Product Operations Director

Accountabilities: As Product Operations Director, you will own the strategy, infrastructure, governance, and operating mechanisms that enable Product and Engineering teams to work efficiently, make informed decisions, and deliver measurable outcomes. Lead AI enablement across Product and Engineering by defining strategies, standards, and governance for AI-powered workflows, agents, skills, connectors, and automations. Own the shared AI infrastructure, including skill registries, integrations, access controls, data guardrails, and automation capabilities. Evaluate and select AI tools, establish adoption standards, measure business impact, and develop training programs that help teams integrate AI into their daily workflows. Oversee the product operations technology ecosystem, including integrations between analytics, roadmap management, customer feedback, and capability-mapping platforms. Establish architecture, ownership, documentation, reliability, and data management standards for the product tooling infrastructure. Manage the product tooling portfolio, including analytics and user behavior platforms, roadmap and discovery solutions, and customer feedback systems. Define tooling strategies, monitor adoption and return on investment, manage platform performance, and determine when to build, purchase, consolidate, or retire solutions. Govern subscription architecture, instrumentation standards, tagging, privacy controls, access provisioning, and usage forecasting. Automate recurring administrative processes and establish clear ownership for day-to-day tooling requests. Partner with Procurement to negotiate vendor contracts, renewals, and expansions, while leading vendor governance and quarterly business reviews. Maintain and continuously improve the product operating system in collaboration with Product and Engineering leadership. Lead cross-functional working groups, change management initiatives, and adoption efforts supporting the transition to the 2027 operating model. Establish central planning calendars, meeting agendas, pre-read standards, and criteria for eliminating unnecessary meetings. Develop mechanisms for collecting and integrating customer feedback from Sales, Support, Customer Experience, and Adoption teams into annual planning and resource allocation decisions. Standardize product lifecycle practices through minimum-specification templates, launch-readiness scorecards, and telemetry and instrumentation standards. Train product teams on operating processes, templates, and tools while ensuring consistent adoption across the organization. Build the measurement infrastructure, dashboards, and reporting capabilities needed to track operational effectiveness, including meeting load, template adoption, and telemetry coverage. Collaborate with portfolio strategy leadership to translate strategic performance metrics into actionable reporting and measurement systems. Requirements The ideal candidate combines extensive product operations experience with strong expertise in AI enablement, enterprise tooling, infrastructure integration, and organizational change management. 12+ years of professional experience, including at least 10 years in product operations, product management, program management, and/or project management. Demonstrated experience enabling teams through AI-powered tools and workflows, including agents, skills, connectors, and automations. Proven ability to establish AI governance frameworks, manage access and data policies, and demonstrate measurable improvements in efficiency or quality. Extensive experience owning product tools and platforms end to end, including strategy, implementation, adoption, ROI measurement, vendor negotiations, and contract management. Strong technical understanding of integrated tooling infrastructure, including system integrations, data flows, dashboards, and reporting architecture. Experience building operating models, scalable processes, and repeatable organizational frameworks from the ground up. Proven change management capabilities, with the ability to drive adoption of new processes and operating standards across multidisciplinary teams. Strong leadership skills and the ability to influence stakeholders without relying on formal authority. Credibility when collaborating with engineers, product leaders, and C-suite executives. Excellent written communication and data analysis skills, with the ability to independently retrieve, interpret, and present data when existing reporting is insufficient. Strong facilitation and stakeholder management skills, particularly when leading high-stakes cross-functional discussions and driving decisions. Genuine curiosity about insurance technology and the evolving needs of the insurance industry. Additional strengths that could set you apart: Experience establishing AI enablement programs for product organizations, including skill registries, connector standards, governance frameworks, and adoption measurement. Experience developing product tooling and infrastructure roadmaps, including multi-subscription analytics architectures, budget planning, system integration strategies, and vendor management. Demonstrated ability to design and implement product operating systems, from initial frameworks to organization-wide adoption. Experience creating standardized product templates, launch-readiness processes, and supporting teams through the implementation of new operating models. Ability to establish cross-functional customer feedback mechanisms that directly inform annual planning, portfolio allocation, and strategic priorities. Benefits Competitive annual compensation ranging from $150,000 to $190,000 CAD, including base salary and, where applicable, variable or incentive compensation. Medical, dental, and vision coverage. Holiday and vacation time. Dedicated health and wellness days. A day off to celebrate your birthday. Remote work opportunity. Meaningful ownership of strategic decisions and initiatives with organization-wide impact. Opportunities to work on products and programs supporting agencies, carriers, and teams across the insurance lifecycle. Professional growth through challenging projects, cross-functional collaboration, learning opportunities, and expanded responsibilities. Collaborative environment built around expertise, curiosity, innovation, and shared accountability. How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1