Square One Insurance Services

Role Description 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. Your primary 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. - System Design: Lead idea sessions and develop requirements 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. Qualifications - Education: Degree or diploma in a technical or business-related field. - Experience: 3+ years in a Business Systems Analyst role or similar. - Technical Aptitude: A practical understanding of how technology (including AI) solves real-world business challenges; active use of AI in understanding system design and refining requirements. - AI Fluency: Experience and a strong working knowledge of LLM capabilities and how they can be applied to business automation. - Data Skills: Strong investigative skills using SQL Queries to analyze data and inform system requirements. - Communication: Exceptional ability to translate abstract concepts into clear, actionable technical requirements for developers. - Execution: Proven track record of meeting deadlines and adapting to changing business needs under pressure. Requirements - Nice-to-haves: - UX/UI Design: Experience with wireframing and prototyping tools. - Advanced AI Integration: Experience developing business or functional requirements 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. Benefits - 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.

Role Description At Square One, we didn’t just join the insurance industry; we reinvented it. We are the leading online home and auto insurance provider in Canada. And we’re the only ones in Canada that let clients choose what they want to insure so they only pay for what they need. We are obsessed with the user experience—both online and offline—and we need a leader who shares that obsession. As our Property Product and Underwriting Manager, you’ll work directly with our leadership team to steer a growing and successful home insurance portfolio. With the Product and Underwriting team, you will manage existing products and underwriting guidelines and develop new ones. You will play a critical role in delivering on our customer-focused digital experience while remaining innovative, stable, and profitable. Your success comes from balancing a "big picture" strategy with superior underwriting fluency, the meticulous organizational skills needed to balance competing priorities, and professional judgement required to communicate effectively. At Square One, you’ll find a culture that values expertise over ego. We provide the roadmap, while you provide the drive. We never leave you in the dark, instead, you’ll have the coaching, tools, and professional support required to lead with confidence and accelerate your own trajectory of success. Qualifications - Advanced expertise in property and casualty insurance underwriting principles. - Superior organizational, analytical, communication, and research skills. - Exceptional ability to conduct secondary market and competitive research online. - Creativity and resourcefulness to identify opportunities and overcome challenges. - Solid understanding of standard insurance profitability and performance metrics. - Natural curiosity and commitment to learning and self-development. - Ability to provide feedback that inspires growth rather than just correcting errors. - Fluency in English (French is an asset). Requirements - A degree in business, commerce, economics, or marketing or equivalent education plus work experience may be considered. - 5 years of property insurance underwriting experience, with at least 2 years in a leadership role. - 2 years of product management or underwriting development experience. - A high level of proficiency with Microsoft Office applications, and the ability to learn new technologies. - Familiarity with project management and product development principles. - A CAIB, CIP/ACIP, CRM or FCIP designation is preferred. - Fluency in English; French is a desirable asset. Benefits - Annual salary range: $86,000 - $114,000. - 4-weeks of vacation to start and an additional week after only 3 years. - Flexible medical, dental, vision and extended health care coverage. - Long-term disability coverage. - In-house and external training paid by Square One. - Full remote work option. - A company profit share plan.