Education Success Specialist

Canada - Remote

Guidewire Software logo
Guidewire Software
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 400 insurers, from new ventures to the largest and...
Apply now Apply later

Are you passionate about learning and helping customers keep pace with digital technology? We need an experienced Education Success Specialist who is passionate about learning and adept at helping clients execute training plans to master our Guidewire products and supporting partner technologies.  You will use your knowledge, skills, and experience to build client relationships and foster product adoption and competency.   With an eye for detail and a passion for optimizing client success, you know how to quickly establish rapport and add value through brief, recurring conversations.  As a client advocate for Guidewire’s small to mid-size carriers, you will work with your co-workers in Education Services and supporting business departments to help customers optimize training plans, maximize training consumption, and enable product competency.  You’ll run and analyze training reports to verify learner progress against the client’s goals; you will highlight risks associated with knowledge gaps; and you will track trends across clients to recommend process and program improvements.  For large carriers with more complex system implementations, you will use these same skills to support the Education Success Lead in our quest for optimal education planning. Your skills and experience will help customers accelerate proficiency and productivity with Guidewire products to reduce their TCO and improve their ROI.     In addition to the more strategic objectives noted above, you will also be responsible for supporting the customer’s end to end journey through our Education systems including:-          User enrollment in Guidewire’s Learning Management System-          Virtual Machine set-up-          Coordination of instructor led classroom training-          Troubleshooting system related issues experienced by learners-          Creating custom training report requests  The Education Services team is growing to keep pace with Guidewire’s digital transformation. We design, develop, and maintain content that teaches our customers, partners, employees, and third parties how to implement and integrate our highly configurable products.  We also build certifications that validate competency to improve implementation efficiency and quality.  Our training is often the first time the customer’s project team sees the Guidewire products that they will be implementing.  Your work will help elevate their first impression of Guidewire, our Services team, the education content we provide, and the value that only mastery can unlock.  Ultimately, your work will help customer teams deepen their knowledge, demonstrate their competency, and increase their self-sufficiency with Guidewire products.  To learn more about Guidewire Education, visit us at

Key Assignments

  • Serve as the client education advocate to enable their training goals and project success
  • Set early expectations with the client and provide direction throughout the customer lifecycle to ensure Guidewire Education delivers as promised
  • Optimize the client experience by leading operational onboarding activities
  • Establish initial training plans, create and maintain personalized learner maps, and recommend incremental training activities
  • Advise the customer on recommended curriculum, prerequisites, and exam sequence to enable competency

Core Responsibilities

  • Handle all contract, order, invoicing, and other ad hoc education queries
  • Build and publish recurring reports to track training and certification progress and other key metrics
  • Research and communicate training and certification gaps that may impact project success
  • Provide timely follow-up on customer requests and drive action items to completion
  • Ensure the customer can access our LMS and training content, troubleshooting as needed
  • Create and maintain processes and procedures for transparency and repeatability
  • Champion improvements in processes and systems to increase efficiencies and customer satisfaction
  • Create and distribute recurring progress reports to customer/partner teams
  • Escalate issues and risks that impact customer success or satisfaction
  • Collaborate with Services, Alliances, Sales, and other Guidewire teams to help ensure project readiness
  • Identify and enable operational efficiency between Education and other departments


  • 3-5 years of customer account management experience
  • 2-4 years defining processes and workflow improvements across complex systems
  • Significant experience in a leadership role that ensured customer success
  • Impeccable customer relationship skills with an ability to quickly establish trust and manage customer expectations
  • Passion for excellence and helping others achieve success
  • Self-driven and proactive with demonstrated leadership qualities
  • Skilled at presenting complex topics and workflows in a simple, consumable way
  • Exceptional written and verbal communication skills
  • Experience presenting to middle management and executive audiences
  • Knowledge of customer success processes and related industry best practices
  • Works well independently but also thrives on a small, nimble team
  • Remarkable focus on quality
  • Proven ability to work across geographic and cultural boundaries to support complex projects with a variety of stakeholders
  • Strong problem-solving skills with ability to see patterns, recommend improvements, and deploy solutions
  • High computer literacy and proven ability to master new systems and complex processes with ease
  • Strong knowledge of Microsoft products with advanced knowledge of Excel
  • Outstanding time management and organizational skills
  • Experience with a customer-facing Learning Management System (LMS) or Customer Relationship Management (CRM) system is a plus
  • Experience providing end user training is a plus
  • Business analyst and/or quality analyst experience is also a plus
  • Some flexible hours may be required due to the global nature of our team  

About Guidewire
Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently.
Guidewire combines core, data, digital, analytics, and AI to deliver our platform as a cloud service. More than 400 insurers, including 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 1000+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of add-ons that accelerate integration, localization, and innovation.
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.
We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation. 
Job perks/benefits: Career development Flex hours
Job region(s): North America
Job stats:  4  2  0

Explore more Remote Work and WFH career opportunities