--- title: 'Software Engineer Manager (Remote) at PolicyMe' canonical: 'https://feeny.ai/job/software-engineer-manager-remote-policyme-ontario-gxvma1t6r5rz' type: 'job' last_seen: '2026-09-07' --- # Software Engineer Manager (Remote) at PolicyMe - **Company:** PolicyMe - **Location:** Ontario, Canada - **Employment:** full-time - **Work type:** remote - **Posted:** 2026-08-05 - **Last confirmed live:** 2026-09-07 - **Apply:** https://jobs.lever.co/policyme/06e07d96-e93e-40d5-91ae-a6a405a2b372 ## 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 has 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 Software Engineering Manager to help us build the future of insurance in Canada and beyond. As an AI Engineering Manager at PolicyMe, you will be responsible for leading and scaling a high-performance team developing an AI-powered product suite that modernizes the insurance experience. Leveraging cutting-edge AI/ML technologies, your team will build groundbreaking intelligent applications to drive PolicyMe's mission of becoming one of the biggest insurance brands in Canada. You'll bring your leadership experience and deep expertise in AI engineering to guide the team in architecting scalable, secure AI systems. Under your direction, the team will employ AI capabilities like natural language processing, computer vision, and recommendation engines to create innovative products that streamline operations and deliver data-driven insights. You’ll use your leadership and technical experience to guide the team in making strategic decisions, optimizing AI development processes, and maintaining rigorous practices for deploying AI responsibly and at scale. What you'll be doing: - Lead and manage a team of fullstack/AI engineers, provide mentorship, performance feedback and enable career growth for the team - Oversee technical design, development and deployment of fullstack web applications backed by AI technology - Collaborate with product, design, and QA teams to ensure seamless execution and delivery of cross-functional projects. - Drive architecture decisions for scalable, reliable, secure cloud-based AI platforms that align with business objectives - Foster an innovative environment for exploring state-of-the-art AI techniques - Lead technical decision-making ensuring alignment with product/company objectives - Promote continuous learning and uplift team's expertise in emerging AI technologies What we are looking for: - 7+ years in software development, with 2+ years managing engineering teams - Strong technical leadership building and operating production AI systems at scale - Proven expertise in AI/ML disciplines like NLP, computer vision, recommendation systems - Strong technical background in web development, ideally in a full-stack environment with expertise in React, Python, and [Node.js](http://Node.js) - Experience with cloud architecture, DevOps, data/ML pipelines and infrastructure - Exceptional people management skills to motivate, mentor and grow high-performers - Excellent communicator able to simplify technical AI/ML concepts for cross-functional teams - Proven ability to lead teams in an agile, fast-paced environment, with a strong focus on collaboration and stakeholder management - A track record of delivering complex projects with a focus on scalability, reliability, and security Reports to: VP of Engineering 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 ensure you reach your highest potential - Work with an empathetic, high-performing team in a flexible, results-oriented environment - Compensation: The total target cash compensation for this role is $170,500 - $192,500 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) ## Other roles at PolicyMe - [Talent Acquisition Partner](https://feeny.ai/job/talent-acquisition-partner-policyme-toronto-1y268852y63x) — Toronto, Canada - [Customer Success Specialist (Remote)](https://feeny.ai/job/customer-success-specialist-remote-policyme-ontario-6jnrw8nkh5at) — Ontario, Canada - [Junior Software Engineer (Remote)](https://feeny.ai/job/junior-software-engineer-remote-policyme-ontario-8akdx2tg7yhg) — Ontario, Canada - [Senior Software Engineer (Remote)](https://feeny.ai/job/senior-software-engineer-remote-policyme-ontario-61wjhacyf0ns) — Ontario, Canada - [Principal Product Manager, Accounts & Automation (Remote)](https://feeny.ai/job/principal-product-manager-accounts-automation-remote-policyme-toronto-s0jrdc1h9kbz) — Toronto, Canada - [Software Engineer (Remote)](https://feeny.ai/job/software-engineer-remote-policyme-ontario-vdpxqct709qq) — Ontario, Canada - [Bilingual Licensed Insurance Advisor (Remote)](https://feeny.ai/job/bilingual-licensed-insurance-advisor-remote-policyme-toronto-y6n7amgjc5me) — Toronto, Canada - [Bilingual Quebec Licensed Insurance Advisor (Remote)](https://feeny.ai/job/bilingual-quebec-licensed-insurance-advisor-remote-policyme-in-j9djcw1ym12p) — IN, Canada - [Join PolicyMe’s Talent Network for future opportunities!](https://feeny.ai/job/join-policyme-s-talent-network-for-future-opportunities-policyme-remote-qtek7ezebbhq)