VP, Office of the General Counsel

Though we prefer NY Metro-based candidates, we are open to candidates based on the East Coast who can work remotely.

About you and the role:

Serve as a core partner to the General Counsel in driving the operational execution of the Legal function. This role acts as the central point of coordination across Legal, ensuring alignment, visibility, and disciplined execution of the General Counsel’s priorities. The role brings together Legal stakeholders, processes, and reporting to enable a more coordinated, scalable, and effective Legal function.

What you will be doing:

Key Accountabilities / Deliverables • Coordinate activity across Legal towers (M&A, Corporate, Governance, Litigation, Compliance) to ensure alignment, communication, and timely delivery • Partner with the General Counsel and Legal leadership team to drive execution of Legal department priorities • Establish and enforce execution standards, timelines, and service level expectations across Legal towers, with clear escalation mechanisms when deliverables are at risk • Lead Legal’s operational planning, including budgeting, resource allocation, and prioritization in partnership with Finance, the FP&A and HR teams • Oversee the process for outside counsel relationship management, vendor management, and legal department spend tracking / cost centre management • Oversee and facilitate LegalOps contributions to legal reporting, including KPIs, dashboards, and executive updates • Prepare materials and reporting to support decision-making and stakeholder communication • Develop the strategy for Legal technology tools in collaboration with the GC Office • Identify operational gaps and implement process improvements to enhance efficiency and scalability • Work with the GC Office to agree Legal’s operating model, and oversee or work with the team responsible for implementing the intake processes, workflow coordination, and role clarity • Manage internal Legal communications to ensure visibility of priorities and progress • Support organizational planning, including capacity assessment, role definition, and team development • Identify and oversee the team implementing practical AI and automation use cases to improve efficiency, consistency, and team capacity • Drive adoption of AI tools and workflow automation in day-to-day Legal processes • Liaise with the General Counsel’s executive assistant on matters of relevance

What you will bring:

• 5-10+ years of experience in Legal Operations, Chief of Staff, or similar operational leadership roles
• Experience working closely with a General Counsel or senior leadership team
• Experience managing legal spend, vendors, and outside counsel relationships
• Experience implementing process improvements, technology solutions, or operational initiatives
• Experience operating in a complex, transaction-driven, multi-stakeholder environment
• Legal operations, including budgeting, vendor management, and service delivery models
• Legal technology tools (eBilling, workflow, and reporting systems)
• Development of reporting frameworks, including KPIs and dashboards
• Process design and workflow optimization in a Legal or professional services environment
• Governance and risk considerations within a Legal function (excluding board administration)
• Demonstrated executive presence and ability to influence senior legal leaders and business stakeholders
• Strong organizational and project management skills across complex, multi-stakeholder environments
• Ability to operate as a trusted advisor to the General Counsel and senior Legal leadership
• Strong communication and reporting skills, including preparation of executive-level materials
• Ability to translate priorities into actionable plans and track delivery
• High level of accountability, attention to detail, and follow-through
• Ability to build alignment and influence stakeholders without direct authority

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 $135,000-$175,000*

*Target full-time equivalent base salary range is based on relevant market data. The actual salary offered will depend on applicable market data for hiring location and relevant candidate 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. </span&