Senior Product Manager

We're building applied AI systems for high-stakes, real-world decisions. Our platform ingests and reasons over large, messy data to surface evidence with hard constraints around fairness, auditability, and low bias.

The single gnarliest, most impact-heavy place this problem shows up is in insurance claims, so that's where we're deployed today, running in production at some of the largest carriers in North America.

We're seeking an ambitious Senior Product Manager to lead the creation of a new product line. In this role, you'll own discovery through delivery across multiple workstreams, applying the latest in AI, SaaS workflows, and data sourcing to transform the insurance industry. You'll partner closely with sales, marketing, customer success, engineering, and design to ship products that delight enterprise customers.

We have engineering hubs in New York City, Vancouver, and Toronto, and this role is 5 days per week onsite in our Toronto office. We optimize for people who like to think deeply, whiteboard with other sharp colleagues, and ship ambitious products together in person.

What you'll do:

• Lead cross-functional initiatives on a B2B enterprise product, driving execution, continuous discovery, JTBD frameworks, and A/B testing.

• Oversee discovery and delivery across multiple workstreams, working closely with internal development teams and external partners.

• Define and test novel solutions using ML/AI, data, and SaaS workflows that deliver meaningful value for insurance companies.

• Conduct market research and competitive analysis to ensure Owl maintains a sustainable competitive advantage.

• Move fluidly between long-term strategy and hands-on execution, bringing structure to ambiguity and removing roadblocks to keep initiatives moving.

• Create clear, concise product specifications and customer-facing materials, and triage feedback to rapidly iterate on the product and messaging.

Ideal Profile:

• 6+ years of Product Management experience, most at a Senior level or higher, with a proven track record of delivering products that delight customers.

• 2+ years of B2B PM experience, including working with large enterprises.

• Successfully launched a new product at a growth-stage startup.

• Experience with both SaaS and AI products.

• Outstanding written and verbal communication with business, technical, and executive stakeholders, and a demonstrated analytical, data-driven approach to problem-solving.

• Insurtech and/or healthcare data experience is a plus.

• Located in Toronto and excited to work 5 days a week in-office with our local team.

Benefits

• Industry Leaders : Our technical leadership comes from Meta, Microsoft, X, and Goldman Sachs, bringing world-class expertise to our agile team.

• Market Leadership : We hold the largest market share in our space, offering a proven ROI and maintaining a 100% customer retention rate , with renewals consistently doubling their previous terms.

• Lean & Impact Driven Team : Our small, nimble team makes swift decisions and encourages direct communication and innovation through a flat organizational structure. You’ll make real, meaningful contributions right from the start.

• Established Product-Market Fit : AI-Driven Product that helps shape an AI-powered enterprise solution for insurance companies across the US and Canada.

• Healthcare benefits: We cover 100% of the premiums for you and your family (medical, dental & vision)

• RRSP matching to help you save for your future

• Recharge: 4 weeks of paid time off & 5 additional personal/sick days ⛱️

• Daily team lunches

• Bi-annual offsites: we'll make sure everyone at Owl has an opportunity to can hang out with teammates IRL at least twice a year

Salary Range: CAD $170,000 - $220,000

Our salary ranges are benchmarked and are determined by role and level. The range displayed on each job posting reflects a range target for new hire salaries for the position and could be higher or lower based on a multitude of factors, including job-related skills, experience, location, and relevant education or training.