Job details

Technical Training Instructor, Customer and Cloud Operations

  • Department: Cloud and Customer Success
  • Location: US - Remote
  • Country: United States of America

Guidewire’s Customer and Cloud Operations (CCO) organization operates and maintains Guidewire Cloud products and provides 24x7 technical support to Guidewire’s enterprise customers. CCO is seeking a dedicated Training Instructor to develop or improve training content and deliver it to new and existing employees.

The Role:

As a successful Training Instructor, you are expected to become proficient in the usage and operation of our products, as well as with our processes and best practices for cloud operations and customer support. You will be responsible for delivering classroom, remote, and recorded training, and for guiding students through the internal certification process.  In addition, you will improve and create new training content as needed for our teams. As one of the primary education resources within CCO, you will work with the teams to ensure training is delivered consistently and will provide new hires and current employees with training and tools to make them effective and efficient in their jobs.

Your initial focus will be the delivery of CCO Foundation Training in various locations globally as we onboard new Support team members. You will then work with the individual students while they complete post-training certification projects, mentoring them through the process and evaluating their performance. In addition, you will contribute to improvements in our training materials and methods of delivery and will review new training materials before they are finalized. Lastly, you will work closely with the Professional Services Education and CCO Enablement teams to develop onboarding and performance-development curriculum for various departments within CCO.

Key responsibilities include:

  • Adhering to Guidewire’s core principles of integrity, rationality, and collegiality in everything that you do.
  • Delivering technical, process, soft skills, and methodology training to new and existing CCO employees.
  • Serving as a coach and mentor to employees during Guidewire CCO Professional Certification.
  • Working with students to troubleshoot on the spot to guide them through exercises and help enable understanding.
  • Providing feedback on new and existing training programs and materials to ensure they effectively prepare students for their roles in the organization.
  • Developing and updating of training curriculum.


  • Strong oral and written communication skills
  • 5+ years’ experience as an instructor on enterprise application software
  • 5+ years’ experience in curriculum development and/or instructional design with a motivation to develop and deliver engaging hands-on training
  • Experience with complex enterprise application software
  • Demonstrated ability to teach business and technical concepts for software products in both live classroom and virtual web settings
  • Comfort presenting complex ideas in simple ways to a diverse learner audience
  • Ability to troubleshoot issues on the spot to enable students to complete exercises
  • Experience with Java/JVM, SQL, development IDEs
  • A flexible and enthusiastic approach to work
  • Availability to travel approximately 35% globally (Primary travel locations include San Mateo, CA, US; Toronto, Canada; Dublin, Ireland; Madrid, Spain; and Kuala Lumpur, Malaysia).

Desired skills/experience include:

  • Experience in training business and technical teams on new products and process flows
  • Experience in technical support, support processes, or customer service
  • Working knowledge of Salesforce or other CRM product
  • Working knowledge of Jira or other ticketing systems
  • Experience with troubleshooting techniques, Java/OS diagnostic tools
  • Familiarity with the P&C Insurance domain

Why Guidewire?

Guidewire exists to deliver the industry platform that P&C insurers rely upon to adapt and succeed in a time of accelerating change—and to ensure that every customer succeeds in the journey. We provide the software, services, and partner ecosystem to enable our customers to run, differentiate, and grow their business.

Guidewire InsurancePlatform is the P&C industry platform that unifies software, services, and partner ecosystem to power our customers’ business. InsurancePlatform provides the standard upon which insurers can engage their customers, optimize their operations, drive smart decisions, and innovate quickly. We are privileged to serve more than 350 P&C insurers in 32 countries. We invest heavily in R&D to build a technology platform that combines three elements—core processing, data and analytics, and digital engagement—to enhance insurers’ ability to engage and empower their customers and employees.



Guidewire Software Inc. provides equal employment opportunities to all applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.