upwork

Principal Product Manager, Business Plus

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At a Glance

Location
Toronto, Ontario, Canada
Posted
2026-04-13T14:42:15-04:00

Key Requirements

Required Skills

Machine Learning

Domain Knowledge

  • Accounting
  • Engineering
  • Finance
  • Marketing
  • SaaS

Responsibilities

Define and drive long-term product strategy for SMB and Business Plus offerings, delivering measurable improvements in adoption, retention, and revenue growth

Own and evolve the end-to-end product roadmap, translating ambiguous opportunities into shipped, high-impact features that improve multi-project workflows

Establish and operationalize success metrics such as adoption, expansion, and monetization, using data to continuously refine product direction and priorities

Lead cross-functional initiatives across engineering, analytics, research, and go-to-market teams to deliver scalable product experiences aligned to customer needs

Shape pricing and packaging strategies, developing clear value propositions that increase conversion and willingness to pay across segments

Drive experimentation strategy, including A/B testing and pricing experiments, to generate validated learnings that inform product and growth decisions

About the Company

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We are seeking a Principal Product Manager to lead the strategy and evolution of our Business Plus offering for small and mid-sized businesses. This is a high-impact individual contributor role where you will define how growing clients transition from transactional hiring to managing ongoing, multi-project work across teams. You will operate at the intersection of product, growth, and monetization, shaping end-to-end experiences that deliver meaningful customer value while driving durable revenue outcomes.

This role is ideal for a builder who thrives in ambiguity, operates with a GM mindset, and is motivated by owning outcomes end-to-end. You will take undefined problem spaces and turn them into shipped products, balancing long-term vision with near-term execution. As a domain leader, you will influence company direction, partner deeply across functions, and remain close to the work, ensuring strategy translates into measurable impact at scale.