CS Strategy & Ops Program Manager, AI-Driven (Hybrid)

DocuSign; Chicago (IL); Hybrid; USD 133,000 - 207,000; Full time

Benefits offered by this job

RSUs

Bonus eligibility

Health benefits

Paid time off

Retirement plan

Learning & development

Parental leave

Job summary

DocuSign seeks a seasoned CS Strategy & Operations Program Manager to design, own, and drive transformation programs across Customer Success. You will lead multi-workstream efforts, align initiatives with leadership, and deliver measurable business value while mitigating risks and guiding stakeholders from the executive level.

Reporting to the Senior Director, Customer Success Strategy & Analytics, this role emphasizes automation, AI-enhanced processes, and a data-driven approach to improve

Qualifications

• 8+ years of combined strategy/operations and program management/enterprise transformation experience.
• 5+ years of experience in Customer Success, Sales, or GTM within SaaS or subscription-based business.
• Demonstrated ability to influence and build consensus with senior leadership and C-level executives.
• Extensive experience driving digital transformation with cross-functional programs.
• Excellent executive communication and interpersonal skills.

Responsibilities

• Own and help define the CS Strategy & Operations program roadmap and vision for major CS initiatives, with automation focus.
• Collaborate with senior leaders to plan objectives, scope, deliverables, and manage expectations to improve customer experience and business performance.
• Design and facilitate strategic sessions with SMEs and CS leaders to surface and test new initiatives before they enter the roadmap.
• Lead cross-functional activities and drive shared accountability across workstreams and with the C-suite as needed.
• Lead executive-level communications and Steering Committee updates to show status, value, and impact.

Skills

Strategy execution

Stakeholder management

Executive communication

Digital transformation

Agile methodologies

Education

BS/BA degree

Tools

Jira

Confluence

SmartSheet

Job description

DocuSign seeks a seasoned CS Strategy & Operations Program Manager to design, own, and drive transformation programs across Customer Success. You will lead multi-workstream efforts, align initiatives with leadership, and deliver measurable business value while mitigating risks and guiding stakeholders from the executive level.

Reporting to the Senior Director, Customer Success Strategy & Analytics, this role emphasizes automation, AI-enhanced processes, and a data-driven approach to improve