VP, Guidewire Readiness

Summary

About Guidewire: At Guidewire, we prioritize our customers’ success and pride ourselves on delivering innovative, high-impact solutions. We foster an environment of engineering excellence, accountability, and continuous improvement, ensuring our team thrives in an ever-evolving industry.
The Opportunity: Guidewire is embarking on a transformative initiative, to revolutionize how we enable and train individuals to maximize their impact both professionally and on our cloud solutions. Developing a unified company-wide enablement strategy will become a differentiator in the market.
We envision being a market leader in SaaS readiness, ensuring every member of the Guidewire community is equipped with the skills to thrive, ultimately driving greater customer success. This critical role will lead the strategic shift to an AI-driven readiness model, transforming content creation and enablement experiences. The Academy will integrate AI to auto generate documentation of our applications and build immersive, interactive learning experiences, moving beyond traditional documentation to a dynamic and personalized learning journey. This is a unique opportunity to lead a significant operational leverage initiative.

Job Description

Key Responsibilities:

• Strategic Leadership & Vision: Lead the strategy, design, and execution of the Guidewire Readiness Academy, unifying disparate learning and enablement functions into a world-class organization. Champion the vision of an AI-powered learning engine that maximizes impact for the Guidewire community.

• Organizational Transformation: Drive the transformation of Guidewire's learning and enablement operating model, establishing scalable, best-in-class processes to drive growth, efficiency, and innovation. This includes leading efforts to reduce content creation overlap, improve asset generation, and meet the needs of our audience.

• AI Integration & Innovation: Oversee the integration of AI into documentation, training, and enablement processes, ensuring Guidewire maintains its competitive edge and positions itself as a leader in AI-driven readiness. Spearhead the creation of AI-powered documentation and AI-generated learning experiences.

• Team Leadership & Development: Recruit and lead a high-performing team, initially driving a new dedicated POC team (AI/ML Engineer, Senior Instructional Designer, Technical Subject Matter Expert, Program Manager) and beginning to form the future of enablement and the education teams. Foster a culture of excellence, accountability, and continuous improvement within the Readiness Academy.

• Process Optimization & Governance: Design and implement scalable, efficient, and compliant business processes for content creation and delivery. Develop and enforce governance frameworks, driving critical cross-functional decisions to balance business needs with operational efficiency.

• Data-Driven Decision Making: Ensure well-governed processes produce actionable data for advanced analytics, improved reporting, and strategic decision-making within the learning and enablement function.

• Cross-functional Collaboration: Partner with executive leadership to drive alignment and ensure operational changes support company-wide objectives. Collaborate with Business Technology and Product teams to enhance customer and employee experiences.

• Execution & Delivery: Oversee the execution of a focused Proof-of-Concept (POC) for the AI-driven model, delivering measurable results and a data-backed recommendation for a full-scale rollout.

Qualifications:

• Experience: 10+ years of experience in business process architecture and business transformation for SaaS and product-led growth organizations. Experience with Salesforce and M&A post-merger integrations strongly preferred. Proven track record of successfully leading cross-functional teams and driving strategic initiatives with a strong, confident leadership style.

• Education: Bachelor’s degree in Business, Technology, Engineering, or a related field. MBA or Master’s degree preferred.

• Leadership & Communication: Strong, confident leadership style with excellent communication and negotiation skills, capable of navigating complex, multi-stakeholder environments. Assertive and confident decision-maker, able to handle challenging conversations and ensure alignment across teams with varied perspectives.

• Technical Acumen: Expertise in business process design, process re-engineering, and change management. Proficient in process governance, data quality, and process automation. Strong understanding of SaaS and PLG business models. Experience with AI offerings like AWS Nova is a plus.

• Decision & Design Skills: Demonstrated ability to make high-stakes decisions and provide authoritative guidance across departments.

• Professionalism: High level of integrity, discretion, and professionalism, particularly when handling confidential information.

Why You Should Join Us:
At our company, we prioritize our customers’ success and pride ourselves on delivering innovative, high-impact solutions. We foster an environment of engineering excellence, accountability, and continuous improvement, ensuring our team thrives in an ever-evolving industry.
We value collaboration and determination, facing challenges with resilience while maintaining humility and openness to feedback. Most importantly, we cherish the strong sense of community within our team, celebrating successes and finding joy even in the toughest moments. If you’re ready to make a meaningful impact and grow with a dynamic, values-driven team, we’d love to hear from you.


The US base salary range for this full-time position is $198,000 - . 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 Accommodations@guidewire.com. 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 Accommodations@guidewire.com 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.