Head of AI, Digital and Technology Compliance

Enstar Group; United States; Hybrid; USD 142,000 - 165,000; Full time

Benefits offered by this job

Medical Insurance (group coverage)

Dental Insurance

Vision Insurance

Health Savings Account (HSA) or FSA

Dependent Care FSA

EAP

Pet & Home/Auto Insurance (optional)

Wellness Reimbursement program

401K with company match (up to 6%)

Job summary

Enstar Group seeks a Head of AI, Digital and Technology Compliance to lead second-line oversight of AI and technology-related regulatory risk across the Group. You will ensure responsible AI and data governance is embedded in business decisions while supporting safe innovation.

You will act as the Group’s subject matter expert, providing independent challenge, and you will oversee governance, risk, and compliance across AI, digital transformation, and emerging technologies, engaging with senior

Qualifications

• Experience in Compliance, Risk, Technology Governance 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 and deliver pragmatic solutions.

Responsibilities

• Provide independent review and challenge of AI use cases and tech initiatives prior to implementation.
• Oversee AI governance frameworks, policies, and approval processes across the Group.
• Lead regulatory impact assessments and guidance for new regulations.

Skills

AI governance

Regulatory risk management

Second line of defense

Executive communication

Tools

Microsoft 365

Copilot

Azure

Purview

Job description

What you will be doing:

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.

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.
• 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
• 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.
• 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).

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.

We offer a range of initiatives and resources to support our people throughout their careers:

• Professional Qualifications and Study Support: We support employees who wish to take professional qualifications aligned to their role and career development.
• Training, Conferences & Seminars: As a global organisation, we work with many professional bodies to provide access to training programmes, conferences, seminars and continuing professional development (CPD) opportunities.
• Digital Learning Hub: Our digital learning hub, LinkedIn Learning, offers a wide range of self-serve resources, including courses, videos, eBooks, and audio books, to help employees build news skills and deepen their knowledge.

We also invest in physical, mental and financial wellbeing initiatives for our employees. Supportive teams, inspiring work and a positive working environment all contribute to our collective wellbeing. Beyond the workplace, we strive to make a positive influence in our communities and to continuously reduce our impact on the environment.

Enstar Inclusivity Policy:

We’re an equal opportunity employer and believe that our inclusive environment creates an authentic working culture. We don’t discriminate on the basis of age, physical or mental disability, gender reassignment, marriage and civil partnership, pregnancy and carer status, race (including colour, nationality, and ethnic or national origin), religion or belief, sex and sexual orientation. Enstar is committed in providing an accessible recruitment experience for all those interested in working with us. Please let your Enstar Recruitment Partner know if you require any reasonable accommodation during the application process due to a disability to enable you to fully participate in our recruitment process.