Executive Assistant

Job Summary

We are seeking a dynamic Executive Assistant to join Guidewire Software and provide comprehensive support to our Chief Information Officer and leadership team, including Vice Presidents of Applications, Strategy & Operations, and Infrastructure Engineering. This critical role operates at the confluence of innovation, operations, and AI, enabling smooth execution of technology and procurement activities at scale.

The ideal candidate will be proactive, inquisitive, technologically adept, and skilled in interpersonal connections. Able to navigate and clarify complex, ambiguous environments, you will collaborate closely with senior directors to enhance the strategic contribution of the Executive Assistant function. This position goes beyond traditional support, acting as a trusted partner in reshaping executive assistance in a technology-driven world.

This hybrid role requires at least two days per week onsite in San Mateo, California.

Responsibilities

• Offer proactive support to the CIO including management of email inbox, coordinating calendars, arranging travel, and overseeing expense reports.
• Organize schedules and logistics for up to four executives, facilitating meetings both internally and externally.
• Plan and coordinate leadership offsite events, team-wide town halls, and recurring departmental forums.
• Communicate effectively across senior leadership, customer executives, and external partners.
• Monitor cross-departmental priorities and connect initiatives across various teams.
• Create polished, executive-level presentations and internal communications.
• Maintain and update team pages and distribution lists to ensure clarity and consistency.
• Support onboarding processes, foster culture-building activities, and manage recognition programs.
• Handle confidential and sensitive matters with utmost discretion, professionalism, and integrity.
• Travel up to 10% for leadership events and onsite assistance as necessary.
• Engage in defining the evolution of the Executive Assistant role by utilizing AI and agentic platforms to enhance productivity, automation, and strategic focus.

Qualifications

• Bachelor’s degree preferred; a minimum of 5 years’ experience supporting VP or C-level executives in a fast-paced technology or client-facing environment (experience in a publicly traded company is an advantage).
• Demonstrated ability to manage sensitive and confidential information discreetly.
• Excellent communication skills, both written and verbal, with clarity and confidence.
• Strong anticipatory skills to address needs and resolve issues proactively.
• Highly organized with superb attention to detail, alongside strong project and time management capabilities.
• Ability to stay calm under pressure, adapt rapidly to shifting priorities, and thrive amid ambiguity.
• Keen interest in emerging technologies, especially AI, with a natural aptitude for learning and applying technological advances.
• Proficiency in Google Workspace tools (Slides, Docs, Sheets); familiarity with Workday, Concur, Coupa, Slack is advantageous.
• Collaborative mindset, accountability, and a drive for delivering exceptional outcomes.
• Innovative thinker committed to improving workflows and enhancing team efficiency.
• Flexibility to work beyond standard hours as required.

Salary and Benefits

The base annual salary range for this position is $82,000 to $163,000, commensurate with experience, education, skills, and location. Full-time employees or those working 30 or more hours weekly are eligible for comprehensive benefits including healthcare (medical, dental, vision), paid time off, and a company-sponsored retirement plan. Additional incentives such as bonuses, commissions, and long-term awards may be offered based on individual and company performance.

Diversity and Accommodations

Guidewire is committed to equal employment opportunity and creating an inclusive workplace that values diverse perspectives and backgrounds. Applicants will be considered without regard to race, color, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, veteran status, or disability.

The company offers accommodations during the hiring process for candidates with disabilities. Requests should be directed to the accommodations contact provided during recruitment. An appeals process is available for decisions regarding accommodations or hiring outcomes, ensuring fair review by an independent decision-maker.

About Guidewire

Guidewire Software provides trusted cloud-based platforms for property and casualty insurers worldwide, integrating digital, core, analytics, and AI capabilities. Our clients include over 540 insurers across 40 countries. We pride ourselves on a strong implementation history, extensive research & development, and a broad partner ecosystem that accelerates innovation and localization.