Summary
The Principal is the Services leader/owner of the Customer Account and the field leader on allimplementation related topics.
You’ll be responsible for the success of the cloud transformation programs, ensuring that projects stay on track and that Guidewire delivers real value to the customer’s business.
You’ll coordinate internal and external teams, manage delivery risks, and serve as a trusted advisor to customer stakeholders. You’ll also work closely with Sales, Product, and other internal teams to ensure smooth delivery, clear communication, and long-term success.
You will advocate for customers’ needs with partners and internal teams while being accountable for the portfolio’s financial performance and revenue growth.
Job Description
Key Responsibilities
Cloud Program Leadership
○ Lead the planning and execution of cloud transformation programs across assigned customer accounts
○ Coordinate key activities like performance testing, cutovers, and handovers to customer success
○ Monitor progress, identify risks, and work with delivery teams to keep programs on track
○ Ensure customer programs align with business objectives and success criteria
Customer Relationship and Advocacy
○ Act as a trusted delivery partner to customer stakeholders and SI (System Integrator) partners
○ Provide strategic input on how customers can best use Guidewire products and services
○ Advocate for customer needs within Guidewire—collaborating with Product, Cloud Ops, and Support
○ Support governance activities like steering committees and executive reviews
Sales and Pre-Sales Support
○ Support sales teams by contributing to cloud transformation proposals and services estimates
○ Participate in early conversations with customers to shape engagement plans
○ Own small to mid-size opportunity proposals and help develop Statements of Work (SOWs)
Program Financial Management
○ Track budgets and forecast delivery costs for your programs
○ Contribute to overall account profitability by managing margin, staffing, and scope alignment
○ Ensure a smooth transition from implementation to BAU support and customer success
KPIs & Success Metrics
● Program Success Rate – % of cloud implementations delivered on time, on scope, and within budget
● Customer Engagement Quality – CSAT scores and stakeholder feedback from assigned accounts
● Delivery Efficiency – Accuracy of delivery forecasting, staffing plans, and margin impact
● Establishing and achieving Account specific Services Revenue, Profitability and Sales targets
Key Skills & Experience
● Experience in enterprise software delivery, consulting, or transformation
● Experience in a customer-facing leadership role
● Hands-on experience with large-scale software or cloud implementations
● Strong communication and relationship-building skills with customer stakeholders
● Familiarity with budgeting, forecasting, and tracking financials at the program level
● Experience coordinating across delivery teams, partners, and customer teams
● High-level understanding of cloud platforms and SaaS delivery models
● Ability to manage and mitigate delivery risks in complex environments
● Proficiency with tools like Jira, Confluence, Power BI, or similar platforms
● Comfortable leading both internal and external stakeholder conversations
● Strong sales acumen, capable of identifying and creating new sales opportunities through strategic thinking and proactive engagement
Preferred Skills & Experience
● Working knowledge of Guidewire Cloud Platform (GWCP) and associated services
● Understanding of P&C insurance industry processes and workflows
● AWS or cloud platform certifications
● PgMP, PMP, or SAFe certifications
● Previous experience working with System Integrator (SI) partners
● Familiarity with regulated industries (e.g., insurance, healthcare, banking)
● Prior experience in customer success, engagement management, or program delivery
● Exposure to commercials—proposals, SOWs, or pricing
● Experience in managing global or multi-region customer programs
● Comfortable working in fast-paced, matrixed environments with shifting priorities
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.
Skills Required
- Experience in enterprise software delivery, consulting, or transformation
- Experience in a customer-facing leadership role
- Hands-on experience with large-scale software or cloud implementations
- Strong communication and relationship-building skills with customer stakeholders
- Familiarity with budgeting, forecasting, and program-level financial tracking
- Experience coordinating delivery teams, partners, and customer teams
- High-level understanding of cloud platforms and SaaS delivery models
- Ability to manage and mitigate delivery risks in complex environments
- Proficiency with Jira, Confluence, Power BI, or similar platforms
- Ability to lead internal and external stakeholder conversations
- Strong sales acumen and ability to identify and create sales opportunities
- Working knowledge of Guidewire Cloud Platform and associated services
- Understanding of property and casualty insurance processes and workflows
- AWS or other cloud platform certifications
- PgMP, PMP, or SAFe certification
- Experience working with System Integrator partners
- Familiarity with regulated industries such as insurance, healthcare, or banking
- Prior experience in customer success, engagement management, or program delivery
- Experience with proposals, statements of work, or pricing
- Experience managing global or multi-region customer programs
- Comfort working in fast-paced, matrixed environments with shifting priorities
Guidewire Software Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Guidewire Software and has not been reviewed or approved by Guidewire Software.
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Flexible Benefits — Flexible work options and distinctive global mobility programs enable remote/hybrid arrangements and short-term or longer-term cross-border work opportunities. Feedback suggests these options are a meaningful differentiator for those valuing location flexibility.
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Leave & Time Off Breadth — Unlimited PTO in the U.S., dedicated volunteer time, and a personal 'My Day' accompany generous parental leave. These elements indicate a broad time-off offering that supports rest, community engagement, and family needs.
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Equity Value & Accessibility — Equity grants (RSUs) and an employee stock purchase plan are positioned as significant parts of total compensation. Stock-based components can enhance overall pay, with value influenced by market conditions.
Guidewire Software Insights
What We Do
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, 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 1,000+ 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.
Why Work With Us
We're focused on each and every employees' personal and professional development, and offer internal career mobility programs and growth opportunities that make Guidewire unique. Other perks like generous PTO, flexible working, our Guidewire Gives Back charitabeland our "Work From Almost Anywhere" program support our employees' work-life balance
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