Technology Operations Director

Technology Operations Director (Hybrid – Greater Toronto Area)

About the Opportunity Leap Recruitment Partners is actively seeking a dynamic, hands-on Technology Operations Director on behalf of a valued client. Our client is a highly respected, award-winning property and casualty (P&C) insurance brokerage based in the Greater Toronto Area. Recognized consistently as a top employer and consumer choice leader in the insurance sector, they specialize in comprehensive personal lines, including home, auto, and specialized recreational vehicle coverage.

The Role In this vital leadership position, you will report directly to the executive team and take complete ownership of the organization’s technology ecosystem. Your mandate is to leverage technology as a catalyst for operational excellence. You will spearhead the IT strategy, manage daily technological operations, oversee vendor relationships, and champion initiatives aimed at automating manual tasks and optimizing workflows. Operating within an agile, privately held business environment, you will serve as both the strategic visionary and the tactical executor, setting the direction while remaining heavily involved in the day-to-day work.

Key Responsibilities

• Direct all facets of IT operations, encompassing cloud environments, network infrastructure, telecommunications, hardware, and end-user support.

• Serve as the primary custodian of core business systems, ensuring seamless data integration with external partners and insurance carriers.

• Identify opportunities for workflow optimization, driving automation initiatives to minimize manual data entry and accelerate client service delivery.

• Supervise and evaluate managed service providers (MSPs) and technology vendors, ensuring strict adherence to service level agreements (SLAs) and budgetary targets.

• Safeguard the organization by managing its cybersecurity posture, access protocols, disaster recovery plans, and adherence to data privacy regulations.

• Shepherd technology projects from initial scoping and requirements gathering through to user acceptance testing (UAT) and final deployment.

• Collaborate with executive leadership to formulate the annual IT budget and construct a comprehensive, multi-year technological roadmap.

• Empower the broader team through targeted training and ongoing support for newly implemented digital tools.

Qualifications

• A minimum of 8 years of progressive IT operations experience, including at least 3 years in a definitive leadership, managerial, or director capacity.

• Professional background in highly regulated sectors, such as insurance, financial services, or wealth management.

• Proven success in leading system integrations, software implementations, workflow automation, and comprehensive UAT processes.

• Deep technical fluency in cloud computing (specifically Microsoft 365), network infrastructure, and enterprise cybersecurity best practices.

• Demonstrated expertise in financial planning, budget management, and vendor negotiation.

• Exceptional communication skills, with the distinct ability to translate complex technical concepts for non-technical stakeholders and staff.

• A roll-up-your-sleeves mentality, thriving in a nimble, fast-paced corporate environment.

Preferred Assets

• Familiarity with prominent broker management systems (BMS) or enterprise platforms.

• Prior exposure to quoting engines, rating platforms, and external carrier system integrations.

• Relevant industry certifications (e.g., ITIL, PMP, CISSP, CRISC, or CBAP).

• A solid understanding of the P&C insurance landscape and Canadian data privacy laws.

Why Join This Team?

• Assume direct ownership of the technology landscape, with a tangible impact on the company’s future trajectory and operational success.

• Work in close partnership with a collaborative, forward-thinking executive leadership team.

• Join a celebrated, award-winning organization renowned for its exceptional workplace culture and stellar reputation for customer service.