Summary

THE ROLE

The Senior Principal is a senior leader within Guidewire’s Professional Services organization, responsible for driving the success, scalability, and strategic value of complex cloud transformation programs. Working across a portfolio of high-impact accounts, the Senior Principal serves as a trusted advisor to customer executives, internal leaders, and delivery partners, ensuring that every transformation maximizes business value and aligns to the long-term vision of both the customer and Guidewire.

This role expands beyond individual program oversight to influence delivery standards, operational strategy, partner collaboration, and internal capability development. Senior Principals bring executive-level relationship management, deep Guidewire knowledge, and proven experience in large-scale SaaS delivery environments.

Job Description

WHAT YOU'LL DO

Customer Success & Strategic Program Oversight

Act as executive sponsor for high-stakes Guidewire Cloud transformation programs, owning customer outcomes and long-term value realization.
Lead coordination of all roles and responsibilities across Guidewire, System Integrators (SIs), and Solution Partners, driving clarity, accountability, and effective decision-making.
Monitor execution against key project milestones, proactively identifying risks, and escalating concerns to Customer leadership as needed.
Act as the primary escalation point for Customer leadership regarding Guidewire and partner delivery challenges, with a focus on transparency, resolution, and partnership health.
Provide transformation guidance on complex program challenges, including architecture, governance, or delivery alignment, and connect customers to the full depth of Guidewire’s resources and frameworks.
Ensure consistent use of standards and governance approaches for operations within the Guidewire Cloud Platform (GWCP), advising on controls that support sustainable success.
Where applicable, support value realization services by aligning KPIs, tracking business outcomes, and advising on actions to maximize ROI throughout the transformation lifecycle.

Portfolio and Revenue Management

Manage a portfolio of strategic accounts across multiple regions or business lines, with accountability for services revenue, margin, and account growth.
Collaborate with Sales, Product, and Customer Success to shape multi-year customer strategies, drive demand generation, and position future services opportunities.
Lead program-level commercial strategies including pricing, resourcing, margin optimization, and contract alignment.

Internal Strategy & Collaboration

Act as a senior voice within Professional Services, influencing product direction, delivery methodologies, and partner enablement based on insights from customer programs.
Partner with Product, R&D, Cloud Ops, and PS Practices to align transformation delivery with evolving product capabilities.
Contribute to cross-functional initiatives that shape the future of Guidewire’s service offerings and global delivery capabilities.

Stakeholder & Partner Alignment

Resolve misalignment between customer, SI, and partner teams that could impact delivery outcomes or business objectives.
Support complex partner dynamics by fostering collaborative approaches, enforcing accountability, and aligning on shared goals.
Provide governance advisory support across program stakeholders to maintain strategic alignment and transparency

Team & Leadership Development

Mentor and guide Principals and Engagement Leaders to grow delivery maturity, customer leadership, and consultative acumen.
Help build organizational delivery capability by contributing to workforce planning, talent development, and onboarding efforts.

WHO YOU ARE

Skills

Strategic Leadership: Ability to lead multi-year transformation strategy, integrating product evolution, delivery operations, and customer goals.
Executive Influence: Confident operating at CxO level, with a strong ability to negotiate and resolve high-stakes challenges with diplomacy.
Program Governance & Oversight: Deep experience with enterprise program delivery frameworks, risk management, and stakeholder governance.
Partner & Multi-Party Coordination: Skilled in navigating complex delivery environments involving SIs, solution partners, and internal teams.
Commercial Acumen: Strong understanding of services business models, including P&L, pricing, and opportunity development.
Cloud & Technical Knowledge: Advanced understanding of cloud-native delivery models and the Guidewire Cloud Platform. AWS certification strongly preferred.
Insurance Domain Knowledge: Deep knowledge of insurance business models, regional market dynamics, and transformation challenges.
Guidewire Expertise: Mastery of Guidewire's full solution suite and delivery frameworks.

Qualifications

12+ years in enterprise software or SaaS consulting roles, including 3–5+ years in senior customer-facing leadership.
Demonstrated experience managing complex cloud or digital transformation programs with multiple internal and external stakeholders.
Track record of successfully advising senior customer leadership and influencing internal cross-functional teams.
Bachelor’s degree required; advanced degree preferred.
Guidewire Cloud, AWS certification and/or significant cloud architecture knowledge highly preferred.

The US base salary range for this full-time position is $192,000 - $300,000 . Your base pay will depend on your experience, skills, education, training, and location among other factors. All full-time positions or part-time roles working 30 hours or more a week at Guidewire are eligible for benefits that support their health and well-being including health, dental, and vision insurance, paid time off, and a company sponsored retirement plan. In addition, some roles may be eligible for the annual company bonus plan, commissions, and/or long term incentive awards which are contingent on a variety of factors including, but not limited to, company and employee performance.

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.