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Overview
At Gigster, we partner with top-tier freelance talent to deliver transformative software solutions. We are looking for a Product Manager – Applied AI to lead the definition and delivery of AI-driven features, experiments, and solutions across a range of projects. This role is perfect for someone who can bridge the gap between business objectives and advanced AI capabilities - ensuring every solution is purposeful, measurable, and technically feasible.
- Identify and assess AI opportunities across client engagements or internal products.
- Translate complex business and user needs into clear AI product requirements and success metrics.
- Prioritize AI use cases, working closely with engineering and data science to define model objectives and validate feasibility.
Coordinate cross-functional teams—engineering, design, MLOps, and stakeholders—to deliver POCs and features efficiently. - Own the product roadmap for AI initiatives, with a focus on iterative learning, fast experimentation, and value delivery.
- Support stakeholder alignment by clearly articulating AI trade-offs, timelines, and performance KPIs.
- 5+ years of experience in Product Management, with at least 2+ years focused on AI, data, or ML products.
- Proven ability to ship AI-driven or ML-based features or platforms, ideally in startup or consulting environments.
- Deep understanding of AI use cases, model types (e.g., LLMs, agents, classifiers), AI system architectures, and the tooling ecosystem (e.g., LangChain, Vertex AI, OpenAI, HuggingFace, etc.).
- Comfortable evaluating trade-offs between open-source, proprietary, and platform-based AI implementations.
- Familiar with full AI lifecycle: Strategy → Data Prep → Model Build → Deployment → Feedback loops.
- Excellent communication and leadership skills in remote and async teams.
- Experience with standard PM tools like JIRA, Productboard, Confluence, or similar.
- Experience or familiarity with tools like GitHub Copilot, Cursor, or Windsurf is a plus.
Why Gigster?
- Be part of an elite, global talent network delivering cutting-edge solutions.
- Collaborate with world-class engineers, designers, and data scientists.
- Enjoy autonomy and flexibility in a fully remote, async-friendly environment.
- Work on high-impact projects with startups, scale-ups, and enterprise clients.
This is a freelance/contract role. You’ll be matched with projects based on availability, skills, and fit.
What you need to know about the Toronto Tech Scene
Although home to some of the biggest names in tech, including Google, Microsoft and Amazon, Toronto has established itself as one of the largest startup ecosystems in the world. And with over 2,000 startups — more than 30 percent of the country's total startups — Toronto continues to attract new businesses. Be it helping entrepreneurs manage their finances, simplifying business operations by automating payroll or assisting pharmaceutical companies in launching new drugs, the city's tech scene is just getting started.
