Summary

At Guidewire, we deliver the software that Property and Casualty (P&C) insurance companies rely on to protect their customers during crises, natural disasters, accidents, and cyber risks. Our core applications enable insurers to sell and underwrite policies, settle claims, and bill their customers. We also offer a suite of innovative products for data management, digital portals, and predictive analytics.

Hundreds of insurers worldwide use Guidewire's products, running on our cutting-edge Guidewire Cloud Platform, to handle billions of dollars in business. We are dedicated to providing the tools and technology that help insurers protect and support their customers when they need it most.


We are searching for a Director of Site Reliability Engineering (Application) to lead a regional SRE organization, uniting our talented engineers under a single banner of reliability, scalability, and performance. You will be responsible for a full stack of applications and services within your geographic region, acting as a strategic, battle-tested leader accountable for the operational excellence of the Guidewire Cloud Platform.

This is a critical leadership role where you will champion the SRE philosophy, drawing from foundational principles like those in the Google SRE handbook. You will drive the evolution of our SRE practice, moving beyond traditional operations to a software-first approach to solving complex application, infrastructure and reliability challenges. Your mission is to build and lead a world-class team that ensures our cloud-based solutions are the most reliable and performant in the industry.

Job Description

What You'll Do:

Lead, mentor, and inspire a regional SRE organization, fostering a culture of ownership, innovation, and continuous improvement across multiple teams and senior technical leaders.

Champion and implement SRE best practices, establishing and maturing core pillars including observability (The Four Golden Signals), reliability engineering, proactive incident management, and Production Readiness Reviews (PRRs).

Partner with executive leadership and product engineering to define the long-term strategic roadmap for the reliability and scalability of the Guidewire Cloud Platform, articulating technological trade-offs and vision.

Drive a culture of automation to eliminate toil, improve operational efficiency, and empower engineering teams to focus on delivering business value.

Develop and empower your team of SRE managers and engineers, fostering a high-performance culture through effective performance management, coaching, and career development to raise the bar for talent.

Oversee the regional incident management process, acting as a point of escalation, directing major incident response, and ensuring that blameless postmortems drive meaningful, preventative actions.

Manage departmental budgets, resource allocation, and schedules to meet corporate and functional objectives, ensuring operational effectiveness.

Represent the technical direction of your initiatives in executive management meetings and potentially at external technical conferences, demonstrating Guidewire's thought leadership.

What You'll Bring:

A deep-seated belief in core SRE principles, with a clear understanding of the difference between reactive operations support and proactive reliability engineering.

Extensive experience in a senior leadership role within Site Reliability Engineering, Software Engineering, or a related field, with a proven track record of managing managers and scaling teams.

Demonstrated excellence in people management, with a track record of building, scaling, and empowering high-performing, geographically distributed teams.

A strategic mindset with the ability to articulate a long-term technical vision to both executive and engineering audiences, effectively managing complex trade-offs.

Exceptional problem-solving capabilities, with the ability to analyze complex distributed systems, anticipate potential problems, and guide teams to innovative solutions.

Outstanding communication and negotiation skills, capable of reconciling multiple stakeholder views to drive business results and influence product strategy.

Typically requires a minimum of 15 years of related experience with a Bachelor’s degree; or 12 years and a Master’s degree; or a PhD with 8 years experience; or equivalent work experience.

Required Skills:

Proven experience implementing and scaling SRE principles (SLIs/SLOs, error budgets, toil reduction, blameless postmortems) across a large engineering organization.

Expertise in leading major incident management for large-scale systems, ideally with hands-on experience as an Incident Commander.

Deep expertise in building, deploying, and running scalable and reliable infrastructure within AWS and Kubernetes ecosystems.

Strong proficiency with Infrastructure as Code (IaC) using Terraform and GitOps principles.

Strong software engineering foundation with architectural knowledge of systems built in Go, Python, or Java.

Experience leading teams that build and support microservices, leveraging frameworks like Spring Framework and React.

Proven experience leveraging modern observability and APM tools, with a strong preference for Datadog (monitoring, dashboards, synthetics, etc).

Experience overseeing CI/CD strategy and pipelines using tools such as Jenkins, TeamCity, or GitHub Actions.

Experience with people management in Workday and managing workstreams using ticketing tools like JIRA Service Management and ideation tools like AHA.

Strong understanding of cloud networking, security, role-based access control (RBAC), and vulnerability management.

Preferred Skills:

AWS and/or Kubernetes certifications (e.g., CKA, CKAD).

Familiarity with Guidewire's product suite (InsuranceSuite) or the Guidewire Cloud Platform is a significant plus.

Knowledge of Guidewire-specific technologies such as Gosu.

Interest or experience in emerging technologies like Kubevela and the application of agentic AI/LLMs to SRE practices.

Experience with enterprise business tools such as Coupa, Concur, and Salesforce.

Why Guidewire

This is an opportunity to join a mission-driven company and make a real impact in the lives of people facing challenges. You'll work with cutting-edge technology, collaborate with talented peers, and grow your skills in a culture that values innovation, teamwork, and work-life balance. We offer competitive compensation, comprehensive benefits, and opportunities for career development.

If you're a Director of SRE who combines deep technical expertise with a passion for problem-solving and a commitment to reliability, we'd love to hear from you. Join us in building the software that helps insurers care for their customers when they need it most.

As a senior leadership position, this role is not part of a formal on-call rotation. However, the Director must remain accessible outside of standard business hours, including evenings, weekends, and holidays, when circumstances require executive involvement. Candidates should be aware of and willing to accept this responsibility as an essential aspect of supporting the needs of the business and our customers.

#LI-AS3

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.