Head of Legal Operations

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Position Overview

Reporting to the Group General Counsel, the Head of Legal Operations will lead the optimization and transformation of our global legal function. This pivotal role will drive operational efficiency, champion data‑driven decision‑making, and align legal services with Ascot’s business objectives. The ideal candidate is a collaborative leader with deep expertise in legal operations and a proven track record of managing complex, high‑stakes environments in the insurance or financial services industry.

This is a hybrid role based in either our Stamford, CT or New York City office.

Key Responsibilities

• Strategic Leadership:
Develop and execute a comprehensive legal operations strategy to support Ascot’s global business goals, ensuring alignment with corporate priorities and regulatory requirements.

• Data‑Driven Insights:
Develop and leverage metrics, analytics, and legal‑industry benchmarking data to evaluate department performance, identify operational and spend trends, and deliver actionable recommendations to senior leadership.

• Process Optimization:
Streamline legal workflows, including contract management, e‑billing, matter management, and compliance processes, to enhance efficiency and reduce costs, incorporating automation where appropriate.

• Technology Integration:
Oversee the selection, implementation, and ongoing management of legal technology platforms (e.g., CLM, e‑discovery, data analytics, AI‑driven tools) to drive innovation, transparency, and scalability.

• Financial and

Risk Management:

Manage the legal department’s budget, forecasting, and vendor/external counsel relationships, ensuring cost efficiency, accurate reporting, and risk mitigation. Build business cases for funding and new initiatives.

• Vendor Management:
Direct relationships with law firms and consultants, designing and managing panels, alternative fee arrangements, and performance assessments to ensure value and quality.

• Stakeholder

Collaboration:

Proactively partner with underwriting, claims, risk, finance, compliance, and IT to support business initiatives, foster innovation, and mitigate legal and operational risks.

• Compliance and Governance:
Ensure adherence to domestic and global regulatory standards, internal policies, and robust governance frameworks, overseeing privacy, information governance, and IT security.

• Knowledge Management:
Facilitate the sharing of best practices and connect internal and external expertise to serve as the guardian of the legal department’s knowledge and history.

• Project and Practice Management:
Oversee ad‑hoc requests, strategic projects, and implement processes/technologies to optimize legal service delivery and enable lawyers to focus on core legal tasks.

• Continuous Improvement & Change Management:
Lead initiatives in process re‑engineering, change management, and service delivery innovation, using KPIs for success evaluation.

• Culture:
Commit to The Ascot Way by fostering colleague engagement, collaboration, inclusivity, and individual accountability.

Requirements

•

Education:

Bachelor’s degree required; JD, MBA, or advanced degree preferred.

•

Experience:

7+ years in legal operations, preferably within insurance, financial services, or a comparably regulated sector.

• Technical Expertise:
Proven success implementing legal tech solutions (CLM, matter management, AI analytics) and driving process improvement.

• Financial Acumen:
Strong budgeting, forecasting, and vendor management skills, with a focus on optimizing legal spend and building business cases for legal technology or resourcing.

• Communication:
Exceptional communication and influencing skills, with experience presenting to C‑suite and cross‑functional stakeholders.

• Adaptability & Problem‑Solving:
Comfort with ambiguity and fast‑paced change; proactive, analytical, and solutions‑focused.

• Travel:
Ability to travel to other offices and on business, domestically and internationally as needed.

Preferred Requirements

• Experience in a global organization with multi‑jurisdictional legal and regulatory exposure.

• Certification in legal operations (CLOC,…