AI Enablement Specialist/Senior

Location: Canada - Toronto

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

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 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, 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, talking points, job aids, and project updates.

Manage digital publishing: Publish and maintain content across intranet and email channels, managing approvals, workflows, version control, accessibility, and metadata.

Create visual materials: Create high-quality visual materials, including Google Slides presentations, videos, infographics, and one-page guides.

Bachelor’s degree in communications, marketing, change management, business, technology, or a related field; equivalent relevant experience may also be considered.

3+ years of experience in change management, internal communications, employee engagement, enablement, event coordination, customer service, or a related area.

3+ years in business process analysis, process mapping, management consulting, or digital transformation roles within enterprise operations (e.g., Finance, Procurement, IT).

1–2 years of practical experience applying generative AI tools, low-code automation, or intelligent workflows to real business processes.

Comfort designing human-in-the-loop checkpoints and agentic interactions.

Ability to rapidly create wireframes, mockups, or low-code pilots to test process ideas with end-users and iterate based on feedback.

Excellent written, verbal, presentation, facilitation, and interpersonal communication skills.

Ability to make technical or operational information understandable for audiences with varying levels of familiarity.

Experience coordinating multiple projects, deadlines, stakeholders, communication channels, and events.

Strong creative and visual-design skills, with the ability to create clear and engaging presentations, videos, graphics, and job aids.

Change-management certification or formal change-management education is an asset.

Experience advising senior stakeholders, facilitating ambiguous problem-solving, and influencing without authority.

Ability to coach teams and build organizational capability.

Experience managing multiple stakeholders, workstreams, dependencies, and competing priorities.