Assistant Vice President, AI Program Lead

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.

Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way.

The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our Client Centric, Risk Centric and Technology Centric strategies

Built to be resilient, Ascot offers clients leading financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot exists to solve for our clients’ brightest tomorrow, through agility, collaboration, resilience, and discipline.

Ascot is embedding artificial intelligence (AI) and automation across the organisation to enhance decision‑making, efficiency, and quality of outcomes. In this role, you will be expected to work confidently alongside AI‑enabled tools, apply sound judgment when interpreting insights, and adapt as technology continues to evolve. We value curiosity, critical thinking, and a willingness to embrace change as part of how we work.

Position Overview:

Ascot’s Machine Learning team is seeking an Assistant Vice President, AI Program Lead to accelerate responsible AI adoption across U.S. operations. Serving as the primary link among business leaders, technology and data teams, and external partners, this role will identify, prioritize, and deliver AI-enabled solutions across underwriting, claims, policy systems, operations, actuarial, finance, and corporate functions.

This business-focused role will report to the Senior Vice President, Predictive Modeling & AI Strategy and will embed AI in strategic initiatives, guide delivery from concept through adoption, and ensure alignment with Ascot’s governance framework, business objectives, and value expectations. This will be an in-office role with a hybrid work schedule.

Responsibilities:

• Partner with North American business and technology leaders to identify and prioritize high-value AI opportunities.

• Translate strategic priorities into an actionable AI roadmap aligned with core platforms and transformation initiatives.

• Lead AI initiatives from concept through deployment, adoption, and continuous improvement.

• Develop business cases, success measures, and value-realization plans; monitor delivery and remove execution barriers.

• Facilitate discovery workshops, requirements gathering, process redesign, and solution design.

• Coordinate business sponsors, technical teams, and partners including Microsoft, Databricks, Palantir, Guidewire, and OpenAI.

• Apply insurance expertise to improve underwriting, risk assessment, broker engagement, claims, policy and billing processes, portfolio management, and operations.

• Ensure compliance with Ascot’s AI governance standards in partnership with Risk, Compliance, Legal, and Information Technology.

• Drive communications, training, AI literacy, stakeholder engagement, and user adoption.

• Monitor AI, insurtech, and specialty insurance trends and convert relevant developments into practical opportunities.

• Demonstrate The Ascot Way by collaborating across teams, embracing inclusivity, and demonstrating accountability while helping build an engaged, high-performing culture.

Requirements:

• A minimum of 10 years of insurance experience with strong knowledge of property and casualty operations and specialty insurance.

• Bachelor’s degree required and AI-related certification, formal training, MBA, or other advanced degree preferred.

• Experience supporting underwriting, claims, policy, actuarial, operations, finance, or distribution functions.

• Proven success leading complex, cross-functional programs and influencing senior stakeholders without direct authority.

• Strong business analysis, process improvement, change management, and execution skills.

• Working knowledge of generative AI, large language models, AI agents, predictive analytics, machine learning, and data-driven decision-making.

• Ability to engage technical teams while maintaining focus on business outcomes, risk, and user needs.

• Familiarity with Microsoft Copilot, Azure AI, Databricks, Palantir, Guidewire, or OpenAI.

• Experience leading AI, data, digital transformation, innovation, or workflow automation initiatives is preferred.
• Experience with AI governance, model risk management, or relevant regulatory considerations is preferred.
• Consulting or transformation leadership experience is preferred.

• Strong communication, facilitation, problem-solving, decision-making, and organizational skills.

• Collaborative, self-motivated, customer-focused, and effective in a fast-paced environment.

**This role can be filled at a different level, depending on experience.**

Compensation:

Actual base pay could vary and may be above or below the listed range based on factors including but not limited to experience, subject matter expertise, and skills. The base pay is just one component of Ascot’s total compensation package for employees. Other rewards may include an annual cash bonus and other forms of discretionary compensation awarded by the Company. The annualized base pay range for this role is: $195,000 - $215,000

Company Benefits:

The Company provides a competitive benefits package that includes the following (eligibility requirements apply):

• Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Life Insurance, AD&D, Work/Life Resources (including Employee Assistance Program), and more
• Leave Benefits: Paid holidays, annual Paid Time Off (includes paid state /local paid leave where required), Short-term Disability, Long-term Disability, Other leaves (e.g., Bereavement, FMLA, Adoption, Maternity, Military, Primary & Non-Primary Caregiver)
• Retirement Benefits: Contributory Savings Plan (401k)