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Senior Executive Assistant to the CEO - San Mateo, California

  • DepartmentOther
  • LocationUnited States - San Mateo, CA
  • Location TypeOn-Site
We are seeking an experienced  professional to fill the role of Senior Executive Assistant to our CEO Mike Rosenbaum. The ideal candidate will be exceptionally organized, possess strong coordination and leadership qualities and be able to think strategically about the company and our objectives. This position involves providing world class administrative support while also ensuring smooth operations and effective communication with internal and external stakeholders as a representative of the CEO office.


Organizational Skills: Strong organizational skills with the ability to prioritize tasks, manage multiple projects, and meet deadlines.

Leadership Skills: Capability to lead and coordinate cross-functional initiatives, collaborating with various departments to achieve organizational goals.

Problem-Solving: Proven ability to analyze complex situations, identify challenges, and implement effective solutions.

Communication: Exceptional written and verbal communication skills to represent the CEO and facilitate clear communication within the executive team.

Adaptability: A flexible and agile mindset to navigate a fast-paced and ever-changing executive environment.

Strategic Thinking: Ability to understand and contextualize the companies and the CEO’s  vision and strategic objectives and actively contribute to the development and prioritization of tactics that support these objectives. 

External Engagement Coordination: Effectively communicate and coordinate engagements with outside parties, including customers, partners, and other representatives. Act as a liaison between the CEO and external stakeholders, ensuring a positive and professional interaction.

Confidentiality: Uphold the highest standards of discretion and confidentiality in handling sensitive information.

Job Responsibilities:

  • Calendar Management: Efficiently manage the CEO's calendar, scheduling meetings, appointments, and travel arrangements.
  • Communication: Serve as the primary point of contact between the CEO and internal/external stakeholders, ensuring clear and timely communication.
  • Document Management: Prepare and review documents, presentations, and reports for the CEO, maintaining accuracy and professionalism.
  • Meeting Coordination: Organize and coordinate executive-level meetings, including agenda preparation, minutes, and follow-up actions.
  • Travel Coordination: Arrange travel plans, itineraries, and accommodations for the CEO, optimizing efficiency and comfort.
  • Strategic Support: Work closely with the CEO to contribute to the development and execution of strategic initiatives.
  • Executive Team Coordination: Facilitate communication and collaboration among executive team members to ensure alignment with organizational goals.
  • Project Management: Lead and oversee special projects, ensuring timely completion and alignment with organizational objectives.
  • Decision Support: Provide analysis and information to aid the CEO in making informed decisions.
  • Office Management: Oversee the day-to-day operations of the CEO's office, ensuring efficiency and productivity.


  • Proven experience as an Executive Assistant supporting C-level executives.
  • Previous experience in a Chief of Staff or strategic support role is highly desirable.
  • Strong interpersonal skills and the ability to work collaboratively in a team environment.
  • The ideal candidate will be able to gain sufficient understanding of Guidewire and our objectives such that they will be able to independently brief the CEO on daily meetings and deliverables.

  •  If you are a motivated and strategic professional, we invite you to apply and contribute to the success of Guidewire.

Salary Information

Salary Range: $134000 - $202000 per year

Our salary ranges are determined by role, level, and location. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific salary range for your preferred location during the hiring process.  We also pride ourselves on being a pay for performance company.
Please note that the compensation details listed in US role postings reflect the base salary only, and do not include bonus, equity, or benefits.

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 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.

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 (650) 356-4940 or 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, call (650) 356-4940 or e-mail 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.
Talent rewards

The perks. The rewards. The good stuff.

We’re proud to shout about our awesome benefits packages. Holistic wellness is a big deal for us. We offer everything you need to support your work and, most importantly, your work-life balance. We’re committed to helping you be the best version of yourself. Inside and outside of work.



Receive market-competitive pay and incentive programs—because you deserve it! To help future-proof your income, we offer generous support through retirement savings plans.



Keep your physical and emotional health in tip-top shape with health insurance for you and your family, an employee assistance program, annual wellness reimbursement, and access to wellness resources.



Work in an environment where you’ll have the freedom and trust to make an impact, with time for your life outside of work.



Relax and kick back through our generous paid time-off programs. Make a difference in your community with three volunteer days each year. Take your own personal day of rest with My Day. We also offer ample paid leave for all new parents.



We encourage self-directed learning, giving you every chance to become a better version of yourself, both professionally and personally. At Guidewire, lifelong learning is here for the taking.



Your career opportunities are only limited by your own imagination. Guidewire’s community is filled with chances to expand your horizons across any of our teams or worldwide‌‌‌‌‌‌‌ locations.