Enstar Group

Head of AI, Digital and Technology Compliance

Work from Home(US) · Full-time

Sponsorship not specified$142k-$165kDetected 2 days ago

AzureCloud PlatformsComplianceCommunicationUnderwriting

About the role

Acting as the Group's subject matter expert, the role provides independent challenge and assurance across AI and technology initiatives, supporting the business to innovate safely while protecting the firm's regulatory standing and reputation.

Extensive experience in Compliance, Risk, Technology Governance, or a related discipline within a regulated environment
Strong knowledge of AI governance, digital regulation, and technology risk frameworks
Experience operating in a second line of defense function providing independent challenge and oversight
Strong understanding of enterprise technology ecosystems, including cloud platforms and AI-enabled tools
Experience engaging with senior governance forums, boards, regulators, and external stakeholders.
Excellent communication and influencing skills, with the ability to translate complex topics into actionable guidance
U.S. and International travel may be required.

Provide independent review and challenge of AI use cases and technology initiatives prior to implementation.
Oversee AI governance frameworks, policies, and approval processes across the Group.
Ensure responsible AI principles and data governance requirements are embedded in business decision-making.
Monitor global AI, digital, and technology regulatory developments and assess business impact.
Ensure technology-related risks are captured within the Group's governance, risk, and compliance framework.
Provide oversight and challenge across key enterprise platforms (e.g., Microsoft 365, Copilot, Azure, Purview)
Assess data access, security permissions, information retention, governance controls, and third-party integrations.
Provide reporting and insights to governance forums, including AI Risk Committees and Boards

Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage.
Access to Health Savings Account (HSA) or Flexible Spending Account (FSA).
Access to Dependent Care FSA to cover daycare expenses.
Access to Employee Assistance Programs (EAP) for health and well-being.
Wellness Reimbursement program (up to $600 annual reimbursement for wellness-related expenses, i.e., gym memberships, massage, etc.).
401K retirement plan (company matches up to 6% of employee contribution).

We are a trusted global re/insurance group and the leading provider of retrospective solutions, with specialist underwriting capabilities. We help our clients manage risk, unlock capital and create the financial freedom to grow. With operations across the world's major insurance hubs and a global network of close to 800 talented professionals, we bring expertise and fresh thinking to some of the industry's biggest challenges.
For more information about Enstar, visit our website: www.enstargroup.com.
For more information about careers at Enstar, visit our LinkedIn Life page or visit our careers site
Why Enstar:
We are a trusted global re/insurance group and the leading provider of retrospective solutions, with specialist underwriting capabilities.
We help our clients manage risk, unlock capital and create the financial freedom to grow.
With operations across the world's major insurance hubs and a global network of close to 800 talented professionals, we bring expertise and fresh thinking to some of the industry's biggest challenges.
Learning and development are a fundamental part of every employee's career journey with Enstar.
Supporting growth and career progression is key to how we engage our people - helping them to learn, grow and succeed at Enstar.

This listing is sourced directly from Enstar Group's careers page and normalized into a canonical job model.