Summary

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, share 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 transparent 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, invitations, presentations, logistics, speaker preparation, and follow‑up activities.
- Coach meeting hosts: Guide meeting hosts on presentation techniques, agenda management, inclusive screen sharing, audio accessibility, and related practices.
- Support employee‑engagement programming: Help deliver programming that supports community, mentoring, engagement, AI fluency, and employee experience.

Content creation and digital publishing

- Translate complex information: Translate technical, operational, and project information into clear, plain‑language communications.
- Create communications and content: Create newsletters, FAQs, intranet content, email messages, Slack posts, internal social updates, presentations,

📌 AI Enablement Specialist/Senior (Toronto)
🏢 Guidewire Software
📍 Toronto