Senior Director, Product Management (Remote) at PolicyMe

Toronto, Ontario, Canada

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Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

InsuranceIndustries

Requirements

8+ years of progressive product management experience, including at least 4+ years in a Sr. leadership role
Track record of success in B2C or D2C digital products - nice to have experience in fintech or insurtech; 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 both internal teams and external stakeholders
Experience managing and growing high-performing teams while balancing execution and coaching
Strong business acumen - you understand 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

Responsibilities

Define & Lead the Product Vision: Evolve 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 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 teams progress towards the long-term vision
Get hands-on: dive into product reviews, write business cases, help unblock teams, etc
Other duties as required
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 building the right things, the right way, at the right time - balancing short-term wins with long-term platform evolution

Skills

Key technologies and capabilities for this role

Product ManagementProduct StrategyProduct VisionOKRsRoadmappingTeam LeadershipCoachingCustomer InsightsInsurance DomainExperimentationUser Empathy

Questions & Answers

Common questions about this position

Is this role remote?

Yes, this is a remote-first role based out of Toronto.

What experience is required for this position?

Candidates need 8+ years of progressive product management experience, including at least 4+ years in a senior leadership role, a track record in B2C or D2C digital products, and experience scaling products and teams at high-growth companies.

What is the salary for this Senior Director role?

This information is not specified in the job description.

What does the company culture emphasize?

The company fosters a remote-first environment, a product-led culture rooted in experimentation, impact, and user empathy, and values building high-performing teams.

What makes a strong candidate for this role?

A strong candidate has proven ability to develop and communicate a compelling product vision, experience managing and growing high-performing teams, and strong business acumen connecting product to revenue, operations, customer success, and compliance.

PolicyMe

Online platform for affordable life insurance

About PolicyMe

PolicyMe simplifies life insurance for Canadians by offering affordable coverage options, including critical illness insurance, through an easy-to-use online platform. Customers can access straightforward advice and apply for policies digitally, which helps reduce costs and allows the company to offer lower premiums. Unlike traditional insurance providers, PolicyMe operates with a digital-first approach, minimizing overhead expenses and passing the savings on to clients. The company is backed by reputable partners, enhancing its credibility and financial stability. PolicyMe aims to ensure transparency and customer satisfaction, handling claims with care and using customer feedback to improve services. Additionally, the company fosters a positive work environment through team-building events, even while operating remotely.

Toronto, CanadaHeadquarters

2018Year Founded

$20.5MTotal Funding

SERIES_ACompany Stage

Fintech, Financial ServicesIndustries

51-200Employees

Benefits

Paid Vacation

Stock Options

Remote Work Options

Professional Development Budget

Flexible Work Hours

Risks

Increased competition from other insurtech startups may erode PolicyMe's market share.

Rapid technological advancements require continuous investment in platform upgrades.

Potential regulatory changes in Canada could increase compliance costs for PolicyMe.

Differentiation

PolicyMe offers the most competitive life insurance pricing in Canada.

The company provides a fully-underwritten term life policy without unnecessary features.

PolicyMe's digital-first approach reduces overhead, offering lower premiums to customers.

Upsides

PolicyMe raised $18 million in Series A funding, boosting its market position.

The launch of Critical Illness Insurance covers 44 conditions, more than average insurers.

Increased demand for digital insurance aligns with PolicyMe's online platform strategy.

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