AI Enablement Specialist/Senior

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 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.

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 employer. We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success. Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.

Guidewire is proud to be a disability inclusive employer. We are committed to providing individualized accommodations and support to candidates for any part of our hiring process. If you think you may need disability-related accommodations, please email EmployAbility at accommodations-gw@employ-ability.org.uk, our disability partner, or schedule a call with an EmployAbility expert (calendar booking slot) for a confidential conversation.

We’re an extraordinary blend of hungry self-starters, intrepid explorers, brainy experts, and loyal allies. Combine all of this, and we make a glorious success story, loaded with down-to-earth, helpful, and passionate people, all on the journey of cloud innovation and best in class technology. Guidewire’s an adventure—and it’s yours for the taking.

About Us

At Guidewire, we are utterly committed to customer success. We combine digital, core, analytics, and AI to deliver our platform as a cloud service to the P&C Insurance industry. And with the largest R&D team, services team, and partner ecosystem in the industry, we continually evolve and innovate to meet our customers’ needs.

We put our values of Integrity, Rationality, and Collegiality first, harboring a culture of honesty and openness that our people never want to lose. And we each bring a little quirkiness—and a little genius—to the table. As the landscape of our industry continues to shift, we respond with flexibility and skill. We’re braving uncharted territory, pushing past the conventional with our products, partners, and people.