Senior Director, Head of Services AI

Summary

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

Job Description

Head of Services AI

This senior leader is responsible for defining and executing a strategy to embed Artificial Intelligence across service delivery, with the goal of dramatically improving efficiency, quality, and speed. The mandate is to achieve a 50–80% reduction in implementation time and effort within 24 months by leveraging AI tools, automation, and innovative practices. As the Head of AI, this role will oversee a small technical team dedicated to AI tooling and model tuning, while collaborating closely with Services delivery, engineering, and consulting teams to ensure AI adoption translates into real business results. This is a highly visible role that requires a blend of strategic vision, hands-on technical know-how, team leadership, and a strong focus on business outcomes.

Core Responsibilities

• AI Strategy & Roadmap: Develop and drive the overall strategy for integrating AI into Professional Services workflows from two standpoints: external services delivery and internal services operations. Identify high-impact areas in the implementation lifecycle (e.g. solution configuration, coding, testing, data migration, knowledge transfer) where AI and machine learning can streamline workflows, reduce costs, and improve quality. Likewise identify high-impact areas in the PS end-to-end business lifecycle (e.g. pipeline generation, solutioning, selling, contracting, staffing, billing, enabling staff, etc.) where AI and machine learning can streamline workflows, reduce costs, and improve quality. 

• AI Tooling & Model Integration: Select and implement the right AI tools and platforms (such as generative AI, machine learning models, NLP/NLG systems, and RPA) to automate or accelerate key services tasks. Oversee the fine-tuning of models to the P&C insurance domain and our product specifics, ensuring AI outputs are accurate and relevant. Evaluate build vs. buy for AI solutions and manage vendor relationships where applicable.

• Implementation of AI Solutions: Lead pilots and full-scale rollouts of AI-enabled processes. Work with delivery teams to embed AI tools into their day-to-day activities, such as using AI for project planning, risk identification, and knowledge management. Ensure that new AI solutions are integrated with existing systems and workflows for seamless adoption. 

• Team Leadership and Development: Build and manage a small, high-impact team of AI engineers, data scientists, and automation specialists. Provide technical guidance and set priorities for this team to develop and maintain AI tools and services. Foster a culture of innovation and experimentation, enabling the team to rapidly prototype solutions while maintaining a clear focus on business value. Mentor team members and promote continuous learning in AI/ML technologies.

• Cross-Functional Collaboration: Serve as the bridge between the PS organization and other departments (Engineering, Product Development, Data Analytics). Collaborate with product engineering to align on data access, APIs, and any product changes needed to support AI-driven services. Partner with delivery and consulting leaders to redesign processes around AI capabilities and ensure buy-in at all levels. Coordinate with the enterprise’s data and security teams to govern AI usage, addressing data privacy, model compliance, and ethical considerations in line with company policies and industry regulations.

• Change Management & Enablement: Champion AI adoption across the PS team. Develop training programs and materials to upskill consultants and project teams on new AI tools — making AI a “co-pilot” for every consultant. Establish an internal AI community of practice to share successes, use cases, and lessons learned. Drive change management efforts to shift the culture towards an “AI-first” mindset in service delivery, helping PS colleagues adapt and make this mindset shift.

• Performance Monitoring & Optimization: Define clear metrics to track the impact of AI initiatives on implementation projects. Monitor progress against the 50–80% efficiency improvement target, including metrics like reduction in average project delivery time, decrease in person-hours per project, automation rates for key tasks, and improvements in profit margin or capacity. Use these metrics to refine the AI strategy continuously. Troubleshoot issues with AI tool adoption or performance and iterate to improve outcomes. Provide regular updates to executive leadership on ROI, including cost savings and value delivered by AI.

• Innovation and Industry Insight: Stay abreast of emerging AI technologies, trends, and best practices, especially as they relate to enterprise software implementation and insurance services. Experiment with new AI capabilities (such as new GPT models, agentic frameworks, or domain-specific AI solutions) that could further shorten implementation timelines or improve quality. Build relationships with industry peers, attend conferences, and bring in fresh ideas on how to maintain a competitive edge through AI. Ensure the company’s PS organization becomes known as a pioneer in AI-driven service delivery, enhancing our brand in the market.

Competency/Skills Requirement

• 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: 5+ years in a technology leadership role (e.g. Director of AI, AI Leader) where you set strategy and led teams to deliver complex technology projects. 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 $171,000 - $296,000 + bonus + equity + benefits. Our salary ranges are determined by role, level, and location. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific salary range for your preferred location during the hiring process.

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.