, machine learning, data science, analytics, design, and marketplace operations.
• Define instrumentation, key metrics, and operating cadences to measure system and product improvements.

Requirements

• Product management experience with search, recommendation, ranking, or large-scale information retrieval systems, preferably in a marketplace or two-sided environment.
• Deep AI/ML fluency, including retrieval methods, ranking signals, embeddings, model tuning, and evaluation.
• Experience owning platform- or infrastructure-level products used by other teams.
• Proven success leading experimentation and A/B testing programs.
• Ability to turn ambiguous user and business needs into technically feasible requirements and make prioritization decisions across teams and time horizons.
• Strong inclusive communication and cross-functional alignment skills in technically complex environments.

Culture & Benefits

• The role will initially be employed through a partner while the Toronto operational hub is established.
• The partner will provide competitive benefits during the initial employment period.
• Potential transition to direct Upwork employment and benefits may become available after the hub is established, subject to business needs and other requirements.
• Interview recording and transcript summarization through BrightHire can be declined by candidates.
• Work in a diverse, inclusive, and equitable environment with access to Upwork resources and growth opportunities.