Product Manager, Insurance Shopping PlatformAbout the roleWhat you’ll doWhat we’re looking for

Ai Stealth Startup

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CAToronto, Canada Until 8/23/2026 First posted March 18, 2026 Last posted March 18, 2026
Job description

Who are we?

We’re a Silicon Valley–based Series A startup backed by top-tier VCs.

Our approach is different from traditional SaaS startups: instead of building software and searching for customers, we acquire traditional service businesses and rebuild them using AI from the inside out.

Our mission is to accelerate the future of work. We’re not merely envisioning the future—we’re actively constructing it.

Our founding team brings a remarkable track record in building and scaling generative AI product for service business, with multiple founders previously helping scale AI companies to unicorn status (including Cresta).

Now we’re applying that experience to rebuild large real-world industries.

About the role

We’re looking for an experienced Product Manager to own the core consumer experience of our insurance shopping platform.

Insurance is a $1T+ industry, yet the consumer experience is still broken. We’re missioned to disrupt the insurance industry by the vertical integration along the value chain and AI transformation.

You will be responsible for building the product that consumers interact with when they discover, compare, and purchase insurance policies.

This is a high-ownership role: you’ll define product strategy, ship quickly with engineering and design, and drive measurable impact on growth and conversion.

You will work directly with founders and have significant influence over the direction of the company.

What you’ll do

  • Own the end-to-end consumer journey for our insurance shopping product
  • Build intuitive experiences that help users discover, compare, and purchase policies
  • Define and execute the product roadmap for growth and conversion
  • Run experiments and use data to continuously improve the product
  • Work closely with design and engineering to ship high-quality consumer products
  • Translate complex insurance policies into simple, understandable user experiences
  • Build AI-powered decision tools that guide users through insurance choices
  • Partner with operations and insurance experts to ensure recommendations are accurate and trustworthy

What we’re looking for

  • 5-7 years of product management experience
  • Experience building consumer-facing products
  • Strong product sense and taste
  • Expertise in use data and experimentation to drive product decisions
  • Comfortable working in fast-moving startup environments
  • Strong cross-functional collaboration skills

Bonus

  • Experience with fintech, marketplaces, or insurance
  • Experience building comparison or shopping experiences
  • Experience building AI-powered consumer products
  • Experience scaling products in the U.S. market

What’s in it for you?

  • Own the core consumer experience end-to-end with direct business impact
  • Define the next generation of AI-powered service businesses
  • Collaborate with a small team of high-caliber builders
  • Competitive compensation and meaningful equity
About this role

Summary

Manage insurance shopping platform, create AI-powered insights, improve user journey, drive growth and conversion

Job title

Product Manager, Insurance Shopping Platform

Experience level

5-7 years

Industry

software

Location requirements

Toronto, Canada, remote work not specified

Salary

Not specified

Management role

No

Skills & keywords

Required skills

product managementdataexperimentationcross-functional collaboration

Preferred skills

fintechmarketplacescomparisonai-powered products

Specializations

consumer experienceaiinsurance
Locations

Structured locations inferred from the posting.

Toronto, ON, Canada

Work arrangement unknown City