Software Engineer Manager (Remote)
PolicyMe
Software Engineering
Ontario, Canada
Posted on Sep 16, 2025
Overview of the role
Join us at PolicyMe! We're modernizing insurance and we'd like your help. The Canadian insurance landscape has remained largely unchanged for decades and we are in the process of changing that. We're a remote-first, Toronto-based startup with big ambitions.
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
- 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: CTO
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
About PolicyMe
At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.
We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit www.policyme.com.
Commitment to Equal Opportunity
PolicyMe is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest — only those selected for an interview will be contacted.
Accessibility Statement
PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please let us know in the "Additional Information" section of the job application. We are committed to working with you to provide support and make reasonable adjustments throughout the process.
