Principal Product Manager - Accounts & Automation, Remote
About the job
- 8+ years of product management experience, including experience owning and scaling customer-facing digital products in high-growth environments.
- Strong track record of leading complex cross-functional initiatives and delivering measurable business and customer outcomes.
- Experience building both customer-facing D2C products and operational/internal tooling products.
- Experience building prototypes with AI.
- Experience scaling products and product practices within high-growth startups or fast-moving technology organizations.
- Proven ability to define and communicate a compelling product vision that aligns teams and stakeholders around long-term outcomes.
- Strong business acumen with a deep understanding of how product decisions impact revenue, operations, customer success, retention, and compliance.
- Exceptional ability to structure ambiguous problems and turn them into clear, actionable plans.
- Strong operational discipline with the ability to manage competing priorities, maintain momentum, and consistently close loops with stakeholders.
- Excellent collaboration and stakeholder management skills with high emotional intelligence and a transparent leadership style.
- Strong documentation and communication skills - able to tailor messaging effectively across executives, engineers, designers, marketers, and operational stakeholders.
- Comfortable leading initiatives with many moving parts and driving alignment across multiple teams.
- Strong sense of prioritization and ability to define MVP scope while balancing speed, quality, and long-term scalability.
- Highly analytical and data-driven, with comfort working with product data, defining metrics, building measurement frameworks, and conducting analyses to inform decisions.
- Define the product vision and evolve strategy to improve customer delight, retention, referral growth, operational efficiency, and cross-product adoption.
- Develop a long-term vision for how to make insurance simple for Canadians, from product discovery to post-sale management.
- Build and champion a roadmap balancing innovation, operational excellence, and long-term scalability.
- Develop deep understanding of customer and operational pain points to shape strategy and prioritization.
- Establish clear OKRs and success metrics that align teams around measurable business and customer outcomes.
- Take open-ended, unstructured problems and break them down into clear opportunities, strategic priorities, and executable plans.
- Bring first-principles thinking to solve complex challenges not solved before in the Canadian insurance market.
- Balance customer needs, technical constraints, operational realities, and business priorities when making product decisions.
- Lead through ambiguity and create clarity for teams and stakeholders across the organization.
- Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration.
- Be highly execution-oriented and willing to dive into the details when needed.
- Balance short-term wins with long-term platform investments to ensure the right things are built, the right way, at the right time.
- Collaborate closely with Product Design and Engineering to build best-in-class customer and internal product experiences.
- Write clear, actionable product specifications that connect business goals, customer needs, operational requirements, and technical constraints.
- Coordinate with Growth, Customer Success, Operations, and other stakeholders to ensure launches are operationally ready and well-supported.
- Drive alignment across teams and act as the connective tissue between stakeholders with competing priorities.
- Define success metrics and measurement frameworks for all major initiatives, including customer engagement, funnel conversion, retention, operational efficiency, and long-term customer value.
- Design and run experiments to validate hypotheses, de-risk larger investments, and accelerate learning.
- Partner closely with Data to build dashboards, analyze product performance, and translate insights into actionable next steps.
- Use data, customer insights, and business context to continuously refine strategy and prioritization.
About the company
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
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Simplify's Take
What believers are saying
- June 2026 launch broadened approvals; many applicants got instant offers without medical exams.
- PolicyMe raised C$30 million through 2025, funding health, dental, and AI expansion.
- Wave’s 300,000-business network gives PolicyMe a fresh B2B2C channel with immediate reach.
What critics are saying
- PolicyMe depends on Securian Canada and Blue Cross Life for product and capital support.
- Complex underwriting rules across life, critical illness, health, and dental raise execution risk.
- Carrier partner withdrawal or regulatory rejection would cripple PolicyMe’s distribution and product roadmap.
What makes PolicyMe unique
- PolicyMe’s June 2026 unified underwriting prices life coverage instantly across risk tiers.
- PolicyMe and Securian Canada power white-labeled digital insurance for Blue Cross Life partners.
- PolicyMe’s March 2026 Wave Perks embed life coverage inside Wave’s small-business workflow.
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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
3%2 year growth
6%PolicyMe, a Canadian digital-first life insurance platform, has launched the country's first unified application that evaluates every applicant across the full life insurance spectrum in a single real-time session. Developed with Securian Canada, the system automatically matches applicants to the best risk-adjusted price they qualify for, from fully underwritten to guaranteed issue coverage. The platform uses over 1,000 reflexive underwriting rules, with most applicants answering around 30 questions. Most PolicyMe applicants in 2025 were approved without medical exams, with the majority receiving instant offers. The system also provides simultaneous real-time decisions on critical illness coverage. PolicyMe's data shows one in four applicants aged 51 and older with pre-existing conditions still qualified for fully underwritten coverage. The platform has helped over 47,000 Canadians secure more than $15 billion in coverage.
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.