Legal Operations Lead

Olo•New York, NY

2d•$120,000 - $150,000•Remote

About The Position

Olo is seeking a Legal Operations Lead to design, build, and scale an AI-forward, data-driven operating model for its Legal Department. This role is broader than contract management, focusing on systems, processes, tools, metrics, and AI-enabled workflows to enhance efficiency, insight, and business impact. The ideal candidate will have daily hands-on experience with AI, a proven track record of implementing AI or automation in a legal or business setting, and a passion for creating practical systems that transform how legal and business teams operate. The Legal Operations Lead will report to the Deputy General Counsel, Privacy and Technology, and collaborate with various internal teams and stakeholders.

Requirements

6+ years of experience in legal operations, preferably in-house or in a high-growth technology environment.
Ability to operate as an owner-builder.
Daily, hands-on use of AI in a professional setting, with a strong ability to design prompts, evaluate outputs, build repeatable workflows, and teach others how to use AI effectively.
Demonstrated experience building, deploying, or managing AI-enabled workflows, automation, or legal technology solutions with measurable business impact.
Demonstrated experience in evaluating, implementing, and managing legal technology, with a deep understanding of AI applications in the legal domain (e.g., for e-discovery, contract analysis, legal research, or workflow automation).
Strong understanding of legal department operations, including intake, workflow design, knowledge management, matter management, contracting operations, privacy operations, reporting, and cross-functional stakeholder support.
Strong data literacy, including experience defining metrics, building dashboards, analyzing operational performance, and using data to drive decisions.
Strong analytical, organizational, and problem-solving skills.
Excellent project management and communication skills, with experience leading cross-functional initiatives.
Comfort working with ambiguity and prioritizing competing needs.
Experience with contract management and automation tools, such as CLMs, Salesforce, and Snowflake.
Experience supporting privacy program operations, including privacy request workflows.
Excellent judgment and ability to prioritize responsibilities, work efficiently, manage, and execute in a timely manner, both independently and collaboratively.
Strategic thinker with the ability to think holistically while focusing on day-to-day project management and driving results.

Responsibilities

Define and own Legal's operations strategy, roadmap, and execution plan.
Build the operating model for an AI-enabled legal department, including workflows, roles, escalation paths, metrics, and continuous improvement loops.
Partner with Legal leadership to identify opportunities to reduce manual work, improve cycle times, increase consistency, and provide faster legal support to the business.
Translate ambiguous legal and business needs into practical, scalable systems, workflows, and tools.
Drive the evaluation, selection, implementation, and adoption of AI-enabled legal technology, automation tools, intake systems, knowledge systems, analytics tools, and other legal operations platforms.
Design, build, and maintain workflows using AI and tools like Jira for legal request intake, approval routing, and reporting.
Partner with IT, Security, Finance, Sales, and other stakeholders to integrate legal tools into Olo's broader technology environment.
Own the strategy, optimization, and integration of Legal's technology stack, including the contract lifecycle management system.
Define metrics to demonstrate Legal's business impact and build dashboards and reporting.
Drive cross-functional projects across Legal.
Use data to prioritize projects, measure the impact of AI and automation, and continuously improve Legal's operating model.
Build and maintain SOPs, playbooks, self-service resources, and knowledge systems for recurring legal processes.
Lead cross-functional legal operations projects from concept through rollout, including stakeholder alignment, requirements gathering, testing, training, adoption, and performance measurement.
Drive change management for new tools and workflows.
Manage Legal team knowledge resources in Confluence to enable self-service for business partners.