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OktaOkta

Head of Legal Operations & Chief of Staff

Leads Legal Operations and serves as the Chief Legal Officer’s operational proxy, overseeing legal technology, AI adoption, budgets, vendors, analytics, and cross-functional initiatives. Requires 10+ years in legal or strategic business operations, executive partnership experience, and a bachelor’s degree.

About the job

Responsibilities

  • Serve as the trusted operational proxy and advisor to the Chief Legal Officer (CLO) in executive forums and key decision-making bodies.
  • Align Legal Department specialties—including Commercial, IP, Privacy, Corporate, and Compliance—with business goals.
  • Coordinate with chiefs of staff and leaders across company departments to align legal strategy and budgets with business objectives.
  • Lead high-impact, cross-functional legal and corporate initiatives from design through execution.
  • Direct and scale Legal Operations infrastructure, intake models, and workflow automation.
  • Oversee the legal technology and AI roadmap, including CLM, e-billing, entity management, and practical AI tools.
  • Establish legal KPIs and operational dashboards tracking performance, turnaround times, and department ROI.
  • Manage outside counsel guidelines, fee negotiations, billing compliance, and alternative fee arrangements.
  • Manage global Legal Department operating budgets and external legal spend with Finance and legal leadership.
  • Redesign workflows between Legal and Sales, Finance, Security, and Product.
  • Lead quarterly business reviews, annual planning, and resource allocation across the global Legal organization.
  • Lead department programs, events, and day-to-day practices that support culture, alignment, and employee impact.

Requirements

  • 10+ years of experience in legal operations, chief of staff, or strategic legal/business operations within a high-growth technology environment.
  • Experience scaling legal operations and implementing CLM, e-billing, and AI-enabled technology.
  • Experience creating and improving legal department processes and managing outside counsel spend.
  • Strong departmental budget management, vendor negotiation, and data-driven reporting experience.
  • Ability to partner with C-suite leadership, influence cross-functional teams, and manage cross-functional teams.
  • Exceptional judgment, discretion with sensitive matters, executive presence, and collaboration skills.
  • Strong strategic execution, organization, problem-solving, and deadline management skills.
  • Bachelor’s degree required.

Nice-to-haves

  • Juris Doctor (JD) or Master of Business Administration (MBA).
  • Fluency with Google Workspace, Microsoft Office, and enterprise project management platforms.

Compensation and Benefits

  • Annual base salary: $238,000–$327,000 USD.
  • Equity, where applicable, bonus, health, dental and vision insurance, 401(k), flexible spending account, and paid leave, including PTO and parental leave.

Skills

Legal Operations, Chief Of Staff, Clm, E-Billing, Entity Management, Legal Technology, Artificial Intelligence, Budget Management, Vendor Negotiation, Outside Counsel Management, Workflow Automation, Legal Analytics, Google Workspace, Microsoft Office, Project Management

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