Strategy and Planning Lead

Location: San Francisco, California

Department: IT Infrastructure & Operations

Work Mode: Hybrid

About the Role

Docusign brings agreements to life. Over 1.5 million customers and more than a billion people in over 180 countries use Docusign solutions to accelerate business processes and simplify lives through intelligent agreement management. As the #1 company in e-signature and contract lifecycle management (CLM), Docusign unleashes business-critical data trapped in documents, integrating it with systems of record to drive efficiency and innovation. Join our forward-thinking team to shape the future of agreements with AI-powered transformation. As the Strategy and Planning Lead in IT Infrastructure & Operations, you will drive the strategy, structure, and delivery of enterprise-wide AI initiatives, connecting strategy to execution for DocuSign's intelligent agreement platform. This high-impact, individual contributor role reports to the VP of Strategy, Release and Operations and operates at the intersection of business, technology, data, AI Centers of Excellence (COEs), and GenAI leaders. You'll design and run the operating system for AI at scale—balancing speed, control, and transparency—ensuring initiatives move from idea to measurable impact without silos. Thriving in ambiguity, you'll influence without authority, fostering a cohesive, outcome-driven AI program that enhances e-signature, CLM, and agreement workflows in our innovation-driven culture. Key responsibilities include translating DocuSign’s AI vision into adaptive roadmaps, partnering to prioritize high-value use cases, leading cross-functional governance with Legal, Security, Privacy, and Procurement, and driving AI literacy programs. You'll simplify complexities with dashboards, communicate transparently via scorecards and forums, tackle roadblocks agilely, and shape adoption strategies focused on real usage. This hybrid role (minimum 2 days/week in-office) demands a driver mindset, strategic thinking, and the ability to turn complex AI ideas into action, empowering teams to innovate responsibly. What you bring: 12+ years in program management, operations, or strategy in tech/data orgs; proven delivery of cross-functional initiatives; AI/digital transformation experience with governance expertise; and a passion for challenging norms. Preferred: hands-on operations savvy, storytelling prowess, data geekery, and financial insight. Docusign is an Equal Opportunity Employer committed to diversity, belonging, and accommodations—apply to help make the world more agreeable.

Key Responsibilities

• Translate DocuSign’s AI vision into a clear, adaptive roadmap with priorities, timelines, and success metrics tied to intelligent agreement management
• Partner with functional, product, data, AI COEs, and GenAI leaders to identify and advance highest-value AI use cases for e-signature and CLM
• Build and maintain the core operating model for AI at scale: intake, prioritization, review, approval, and execution tracking
• Lead cross-functional coordination with Legal, Security, Privacy, and Procurement to ensure responsible AI adoption across DocuSign's global operations
• Simplify complex processes, reduce friction, and create visibility through dashboards and structured documentation for AI initiatives
• Drive company-wide AI literacy and enablement programs, empowering employees to leverage AI safely in agreement workflows
• Communicate progress, risks, and decisions via updates, forums, and scorecards to foster trust and alignment
• Turn strategy into action with disciplined planning, milestone tracking, and agile problem-solving to overcome roadblocks
• Manage distributed ownership programs through credibility, collaboration, and influence without direct authority
• Shape adoption strategies focused on measurable usage and impact, encouraging experimentation while ensuring compliance and control
• Help teams adapt to AI-integrated workflows that enhance DocuSign's innovation in e-signature and agreement management

Required Qualifications

• 12+ years in program management, business operations, or strategy roles within technology or data-focused organizations
• Proven ability to deliver complex, cross-functional initiatives with limited direct authority
• Experience in AI, analytics, or digital transformation, with strong understanding of governance and risk management
• Track record of challenging the status quo, connecting dots across functions, and thinking beyond traditional organizational boundaries
• Demonstrated success in enterprise-wide strategy execution within fast-paced tech environments like SaaS or agreement management platforms
• Experience driving AI initiatives that integrate with core business systems such as e-signature and contract lifecycle management (CLM)

Preferred Qualifications

• Hands-on operator with judgment to know when to plan, adapt, or act decisively
• Strong experience in strategy, planning, and operations in AI-driven organizations
• Exceptional communication and storytelling skills to simplify complex AI concepts
• Deep understanding of financial and business metrics with a 'data geek' mindset
• Prior exposure to DocuSign-like ecosystems involving intelligent agreement management and digital transformation

Required Skills

• AI strategy and governance
• Program and portfolio management
• Cross-functional influence and stakeholder management
• Roadmap development and prioritization
• Risk management in AI and digital transformation
• Data analytics and business metrics interpretation
• Agile operating model design
• Communication and storytelling
• Process simplification and dashboard creation
• Financial acumen
• Change management and adoption strategies
• Problem-solving in ambiguous environments
• E-signature and CLM domain knowledge
• Intelligent agreement management platforms
• Bias for action and adaptability
• Collaboration across Legal, Security, Privacy functions

Benefits

• Competitive base salary: California range $157,500 - $254,350, based on location, experience, and skills
• Company bonus plan calculated as a percentage of eligible wages, tied to performance
• Restricted Stock Units (RSUs) eligibility
• Paid Time Off including earned time off and company holidays
• Paid Parental Leave up to six months for birth, adoption, or foster care
• Full Health Benefits Plans with 100% employer-paid options from day one
• Retirement Plans with potential employer contributions
• Learning and Development including coaching, online courses, and education reimbursements
• Compassionate Care Leave for life-changing events

DocuSign is an Equal Opportunity Employer.