What you'll do

As the Strategic Portfolio Management Director for Enterprise Transformation (ET), you drive large-scale strategic initiatives from intake through business outcomes realization by owning company-level portfolio planning, prioritization, and OKR governance across the organization. You 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 establish the planning calendar, long-range planning rhythms, and fiscal interlocks that ensure the broader organization executes the right initiatives with the right resource allocations. You orchestrate cross-functional planning alignment, manage complex dependency clearance workflows, and drive OKR excellence by translating strategy into departmental objectives that cascade down to individual contributor goals. You will also govern Jira, Jira Product Discovery, and Workday goal integration as systems of record to maintain full visibility from strategy through delivery. Your success is measured by the team's ability to deliver 90%+ of planned outcomes for ET-led initiatives, achieve high executive sponsor confidence ratings, and ensure company priorities remain focused, resourced, and measurable.

This position is an individual contributor role reporting to the Vice President, Enterprise Transformation and Program Office.

Responsibility

• Own the planning calendar and establish staged plan maturity gates (60% Directional, 80% Interlocked, 95% Locked) with clear definitions of done and dependency clearance criteria
• Lead the end-to-end annual and quarterly planning cycles, translating company strategy into actionable OKRs and key initiatives
• Partner with Finance to establish fiscal interlocks, business case requirements, and frameworks to track realized benefits against proposed financial targets
• Collaborate with planning leads across all business functions including Sales, Marketing, Product, Engineering, Finance, Operations, HR, and Customer Success to develop departmental OKRs that ladder up to company objectives
• Facilitate quarterly business reviews (QBRs) and planning forums to assess progress toward OKRs, resolve cross-functional conflicts, surface blockers, and adjust resource allocations
• Manage the dependency workflow and clearance process across the organization to capture scope, timing, and resource requirements before initiative onboarding
• Govern Jira and Jira Product Discovery (JPD) configuration, architecture, workflows, and access controls to ensure data integrity and full planning visibility
• Implement Workday goal cascading in partnership with HR and Finance to link individual employee goals directly to company-level OKRs
• Generate executive readouts, real-time dashboards, and portfolio health metrics to communicate alignment, dependency status, and value realization to leadership and stakeholders

Job Designation

Remote: Employee is not required to be in or near an office frequently and works from a designated remote work location for the majority of the time.

Positions at Docusign are assigned a job designation of either In Office, Hybrid or Remote and are specific to the role/job. Preferred job designations are not guaranteed when changing positions within Docusign. Docusign reserves the right to change a position's job designation depending on business needs and as permitted by local law.

What you bring

Basic

• 15+ years of experience in corporate strategy, business planning, portfolio management, or enterprise transformation
• 8+ years of experience managing cross-functional programs at the enterprise level
• Experience with OKR frameworks and plan maturity models
• Experience executing long-range planning cycles in a multi-function environment
• Experience partnering with Finance on budgeting, fiscal interlocks, and business case development
• Experience with Jira and Jira Product Discovery for workflow configuration and dependency tracking
• Experience with performance management platforms such as Workday, Lattice, or 15Five
• Experience with financial analysis, ROI tracking, and resource allocation
• Experience collaborating with C-suite executives, function heads, and operational teams
• Experience working within a hyper-growth or SaaS environment
• MBA or equivalent master's degree in business administration or a related field

Preferred

• Experience designing and implementing company-wide planning or OKR transformation programs
• Experience configuring custom hierarchies, status transitions, and dependency workflows in Jira Product Discovery
• Background in management consulting or strategic advisory roles guiding organizations through planning cycles
• Certification in project management or OKR coaching such as PMP, Agile, or Lattice
• Experience integrating Workday HCM or financial modules with strategic planning tools
• Proficiency in data visualization and executive storytelling

Wage Transparency

Pay for this position is based on a number of factors including geographic location and may vary depending on job-related knowledge, skills, and experience.

Based on applicable legislation, the below details pay ranges in the following locations:

California: $212,100.00 - $342,650.00 base salary

Illinois, Colorado, Massachusetts and Minnesota: $202,100.00 - $285,500.00 base salary

Washington, Maryland, New Jersey and New York (including NYC metro area): $202,100.00 - $299,625.00 base salary

Washington DC: $X/hour - $212,100.00 - $299,625.00 base salary

Ohio: $182,200.00 - $257,350.00 base salary

This role is also eligible for the following:

• 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).

Global benefits provide options for the following:

• 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

Work Authorization Notice: Please note that we do not provide visa sponsorship or immigration support for this position. Applicants must already be authorized to work in the United States on a full-time, permanent basis without the need for current or future sponsorship.

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