Principal Program Manager

Docusign•Seattle, WA

5h•Hybrid

About The Position

As a Principal of Technology & Business Operations at Docusign, you will lead critical programs and operating mechanisms to enable Engineering and Product organizations to execute effectively at scale. This role focuses on translating leadership priorities into disciplined execution through strong operational rigor, cross-functional coordination, and reliable operating signal. You will drive system and process improvements, orchestrate complex technology initiatives, optimize workflows, manage planning and execution inputs, ensure data integrity, and oversee key cross-functional dependencies in support of the CTO organization’s priorities. Acting as a senior execution partner to leadership, you will work closely with Engineering, Product, Finance, People, Communications, and Legal, to ensure alignment, clarity, and predictable delivery. This role requires comfort operating across levels - from hands-on ownership of complex operational work to senior level judgement and cross-functional leadership - and is expected to independently drive initiatives end to end while keeping leadership informed through clear, proactive communication. This position is an individual contributor role reporting to the Senior Director of Technology Development and Operations.

Requirements

15+ years of impactful experience in program or technical program management within strategy and operations, including a minimum of 5 years directly partnering with Product and Engineering organizations
History of driving significant operational excellence within high-growth, global technology environments, transforming challenges into streamlined processes
Experience with engineering metrics, leading productivity frameworks, and cutting-edge operational best practices, with practical experience in establishing or enhancing technical KPIs, OKRs, or scorecards for engineering teams
Experience leading and refining rhythm of business activities, encompassing planning cycles, executive reviews, and comprehensive reporting to foster an efficient operational cadence
A Bachelor's degree in a technical field or equivalent practical experience

Nice To Haves

Masterful communication, collaboration, and stakeholder management skills, allowing you to adeptly influence without authority and forge strong alignment across all organizational tiers, even in complex, matrixed structures
Ability to comfortably navigate fast-paced, ambiguous environments, consistently demonstrating a proactive bias for action and a dedication to continuous improvement
Strong people management skills by influencing diverse stakeholders, resolving conflicts constructively, and expertly leading teams through periods of change
Robust technical and analytical skills, with a proven ability to distill complex data into strategic, actionable insights for executive stakeholders
Experience leveraging data visualization and business intelligence tools like Tableau, Looker, or Power BI to drive insights at scale
Experience in management consulting, strategic operations, or technical operations is highly valued
Demonstrated comfort and effectiveness in collaborating with and presenting to senior leadership (VP-level and above) within executive settings
Familiarity with modern Agile, Lean, or scaled delivery methodologies such as (e.g., SAFe, Scrum@Scale)
An advanced degree (e.g., MBA, MS in Engineering, or a related field) or specialized training in data analysis, systems thinking, or operational strategy
Deep understanding of product development lifecycles and a track record of positively influencing outcomes across both product and engineering teams
Experience in mentoring or guiding junior program managers or operational leads on best practices
Experience navigating and contributing to complex SaaS architectures, particularly within cloud-native and distributed systems

Responsibilities

Serve as a trusted execution and operations partner to senior leadership, driving operational excellence across the CTO organization.
Drive and coordinate rhythm of business activities across Product and Engineering (e.g., townhalls, planning cycles, OKR / program reviews, operational cadences)
Partner closely with Finance and Accounting on budgeting, capitalization, forecasting, and investment tradeoffs, ensuring accuracy, transparency, and compliance
Manage budgets effectively for all of Product & Engineering, including developing financial models, forecasting, analyzing variances, and identifying cost optimization opportunities while maintaining quality and strategic alignment
Partner with executive leadership to truly understand core business needs, rigorously assess current operational states, and develop actionable plans that drive significant process improvements and enhanced operational efficiency
Lead complex, cross-functional initiatives from problem definition through execution, coordinating stakeholders across Finance, Engineering, Customer Support, Marketing, and Product
Drive results without formal authority by cultivating a highly collaborative and high-trust team environment
Apply deep project management expertise to clearly define workstreams, establish precise milestones, and ensure all project activities are appropriately assigned and meticulously tracked to guarantee successful delivery
Identify and manage program risks through rigorous risk assessments, proactively raising prioritization and tradeoff decisions, proposing effective mitigation strategies, and developing alternative solutions in line with a defined risk management framework
Design and optimize workflows for Product & Engineering leads, including tooling, processes, and best practices
Apply project management expertise to define clear workstreams, establish ambitious yet achievable milestones, and ensure all project activities are appropriately assigned and meticulously tracked for successful delivery
Balance strategic vision with operational execution by making real-time decisions, evaluating tradeoffs, and identifying opportunities that enhance program outcomes and drive continuous improvement
Facilitate comprehensive program planning and coordination to drive accountability across teams, ensuring they deliver high-quality results consistently, on time, and within scope
Establish and track critical operational metrics such as cycle time, lead time, deployment frequency, success rates for product launches, resource utilization, and cost efficiency
Design and implement dashboards that provide real-time visibility into program health, operational performance, and key metrics
Establish robust mechanisms for company-wide information flow, ensuring transparency and clarity including developing centralized communication platforms, standardizing reporting cadences, implementing regular cross-functional sync-ups, and fostering a culture of proactive information sharing to break down silos
Cultivate a culture that relentlessly accelerates launches and enhances velocity including championing agile methodologies, promoting continuous improvement, fostering a blameless post-mortem culture, recognizing and rewarding efficient processes, and empowering teams to make rapid, informed decisions
Shape and enhance the Product & Technology culture through initiatives such as internal and external newsletters, orchestrating hackathons, and establishing community forums, all aimed at bringing people together and fostering a cohesive and innovative environment

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

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