About this role.
PolicyMe is hiring a full-time AI-Driven Full Stack Engineer to build insurance technology in a remote-first Canadian environment. The role spans Python, React, Redux, PostgreSQL, AWS, and AI tooling such as LangChain/LangGraph and n8n. Responsibilities include production AI integrations, data pipelines, cloud architecture, observability, frontend experiences, and end-to-end feature delivery. The team emphasizes autonomy, proactive communication, collaboration, experimentation, and a fast-paced but low-ego culture.
Role DNA
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Job Complexity
4/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
4/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Software Engineer role at PolicyMe. My experience building full-stack applications with Python, React, PostgreSQL, AWS, and AI-integrated services aligns closely with your goal of modernizing insurance through intelligent products.
I would bring a practical, customer-focused approach to designing scalable backend systems, reliable data pipelines, and polished user experiences, while collaborating effectively across engineering and QA. I am particularly motivated by the opportunity to help productionize AI capabilities and take end-to-end ownership in a high-performing remote-first team.
Thank you for your consideration; I would welcome the opportunity to discuss how I can contribute to PolicyMe's next product line.
Sample interview questions
I would describe an AI feature as a product workflow rather than only a model integration: define the user problem, select an appropriate model or API, establish evaluation criteria, and design fallbacks for low-confidence outputs. I would instrument latency, error rates, cost, quality signals, and user outcomes, then iterate through controlled releases to ensure the feature creates measurable value.
I would separate domain logic, infrastructure concerns, and external AI-provider integrations through clear interfaces. This enables unit testing with mocks, makes providers replaceable, and allows asynchronous processing, retries, idempotency, and audit logging to be implemented consistently. I would also define API contracts and observability standards early.
I would use structured logs, distributed traces, metrics, dashboards, and actionable alerts across the application and cloud infrastructure. For AI workflows, I would additionally monitor model/API latency, token or usage cost, success and fallback rates, queue depth, data quality, and quality-evaluation results while protecting sensitive customer information.
I would begin with a shared definition of the customer problem, expected behavior, acceptance criteria, and measurable success metrics. I would communicate trade-offs in audience-appropriate language, surface dependencies early, keep decisions documented, and involve QA before implementation is complete so release risks and test cases are addressed proactively.
I would first validate the pipeline's data sources, schemas, freshness, and access controls, then automate validation checks for completeness, drift, and anomalous values. I would make transformations reproducible and versioned, use secure storage and least-privilege access, and ensure inference inputs are monitored so production behavior can be traced back to data and deployment versions.
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:
- Design and develop full stack features for our AI-powered web application using Python, React, Redux, PostgreSQL, and AWS
- Integrate AI models and APIs for tasks like document processing, data extraction, recommendation engines etc.
- Work closely with Sr. Engineers experienced in AI to seamlessly integrate models into production
- Research and prototype new AI applications to continuously enhance our product capabilities
- Construct scalable, secure, and observable cloud architectures for our core AI services
- Implement robust data pipelines to fuel AI model training and inference
- Craft seamless user experiences that surface AI-powered functionality
- Participate in architecture planning, code reviews, and ideation sessions
- Take ownership of feature development end-to-end (once ramped up), coordinating with QA and other teams
- Engage in cross-team communication to help unblock dependencies and improve release flow
- Share ideas during quarterly planning to help shape what we build next
- Participate in company-wide initiatives such as hackathons, engineering guilds, and AI tooling experiments
What we are looking for:
- Strong full-stack development skills with the ability to work across backend and frontend using Python, React, Redux, PostgreSQL, and AWS
- Hands-on experience integrating and deploying AI/ML technology into production environments
- Solid understanding of AI/ML concepts and how to incorporate them to provide value to customers
- Ability to design modular, testable, and scalable backend architectures
- Comfortable learning new frameworks, libraries, and tools quickly
- Expertise in building observability and monitoring for cloud-native applications
- Intellectual curiosity to continuously learn and upskill in emerging AI technologies
- Proven track record of proactive communication with the ability to adapt technical explanations to different audiences
- Self-starter with a career-driven mindset who thrives in an environment with autonomy and accountability
- Collaborative team player with low ego who is open to feedback and eager to help others
- Detail-oriented approach to problem-solving, especially in complex domains
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 $110,000 – $150,000 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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