AI Enablement Specialist

Canada - Toronto

Content

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 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.

Qualifications

• 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.

• Why Guidewire

• At Guidewire, you will work with people who bring diverse perspectives, expertise, and creativity to a shared purpose. Guidewire describes its culture through determination, collaboration, continuous improvement, and bravery, while its employee-value themes emphasize inclusive culture, trusted leadership, career clarity, access to cutting-edge projects, learning, and meaningful impact. In this role, you will help colleagues grow their confidence with technology, strengthen connections across the organization, and contribute to solutions that help P&C insurers modernize and thrive.

• The Canadian CAD base salary range for this full-time position is 94,000.00 - 118,000.00. Your base pay will depend on your experience, skills, education, training, and location among other factors. All full-time positions or part-time roles working 30 hours or more a week at Guidewire are eligible for benefits that support their health and well-being including health, dental, and vision insurance, paid time off, and a company sponsored retirement plan. In addition, some roles may be eligible for the annual company bonus plan, commissions, and/or long term incentive awards which are contingent on a variety of factors including, but not limited to, company and employee performance.

• Interested in this position?

• About Guidewire

• Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 540+ insurers in 40 countries, from new ventures to the largest and most complex in the world, run on Guidewire.

• As a partner to our customers, we continually evolve to enable their success. We are proud of our unparalleled implementation track record with 1600+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of applications that accelerate integration, localization, and innovation.

• For more information, please visit www.guidewire.com and follow us on Twitter: @Guidewire_PandC.

• Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action e