Job Description
Note: The job is a remote job and is open to candidates in USA. Guidewire Software is seeking a visionary leader to drive enterprise transformation initiatives focused on AI competency. In this senior role, the candidate will reshape processes and operating models within the Operations and People team, leading the development of AI strategies for organizational readiness.
- Responsibilities
- Strategy & Readiness Transformation
- AI Readiness Strategy: Develop the specific AI strategy for the readiness transformation, by shifting enablement content creation from manual development to an AI-first model. You will define how AI is used to generate, curate, and maintain high-value enablement materials
- AI-Driven Knowledge Management: Design and implement the strategy for how content is managed and retrieved, moving away from static repositories to dynamic, AI-enabled knowledge bases that serve the right content at the right time
- Operations & People Team Enablement
- Operating Model Design: Design an "Agentic Automation Operating Model" and maturity assessment framework that can be tested within Operations and People teams before broader rollout
- Strategic Governance: Design governance frameworks that enable structured collaboration between business stakeholders and technology teams, ensuring initiatives deliver sustained adoption rather than isolated deployments
- Workforce Capability Building: Design and lead capability-building programs that enable HR and Ops teams to design and run their own AI-assisted processes
- Experiential Learning: Address skills gaps through practical, on-the-job experience with new AI content tools rather than formal training alone. Working closely with our IT team and technical organisations
- Enterprise Scalability & Cultural Change
- Blueprint for Scale: Position the Operations and People functions as the internal standard for AI & automation, using their success to influence internal operations and eventually external, customer-facing activities
- Adoption & Behavior Change: Ensure automation and AI are embedded into day-to-day work, driving long-term behavior change and managing the cultural shift required for an AI-first organization
- Internal Tooling: Partner with the CIO org to design and deliver internal AI tools (based on LLMs) to provide technical and business advisory support to internal users regarding automation maturity
- Skills
- 8–12+ years of experience in Business Transformation, Strategy & Operations, or Sales/People Enablement Leadership and Shared services at an enterprise level
- Proven track record of leading large-scale change initiatives in high-growth technology environments
- Demonstrated ability to design and own enterprise-wide operating models and governance frameworks
- Deep expertise in Generative AI (LLMs) and Agentic Automation
- Experience applying AI to Knowledge Management and Content Lifecycles—shifting from manual creation to AI-driven generation and retrieval
- Expert command of Change Management methodologies with a focus on behavioral transformation
- Ability to drive 'citizen developer' cultures and design capability-building programs that bridge the gap between technical tools and business users
- High emotional intelligence with the ability to operate at a senior leadership level
- Proven success acting as a bridge between technical teams (Product/Engineering/BizTech) and business stakeholders (HR, Sales, Ops) to drive alignment and adoption
- Bachelor's degree required
- MBA or relevant advanced degree in Operations, Organizational Design, or Technology Strategy
- Benefits
- Health, dental, and vision insurance
- Paid time off
- Company sponsored retirement plan
- Annual company bonus plan
- Commissions
- Long term incentive awards
- Company Overview
- Guidewire Software provides core back-end systems software to the global property, casual and worker's compensation insurance industry. It was founded in 2001, and is headquartered in San Mateo, California, USA, with a workforce of 1001-5000 employees. Its website is http://www.guidewire.com.
- Company H1B Sponsorship
- Guidewire Software has a track record of offering H1B sponsorships, with 79 in 2025, 80 in 2024, 85 in 2023, 117 in 2022, 108 in 2021, 148 in 2020. Please note that this does not guarantee sponsorship for this specific role.
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