Director of Legal Operations and Innovation

Five Below•Philadelphia, PA

About The Position

Five Below is seeking a Director of Legal Operations and Innovation to define the strategy, operating model, technology, and business management infrastructure of the Legal Department. This hands-on leader will partner with Legal leadership and business functions to improve service delivery while managing spend, strengthening governance, and scaling legal support across a rapidly growing national retail footprint. The role will use data, AI-enabled workflows, and automation to increase capacity, reduce cycle times, and create a consistent, business-focused experience for internal clients. The ideal candidate combines deep legal operations expertise, strong change leadership, and practical fluency in legal technology, AI, and process improvement.

Requirements

Bachelor’s degree and at least 12 + years of progressive experience in legal operations, legal project management, or a comparable operational role within a corporate legal department, law firm, or legal services organization.
Demonstrated experience building or scaling a legal operations function, with ownership of several core disciplines such as process improvement, legal technology, outside counsel and vendor management, budgeting, spend management, metrics, and reporting.
Hands-on experience evaluating, implementing, administering, and driving adoption of core legal platforms, AI tools, or workflow automation solutions, such as matter management, document management, e-billing, or contract lifecycle management systems.
Strong program and change-management capability, including leading concurrent cross-functional initiatives, aligning stakeholders, managing dependencies, and sustaining adoption across teams with varying levels of technical proficiency.
Strong analytical capability, including defining data standards, developing actionable dashboards and forecasts, and applying working knowledge of generative AI capabilities, limitations, and responsible-use principles to legal workflows.
Excellent judgment, communication, and influencing skills, with the discretion to handle confidential and privileged information and the ability to translate operational, financial, and technical concepts for senior leaders and business partners.

Nice To Haves

Juris Doctor degree, advanced business degree, or relevant legal operations credential.
Experience supporting a large retail, consumer products, restaurant, or other multi-unit, high-growth enterprise.
CLOC certification or active participation in the legal operations professional community.

Responsibilities

Define, build and own the Legal Department’s operating model, translating departmental priorities into an executable roadmap, aligning resources, and measuring progress against strategic goals.
Redesign and automate matter intake, triage, workflow routing, document management, knowledge management, and operational onboarding to remove bottlenecks, improve consistency, and reduce cycle times.
Develop and manage the annual legal budget; oversee spend, forecasting, accruals, invoice processing, and reporting across litigation, commercial, intellectual property, employment, and real estate; and identify sustainable cost-saving opportunities.
Lead provider selection, onboarding, billing guidelines, invoice review, rate negotiations, performance evaluation, and diversity tracking for outside counsel and legal service providers.
Own the strategy behind the use of technology and AI across the legal team, including evaluation, implementation, integration, administration, adoption, of matter management, document management, contract lifecycle management, generative AI, and intelligent automation solutions.
Establish and maintain responsible-use standards for Legal Department AI and automation, including model validation, prompt management, data handling, privilege protection, human oversight, and alignment with enterprise technology, security, privacy, and risk frameworks.
Define data standards and build reporting that tracks matter volume, assignments, capacity, cycle time, contract turnaround, throughput, spend, adoption, and automation impact. Use analytics to identify trends, forecast demand, and support resource decisions.
Maintain and improve standard agreements, clause libraries, playbooks, checklists, and precedent banks. Develop AI-supported contract review and self-service solutions that enable business teams to resolve appropriate routine requests with clear guardrails.
Oversee subsidiary and entity management, corporate housekeeping, state registrations, annual reports, and regulatory calendar tracking across the company’s multi-state retail footprint.
Partner with Finance, HR, IT, Merchandising, Supply Chain, Marketing, and Store Operations to improve how Legal engages with the business. Drive adoption through stakeholder engagement, training, documentation, feedback, and measurable change-management plans.