[Hiring] Director, Transformation @Enstar Group

Role Description

Lead the planning, governance, and coordinated execution of the AF Group integration program, translating integration objectives into actionable delivery plans, measurable outcomes, and sustainable operational results. The role is responsible for supporting integration management disciplines that enable successful delivery, including integration planning and governance, Target Operating Model definition and implementation, Day 1 readiness, TSA transition, and value realization. Working in partnership with business and functional leaders, the role coordinates cross-functional workstreams, manages dependencies and risks, facilitates decision-making, and drives alignment to ensure successful integration outcomes.

What you will be doing

• Lead the planning and execution management of the AF Group integration program, defining objectives, scope, milestones, deliverables, governance, and expected outcomes.
• Maintain the integrated AF Group integration roadmap, including workstream plans, key milestones, dependencies, and critical path activities.
• Lead integration governance structures, including meeting cadence, reporting standards, decision logs, issue management, and escalation processes.
• Coordinate the cross-functional definition and implementation of the post-close Target Operating Model, translating agreed future-state designs into integrated implementation plans, milestones, dependencies, and transition activities.
• Partner with senior leaders to translate the integration strategy and deal objectives into prioritized initiatives, operating-model decisions, and measurable business outcomes.
• Coordinate cross-functional integration workstreams to ensure activities remain aligned, appropriately sequenced, and effectively managed.
• Support Day 1 readiness activities, including planning, tracking, dependency management, issue resolution, and leadership reporting.
• Coordinate TSA transition planning and execution activities, including milestone tracking, risk management, and transition readiness efforts.
• Manage integration risks, issues, assumptions, decisions, and dependencies, escalating concerns and recommendations to leadership as appropriate.
• Partner with business and functional leaders to help ensure integration activities are appropriately resourced, prioritized, and embedded into business plans.
• Coordinate the value realization discipline, including benefits case tracking, synergy and value capture reporting, operational effectiveness measures and coordination with accountable business owners.
• Prepare executive reporting, dashboards, presentations, and governance materials that provide visibility into integration progress, risks, key decisions, and outcomes.
• Facilitate cross-functional workshops, working sessions, and leadership reviews to drive alignment, accountability, and issue resolution.
• Develop and continually improve integration and transformation methodologies, playbooks, templates, governance standards, and tools that support successful integration execution.

Experience

• 10+ years of progressive experience in business transformation, integration management, program management, strategy, consulting, corporate development, or related disciplines.
• Experience supporting or leading complex M&A integrations, business integrations, separations, or large-scale transformation initiatives.
• Experience operating within an Integration Management Office (IMO), Transformation Office, PMO, or similar governance environment.
• Demonstrated success coordinating large cross-functional initiatives that involve multiple stakeholders, competing priorities, and significant organizational change.
• Experience supporting Day 1 readiness, TSA transition activities, operating model implementation, systems/process integration, or post-close integration efforts.
• Experience leading or coordinating Target Operating Model definition and implementation across multiple business and functional areas.
• Strong experience working with senior leadership teams and preparing executive-level communications, reporting, and governance materials.
• Experience within insurance, financial services, or another highly regulated industry preferred.

Knowledge

• M&A integration planning and execution.
• Day 1 readiness planning and post-close integration activities.
• TSA planning, management, and transition execution.
• Program governance, portfolio management, and executive reporting practices.
• Integrated program planning, milestone tracking, dependency management, risk management, and decision governance.
• Benefits realization, KPI tracking, value capture, and operational performance measurement.
• Insurance and/or financial services operating models, regulatory environments, and functional interdependencies.
• Change management, stakeholder engagement, communications planning, and organizational readiness principles.

Skills

• Integration Planning
• Program & Roadmap Management
• Governance & Reporting
• Executive Communications
• Risk & Issue Management
• Dependency Management
• Benefits Realization Tracking
• TSA Transition Management
• Cross-Functional Facilitation
• Operational Execution

Leadership Skills

• Executive Presence
• Communication
• Stakeholder Management
• Influence Without Authority
• Consensus Building
• Problem Solving
• Negotiation & Conflict Resolution
• Cross-Functional Leadership
• Change Leadership

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.