Head of AI, Digital and Technology Compliance

About you and the role:
The Head of AI, Digital and Technology Compliance leads the second-line oversight of AI and technology-related regulatory risk across the Group. The role ensures that artificial intelligence, digital transformation, and emerging technologies are deployed in a manner consistent with regulatory requirements, governance standards, and responsible AI principles.
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.

What you will be doing:
Global Accountabilities

AI Governance & Oversight
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.

Regulatory Compliance & Horizon Scanning
Monitor global AI, digital, and technology regulatory developments and assess business impact.
Lead impact assessments, gap analysis, and implementation guidance for new regulations.
Support the rollout and communication of regulatory changes across the Group.

Risk Assessment & Assurance
Lead compliance risk assessments across AI, digital transformation, and emerging technologies
Ensure technology-related risks are captured within the Group’s governance, risk, and compliance framework.
Develop and oversee monitoring programs to assess compliance, controls, and employee usage of AI technologies

AI & Technology Ecosystem Oversight
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.

Stakeholder Engagement & Reporting
Provide reporting and insights to governance forums, including AI Risk Committees and Boards
Support regulatory engagement on AI governance and digital operational resilience
Collaborate across Compliance, Risk, Legal, Technology, and Data functions to ensure aligned and effective governance

Culture & Capability
Promote awareness of AI regulatory requirements and responsible AI practices across the business.
Support development of compliance training and communication programs for AI and technology risks

What you will bring:
Required Capabilities
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
Proven ability to assess complex technology risks, perform regulatory impact assessments, and deliver pragmatic solutions.
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
Demonstrated ability to build effective cross-functional relationships while maintaining independence and challenge.

Conduct and Regulatory Expectations
Operate in accordance with internal policies, applicable laws and regulations, and regulatory expectations. Maintain high standards of integrity, governance, and stakeholder protection, including appropriate engagement with regulators and oversight of delegated responsibilities.

General
High executive maturity, global mindset, and embracing change.
Comfortable navigating ambiguity and complex geopolitical considerations.
Strong integrative thinking with enterprise-first orientation.
Collaborative, influential, and able to drive alignment across organizational boundaries.
Global role with hybrid flexibility.
U.S. and International travel may be required.

Your Benefits:
Enstar offers best-in-class Medical, Dental, and Vision healthcare for single and family coverage.
Board-certified doctors and pediatricians are available virtually 24/7 for urgent care.
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.
Optional Pet & Home/Auto Insurance.
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).
One paid annual volunteer day.

General Info
The target base salary pay range for this role is $142,000-$165,000*
*Target full-time equivalent base salary range is based on relevant market data. The actual salary offered will depend on applicable market data for the hiring location and the relevant candidate's knowledge, skills/experience. This salary range is not inclusive of applicable discretionary incentives.

Who we are:
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:
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