Principal Product Manager, Business Plus

Upwork • Toronto, ON

17d • Hybrid

About The Position

Upwork Inc.’s (Nasdaq: UPWK) 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. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.
Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.
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.

Requirements

• Demonstrated track record of owning and shipping 0 to 1 or highly ambiguous products that deliver meaningful business impact in growth, monetization, or platform environments
• Strong product judgment with the ability to balance customer needs, business goals, and technical constraints while operating with high autonomy
• Experience building in marketplace, labor marketplace, or SaaS environments, with an understanding of multi-sided dynamics and scaling challenges
• Data-driven approach to product development, with fluency in analytics, experimentation, and using insights to guide strategy and execution
• Ability to integrate AI into product and decision-making workflows, using it to accelerate insight generation, refine strategy, and improve outcomes through iteration

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
• Influence senior stakeholders through clear product vision, structured communication, and consistent delivery of high-quality, business-critical outcomes

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed
• Number of Employees: 251-500 employees