Principal Product Manager is a software company that enables insurers to fight illegitimate claims at scale while removing human bias from the process. Our clients are the top insurance companies across North America, and they are achieving incredible results through our AI-powered, evidence-based platform. We are on a mission to bring state-of-the-art ML and NLP methods to transform this traditionally manual activity into an equitable process. We are well-funded and have engineering offices in New York City, Toronto, and Vancouver.

About the Role: We're looking for an ambitious Principal Product Manager to lead the creation of a new product line. This is an opportunity to apply the latest in AI technologies, SaaS workflows, and data sourcing to transform a massive industry.

What You'll Be Doing:

  • Conduct quantitative and qualitative research to rapidly learn about the insurance industry from peers, advisors, customers, and Owl data
  • Conduct market research and competitive analysis to ensure that Owl maintains a sustainable competitive advantage
  • Create a clear vision/roadmap for the product
  • Define and test novel solutions using ML/AI, data, and SaaS workflows that deliver meaningful value for insurance companies
  • Create clear, concise product specifications and customer-facing materials
  • Do what it takes to ship high-quality products on time
  • Drive successful early adopter releases
  • Triage feedback to rapidly iterate and improve the product and messaging
  • Work closely with sales, marketing, customer success, engineering, and design across all activities to ensure successful delivery and buy-in

Ideal Experience:

  • 6+ years of Product Management experience, most of which is at a Senior level or higher
  • 2+ years of B2B PM experience, including working with large enterprises
  • Successfully launched a new product at a growth startup
  • Experience with both SaaS and AI products
  • Demonstrated outstanding written and verbal communication skills with all types of business, technical, and executive stakeholders
  • Demonstrated analytical and data-driven approach to problem-solving
  • Previous insurtech experience is a plus


  • $1,200 ($100 monthly) per year into a Wellness or Healthcare Spending Account
  • RRSP matching up to 4% of base salary
  • 4 weeks of vacation, 10 public holidays, plus 5 personal days
  • Hybrid work model
  • Dog-friendly office
  • Weekly team lunches in the office