Full-Time
Staff Product Manager
PolicyMe
51-200 employees
Online platform offering affordable life insurance
Compensation Overview
CA$160k - CA$180k/yr
Toronto, ON, Canada
Remote
Remote-first role; option to work from home or at the Toronto office; in-person team socials twice a year.
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- Relevant product experience: 4-6 years of experience in product management, with experience building customer-facing direct-to-consumer products and exposure to internal-facing products. You can speak to your track record of leading projects and delivering measurable results.
- Exceptional collaboration skills: You have high emotional intelligence and can "be the glue" between many different stakeholders in the organization.
- Strong documentation skills: You write clear, concise, and well-informed product specifications/requirements.
- Ability to structure ambiguous problems: You have the ability to take an ambiguous problem and structure it. You are someone who can start with an idea and manage it from concept to deployment.
- Demonstrated experience leading: You are comfortable bringing people together, leading teams and managing projects with many moving parts. You have a sense of ownership and are excited about driving a project from start to finish.
- Strong communication: You know how to tailor your communication style to meet different audiences. You know when to lead conversations, but also when to listen. You know how to set expectations with different stakeholders and when to ask these stakeholders for help. You can take a complex topic and explain it succinctly in an easy-to-understand manner.
- A strong sense for prioritization: You know how to prioritize different builds and define what is truly part of an MVP to optimize developer productivity. You know how to balance agile market feedback with our customers' product expectations.
- Curiosity and comfort with technical topics: While you do not need a technical background, you are naturally curious about how everything works. You know when to ask clarifying questions and are not shy about diving into complex topics.
- An analytical mindset: You are comfortable working with product data, defining its structure and running analyses to answer key questions.
- Shape our Product Vision: Evolve our product strategy to improve how our post-sale experience delivers greater customer delight, retention, referral growth and cross-product adoption.
- Partner with leadership to develop a compelling vision for how our accounts platform can evolve and set a new standard for how Canadians manage insurance.
- Bring the vision to life by building and championing a product roadmap that balances innovation and operational excellence.
- Solve Ambiguous Problems: Develop a deep understanding of both PolicyMe customers and internal customers - use this knowledge to build products and features that your users love.
- Take open-ended, unstructured problems and break them down into clearly defined bodies of work.
- Come up with creative solutions to solve our most complex problems.
- Drive End-to-end Execution and Delivery: Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration
- Ensure we build the right things, the right way, at the right time - balancing short-term wins with long-term platform evolution.
- Collaborate closely with Product Design to build best-in-class customer experiences.
- Write clear, actionable product specs that connect business goals, customer needs, and technical constraints.
- Partner closely with engineering management to ensure initiatives are well-scoped, appropriately sized, and resilient.
- Coordinate go-to-market with Growth, CS, and Operations, ensuring launches are operationally ready and well-supported.
- Measurement, Experimentation and Iteration: Define success metrics and measurement plans for each initiative.
- Design and run experiments to validate hypotheses and de-risk larger bets.
- Partner with Data to build dashboards, analyze performance, and translate results into next steps — including when to pivot, double down, or sunset work.
PolicyMe provides life insurance products for Canadians through an online, digital-first platform that aims to simplify purchasing and lower costs. It offers affordable options such as critical illness insurance with guided support and a streamlined application process, helping customers secure coverage with reduced overhead. Revenue comes from commissions earned from partner insurers, while the platform stands out through a transparent, customer-centric experience backed by established partners. The goal is to make life insurance more accessible and affordable for Canadians while ensuring clear communication and supportive claims handling.
Company Size
51-200
Company Stage
Series A
Total Funding
$21.1M
Headquarters
Toronto, Canada
Founded
2018
Simplify's Take
What believers are saying
- Expansion into health, dental, and disability insurance diversifies revenue beyond term life.
- AI-powered underwriting reduces application time and improves risk assessment accuracy.
- $51M total funding from Blue Cross Life and Securian validates model and enables scaling.
What critics are saying
- Health and dental expansion dilutes core expertise and invites competition from established incumbents.
- Wave partnership attracts high-lapse small business owners facing business failure risks.
- Dependence on Canadian Premier and Securian for underwriting creates existential partner risk.
What makes PolicyMe unique
- Commission-free advisors and transparent pricing eliminate conflicts of interest versus traditional insurers.
- Covers 44 critical illness conditions, 10-15 more than average Canadian competitors.
- Wave partnership reaches 300,000+ small business owners through existing trusted platform.
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Your Connections
People at PolicyMe who can refer or advise you
Benefits
Paid Vacation
Stock Options
Remote Work Options
Professional Development Budget
Flexible Work Hours
Growth & Insights and Company News
6 month growth
↓ -3%1 year growth
↓ -1%2 year growth
↑ 0%PolicyMe partners with Wave. March 31, 2026 New collaboration brings life and critical illness insurance to small business owners. PolicyMe and Wave have partnered to give small business owners access to affordable life insurance and critical illness coverage. Together, they're helping protect entrepreneurs and self-employed Canadians protect their families and their businesses from unexpected financial challenges. How can small business owners get life insurance? For small business owners, securing life insurance has traditionally been complicated and time-consuming. Unlike employees who often have access to group insurance benefits through their workplace, small business owners typically need to navigate the insurance market on their own. Many put it off entirely, leaving both their families and their businesses vulnerable. This partnership changes that. Through Wave Perks, small business owners can now access PolicyMe's life and critical illness insurance products with a fully digital application process that takes just minutes to apply. PolicyMe's online process removes the need for in-person meetings, making it easier for busy entrepreneurs to secure coverage quickly and affordably. "At Wave, we've always believed small businesses deserve the same financial tools and protections as large enterprises. By partnering with PolicyMe, we're giving entrepreneurs access to insurance coverage that protects what they've worked so hard to build." - Adnan Glavas, Director of Strategic Partnerships at Wave Do small business owners need life and critical illness insurance? Running a small business comes with unique financial risks. Many entrepreneurs personally guarantee business loans, leases, and credit lines. Without life insurance for small business owners or critical illness coverage, these obligations could fall on their families in the event of serious illness or unexpected death. Unlike traditional employees with employer-sponsored benefits, self-employed individuals and small business owners need to proactively secure their own safety net. Life insurance and critical illness insurance provide that protection - ensuring personal assets are safeguarded and businesses can continue operating during difficult times. "Small business owners shouldn't have to choose between growing their business and protecting their family. Our referral partnership with Wave brings affordable, modern insurance to small business owners through a platform they already trust and use." - Andrew Ostro, CEO of PolicyMe Benefits of life & critical illness insurance for small business owners The new offering through Wave Perks is designed to help small business owners: * Protect personal assets: Ensure families aren't burdened by business debts or personal financial obligations in the event of illness or death. * Maintain business continuity: Access lump-sum payouts that can cover operational costs, payroll, or outstanding loans - keeping the business running during challenging times. What insurance options are available? Life insurance PolicyMe offers life insurance with flexible coverage amounts and terms ranging from 10 to 30 years, giving small business owners the ability to tailor coverage to their needs and budget. Coverage provides a tax-free payout to beneficiaries and can help cover debts, replace income, or support business continuity. Critical illness insurance Critical illness insurance provides a lump-sum, tax-free payment if you're diagnosed with a covered condition. These funds can be used however you need - whether for medical expenses, living costs, or keeping your business running. Wave supports entrepreneurs at every stage This partnership reflects Wave's ongoing commitment to championing small businesses throughout their journey, from starting to thriving. More than 300,000 small businesses rely on Wave for invoicing, payments, and accounting. Now, those same entrepreneurs can access critical financial protection with life and critical illness insurance through Wave Perks, alongside the tools they already use. Wave continues to evolve alongside the needs of the small business community, ensuring they have the resources to build sustainable, resilient businesses. Through this partnership, PolicyMe extends that support by providing accessible, modern insurance designed for small business owners. Together, PolicyMe and Wave are helping entrepreneurs build stronger, more resilient businesses. Small business owners can explore PolicyMe's life and critical illness insurance offerings, as well as many other offerings, through Wave Perks. Learn more.
The data comes from the 2025 Insurance Access and Affordability Study by PolicyMe, a Toronto-based insurance technology company, in partnership with the Angus Reid Forum.
PolicyMe, a Canadian digital insurance provider, has raised C$30 million in new funding, following its C$3.3 million Seed Round (2020) and C$18 million Series A (2022). The funding, from partners like Blue Cross Life and Securian Canada, will support expansion into health and dental coverage. This aligns with PolicyMe's mission to offer simple, affordable insurance and strengthens its strategic partnerships to reshape Canada's insurance landscape.
StreamSettle, developer of encrypted negotiation software designed to streamline the resolution of disputed insurance claims, graduated from Global Insurance Accelerator as part of its Accelerator Program and received $50,000 in funding in the form of SAFE notes.
PolicyMe raises $30M to expand digital insurance products.