Senior Director of Support, AMER Region

Summary

Guidewire is seeking a Senior Director to lead the AMER region of Guidewire Global Support (GGS). The Senior Director is responsible for leading a team of ~200 technical support engineers as they research and resolve all incoming support cases from Guidewire’s customer base. This position requires strong managerial and leadership skills, a deep commitment to customer satisfaction, and experience in driving effective process improvement.

This is a full-time in-office role based at Guidewire’s office in San Mateo, California or in Mississauga Ontario, Canada. The job requires occasional travel (up to 10%) to visit other Guidewire offices or for company events.

Job Description

Responsibilities

Operational Management

• Oversee day-to-day operations of the Application and Platform Support teams in the USA, Canada, and Brazil, ensuring KPI delivery across Guidewire’s diverse product suite. Balance ensuring a globally consistent and scalable approach to support with regional customization to ensure success of the business.

• Set goals and monitor KPIs such as CSAT, Initial Response, Time to Resolve, and Escalation Rates, ensuring data-driven decision-making.

• Drive continuous improvement through existing and future team performance and quality frameworks, leveraging analytics and benchmarking to identify gaps and optimize processes.

• Develop and adopt AI-powered support delivery mechanisms to improve efficiency and service quality.

Team Development & Leadership

• Build and lead high-performing Application and Platform support teams, including recruitment, onboarding, and career development initiatives.

• Measure and track employee attrition as a success measure.

• Drive a culture of accountability, collaboration, transparency, customer obsession, and data‑driven decision‑making across diverse teams.

• Foster a sense of urgency to resolve customer issues and encourage high levels of customer interaction.

• Conduct regular performance reviews, succession planning, and leadership coaching to ensure organizational resilience.

• Lead the regional team through periods of transformation and growth, ensuring employees are supported, informed, and empowered as the business evolves.

Strategic Leadership

• Develop and execute regional support strategies aligned with global objectives and growth targets.

• Determine required staffing levels in each office location to ensure adequate time zone coverage and effective regional hand-offs.

• Collaborate with other leaders both within GGS and across the Product Development & Operations organization on transformation initiatives to scale support operations, including automation, self-service, and AI-driven support tools.

• Represent the voice of the customer in regional and global leadership forums, influencing product roadmaps and service enhancements.

• Maintain readiness to contribute to global strategic planning and decision-making when required.

Customer Experience & Escalation Management

• Own regional escalation visibility to the senior leadership team, ensuring timely and effective resolution of high-impact issues. Help to organize and participate in on-shift and on-call rotas as required to ensure engineer and leadership coverage.

• Provide weekly reporting on regional support performance, highlighting trends and improvement opportunities.

Cross-Functional Collaboration

• Partner with Product Engineering and Customer Success to align support capabilities with evolving customer needs and product changes.

• Collaborate with HR, Finance, and Legal on workforce planning, budgeting, and compliance matters.

• Lead regional communications and change management efforts, ensuring alignment with global initiatives.

Required Skills and Experience

• Bachelor’s Degree in Computer Science or related field.

• 10+ years in customer support leadership roles, ideally in high-growth B2B SaaS or technology environments.

• At least 8 years of experience leading geographically-dispersed teams of 60 people or more.

• Successful experience managing teams at scale, including remote and multilingual support functions.

• Proven success in scaling support operations across multiple regions or business units.

• Strong understanding of support metrics, tooling (e.g., Salesforce, Jira), automation strategies, and AI-driven solutions.

• Ability to operate effectively at an executive level, influencing global priorities and contributing to strategic decisions.

• Familiarity with global support models, including follow-the-sun and tiered support structures.

• Experience with tiered-level support opportunities and challenges, including cultural requirements and language needs, and time zone coverage.

• Proven ability to lead through influence, build cross‑functional alignment, and translate strategy into measurable results.

• Exceptional communication, executive presence, and the ability to inspire teams through change.

• Background in implementing automation, AI, or self-service strategies.

• Experience implementing and leveraging AI-enabled support technologies (e.g., chatbots, agent assist, automation, intelligent routing, workflow optimization) to drive efficiency and enhance customer outcomes.

Preferred Experience

• Innovative Disruptor: A documented history of challenging assumptions and bringing new, "courageous" ideas to shape Cloud Success strategies.

• High EQ Leadership: Demonstrated "low ego" with the natural authority to inspire others and remain resilient in the face of setbacks.

• Product Influence: Experience directly influencing product development lifecycles or engineering priorities based on support data and trends.

Benefits

• Competitive Market Salary

• Annual Bonus

• LTI (Long-Term cash or stock  Incentive)

• FlexWork options

• Group Medical Insurance

• Annual Wellness Reimbursement

• Unlimited paid time off

• 26 weeks paid maternity leave

• 16 weeks paid paternity leave

• 3 paid days volunteering and many more

The US base salary range for this full-time position is $174,000 - $334,000. 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 Accommodations@guidewire.com. 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 Accommodations@guidewire.com 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.