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The Guidewire Enterprise Readiness Team is a critical strategic organization developed to align information, learning and communication experiences to support readiness and adoption goals across all Guidewire personas - Customer, Partner, and our internal Guidewire team. Our goal is to build an enterprise training and enablement strategy that becomes a competitive differentiator—ensuring employees, customers, and partners maximize their impact with Guidewire Cloud.As a Program Owner specializing in Go-to-Market Capabilities for the global Customer Success organization, you turn business needs into meaningful learning that helps our teams win. You design, deliver, and continuously improve programs that are simple to use and tied to real business outcomes. You will be accountable for owning a portfolio of work including new hire / role assignment learning, methodology training, and competency development. In addition, you will be accountable for the ownership of the Sales / Adoption methodology (Challenger), applicable to all field-facing organizations.
Job Description
Required Skills / Experience
Experience: 5-8 years in enablement, learning & development, onboarding, or related fields within enterprise software; 3-5 years facilitating live or virtual training sessions. P&C insurance or enterprise SaaS experience preferred.
Instructional design and facilitation: exhibit advanced skills in curriculum design, learning activities, and dynamic presentation/facilitation
Business acumen and P&C industry knowledge: contextualize by domain to ensure strategic relevance and practical adoption.
Complex project management: plan and execute multi‑workstream programs; maintain accurate weekly status in the project tracking system.
Communication and Adaptability: exhibit excellent verbal, written, and presentation skills. Has the ability to multitask and quickly adapt to a changing environment.
Strategic stakeholder collaboration: influence alignment with EBPs and cross‑functional leaders; translate needs into effective enablement solutions.
Integrity, Rationality, & Collegiality: operate within the Guidewire values; integrity by building truthful relationships, with rationality by making evidence-based decisions, and with collegiality by working as a professional equal among your peers.
Tools proficiency: Google Workspace; LMS and survey/analytics; authoring platforms; virtual delivery tools; AI tools, project tracking (e.g., Monday.com).
Key Responsibilities
Accountable for the functional onboarding program for the Customer Success organization, including design and delivery of an effective self-study curricula program for each templated role. Roles include Customer Success Managers, Client Partners, Operational Roles, and Alliances functions. Success is measured by achievement of role readiness at the 6-month mark of employment or new hire assignment.
Maintain the Customer Success program currency, ensuring programs are regularly enhanced, communicated and measured against business expectations. Ensure new programs are loaded into appropriate LMS and new changes are communicated effectively to business leadership and owners.
Responsible for ensuring your new hires are appropriately registered for Field Onboarding or technical certification courses as assigned. Assess ongoing feedback to ensure programs are continually enhanced.
Responsible for delivery of the Sales / Adoption methodology (Challenger or otherwise defined) for the entire Field organization. Ensure methodology is incorporated into new hire approaches for Sales, Customer Success, Alliances, and Services. Organize ongoing learning experiences and recertifications across the field organization to assess skills as required.
Responsible for program development of ad-hoc role / functional training to further elevate the skill development of the Customer Success organization. Partner with the Sales / Adoption Business Partner to ensure delivery aligns with other in-person learning events.
Ensures all projects are appropriately managed using readiness methodology, including completion of needs assessments, training / readiness plans, and curation / development of content. Build the right content/format for the program (live, virtual, self‑serve, tool guides). Partner with the business for sign-off on plan, content and outcome measurement.
Partners with Readiness Business Partners to plan and deliver ongoing training associated with new hire programs or in-person field events such as Regional Kick-Offs, Sales Reviews, etc.
Tracks program success based on business performance, usefulness, and completion rates.
Supports the future readiness strategy, delivering enablement projects to internal personas. Supports the overall readiness transformation program, aimed at migrating away from a push strategy to a pull strategy, utilizing AI capabilities to provide content in context.
Key Performance Indicators (KPIs)
Stakeholder Satisfaction: Internal and external satisfaction with the strategic partnership and execution of enablement activities.
Business Performance: Correlation of readiness program to a specific, measurable performance improvement including new hire readiness and increased skill attainment.
Program Usefulness Score: Average post-learning usefulness score reflecting the quality, accuracy, and relevance of enablement program content.
Program Completion Rate: The percentage of the target audience who complete the enablement program within the designated timeframe.
New Hire Readiness: The percentage of Field managers who believe employees are functionally prepared after first 6 months of new role orientation.
Program Management: Adherence to program methodology, appropriately tracking tasks and measure outcomes via tools such as Monday.com.
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.
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