Product Operations Director

Accountabilities: Define and lead the AI enablement strategy for Product and Engineering, including AI tools, agents, skills, connectors, shared automations, governance standards, and data-access guardrails. Evaluate AI solutions, establish adoption and performance metrics, and develop training programs that help teams use AI effectively while improving efficiency and quality. Own the product operations technology infrastructure, including integrations across analytics, roadmapping, customer feedback, and capability-mapping platforms. Establish architecture, documentation, reliability, data-flow, dashboard, and automation standards to ensure the product technology stack is connected, scalable, and AI-ready. Manage the product tooling portfolio, including product analytics and user behavior platforms, roadmap and discovery systems, and customer idea-management tools. Assess adoption, return on investment, and opportunities to build, buy, consolidate, or retire solutions. Oversee tenant configuration, subscription architecture, instrumentation, tagging, privacy, access provisioning, and usage forecasting, while establishing standards and delegating routine requests. Manage vendor relationships and contracts in partnership with Procurement, including evaluations, negotiations, renewals, expansions, and quarterly business reviews. Maintain and continuously improve the product operating model in collaboration with Product and Engineering leadership, leading working groups, adoption initiatives, and change management. Establish effective operating mechanisms, including central calendars, meeting agendas, pre-read standards, and criteria for reviewing or retiring unnecessary meetings. Develop structured processes for collecting customer feedback across Sales, Support, Customer Experience, and Adoption teams and incorporating insights into annual planning and resource allocation. Standardize product lifecycle practices through minimum requirements templates, launch-readiness scorecards, and telemetry and instrumentation standards. Build the measurement and reporting infrastructure for operational performance, including meeting load, process adoption, and telemetry coverage. Facilitate cross-functional discussions, drive decisions, and communicate progress and outcomes through clear written updates and data-driven reporting. Requirements: At least 12 years of professional experience, including 10 or more years in product operations, product management, program management, and/or project management. Demonstrated experience introducing AI tools and workflows across teams, including agents, skills, connectors, and automations, with appropriate governance and measurable improvements in efficiency or quality. Proven end-to-end ownership of product tools, covering strategy, implementation, adoption, ROI measurement, vendor negotiations, and contract management. Experience designing and managing integrated technology infrastructure, including system integrations, data flows, dashboards, and automations. Track record of creating operating models and repeatable processes from the ground up and successfully leading organizational change to secure adoption. Strong ability to influence without formal authority and establish credibility with engineers, product leaders, and executive stakeholders. Excellent written communication and data analysis skills, with the ability to independently retrieve and interpret data when standard reporting is unavailable. Strong facilitation and stakeholder management skills, particularly in high-impact cross-functional discussions that require clear decisions and alignment. Strategic thinking combined with a practical, hands-on approach to solving operational challenges. Genuine curiosity about insurance technology and the opportunities to improve the industry through better products, data, and intelligent systems. Additional experience that could set you apart: Experience establishing AI enablement programs for product teams, including skill registries, connector standards, governance frameworks, and adoption measurement. Experience defining product tooling and infrastructure roadmaps, including multi-subscription analytics architectures, budgeting, integrations, and vendor strategies. Experience developing and rolling out product operating frameworks, minimum-specification templates, and launch-readiness processes. Experience building cross-functional customer feedback mechanisms that inform annual planning, prioritization, and resource allocation. Benefits: Annual compensation range: CAD $150,000–$190,000, including base salary and, where applicable, variable or incentive compensation. Medical, dental, and vision coverage. Holiday and vacation time. Health and wellness days. A day off for your birthday. Fully remote work arrangement. Opportunities to own meaningful decisions and contribute to products and programs supporting the insurance industry. Cross-functional collaboration and exposure to a broad range of business and technology priorities. Professional growth through meaningful projects, learning opportunities, and expanded responsibilities as the organization evolves. Compensation is determined based on the role's scope, experience, skills, and location.