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Head of AI, Digital and Technology Compliance Work from Home

Remote / Online - Candidates ideally in
Northern, Floyd County, Kentucky, USA
Listing for: Enstar Group
Full Time, Remote/Work from Home position
Listed on 2026-09-01
Job specializations:
  • IT/Tech
Salary/Wage Range or Industry Benchmark: 142000 - 165000 USD Yearly USD 142000.00 165000.00 YEAR
Job Description & How to Apply Below
Position: Head of AI, Digital and Technology Compliance Work from Home(US)
Location: Northern

Head of AI, Digital and Technology Compliance

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.
  • 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…
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