AI Enablement Specialist/Senior

Canada - Toronto Business Technology/Full time/Hybrid Guidewire is hiring an AI Enablement Specialist to make complex technology accessible and empower employees to embrace AI-driven ways of working. In this role, you will lead end-to-end process reimagination by challenging legacy assumptions, prototyping AI solutions, and designing high-impact digital experiences. By blending change management, strategic communications, and hands-on engagement, you will act as a trusted internal advisor to elevate company-wide AI fluency. You will help Guidewire advance its mission to transform how the world’s P&C insurers do business by enabling colleagues to work effectively with trusted technology and information. The role offers opportunities to learn, collaborate globally, and make a meaningful impact in a culture grounded in determination, collaboration, continuous improvement, and bravery. Job type: Hybrid Location: Mississauga, Canada Job Description AI Enablement Specialist Employment type: Full-time Job type: Hybrid Location: Mississauga, Canada Department: Business Technology Strategy & Operations Roles and responsibilities AI process design Build reusable frameworks and playbooks: Create standards, design patterns, and best practices for AI-enabled process design so teams across Guidewire can apply them consistently and at scale. Act as a coach, trainer and advisor: Educate leaders and teams on what’s possible with AI, emerging trends and lessons learned, and foster a culture of continuous improvement and experimentation. Challenge existing process assumptions: Facilitate workshops and discovery sessions to question why steps, approvals, handoffs, and systems exist, and determine which can be eliminated, automated, or fundamentally rethought. Lead end-to-end process reimagination: Partner with Guidewire employees to map current-state processes that span across functions (e.g., IT, Finance, Procurement, etc.), identify friction, and redesign them from first principles for an AI-native world rather than layering AI onto legacy workflows. Identify and prioritize high-impact opportunities: Build a pipeline of AI use cases and process transformation candidates, using a clear framework (value, feasibility, risk, adoption readiness) to guide investment and sequencing. Prototype and pilot rapidly: Use approved AI platforms and agile methods to test redesigned processes with real users, gather feedback, and iterate before full-scale rollout. Establish success metrics and measure outcomes: Define baselines and KPIs (cycle time, cost to serve, quality, employee and customer experience, adoption) and track realized value against the business case. Change management and adoption Conduct change and stakeholder assessments: Perform organizational-readiness, change-impact, stakeholder, and adoption assessments; use stakeholder data to identify audiences, tailor engagement approaches, and inform change decisions. Lead change-management planning: Develop and execute change-management plans across the project lifecycle; apply appropriate change-management frameworks and methods to communications, learning, and adoption activities. Deliver adoption and reinforcement: Design and deliver user-adoption, training, and reinforcement initiatives. Partner across teams and advocate for employees: Partner with project teams, business stakeholders, and functional departments to support successful implementation and sustained usage; advocate for employees affected by change and bring empathy, clarity, and respect to each engagement. Monitor adoption and feedback: Define and monitor adoption measures, feedback mechanisms, and continuous-improvement actions. Events and employee engagement Coordinate employee events: Organize, promote, and facilitate Employee Engagement Advocate events, including All Hands, VP Huddles, office lunches, Guidewire Gives Back activities, leadership visits, lunch-and-learns. Manage event logistics: Coordinate agendas, invi…

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