CS Strategy & Ops Leader: AI-Driven Transformation

Docusign; Chicago (IL); Hybrid; USD 150,000 - 210,000; Full time

Benefits offered by this job

Bonus eligibility

RSUs

Paid time off

Job summary

DocuSign is seeking a CS Strategy & Operations Program Manager to design, own, and drive transformation programs within Customer Success. You will lead initiatives, align with senior leadership, identify risks, and deliver measurable business value across multiple workstreams.

The role reports to the Senior Director, Customer Success Strategy & Analytics, and emphasizes cross-functional leadership, strategic planning, and executive communication in a hybrid work setting.

Qualifications

• 8+ years of combined strategy/operations and program management/enterprise transformation experience, with a proven track record of owning and delivering multiple, large-scale programs.
• 5+ years of experience specifically with Customer Success, Sales, or broader GTM Space within a SaaS or subscription-based business.
• Demonstrated ability to influence and build consensus with working teams, senior leadership and C-level executives.
• Strong problem solver and sense of urgency
• Extensive experience driving digital transformation with a focus on cross-functional, interdependent programs.
• Exceptional skills in simplifying highly complex issues and developing strategic frameworks to facilitate broad organizational understanding and action.
• BS/BA degree or equivalent relevant experience
• Excellent executive communication skills and interpersonal aptitude

Responsibilities

• Own and help define the overarching CS Strategy & Operations program roadmap and vision for major Customer Success Operations initiatives, with a bias to agentification and automation
• Collaborate with senior leaders to proactively plan program objectives, scope, and deliverables, and manage expectations on an ongoing basis to ensure outcomes that materially improve customer experience and business performance.
• Design and facilitate strategic brainstorming and working sessions with SMEs, cross-functional stakeholders, and CS leaders to surface, shape, and pressure-test new initiatives before they enter the program roadmap.
• Enable all activities from strategic inception through to successful delivery and adoption, directing cross-functional program activities, and driving a shared understanding and accountability across multiple workstreams and with stakeholders at all levels, including the C-suite as needed.
• Lead the development and presentation of executive-level communications, including Steering Committee updates, to ensure a shared understanding of program status, strategic value, and business impact.
• Create and manage program-level artifacts, including long-range strategic plans, cross-program dependency maps, and holistic risk and issues logs that inform and guide executive decision-making.
• Define and track program-level success metrics tied to business outcomes (e.g., adoption, GRR, efficiency gains)
• Model and champion AI-augmented program management practices: using AI tools to synthesize cross-functional updates, surface risks earlier, accelerate reporting/Steering Committee prep, and scale program oversight across a growing initiative portfolio.
• Lead and evolve our CS Strategy & Operations program management methodology and best practices, sharing lessons learned and driving a culture of continuous improvement across the organization.

Skills

Strategy & operations

Program management

Executive communication

Cross-functional collaboration

Problem solving

Digital transformation

Education

BS/BA degree or equivalent

Tools

Agile methodologies

SmartSheet

Jira

Confluence

Job description

DocuSign is seeking a CS Strategy & Operations Program Manager to design, own, and drive transformation programs within Customer Success. You will lead initiatives, align with senior leadership, identify risks, and deliver measurable business value across multiple workstreams.

The role reports to the Senior Director, Customer Success Strategy & Analytics, and emphasizes cross-functional leadership, strategic planning, and executive communication in a hybrid work setting.