Chief of Staff

Summary

The Chief of Staff to the Chief Customer Success Officer plays a pivotal role in amplifying the impact of the Customer Success and Alliances organization. This individual serves as a trusted advisor, program leader, and strategic operator who drives alignment, communication, and execution across key initiatives that enhance customer engagement, organizational culture, and executive visibility.

Job Description

The Chief of Staff to the Chief Customer Success Officer plays a pivotal role in amplifying the impact of the Customer Success and Alliances organization. This individual serves as a trusted advisor, program leader, and strategic operator who drives alignment, communication, and execution across key initiatives that enhance customer engagement, organizational culture, and executive visibility.

This role requires a strong balance of strategic thinking, operational excellence, and hands-on program execution. The Chief of Staff will ensure the Customer Success and Alliances organization runs smoothly, effectively communicates its impact, and maintains strong alignment with both internal and external stakeholders.

Key Responsibilities

Customer & Partner Engagement Programs

• Lead and execute key customer feedback forums and executive meetings, including the Global Strategic Advisory Council (GSAC), Business Advisory Council (BAC), and User Groups, ensuring meaningful outcomes and follow-through on customer feedback.
   

• Coordinate Customer and System Integrator (SI) tours and visits to drive deeper partnership engagement and showcase the organization’s value.
   

• Support planning and delivery of Executive Symposiums, Customer Connections, and GIFs (Global Influencer Forums) to enhance strategic alignment and customer advocacy.

Organizational Communications & Engagement

• Develop and manage Quarterly All-Hands content, agenda, and messaging to ensure alignment across the Customer Success and Alliances organization.
   

• Serve as the owner of Employee Net Promoter Score (eNPS) programs, including survey management, analysis, and execution of improvement actions.
   

• Oversee internal recognition programs such as Rockstar of the Quarter and other engagement or reward initiatives.
   

• Partner with the CCSO to craft and deliver key executive communications, including Quarterly Board of Directors presentations, executive readouts, and strategic internal updates.
   

Strategic Programs & Operations

• Partner with the Chief Customer Success Officer to manage strategic priorities, special projects, and ad-hoc executive requests, ensuring timely and high-quality execution.
   

• Support annual and regional event planning, including Synergy, Regional Kickoffs, and Connections, working closely with Enablement, Marketing, and HR teams on logistics, attendee engagement, and recognition moments.
   

• Coordinate and manage board-related experiences and executive briefings that highlight Customer Success achievements and customer impact stories.
   

Leadership Enablement & Execution

• Act as a thought partner to the CCSO in shaping organizational strategy, identifying opportunities for efficiency, and driving alignment across cross-functional teams.
   

• Drive operational excellence through consistent tracking of key initiatives, communication cadences, and executive reporting.
   

• Ensure strong collaboration across Customer Success, Sales, Marketing, Product, and Partner organizations.

Qualifications

• 5+ years of professional experience in Customer Success, Business Operations, or Program Management roles within a SaaS or technology organization.
   

• Proven ability to lead cross-functional initiatives and drive results through influence rather than authority.
   

• Strong executive communication and storytelling skills — able to translate complex ideas into compelling narratives.
   

• Excellent organizational skills, with a demonstrated ability to manage multiple programs and priorities simultaneously.
   

• Experience managing executive forums, customer advisory boards, or internal communications programs preferred.
   

• Demonstrated success in employee engagement, event planning, or culture-building initiatives.

Personal Attributes

• Strategic thinker with a hands-on, “get it done” mindset.
   

• Highly collaborative, adaptable, and capable of operating in fast-paced, evolving environments.
   

• Discreet and professional when handling sensitive information.
   

• Passionate about customer advocacy, organizational culture, and operational excellence.

The US base salary range for this full-time position is $141,000 - $211,000 . 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.