Senior Director, Product Management (Remote)

Senior Director, Product Management (Remote) Join to apply for the

Senior Director, Product Management (Remote)

role at

PolicyMe

Overview of the role:

We’re on a mission to modernize insurance - making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that’s remained largely untouched by the digital revolution, and PolicyMe is here to change that. As a remote-first, Toronto-based startup with big ambitions, we’re looking for a product leader to help us build the future of insurance in Canada - and beyond.

We’re now seeking a

Senior Director

of

Product Management

to scale our product organization and take end-to-end ownership of the product vision, strategy, and execution across new and existing product lines. This is a pivotal role, reporting to the VP of Product and working closely with multiple teams across the organization.

What you'll be doing

Define & Lead the Product Vision: evolve our product strategy to meet ambitious growth, retention, and customer impact goals that you will own

Set a compelling long-term product vision, aligned with business priorities and grounded in customer insights

Champion a roadmap that balances innovation with operational excellence

Understand your product and customer context deeply - build strong domain knowledge and be an expert in your category, applying it to the vision for your portfolio

Bring creative new ideas to solve complex problems that haven't been solved before in Canada

Establish OKRs that help your teams progress toward the long-term version

While you’ll shape the big picture, you’ll also roll up your sleeves—participating in product reviews, writing business cases, and helping unblock teams

Scale the Product Function: build, lead, and coach high-performing product teams (PMs, designers, etc.)

Foster a product-led culture rooted in experimentation, impact, and user empathy

Drive Strategic Product Development: oversee full lifecycle development of improvements to existing insurance products and net-new offerings

Partner with Engineering, Growth, and CS to define go-to-market strategies and deliver frictionless customer experiences

Ensure we build the right things, the right way, at the right time - balance short-term wins with long-term platform evolution

Other duties as required

What we are looking for

8+ years of progressive product management experience, including at least 4+ years in a senior leadership role

Track record of success in B2C or D2C digital products - fintech or insurtech experience is a nice-to-have but not required

Experience scaling products and product teams at high-growth companies (e.g., Series A-D startups or tech-forward incumbents)

Proven ability to develop and communicate a product vision that inspires internal teams and external stakeholders

Experience managing and growing high-performing teams while balancing execution and coaching

Strong business acumen - understands how product connects to revenue, operations, customer success, and compliance

Comfortable leading through ambiguity and structuring ambiguous problems into measurable outcomes

Data-driven decision-maker with fluency in OKRs, KPIs, funnels, and experimentation

Adept at prioritizing tradeoffs, managing competing needs, and maintaining velocity without sacrificing quality

High emotional intelligence with a collaborative, transparent leadership style

Strong communicator who can tailor messages to executives, engineers, marketers, and everyone in between

Committed to building a diverse, inclusive, and mission-driven team culture

Why join us

Generous PTO - 20 vacation days

Access to stock options and a comprehensive benefits plan

A remote-first team with company-paid in-person socials and the option to work from our Toronto-based office

Resources to help your professional development, including an L&D budget, performance reviews twice a year and ongoing feedback to help you reach your potential

Work with an empathetic, high-performing team in a flexible, results-oriented environment

About PolicyMe PolicyMe is Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, with B2B2C solutions also available. Since our launch in 2018, we have grown significantly, serving Canadians with digitally-enabled insurance options. We operate a remote-first culture and welcome talent from across Canada.

Commitment to Equal Opportunity PolicyMe is an equal opportunity employer. All applicants will be considered for employment without regard to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest; however, only those selected for an interview will be contacted.

Accessibility PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please indicate this in the Additional Information section of the application. We are committed to providing support and reasonable adjustments throughout the process.

Seniority level Not Applicable

Employment type Full-time

Job function Product Management and Marketing Industries: Insurance

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