Chief of Staff/Office of the CEO

Summary

We seek an exceptional, strategy-driven leader with sharp market insight, structured problem-solving expertise, and unparalleled execution ability. This highly visible, strategic role requires executive presence, deep business acumen, and expertise in the international P&C insurance market.
You will act as an internal management consultant to the CEO and executive team, owning the end-to-end process of developing, stress-testing, communicating, and tracking the annual corporate strategy. Serving as the trusted partner and operational extension of the CEO, you will maximize their impact by effectively managing their time, focus, and priorities. You will not only report the strategy but also build the intellectual scaffolding and execution engine to achieve it. Partnering with the Chief People Officer to align on communication, operations, and readiness globally in connection with VPMom events. This role is a catalyst opportunity to work alongside a strong CEO and get the exposure and experience working across the organization globally to deliver and provide insight to CEO and partnership with the leadership team, employees and customers.

Job Description

Responsibilities:

• Structure & Lead Annual Strategy:
  Own the full lifecycle of our annual and multi-year corporate strategy. This includes driving the creation each year with the CEO and President, and bringing core business challenges, market trends, customer feedback, and competitive landscape to the conversation to help define where we play and how we win.

• Facilitate Executive Alignment & Consensus: 

Act as a skilled facilitator and trusted advisor to the CEO and executive team. You must be able to structure and facilitate tough discussions, challenge underlying assumptions, and distill complexity into crisp, actionable decisions that drive alignment across diverse executive viewpoints.

• Synthesize Insights & Drive Recommendations:
  Continually scan the market, customers, VPMOM methods and competitors. Combine external intelligence with rigorous internal analysis of data across the organization to proactively bring data-backed recommendations to the executive conversation.
   

• Lead Strategic Cadence:
  Oversee the planning and execution of quarterly in-person leadership meetings, monthly method reviews with the CEO, and our annual global kick-off. Ensure these gatherings drive accountability, foster alignment, and keep our strategy alive and evolving. 

• Enable CEO Effectiveness & Communications:
  Manage the overall Executive Office operating rhythm, including the quarterly business review process, board preparation, and weekly executive staff meetings. Serve as the primary liaison for the CEO, triaging and directing communications and priorities to the appropriate leaders and teams. Draft and prepare high-stakes internal and external communications for the CEO, including presentations, internal updates, and town hall content. Oversee and manage the preparation and follow-up for the CEO’s key meetings, ensuring pre-read materials are accurate and post-meeting actions are assigned and tracked. 

Success Profile:

• Executive Presence: The confidence to lead and drive conversations at the highest levels of the organization, coupled with the grace and emotional intelligence to navigate sensitive, high-stakes discussions. Unwavering discretion and integrity when handling highly sensitive and confidential executive and personnel information.

• Expert Industry Knowledge: Deep understanding of the international Property & Casualty insurance market, its trends, competitive dynamics, and strategic levers for growth and efficiency.

• Analytical Acumen: Ability to connect disparate data points— financials, customer needs, competitive moves—and create a compelling, coherent strategic narrative. 

• Impact-Driven: A track record of not just advising, but building momentum—moving quickly from ideas to outcomes and keeping cross-functional teams focused on measurable results
   

Qualifications:

• Experience: 10–15+ years in corporate strategy, strategic or business operations, or a similar executive-level function. Experience within (or advising) international P&C insurance organizations strongly preferred. Experience developing strategies, enterprise wide events, management consulting and program management in the software industry. Must be fluent in AI and leads an AI first approach in all areas.
   

• Education: Bachelor’s degree required; Military experience, advanced degree (MBA or similar) a plus.
   

• Leadership: Proven success leading high-impact strategy development and large scale transformation efforts that cross functions and regions.
   

• Communication: Exceptional written and verbal communicator who can engage both broad audiences and small executive teams with consulting-grade clarity, concision, and inspiration. Proven ability to ghostwrite and synthesize the voice and perspective of an executive leader for various internal and external audiences.

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 $165,000 - $247,000 . 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.