Director, Strategy & Program Management

Docusign • San Francisco, CA

2d • Hybrid

About The Position

As the Director of Strategy & Program Management, you will serve as the primary strategic partner and "force multiplier" for the VP of Strategy, Release & Operations. This is a high-visibility leadership role that sits at the intersection of enterprise strategy, technical execution, and operational excellence.
You are responsible for turning vision into a structured reality. You will bridge the gap between business, technology, and data leaders, ensuring that our most critical initiatives move in sync and deliver measurable impact. Beyond program delivery, you will act as a trusted advisor, proxy, and strategic backup for the VP, with the explicit goal of being groomed as their long-term successor.
You’ll design and run the program structure, governance and managing risks at scale; balancing speed, control, and transparency. The ideal candidate thrives in ambiguity, brings a driver mindset, and can influence across functions without direct authority. This role demands agility, practical problem solving, critical thinking, thought leadership, high bias for action, and the ability to turn complex ideas into action.
This position is a people manage role reporting to the VP of Strategy, Release & Operations.

Requirements

• 12+ years of experience in Program Management, BizOps, or Strategy within high-growth technology or data-centric organizations
• Ability to influence at the C-suite and VP level without direct authority
• Expereince with financial metrics, business operations, and the technical nuances of AI and Analytics

Nice To Haves

• Comfortable challenging the status quo and "speaking truth to power" gracefully
• A storyteller who can take a mess of data and "simplify the complex" into a compelling strategy or scorecard
• "Hands-on" operator with the judgment to know when to pivot and when to persevere
• Possess a high bias for action
• Experience in high-level strategic planning and financial modeling
• A self-described "Data Geek" who uses metrics to drive accountability
• Previous experience in a Chief of Staff or "Head of Staff" capacity

Responsibilities

• Act as a surrogate and proxy for the VP in key forums, decision-making bodies, and executive sessions
• Be mentored to step into broader leadership responsibilities, increasingly owning the strategic agenda
• Manage the leadership rhythm of business (staff meetings, offsites, QBRs), synthesizing complex data into executive-level narratives, and ensuring the VP’s time is focused on the highest-leverage activities
• Design and lead the operating model for large-scale company initiatives
• Manage intake, prioritization, and risk at scale—balancing speed with necessary governance
• Align Application Engineering, Product Management, and Global Data teams to ensure unified execution of the Annual Operating Plan (AOP)
• Translate high-level strategy into a living roadmap
• Unblock teams, solve complex architectural or political roadblocks, and ensure "idea-to-impact" isn't just a phrase, but a disciplined process
• Drive adoption of new workflows, particularly AI-integrated ways of working, ensuring that digital transformation results in real-world usage and cultural shift

Benefits

• Bonus: Sales personnel are eligible for variable incentive pay dependent on their achievement of pre-established sales goals. Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.
• Stock: This role is eligible to receive Restricted Stock Units (RSUs).
• Paid Time Off: earned time off, as well as paid company holidays based on region
• Paid Parental Leave: take up to six months off with your child after birth, adoption or foster care placement
• Full Health Benefits Plans: options for 100% employer paid and minimum employee contribution health plans from day one of employment
• Retirement Plans: select retirement and pension programs with potential for employer contributions
• Learning and Development: options for coaching, online courses and education reimbursements
• Compassionate Care Leave: paid time off following the loss of a loved one and other life-changing events

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed