Engagement Director

Summary

As an Engagement Director for the AMER region, you will lead strategic delivery efforts across multiple key Guidewire customers. Your role is critical in ensuring that our most complex and high-value programs are executed successfully, that customer relationships are strong, and that engagements deliver measurable value.
You’ll be responsible for overseeing senior-level engagement managers and ensuring alignment between delivery, business outcomes, and Guidewire’s regional strategy. This includes overseeing project timelines, deliverables, and stakeholder communication to drive project success. For our self-managed customers, the Engagement Director will continue to act as their trusted advisor and provide strategic direction and executive delivery oversight for Guidewire customers and owns and develops long-term client relationships on behalf of Guidewire, cultivating business with clients to achieve revenue growth, profitability, and customer satisfaction.
Acting as both a strategic partner to our clients and a senior leader within Professional Services, you’ll help shape the success of our delivery organization across North America and Latin America.

Job Description

Responsibilities

Regional Leadership and Delivery Oversight

• Lead a portfolio of customer programs across the AMER region, establishing and leading governance frameworks for customer engagements.

• Provide oversight and coaching to senior engagement managers and delivery leads

• Own the strategic delivery posture for Guidewire’s top-tier AMER clients

• Drive consistency and excellence in delivery execution and customer experience

Customer Relationship Management

• Serve as an executive point of contact for regional customers, building trusted partnerships

• Align Guidewire’s delivery services to customers’ long-term business objectives

• Support customer success through strategic account planning and governance leadership

• Anticipate and manage complex customer challenges and escalations

Program Strategy and Execution

• Guide the successful delivery of large, complex programs—often spanning multiple workstreams or products

• Proactively identify, assess, and mitigate risks at project and strategic levels.

• Lead or support governance forums (steering committees, executive reviews, QBRs)

• Ensure projects stay on track with respect to scope, budget, timeline, and quality

• Take full responsibility for the financial performance of customer engagements, including budgeting, forecasting, and profitability analysis.

• Drive accountability across all stakeholders and delivery contributors

Financial and Commercial Management

• Own regional engagement profitability, including forecasting, margin improvement, and budget adherence

• Review and approve Statements of Work (SOWs), Change Orders, and project estimates

• Collaborate with Sales on renewals and new opportunities; identify upsell potential during delivery

• Ensure commercial terms are aligned with delivery expectations and customer success

Sales Support and Opportunity Management

• Engages as client lead for strategic top tier clients at any given time, leading primarily Guidewire-owned projects, including strategic engagements and implementation programs.  

• Monitor financial metrics and implement strategies to achieve or improve projected engagement profitability.

Account and Resource Management

• Work closely with internal teams, such as Product Development, Professional Services, and Support, to ensure cohesive service delivery.

• Advocate for customer needs and contribute to continuous improvement initiatives.

• Facilitate strategic discussions to support business growth, value realization, and innovation opportunities.

• Collaborate with Sales and Business Development teams to drive Value Roadmap engagements during sales cycles and then translate those engagements into compelling services proposals.

• Reviews, approves, and in smaller engagements, will draft Work Orders (WOs) and Statements of Work (SOWs) within a certain threshold for self-managed projects in the portfolio.

• Proactively develops and communicates escalation mitigation plans when customers are off track with schedule, scope, and budget. 

Competency/Skills Requirement

• Delivery Management: Proven experience in program, portfolio, or professional services leading large-scale software or cloud implementation programs.

• Executive Communication and Influence: Exceptional ability to communicate with and influence C-level executives.

• Strategic Thinking and Planning: Strong capability to develop and execute long-term strategic plans that align with customer goals and drive mutual success.

• Business Acumen: Deep understanding of business operations, financial management, and organizational dynamics. Skilled in identifying business development opportunities and driving growth initiatives.

• Leadership and Team Management: Demonstrated ability to lead cross-functional teams and foster a collaborative environment. Experience in mentoring and developing talent within the organization.

• Analytical and Problem-Solving Skills: Strong analytical abilities to assess complex situations and devise effective solutions. Proactive in identifying potential issues and implementing preventative measures.

• Sales Support:  Strong sales acumen with an entrepreneurial mindset, capable of identifying and creating new sales opportunities through strategic thinking and proactive engagement.

• Guidewire Knowledge: Understands the Guidewire catalog and capabilities at a high level and maintains certification

• Cloud Knowledge: Understand Guidewire Cloud and maintain AWS certification

• Insurance Industry Knowledge: Understand Insurance Industry for the country/region in which they operate

Preferred Skills & Experience

• A minimum of 10 years leadership experience within Professional Services 

• Deep understanding of the Guidewire Cloud Platform (GWCP) and product suite

• Knowledge of the North American insurance market, particularly P&C insurance

• Experience operating in regulated industries such as insurance, banking, or healthcare

• PgMP, SAFe SPC, or other advanced delivery certifications

• AWS or cloud-related certifications

• Experience leading multi-region or global delivery programs

• Track record of building and scaling delivery teams in a matrixed environment

• Success in managing executive escalations and complex stakeholder landscapes

• Demonstrated impact on revenue growth or retention through delivery excellence

• Ability to guide clients through complex change, modernization, or transformation journeys

The US base salary range for this full-time position is $155,000 - $233,000 . 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 [email protected]. 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 [email protected] 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.