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SquareSquare

Legal Innovation & Operations Lead

Leads legal technology strategy and operational excellence across the Counsel organization, overseeing systems, vendors, budgets, and cross-functional automation and AI initiatives. Requires 8+ years in legal operations, technology strategy, or a related operations role.

About the job

Responsibilities

  • Define and drive the Legal Innovation & Operations legal technology strategy, including the vision, roadmap, and delivery of productivity tools.
  • Oversee legal systems such as contract lifecycle management, eBilling, knowledge management, and workflow platforms; optimize integrations and alignment with business processes.
  • Manage core digital platforms for efficiency, usability, and cost control.
  • Partner with Legal, Policy, IT, Finance, Business Operations, and other teams to evaluate and implement technology solutions.
  • Translate business needs into effective technology and process solutions.
  • Manage vendor relationships and ensure measurable value from technology investments.
  • Lead multi-quarter, cross-functional automation, AI, and data-driven initiatives.
  • Improve operational excellence across the organization.

Requirements

  • 8+ years of experience in legal operations, technology strategy, or a related operations-focused role.
  • Experience leading automation or AI initiatives that deliver measurable improvements.
  • Experience managing budgets, timelines, and stakeholders with strong attention to detail and follow-through.
  • Ability to communicate technical details as clear business value.
  • Collaborative, curious, and adaptable approach to experimentation and process improvement.
  • Experience building trust with senior leaders and individual contributors.

Nice-to-haves

  • Familiarity with DocuSign CLM or workflow automation tools.
  • Hands-on legal technology implementation experience.

Compensation and Benefits

  • Annual salary range of $217,800–$326,800 USD.
  • Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning.

Skills

Legal Operations, Legal Technology, Technology Strategy, Automation, Artificial Intelligence, Contract Lifecycle Management, Docusign Clm, Ebilling, Workflow Automation, Knowledge Management, Data Analytics, Vendor Management, Budget Management

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