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DocuSign is seeking a Strategic Portfolio Management Director for Enterprise Transformation to drive large-scale strategic initiatives from intake through business outcomes realization. In this individual contributor role reporting to the VP of Enterprise Transformation and Program Office, you will own company-level portfolio planning, prioritization, and OKR governance across the organization.
You will serve as the central connective hub translating high-level company strategy into a disciplined, end-to-end planning process with clear prioritization, business case rigor, and measurable outcomes. Working closely with Finance and business function leaders, you will establish the planning calendar, long-range planning rhythms, and fiscal interlocks that ensure the broader organization executes the right initiatives with appropriate resource allocations.
Key responsibilities include: owning the planning calendar and establishing staged plan maturity gates (60% Directional, 80% Interlocked, 95% Locked); leading annual and quarterly planning cycles that translate company strategy into actionable OKRs and key initiatives; partnering with Finance on fiscal interlocks, business case requirements, and benefit tracking frameworks; collaborating with planning leads across Sales, Marketing, Product, Engineering, Finance, Operations, HR, and Customer Success to develop departmental OKRs that ladder to company objectives; facilitating quarterly business reviews and planning forums to assess OKR progress and resolve cross-functional conflicts; managing dependency workflows and clearance processes; governing Jira and Jira Product Discovery configuration for planning visibility; implementing Workday goal cascading; and generating executive readouts and portfolio health metrics.
You bring 15+ years of experience in corporate strategy, business planning, portfolio management, or enterprise transformation, with 8+ years managing cross-functional programs at the enterprise level. Required expertise includes OKR frameworks, plan maturity models, long-range planning cycles, Finance partnership on budgeting and business cases, Jira and Jira Product Discovery configuration, performance management platforms (Workday, Lattice, 15Five), financial analysis and ROI tracking, C-suite collaboration, and experience in hyper-growth or SaaS environments. An MBA or equivalent master's degree is required. Preferred qualifications include designing company-wide planning or OKR transformation programs, custom Jira hierarchy and workflow configuration, management consulting or strategic advisory background, project management or OKR certifications (PMP, Agile, Lattice), Workday HCM integration experience, and data visualization proficiency.
