We are looking for an extraordinary Vice President of Technology Development and Business Operations. This leader will oversee a high-impact Program Management Office (PMO), responsible for managing complex, cross-functional initiatives and ensuring that projects align with business objectives and are delivered on time and within budget. Together with the Technology leadership team, you will play a critical role to unlock the potential of the entire organization by introducing strong operating rhythms, revenue optimization programs, and new ways of working. This is a highly visible role that serves as an enabler of Product Technology to drive revenue and efficiency for DocuSign, and requires excellent communication, project management, and leadership skills. This position is a people manager role reporting to the Chief Technology Officer. Responsibility Act as a trusted advisor and partner to the CTO, aligning department goals with company vision and strategic priorities Define the governance framework and operating model for the Product & Engineering Program Management Office, establishing long-term standards for technical delivery, financial transparency, and risk management across the global organization Facilitate planning, prioritization, and execution of strategic initiatives within Technology and Engineering, ensuring alignment with business goals and timelines Architect the strategic portfolio management framework, ensuring that the technology investment roadmap is consistently aligned with the long-term corporate vision and revenue optimization targets Oversee budgeting, resource planning, and capacity management for programs, ensuring appropriate resource allocation and financial tracking Establish a comprehensive framework for measuring and reporting the Return on Investment (ROI) for the entire technology portfolio, providing the C-suite with data-driven insights into how technology spend drives business performance Manage enterprise-level relationships with key technology vendors and external partners, negotiating high-impact agreements that influence the organization’s cost structure and technical capabilities Own the lifecycle of large-scale, cross-functional projects, ensuring timely execution and accountability across all project phases, from initiation to completion Identify and mitigate risks proactively, implementing strategies to navigate challenges and ensure successful project outcomes Establish and monitor KPIs for project success, adjusting strategies and tactics as needed to optimize performance and efficiency Standardize and streamline processes to enhance the scalability, efficiency, and reliability of program and project execution Collaborate closely with product, engineering, and business leaders to translate technical and operational goals into actionable projects and deliverables Act as a strategic bridge between Executive Leadership and the Technology organization to translocate complex, long-term business goals into multi-year technology roadmaps and resource investment plans Lead and develop a team of program and project managers, providing mentorship, guidance, and opportunities for growth to ensure high team engagement and performance Build a culture of accountability, collaboration, and continuous improvement within the PMO and across all project management functions Drive cross-functional communication, breaking down silos between technology, engineering, and other business units to ensure seamless project execution Implement training and development initiatives to continually elevate the skills and expertise of the program management team Serve as a liaison between the Technology and Engineering teams and other business units, ensuring clear communication of project statuses, roadblocks, and outcomes Prepare and present executive-level briefings on program and project performance, providing insights and recommendations for decision-making Manage stakeholder expectations and foster alignment across all levels of the organization, balancing competing priorities to drive consensus Develop and maintain relationships with external partners, vendors, and consultants to support project and program objectives Lead continuous improvement initiatives, implementing best practices, tools, and methodologies to optimize project delivery and program management processes Oversee change management processes to ensure smooth transitions during large-scale technology and engineering initiatives Encourage an innovative approach to project management, seeking opportunities to integrate automation and digital tools to enhance productivity and results