Executive Assistant- West Coast

Summary

Our Product Strategy organization shapes the future of Guidewire’s cloud, AI, and data-driven product portfolio, ensuring we deliver secure, scalable, and high‑value solutions for P&C insurers worldwide. The team focuses on operational excellence, transformative innovation, and customer‑centricity, closely partnering with Product Development, Professional Services, and Go‑to‑Market to bring new capabilities to market. You’ll join a highly collaborative environment that blends deep insurance expertise with cutting‑edge technology.
As Executive Assistant, you will support three Vice Presidents within Product Strategy, enabling them to focus on advancing Guidewire’s AI‑infused platform, new product categories, and global expansion initiatives. You’ll manage complex calendars, communications, travel, and key meetings while “connecting the dots” across teams to keep strategic work moving. This role is ideal for a highly organized, tech‑savvy EA who enjoys operating in a fast‑paced environment, using judgment and discretion to drive impact behind the scenes.
Your Impact
We believe in clarity and setting you up for success. In your first six months, you’ll build strong operating rhythms with three Product Strategy VPs, learning their priorities around operational excellence, AI/GenAI initiatives, and global product expansion. You’ll streamline their calendars, reduce administrative friction, and create reliable cadences for leadership meetings and communications—ensuring decisions and actions tied to the Product VPMOM are clearly documented and followed through. As you grow in the role, you’ll become a trusted hub for information flow across Product Strategy, PDO, Go‑to‑Market, and Professional Services, helping the organization move faster and more effectively in delivering AI‑enabled, cloud‑based solutions that transform how P&C insurers operate and serve their customers.
You’ll also participate in our in‑person orientation experience, where you’ll meet colleagues from across Guidewire, learn how we combine digital, core, analytics, and AI to power the future of P&C insurance, and start building the relationships that will help you thrive here.

Job Description

What you’ll do

• Provide comprehensive executive support to three Product Strategy VPs, including proactive email triage, drafting correspondence, travel arrangements, and timely expense management.

• Own and optimize multiple complex calendars—prioritizing time against key Product VPMOM initiatives, anticipating conflicts, and coordinating high‑stakes internal and external meetings across time zones. 

• Coordinate strategically across Product Strategy, Product Development & Operations, Go‑to‑Market, and Professional Services to keep initiatives like AI/GenAI adoption, new product launches, and market expansion on track. 

• Create polished, executive‑ready presentations, visuals, and briefing materials that clearly communicate priorities such as the Agentic AI Platform, Claims/Underwriting solutions, and international product rollouts. 

• Lead end‑to‑end logistics for leadership meetings, offsites, town halls, and cross‑functional workshops—including agenda design, attendee coordination, room/virtual setup, catering, materials, purchasing, and on‑the‑day execution.

• Capture key decisions, next steps, and owners from leadership meetings; ensure actions are documented, tracked, and followed through to support operational excellence.

• Use AI and productivity tools (e.g., ChatGPT, Gemini, NotebookLM) to streamline information gathering, draft content, summarize documents, and improve workflow efficiency, while applying strong judgment and data privacy awareness.

• At Guidewire, we foster a culture of curiosity, innovation, and responsible use of AI—empowering our teams to continuously leverage emerging technologies and data-driven insights to enhance productivity and outcomes. 

• Through this work, you’ll help Product Strategy execute on Guidewire’s mission to transform how the world’s P&C insurers do business by combining digital, core, analytics, and AI on our cloud platform. 

What you’ll bringRequired

• Demonstrated ability to embrace AI and apply it to your current role as well as data-driven insights to drive innovation, productivity, and continuous improvement. 

• 5+ years of experience as an Executive Assistant supporting VP‑level or above leaders in a fast‑paced technology or SaaS environment, preferably supporting multiple executives simultaneously.

• Exceptional calendar management skills with proven experience handling competing priorities, complex time zones, and frequent changes while maintaining calm and clarity.

• Outstanding verbal and written communication skills, with the ability to draft concise executive‑level communications, anticipate information needs, and escalate conflicts appropriately.

• High level of organization and attention to detail; you consistently follow through, close loops, and maintain accurate documentation and records under time pressure.

• Proficiency with Google Workspace (Gmail, Calendar, Docs, Sheets, Slides) and comfort learning new enterprise tools; experience with travel and expense platforms such as Concur or Navan is a plus.

• Demonstrated discretion and sound judgment in handling confidential information and sensitive topics.

• Ability to work effectively across time zones and adapt to changing priorities, including occasional early/late meetings aligned to global Product initiatives.

• Preferred

• Experience supporting leaders in Product, Strategy, or R&D organizations—ideally in cloud, data, or AI‑driven product companies.

• Hands‑on experience using AI tools (e.g., ChatGPT, Gemini, NotebookLM, or similar) to draft content, summarize information, or optimize workflows.

• Experience planning and executing multi‑day leadership offsites or global virtual events.

• Familiarity with P&C insurance or enterprise software environments, a plus

What’s in it for you
The people we employ give their all, and in return, we offer flexibility wherever we can, such as:

• Flexible work environment

• Health and Wellness benefits

• Paid time off programs including volunteer time off

• Market-competitive pay and incentive programs

• Continual development and internal career growth opportunities

The US base salary range for this full-time position is $82,000 - $124,000 . 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.