Senior Software Engineer (Winnipeg)

Senior Software Engineer (Winnipeg)

21 Oct
|
Userc Dehradun
|
Winnipeg

21 Oct

Userc Dehradun

Winnipeg

Canada Full-Time CAD 154000–176000 / Posted 1 day ago

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Location Canada

Job type Full-Time

Salary CAD 154000–176000 /

Posted 18 Oct 2026 (1 day ago)

Region Canada

Category Software Engineering

Source Jobicy

Work mode Remote

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 workplace 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

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





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.

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.

About PolicyMe

At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast

📌 Senior Software Engineer (Winnipeg)
🏢 Userc Dehradun
📍 Winnipeg

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