Founding Product Lead - B2b2c Insurtech

About Simple VenturesSimple Ventures is a Canadian venture studio building the next generation of great Canadian companies.
Our thesis is simple: Canada is overlooked and under-appreciated. We identify compelling business opportunities from around the world and partner with exceptional operators to build and scale them in Canada.
We're backed by leading Canadian founders and operators, including leaders behind Wealthsimple, Shopify, Ada, and more.
The OpportunityWorking alongside one of Canada's leading insurers, we're building a new platform with the potential to reach millions of consumers.
Insurance is one of Canada's largest and most established industries, yet much of the customer experience remains fragmented, reactive, and underserved by modern technology. Advances in AI create an opportunity to move beyond one-off transactions toward intelligent, personalized experiences that anticipate people's needs and help them take action.
We're looking for a Founding Product Lead to help shape this product from its earliest stages. You'll work directly with the founding team and enterprise partners to define the product, design and test early experiences, and turn what works into a scalable platform.
This isn't a traditional product role. You won't just manage a roadmap or coordinate engineering teams. You'll be hands-on in shaping the experience, building prototypes, and shipping new capabilities, with real ownership over what gets built and how it evolves.
What You'll Do
Work directly with enterprise partners:
Translate business needs and stakeholder feedback into practical product decisions, balancing partner requirements with what consumers actually want.
Build and ship product:
Take ideas from concept to working product, rapidly prototyping, testing, and improving consumer-facing experiences and supporting tools.
Shape the product experience:
Design intuitive, engaging experiences that simplify complex processes and give users compelling reasons to return.
Build with AI:
Use modern development tools to accelerate execution, and ensure the resulting experiences are useful and reliable.
Run experiments and pilots:
Get products into users' hands, learn from their behaviour, and use real-world feedback to determine what to build next.
Connect product and operations:
Design the workflows and supporting systems that make the end-to-end customer experience work, not just the interface.
Own product priorities:
Help define the roadmap, make thoughtful trade-offs, and measure whether what we're building is creating meaningful value.
Who You Are
You're a builder. You've taken products 0 → 1 and enjoy being directly involved in creating things, not just managing their development.
You have strong product and design instincts. You can turn complicated problems into simple, intuitive experiences and care deeply about the details.
You're AI-native. You actively use tools like Claude Code, Cursor, or Codex to prototype, build, and work faster. You're excited by what emerging technology makes possible.
You're technically fluent. You understand how software gets built, can work effectively with engineers, and ideally have experience shipping working products yourself.
You understand users and businesses. You can speak with customers, collaborate with senior stakeholders, and turn competing needs into clear product decisions.
You move quickly. You're comfortable testing imperfect ideas, learning from real feedback, and iterating rather than waiting for perfect information.
You're resourceful and independent. You thrive in early-stage environments where there isn't a playbook and are comfortable taking ownership from problem to solution.
Bonus: Experience with mobile products, AI-powered applications, B2B2C platforms, or building products alongside enterprise customers.
This is perfect for someone ready to move beyond managing someone else's roadmap and eager to lead product at a new venture from the ground up.
Why Join Now
Large commercial opportunity: Help develop and validate a new product alongside established industry partners.
Build from the ground up: Join at a stage where you can meaningfully shape the product, the technology, and the company.
Real ownership: Make product decisions, build, experiment, and see the direct impact of your work.
AI-native development: Use emerging tools and technologies to build faster and rethink what's possible.
Strong backing: Work alongside Simple Ventures and its network of experienced founders and operators.
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