About this role.
PolicyMe is hiring a full-time AI Engineering Manager to lead a team of full-stack and AI engineers building AI-powered insurance products. The role combines people management, technical leadership, cloud-platform architecture, and delivery of reliable, secure production AI systems. Candidates need at least seven years of software-development experience, including two years managing engineering teams, plus strong AI/ML and full-stack expertise. The organization is remote-first and explicitly recruits talent across Canada, with an optional Toronto office. The role reports to the CTO and operates in a collaborative, fast-paced environment.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the AI Engineering Manager role at PolicyMe, bringing experience leading engineering teams and delivering scalable, reliable AI-powered products. My background in full-stack development, cloud architecture, and production ML systems would enable me to guide technical strategy while mentoring engineers and strengthening delivery practices. I am particularly drawn to PolicyMe's customer-first mission and the opportunity to apply responsible AI to simplify insurance for Canadians. I would welcome the opportunity to help your team build secure, high-impact intelligent applications at scale.
Sample interview questions
I would begin by aligning on the user problem, success metrics, risk tolerance, and operational constraints. I would select the simplest model approach that can meet those requirements, establish offline and production evaluation criteria, and use staged releases with monitoring, rollback plans, and human-review paths where appropriate. I would also ensure privacy, security, and model-governance requirements are built into the delivery process from the start.
I use a clear decision framework: customer and business impact, technical risk, reversibility, cost, and time to learn. For major decisions, I solicit input from relevant engineers and partners, document options and trade-offs, then make and communicate a timely decision. After implementation, I revisit the outcome through metrics and retrospectives so the team can refine its approach.
I set explicit expectations through regular one-on-ones, growth plans, actionable feedback, and meaningful ownership opportunities. I tailor coaching to each engineer's goals while maintaining a high bar for quality, collaboration, and accountability. I also create opportunities for senior engineers to lead designs and mentor others, which scales leadership across the team.
I would define measurable service and model-health indicators, such as latency, error rates, prediction quality, drift, cost, and user-impact metrics. The team would maintain dashboards, alerts, runbooks, and clear ownership for responding to incidents. Regular reviews of production outcomes would feed back into data quality, evaluation, retraining, and architectural improvements.
I translate technical choices into the outcomes stakeholders care about, such as customer experience, risk reduction, delivery timelines, and operating cost. I avoid unnecessary jargon, state trade-offs directly, and use concise written decision records and regular checkpoints to maintain alignment. When uncertainty is high, I propose an experiment or phased rollout that produces evidence for the next decision.
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
- 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
- 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.
Compensation
Additional Information
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.
Additional Notes
– Job Vacancy: This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.
– Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
– Accessibility Statement: We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.
We thank all applicants for their interest, however, only those selected for an interview will be contacted.
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