Transformation Program Manager to the Chief People Office

Summary

Guidewire is transforming from an industry leader software provider to an AI-first cloud platform that is the backbone of the $2 trillion Property & Casualty (P&C) insurance industry. To do this, we must transform how we work. This role is central to that evolution. The Chief People Officer (CPO) is spearheading a global initiative to scale Guidewire’s people, operations, and culture through intelligent automation and AI-driven talent strategies.
As the CPO’s Transformation Program Manager (a 'force multiplier'), you will be the key operational driver for the People Strategy. You will ensure that our shift toward AI and automation not only increases efficiency but also unlocks human potential, making our global workforce more curious and empowered. This role operates at the critical intersection of strategy and hands-on execution within a high-growth, fast SaaS environment.

Job Description

Key Responsibilities

1. People Strategy Orchestration & Transformation Leadership

• Change Management: Serve as a primary lead for change management methodology, guiding the organization through the organizational, cultural and operational shifts that accompany major technology and operating model evolutions (re-skilling, up-skilling, and influencing the "people side" of automation adoption).

• The AI Roadmap: Partner directly with the CPO and People Leadership Team (PLT) to ensure the AI integration and automation into the full employee lifecycle meets its deliverables.

• Transformation Agent: Lead high-impact, cross-functional projects that drive workforce productivity and AI literacy across the organization, ensuring these initiatives are perfectly synced with Guidewire's broader Cloud-First and AI-Enabled business objectives.

2. Intelligent Operations & Rhythm Management

• Leading the Quarterly Go-Live planning process for all People initiatives.

• Ensuring the success of the Annual People Team Roadmap, ensuring alignment with enterprise comms and enablement calendars.

• Designing and maintaining the People Team Operating Guide, codifying key rituals, decision-making cadences, and collaboration norms.

• CPO Office Management: Manage the CPO's operating rhythm, including PLT meetings, offsites, and All-Hands, ensuring discussions convert into trackable decisions, owners, and outcomes.

• Transparent Communications: Partner with Exec Comms to deliver communications, board decks, and presentations that clearly articulate the CPO’s vision for a scaled, automated future and the People + Enablement organization’s impact on the business.

3. Culture of Curiosity & Employee Experience at Scale

• Voice of the Employee (VoE): Partner with the Employee Experience team to integrate VoE and feedback loops (e.g., Peakon, focus groups) into People Team planning, retros, and leadership discussions, ensuring a visible, repeatable “You Said, We Did” practice.

• Self-Service & Scaled Support: Partner with People Operations and BizTech to scale employee self-service, including the development and promotion of AI/chatbot capabilities to handle common HR questions, driving adoption of self-service tools.

• Brand and Awareness: Co-lead the People Team brand, access, and awareness strategy, ensuring a clear, user-friendly intranet experience and internal roadshows that clarify "Who we are / What we do" for employees and managers.

Experience

8-10 years in HR Strategy, Management Consulting, Business Operations, or a Transformation/Chief of Staff role within a fast-paced, technology-driven SaaS environment. Direct experience with C-suite leadership is essential.

AI Competency

A deep curiosity for Generative AI and demonstrated ability to apply data-driven insights to drive innovation and continuous improvement in People/HR workflows. Hands-on experience with AI-enabled self-service, chatbots, or knowledge management tools is preferred.

Program Mastery

Proven experience designing and running comprehensive operating rhythms (planning cycles, portfolio reviews, launch calendars) across multiple functions. Track record of turning programs into full internal go-to-market motions (intake, positioning, comms, enablement).

Change Mastery

Strong change management skills and building a company-wide methodology with a proven ability to guide organizations through complex transformations (new operating models, technology adoption, or organizational design changes).

Influence

Exceptional communication, storytelling, and executive presence. The ability to synthesize complex information, craft compelling narratives, and act as a trusted, neutral sounding board and thought partner to senior leaders.

Guidewire Core Values: This role must lead with Integrity, Rationality, and Collegiality while pushing the boundaries of what is possible in the future of work.

The US base salary range for this full-time position is $176,000 - $264,000 . 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.

Disability Accommodations and Guidewire’s Appeals Process. Guidewire provides accommodations to the hiring process to create a fair opportunity for candidates with disabilities to contend for open positions. Accommodation requests should be directed to [email protected]. If things do not go as hoped, we invite you to use our appeals process. Guidewire promises to independently review any denied accommodation and any decision not to offer you the position. The appeals process is the same in either case. Within five business days of receiving a notice of denial of an accommodation, or receiving a notice of your non-selection for a vacancy, e-mail [email protected] to make an appeal. Guidewire will assign a new decision-maker to review the request and/or hiring decision, who will then notify you in writing of a decision within 10 business days.

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.