Executive Assistant

Guidewire•San Mateo, CA

5d•Hybrid

About The Position

Join Guidewire at the intersection of innovation, operations, and AI. Guidewire is hiring a high-impact Executive Assistant to support our Chief Information Officer and his leadership team, including the VPs of Applications, Strategy & Operations, and Infrastructure Engineering. This is a visible, fast-paced role at the heart of how we run technology and procurement at scale. We need someone who is curious, proactive, tech-savvy, and people-savvy—a natural connector who thrives in ambiguity, and finds clarity in complexity. You’ll partner closely with our Sr. Director of Portfolio Management & Operations and be a key voice in evolving how the EA function adds strategic value. This isn’t a traditional support role. You’ll be a trusted business partner, helping to redefine what executive support looks like in a world of AI and agentic platforms. If you’re energized by the opportunity to make things smoother, smarter, and more impactful -this role is for you. This is a hybrid role requiring a minimum of 2 days per week onsite in San Mateo, California.

Requirements

Bachelor’s degree preferred; 5+ years supporting VP/C-level execs in a high-growth tech or client-facing environment (public company experience a plus)
Proven ability to manage sensitive and confidential information with discretion
Exceptional communicator—clear, concise, confident in both written and verbal formats
Anticipates needs, solves problems before they surface, and stays three steps ahead
Highly organized and detail-driven, with strong project and time management skills
Calm under pressure; thrives in ambiguity and adapts quickly when priorities shift
Strong interest in technology, a keen curiosity for advancements in the field, and a natural aptitude for AI
Expert in Google Workspace (Slides, Docs, Sheets); familiarity with Workday, Concur, Coupa, Slack, etc., is a plus
Collaborative, accountable, and motivated by delivering high-quality outcomes
Creative thinker who improves workflows and helps the team work smarter
Willing to be flexible and available outside standard hours when needed.

Responsibilities

Provide proactive support to the CIO: inbox management, calendar coordination, travel planning, and expense reporting
Manage schedules and logistics for up to 4 executives; coordinate internal and external meetings
Plan and execute leadership offsites, team town halls, and recurring department forums
Communicate seamlessly across senior leaders, customer executives, and partners
Track cross-functional priorities and connect the dots across teams and initiatives
Build polished, executive-ready presentations and internal communications
Maintain and update internal team pages and distribution lists for clarity and consistency
Support onboarding, culture-building, and recognition programs
Handle sensitive matters with discretion, integrity, and professionalism
Travel up to 10% for leadership events and in-person support; this is a hybrid role requiring a minimum of 2 days per week onsite in San Mateo, California.
Help define the future of the EA role by leveraging AI and agentic platforms to unlock greater productivity, automation, and strategic focus