Head of Legal Operations

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.

Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way.

The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric.

Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot exists to solve for our clients’ brightest tomorrow, through agility, collaboration, resilience, and discipline.

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, a passion for leveraging technology, 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 for continuous improvement and competitive alignment.

• 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, and AI-driven tools) to drive innovation, transparency, and scalability.

• Financial and Risk Management: Oversee the legal department’s budget, forecasting, and management of vendors/external counsel relationships, ensuring cost efficiency, accurate reporting (including MI), 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, and advocating for legal exceptionalism when warranted.

• 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.

•  Change Management & Adoption: Lead change management initiatives to ensure successful adoption of new processes and technologies, including training programs, communication strategies, and stakeholder engagement plans that foster buy-in, minimize disruption, and promote a culture of continuous improvement.

• Culture: Commit to The Ascot Way: Demonstrate The Ascot Way in his/her daily interaction with colleagues, fostering colleague engagement and development, collaboration, inclusivity, and individual accountability.

Requirements:

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

• Experience: 7+ years in legal operations, preferably with experience within insurance, financial services, or a comparably regulated sector.

• Technical Expertise: Proven success implementing legal tech solutions (CLMs, 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 experience 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 on an as needed basis.

Preferred Requirements:

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

• Certification in legal operations (CLOC, ACC Legal Ops) or project management (PMP).

• Track record managing transformation or technology adoption projects in legal services.

***This position may be filled at a different level, depending on experience***

Compensation 
Actual base pay could vary and may be above or below the listed range based on factors including but not limited to experience, subject matter expertise, and skills. The base pay is just one component of Ascot’s total compensation package for employees. Other rewards may include an annual cash bonus, and other forms of discretionary compensation awarded by the Company. 

The salary range for this position is $150,000 - $165,000

Company Benefits

The Company provides a competitive benefits package that includes the following (eligibility requirements apply):

Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Life Insurance, AD&D, Work/Life Resources (including Employee Assistance Program), and more

Leave Benefits: Paid holidays, annual Paid Time Off (includes paid state /local paid leave where required), Short-term Disability, Long-term Disability, Other leaves (e.g., Bereavement, FMLA, Adoption, Maternity, Military, Primary & Non-Primary Caregiver)

Retirement Benefits: Contributory Savings Plan (401k)

Please be aware that Ascot Group’s job opportunities will be posted on our official careers page. All official communication comes from @ascotgroup.com email addresses, if you receive a job offer or recruitment communication from Ascot Group that you suspect might be fraudulent, do not hesitate to contact us directly to verify its legitimacy. We will never ask for payment or sensitive personal information during any stage of the recruitment process. Your privacy and trust are of utmost importance to us, and we strive to ensure that you have a positive experience with Ascot Group.

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