---
title: 'Senior Software Engineer (Remote) at PolicyMe'
canonical: 'https://feeny.ai/job/senior-software-engineer-remote-policyme-ontario-61wjhacyf0ns'
type: 'job'
last_seen: '2026-09-07'
---

# Senior Software Engineer (Remote) at PolicyMe

- **Company:** PolicyMe
- **Location:** Ontario, Canada
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-08-06
- **Last confirmed live:** 2026-09-07
- **Apply:** https://jobs.lever.co/policyme/5035599c-756a-495d-aab3-ce4de6406de9

## Job description

## 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 building the future of insurance in Canada and beyond.

We're building a groundbreaking new product line that will transform the insurance broker experience through AI and machine learning. As an AI-Driven Full Stack Engineer, you'll be part of a team charting new territory - designing and implementing intelligent systems that automate manual processes and unlock powerful data-driven insights.

You will work across the stack, contributing to front end, back end, and AI/ML initiatives, while also participating in architecture discussions, release planning, and company-wide engineering initiatives. Our core stack includes Python, React, Redux, PostgreSQL, n8n, LangChain/LangGraph and AWS, and we are always open to adopting new tools and technologies that help us deliver better results

What you'll be doing:

- Leading the design and development of full stack features for our AI-powered web application using Python, React, Redux, PostgreSQL, and AWS
- Defining the technical vision and architectural principles for AI/ML systems
- Driving innovation by researching and prototyping cutting-edge AI technologies
- Ensuring security, scalability, and observability best practices across cloud architecture
- Work within a cross-functional environment partnering closely with product, design, and business teams to communicate technical designs/strategies
- Serve as a role model for engineering standards and bring consistency across systems and processes while mentoring junior and intermediate engineers
- Help drive sound technical decision-making across ambiguous, system-spanning problems

What we are looking for:

- A strong technical background with 5+ years of experience in fullstack web development and production AI/ML systems
- Deep expertise in AI/ML domains like NLP, computer vision, recommendation engines etc.
- Proficiency with cloud infrastructure, distributed systems, microservices
- Proven ability to architect and lead end-to-end AI projects, including security best practices
- Exceptional technical communication and knowledge sharing abilities
- Track record of managing ambiguity and delivering innovative solutions
- An appreciation for fast-paced startup environments and experience building foundational systems
- Demonstrated ability to take ambiguous technical challenges and drive them to resolution with cross-functional teams
- Strong development skills in React, Python, and Node, or equivalent technologies with the ability to ramp up quickly

Why join us:

- Generous PTO - 20 vacation days
- A comprehensive benefits plan with premiums paid in full by PolicyMe
- Investment in your professional development, including an L&D budget, AI tooling budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
- An extremely high performing, low-ego, remote-first team that is truly disrupting an old industry
- Option to work from home or our Toronto-based office (bonus: we cover the costs to bring all our employees in-person twice a year for experiential socials!)
- Access to stock options based on performance
- Compensation: The total target cash compensation for this role is $154,000 - $176,000 CAD, based on experience. We’ll walk through the details together during the interview.

## About PolicyMe

## Company Overview
- **One-liner**: PolicyMe is a Canadian digital insurance platform that makes life, health, and home & auto coverage simple, affordable, and honest by combining smart technology with licensed advisors.
- **Entity Type**: Private (venture-backed, $43.7M total funding)
- **Headquarters**: Toronto, Ontario, Canada
- **Founded**: 2018
- **Founders**: Andrew Ostro (CEO), Laura McKay (COO), Jeff McKay (CTO)

## Core Business
- **Primary industry/industries**: Insurance (Life, Critical Illness, Health & Dental, Home & Auto)
- **Target customers**: B2C – individual Canadians seeking personal insurance coverage
- **Mission or purpose statement**: "Ensuring every Canadian has access to fair and comprehensive coverage, backed by smart technology and people who care."

## Products & Services
- **[Life Insurance]**: Direct-to-consumer term life insurance, fully online, with guaranteed coverage options. Issued by Securian Canada.
- **[Critical Illness Insurance]**: A tax-free lump-sum payout upon diagnosis of a covered condition. PolicyMe covers more conditions than any other Canadian provider.
- **[Health & Dental Insurance]**: Coverage for prescriptions, dental care, vision, and paramedical services. Individual and family plans available.
- **[Home & Auto Insurance]**: Brokerage service – compares partner insurers to find the best price for home and car coverage (currently available only in Ontario).
- **[White-Label Platform]**: Powers insurance products behind some of Canada’s largest insurance brands – their technology and products under a partner’s name.

## Market Standing
- **Valuation/Market Cap**: Not disclosed
- **Key Metrics**:
  - Annual Revenue: $19.5M (LinkedIn estimate)
  - Total Funding: $43.7M across 8 rounds
  - Coverage issued: $15B+ in coverage
  - Customers: 50,000+ families covered
- **Notable Investors/Partners**: Not explicitly listed in available sources; backed by venture capital (details not public). Insurance partner: Securian Canada (Canadian Premier Life Insurance Company).
- **Growth Signals**:
  - Headcount: 100 employees (+28.7% YoY)
  - Named to Globe & Mail’s Top Growing Companies list (2025)
  - Deloitte’s Technology Fast 500 (2025)
  - A+ rating from Better Business Bureau
  - Expanding product lines and geographic coverage

## Competitive Advantages
- **Direct-to-consumer model** for life, critical illness, and health & dental – eliminates middlemen and overhead, lowering premiums.
- **Technology-driven but human-backed** – online application in ~20 minutes with optional support from licensed advisors (no chatbots, no call centres).
- **Broader coverage** – critical illness policy covers more conditions than any other Canadian insurer.
- **White-label platform** strength – underlying technology powers products for major Canadian insurance brands, demonstrating trust and scalability.
- **Remote-first culture** with no in-office mandate, attracting top talent across Canada.

## Strategic Focus
- Continue to grow the direct-to-consumer insurance business across all Canadian provinces and territories.
- Scale the home & auto brokerage to more regions (currently Ontario-only for those products).
- Deepen partnerships with large insurance brands via the white-label platform.
- Invest in technology and automation to further simplify the customer experience and reduce costs.

## Why Work Here
- **Remote-first**: No in-office mandate; work from anywhere in Canada with the option to use a downtown Toronto office.
- **Compensation & Benefits**: Competitive total compensation reviewed annually; comprehensive benefits from day 1; 4 weeks paid time off.
- **Professional Development**: Learning resources, unique growth opportunities, and support for continuous skill-building.
- **Culture**: Emphasis on trust, open dialogue, and continuous feedback. Regular in-person and virtual team events (e.g., summer island party, holiday celebrations).
- **Engineering Culture**: Modern tech stack (details not public), focus on building large-scale distributed systems; leadership includes CTO with Bloomberg background.
- **Open Roles**: Software Engineer (Junior, Senior, Manager), Principal Product Manager, Licensed Insurance Advisors, Talent Acquisition Manager – all remote.

## Sources
1. [PolicyMe Careers Page](https://www.policyme.com/careers)
2. [PolicyMe About Us](https://www.policyme.com/about-us)
3. [PolicyMe Main Site](https://www.policyme.com/)
4. [PolicyMe LinkedIn Company Page](https://linkedin.com/company/policymeinsurance)
5. [PolicyMe Job Postings on Lever](https://jobs.lever.co/policyme)

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