Freelance Software Engineer Jobs in Toronto, ON (NOW HIRING)

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.

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.

• 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.

• 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.
• Track record of owning platform- or infrastructure-level product work, where your roadmap shaped capabilities other teams depended on, not just user-facing features.
• 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.

Upwork is establishing an operational hub in Toronto, Canada. The new office is expected to be fully operational by Q4 2026. This role will require 3 days in office once we have an office open.

This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork, depending on business needs and other requirements. While employed by the partner, you'll work as part of Upwork's team, with access to our resources, culture, and growth opportunities.

Our partner will offer competitive benefits. When Upwork's hub is established, we will be excited to offer employment and benefits directly as business needs require.

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.

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