Senior Product Manager

Owl.co

• $170K — $220K *
Finance & Insurance
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 6+ years of senior-level Product Management experience with a successful product delivery track record.
  • 2+ years of experience in B2B Product Management with large enterprises.
  • Proven achievement in launching new products at growth-stage startups.
  • Experience with SaaS and AI product development.
  • Strong communication skills with business, technical, and executive stakeholders.
  • Experience in the insurtech or healthcare data sectors is a plus.
  • Located in Toronto and available for in-office work 5 days a week.

Responsibilities

  • Lead cross-functional initiatives for a B2B enterprise product, driving execution and user-focused frameworks.
  • Oversee discovery and delivery processes across multiple workstreams with internal teams and external partners.
  • Define and test innovative solutions leveraging ML/AI and SaaS workflows for the insurance sector.
  • Conduct market research and analyze competitors to maintain a competitive edge.
  • Balance long-term strategy with hands-on execution to navigate ambiguity and keep projects moving.
  • Craft detailed product specifications and customer-facing communications, iterating based on feedback.

Benefits

  • Work with industry leaders from major tech companies, enhancing your skills and knowledge.
  • Join a market leader with established product-market fit and a strong customer retention rate.
  • Be part of a small, nimble team that fosters direct communication and innovation.
  • Enjoy comprehensive healthcare benefits covering 100% of premiums for you and your family.
  • Participate in RRSP matching to support your retirement savings.
  • Take advantage of 4 weeks of paid time off plus 5 additional personal/sick days.
  • Benefit from daily team lunches that promote camaraderie.
  • Attend bi-annual offsites to strengthen team bonds and collaboration.
Full Job Description
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 â›±
  • 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.

Department Engineering Locations Toronto Yearly salary CAD170,000 - CAD220,000 Employment type Full-time

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