Our Company As the first and fastest-growing Canadian Insurtech, software is the heartbeat of Square One . We recognize the transformative power of technology, especially when disrupting a "sleepy" industry. Our entire team is dedicated to continuous technological evolution—scaling our business and making insurance interactions effortless for our customers.

ca/reviews to see why our customers love us. As we grow across Canada, so do our ambitions. We are expanding our high-performance product development team to launch new features, automate complex business processes, and integrate AI and Large Language Models (LLMs) to further enhance our customer experience and streamline our operations.

Your Role Square One’s focus on technology is redefining the insurance landscape. We’ve built a modern, proprietary web-based platform from scratch that handles: Customer Management Online Sales & Support Policy Lifecycle Management Claims Reporting & Fulfillment As a Business Systems Analyst , you are at the intersection of business strategy and technical execution. We are big enough to provide world-class resources and small enough that your work—including initiatives that incorporate AI-driven workflows—will be felt by thousands of users daily.

We value doing things right over doing them fast, ensuring a stable, long-term impact. You will be directly involved in the evolution of our platform.

Responsibilities

include: Requirement Architecture: Liaise with business groups to capture change requests, perform gap analysis, and translate business needs into detailed functional

Requirements

AI Integration & Automation: Identify opportunities to leverage LLMs and AI tools to automate manual tasks, enhance customer support workflows, and improve data extraction processes.

for new systems to optimize business processes and information flow. Quality Advocacy: Partner with the QA team to ensure test plans are exhaustive and align with the original business intent. Documentation: Maintain high-quality system documentation that serves as the "source of truth" for our evolving tech stack.

You are a self-directed expert who thrives in a purpose-driven environment. You are someone who balances technical rigor with a curious, innovative mindset. Must-haves: Education: Degree or diploma in a technical or business-related field.

Experience: 3+ years in a Business Systems Analyst role or similar.

AI Fluency: Experience and a strong working knowledge of LLM capabilities and how they can be applied to business automation.

. Communication: Exceptional ability to translate abstract concepts into clear, actionable technical

for developers. Execution: Proven track record of meeting deadlines and adapting to changing business needs under pressure.

for projects involving AI-driven workflows or AI-enabled product features. Industry Knowledge: Experience in Insurance (Home/Auto), Fintech, or a high-growth startup environment.

Compensation

just like we personalize our policies: Competitive base salary and participation in the corporate profit-sharing plan. Generous Vacation: 3 weeks to start; 4 weeks after 3 years. Flexibility: The ability to work from home Comprehensive Health: Flexible medical, dental, vision, and extended health care.

Support: Employee assistance program, short-term and long-term disability coverage.

Business Systems Analyst (ON, AB, or BC)