Director of Legal Operations and Innovation

At Five Below our growth is a result of the people who embrace our purpose: We know life is way better when you are free to Let Go & Have Fun in an amazing experience, filled with unlimited possibilities, priced so low, you can always say yes to the newest, coolest stuff! Just ask any of our over 35,000 crew members who work at Five Below and they’ll tell you there’s no other place like it. It all starts with our purpose and then, The Five Below Way, which is our values and behaviors that each and every crew member believes in.

It’s all about culture at Five Below, making this a place that can inspire you as much as you inspire us with big ideas, super energy, passion, and the ability to make the workplace a WOWplace!

Position Overview

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.

Key Responsibilities

• Legal operations strategy: 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.

• Process design and service delivery: Redesign and automate matter intake, triage, workflow routing, document management, knowledge management, and operational onboarding to remove bottlenecks, improve consistency, and reduce cycle times.

• Financial management: 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.

• Outside counsel and vendor management: Lead provider selection, onboarding, billing guidelines, invoice review, rate negotiations, performance evaluation, and diversity tracking for outside counsel and legal service providers.

• Technology, AI, and automation: 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.

• AI governance and risk: 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.

• Data, analytics, and performance: 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.

• Knowledge and self-service: 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.

• Corporate operations: Oversee subsidiary and entity management, corporate housekeeping, state registrations, annual reports, and regulatory calendar tracking across the company’s multi-state retail footprint.

• Cross-functional partnership and change leadership: 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.

Qualifications and Experience

Required Qualifications

• 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.

Preferred Qualifications

• 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.

Explore our benefits site to discover all the perks and support we offer! From health coverage to financial and personal wellness, we've got you covered—check it out today!

Five Below is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, age, national origin, disability, protected veteran status, gender identity or any other factor protected by applicable federal, state, or local laws.

Five Below is committed to working with and providing reasonable accommodations for individuals with disabilities. If you need a reasonable accommodation because of a disability for any part of the employment process, please submit a request and let us know the nature of your request and your contact information.

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