Senior Director, Head of Services AI Solutions

Summary

The Head of Services AI will lead the AI-driven transformation of our 900-person Professional Services (PS) organization.

Job Description

Role Summary

The Senior Director, Head of Services AI Solutions plays a critical role in the transformation of our Professional Services (PS) organization through the development and deployment of cutting-edge AI technologies. 

Head of AI/ML Solutions will lead the design, development, and delivery of AI and machine learning-based solutions across our software services portfolio. This role combines strategic solution delivery leadership with hands-on innovation to drive value for clients through intelligent automation, predictive modeling, and advanced data insights.

As the technical counterpart to the Head of Services AI, this role will lead the architecture, development, and integration of AI tools and platforms that accelerate services delivery and operational efficiency. This individual will translate business goals into scalable, technically sound AI solutions and ensure their successful implementation across the PS lifecycle.

Core Responsibilities

AI Architecture & Tooling Execution

• Overall ownership of solution architecture, platform integration, prototyping, model tuning for Professional Services AI use cases.

• Lead the design and development of AI-driven solutions for use in customer implementations and internal operations (e.g., project planning, forecasting, configuration, testing, and staffing).

• Architect scalable, domain-tuned solutions using generative AI, NLP/NLG, code generation, and RPA technologies.

• Evaluate, prototype, and integrate AI tools and platforms aligned to the unique needs of the P&C insurance domain and our SaaS architecture.

• Partner with the enterprise Data and AI teams to leverage shared tools, models, and infrastructure.
   

Prototyping & Delivery Readiness

• Rapidly prototype AI capabilities (e.g., chatbot requirement gatherers, config generators, test script builders) and transition them into production use with clear MLOps practices.

• Build and maintain reusable AI components, APIs, and service wrappers for internal and customer-facing PS use cases.

• Partner with delivery teams to test and refine AI tools in live environments to ensure stability, performance, and ROI.
   

Product & Engineering Collaboration

• Work closely with Product Development teams to understand native AI capabilities in our core product and identify integration points.

• Influence product roadmaps by identifying platform-level enablers needed to support scalable AI-assisted delivery.

• Ensure seamless integration of AI solutions with product APIs, data models, and deployment pipelines.
   

Operational Optimization with AI

• Partner with internal PS operations teams to automate and optimize planning, estimating, staffing, and project execution tasks using AI.

• Support internal data models and systems that enhance predictability, staffing optimization, and delivery margin improvements.
   

Cross-Functional Collaboration & Governance

• Contribute to AI governance, model testing standards, and compliance guardrails across PS workflows.

• Support the Head of Services AI in defining ethical AI practices and ensuring data privacy/security in model development and use.

• Serve as a technical liaison to enterprise architecture, security, and compliance teams as AI capabilities scale.
   

Team & Capability Development

• Mentor and guide PS AI developers and automation engineers in building and maintaining high-value tools.

• Cultivate an internal developer community around AI capabilities, reusable assets, and APIs.

• Drive continuous learning and upskilling across the team on emerging AI technologies and development practices.

Success Metrics

• AI tools deployed with measurable impact on implementation speed and quality.

• Scalable architecture and platform integrations for sustained usage.

• Technical innovation that supports business goals of reducing delivery footprint by 50–80%.

• Internal operational efficiencies achieved through intelligent automation.

• Successful collaboration across product, delivery, and operational teams

Qualifications / Requirements

• AI/ML Expertise: Proven experience (10+ years) in data science, machine learning, or AI engineering roles, including hands-on knowledge of modern AI techniques (NLP/NLG, generative AI, predictive modeling, machine learning frameworks). Experience selecting, training, and deploying AI/ML models in a business environment is essential – from initial POCs to scaled solutions.

• Technology Leadership: 3+ years in a technology leadership role where you led strategy teams to deliver nascent technology solutions with ability to translate cutting-edge tech into practical solutions that drive business value. Prior experience managing technical teams (developers, data scientists) including hiring and mentoring talent.

• Professional Services/Delivery Experience: Strong understanding of the software implementation lifecycle and professional services operations. Experience working in or with large consulting/professional services teams (e.g. as a solutions architect, engagement manager, or tech lead on implementations) is highly valued. You should understand how enterprise software is delivered and where common inefficiencies lie, so you can target AI to solve real pain points (such as lengthy requirement gathering, custom coding, testing cycles, etc.).

• Domain Knowledge – Insurance or Enterprise Software: Familiarity with Property & Casualty insurance or financial services is a big plus. Domain knowledge helps in tuning AI models to industry-specific data and processes (for example, understanding insurance terminology for a requirements chatbot, or typical insurance workflows to automate). If not direct insurance experience, the candidate should have the ability and enthusiasm to quickly learn the P&C insurance domain.

• Strategic Thinking & Execution: Demonstrated ability to develop a strategic vision and execute it. This role requires setting an ambitious transformation agenda (e.g. using AI to cut effort by half or more) and then systematically delivering results. Experience in change management or leading digital transformation initiatives is important – the candidate must know how to drive organizational change alongside technology deployment.

• Cross-Functional Collaboration & Influence: Excellent communication and stakeholder management skills. Proven track record of working across departments (e.g. with engineering, product, business units) and influencing senior leadership. The ideal candidate can articulate the “why” of AI initiatives in business terms and rally different teams towards a common goal. Experience presenting business cases to executives and securing buy-in for innovation projects is required.

• Data & Analytics Orientation: Comfort with data analytics and metrics. Ability to define what success looks like in numerical terms (KPIs, OKRs) and to derive insights from data to adjust course. Experience with business intelligence or analytics in services (e.g. analyzing project data or financial metrics) is helpful.

Education: A Bachelor’s or Master’s degree in Computer Science, Data Science, Engineering, or related field. An MBA or similar business education is a plus, especially if complemented by technical experience, as it indicates ability to balance technical depth with business strategy.

The US base salary range for this full-time position is $174,000 - $262,000 . 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.