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About the RoleAs Director of Product, Commerce, you will lead the product function for our Commerce domain, spanning retail partnerships, logistics, and the gig economy, and reporting to the SVP of Product. You will own product strategy, development, and the end-to-end customer experience, working closely with senior stakeholders, partners, and cross-functional teams to design and launch innovative protection products that drive business growth and partner value. You will also lead, coach, and develop a team of product managers, building a high-performing product organization for the domain.
This is not a traditional portfolio management role. You will be responsible for shaping where commerce protection goes next, including how AI and agentic commerce change the way customers discover and buy protection, and turning those opportunities into scalable products with our partners.
Key Responsibilities:- Own the product vision, strategy, and roadmap for the Commerce domain, spanning our retail partnerships, logistics, and gig economy verticals, aligned with overall company goals and reporting to the SVP of Product.
- Lead product development and the customer experience end-to-end, from partner integration and the point of sale through to policy servicing and claims, ensuring a seamless experience for both partners and their customers.
- Design, validate, and launch new and innovative protection products for commerce partners, including identifying gaps in existing offerings and opportunities in emerging areas such as marketplaces, delivery, and the gig economy.
- Lead vendor evaluation and selection for the domain, including defining requirements, assessing build-versus-buy trade-offs, and managing vendor relationships through to delivery.
- Build, lead, coach, and develop a team of product managers, setting clear expectations, raising the bar on product craft, and creating growth paths for each team member.
- Partner closely with senior internal stakeholders across commercial, partnerships, engineering, design, underwriting, claims, and operations to align priorities and drive execution.
- Act as a senior product counterpart to key partners, building trusted relationships, understanding how they make decisions, and translating their needs into products that drive measurable value.
- Prioritize investment across the Commerce portfolio, making trade-offs based on business value, partner impact, technical feasibility, and time constraints.
- Establish and track key product metrics (such as attach rate, conversion, GWP, and customer satisfaction) to measure success, identify areas for improvement, and inform future product decisions.
- Communicate product strategy, progress, and outcomes clearly to executives, partners, and cross-functional teams.
Skills and Experience:- 8-10+ years of Product Management experience, including at least 3 years leading and developing teams of product managers.
- Proven track record of owning a product domain end-to-end and launching new products that drove measurable revenue and customer outcomes.
- Experience in commerce, marketplaces, logistics, fintech, or embedded products, ideally working with large enterprise partners in a B2B2C model.
- Hands-on experience building and launching AI-powered products, including LLM-based features, conversational experiences, or AI agents in production.
- Strong understanding of how AI is reshaping commerce, including agentic commerce, AI-driven checkout and purchase flows, and emerging standards such as MCP and agent-to-agent protocols.
- Ability to identify where AI creates real customer and business value, and to make sound trade-offs between AI-driven and conventional solutions.
- Experience using AI tools to improve product team productivity, such as rapid prototyping, research synthesis, and data analysis, and coaching others to do the same.
- Experience leading vendor selection and managing third-party providers as part of product delivery, including evaluating AI and LLM vendors.
- Strong understanding of the full product development lifecycle, roadmap prioritization, and customer-driven innovation in a fast-paced environment.
- Understanding of, or hands-on experience with, software development, APIs, and web technologies.
- Experience in high-growth SaaS startups or similar global tech companies.
- Experience in insurance or insurtech is advantageous.
- Bachelor's degree or equivalent practical experience. A background in computer science, engineering, business, or another quantitative discipline is advantageous.
Proficiencies and Attributes:- Driven, energetic, and a "good enough is not enough" mentality.
- Strong sense of ownership over the Commerce domain and its outcomes.
- Exceptional communicator, able to tailor the message for executives, partners, and delivery teams alike.
- Skilled at stakeholder management, building alignment across senior leaders with competing priorities.
- Partner-focused: builds credibility with partners and turns their pain points into product opportunities.
- A natural coach who enjoys developing product managers and building a high-performing team culture.
- Commercially minded: focuses on products that move partner and business metrics, not just features.
- Thinks big-picture while staying close enough to the detail to make sound trade-offs.
- Result-driven with a focus on achieving measurable outcomes.
- Ability to work effectively under pressure and manage multiple priorities.
- Positive approach to change and adaptability.
*The cash compensation range for this role is C$195,000 - C$250,000 base salary.
