Chief of Staff/Office of the CEO

Guidewire Software

5d • $165,000 - $247,000

About The Position

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.

Requirements

• 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
• 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.

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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 1,001-5,000 employees