Remote Legal Innovation & Operations Lead: AI & Automation

Block, Inc.; San Francisco (CA); On-site; USD 218,000 - 327,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning support

Job summary

Block, Inc. is seeking an experienced operations leader to head the Legal Innovation & Operations team within Counsel. You will translate vision into executable strategy, manage multiple workstreams, and champion automation and AI to improve how the legal function operates.

You will own the legal tech roadmap, oversee systems like CLM and eBilling, balance budgets, and partner with Legal, IT, Finance, and Business Ops to deliver measurable value across the organization.

Qualifications

• 8+ years of experience in legal operations, tech strategy, or related roles.
• Experience leading automation or AI initiatives with measurable improvements.
• Budget, timelines, and stakeholders management with attention to detail.
• Translating technical detail into clear business value.
• Familiarity with DocuSign CLM or workflow automation tools.
• Experience building trust with executives and individual contributors.

Responsibilities

• Define and drive the legal tech strategy and roadmap.
• Oversee legal systems (CLM, eBilling, knowledge management and workflows).
• Manage core digital platforms for efficiency and cost control.
• Collaborate across Legal, Policy, IT, Finance, and Ops to roll out tech solutions.
• Lead multi-quarter automation and data-driven initiatives.
• Build vendor relationships to maximize value from tech investments.

Skills

Legal operations

Tech strategy

Automation

Budget management

Stakeholder management

Vendor management

Tools

DocuSign CLM

Job description

Block, Inc. is seeking an experienced operations leader to head the Legal Innovation & Operations team within Counsel. You will translate vision into executable strategy, manage multiple workstreams, and champion automation and AI to improve how the legal function operates.

You will own the legal tech roadmap, oversee systems like CLM and eBilling, balance budgets, and partner with Legal, IT, Finance, and Business Ops to deliver measurable value across the organization.