About this role.
PolicyMe is hiring a Senior Software Engineer to develop AI-powered products that improve the insurance broker experience. The role spans React, Python, Node, PostgreSQL, AWS, distributed systems, and AI/ML technologies such as LangChain and LangGraph. The engineer will lead architecture and full-stack feature delivery, emphasize security and observability, and mentor other engineers. This is a remote-first Canadian role with optional access to a Toronto office and a strong expectation of cross-functional leadership. The company offers CAD 154,000–176,000 in total target cash compensation, plus benefits, PTO, professional-development support, and stock options.
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 Senior Software Engineer role at PolicyMe. My experience building scalable full-stack applications with Python, React, cloud infrastructure, and AI-enabled systems aligns well with your goal of modernizing the insurance experience.
I would bring a pragmatic, security-minded approach to architecture, experimentation, and delivery, while partnering effectively with product and design stakeholders to resolve ambiguous technical challenges. I am also motivated by the opportunity to mentor engineers and help establish durable engineering standards in a high-performing remote-first environment.
Thank you for your consideration; I would welcome the opportunity to discuss how I can contribute to PolicyMe’s AI-powered product line.
Sample interview questions
I would begin by defining the user workflow, measurable outcomes, data sources, and failure modes with product and domain stakeholders. I would then create a small, observable prototype, evaluate model quality and operational risk, and evolve it into a secure service with evaluation datasets, human-review paths, monitoring, and rollback mechanisms.
I use clear service boundaries, asynchronous processing where appropriate, idempotent APIs, and robust observability from the outset. For AI workloads, I would separately monitor model latency, cost, quality, drift, and fallback rates, while using infrastructure-as-code and staged releases to maintain reliability.
I would use a layered approach: least-privilege access controls, encryption in transit and at rest, secret management, data minimization, audit logs, and vendor due diligence. I would also ensure prompts, retrieval sources, and model outputs cannot expose sensitive information, and establish clear retention and incident-response practices.
I communicate trade-offs in terms of customer impact, delivery risk, cost, and future flexibility rather than implementation preference. I document options, recommend a path based on available evidence, align decision-makers, and use a time-boxed experiment when uncertainty is high.
I mentor through pairing, thoughtful code reviews, architecture walkthroughs, and progressively larger ownership opportunities. I set clear quality expectations, explain the reasoning behind standards, and create psychologically safe feedback loops so engineers can grow while delivering effectively.
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.
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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