As a Senior Customer Success Strategy & Operations Analyst supporting Strategy & Transformation, you will help design, build, and execute the initiatives that shape how Docusign’s Customer Success organization operates. You will do this through structured problem-solving, rigorous analysis, and strong cross-functional partnership with leaders across Sales, Product, Digital Technology Services, Finance, and Enterprise Transformation, turning ambiguous strategic questions into clear frameworks, business cases, and executable plans, and helping track their impact once launched. This position is an individual contributor role reporting to the Sr. Director, CS Strategy & Operations. Responsibility Support end-to-end execution of strategic initiatives and transformation workstreams, from problem framing and analysis through stakeholder alignment and implementation Build and maintain frameworks for account/segment prioritization, health scoring, and coverage modeling that inform where the CS organization focuses its efforts Develop business cases, playbooks, and operating models that support strategic investments and transformation initiatives Partner with cross-functional teams including Sales Strategy, Product, Digital Technology Services, Finance, and Enterprise Transformation to translate strategy into scalable, executable plans Structure ambiguous, complex business problems into clear, actionable analysis and recommendations Build executive-ready materials e.g. decks, one-pagers, briefing documents summarizing progress, risks, and recommendations for senior leadership Own program governance for assigned initiatives, including milestone tracking, dependency management, and reporting cadences Support the annual planning process for Customer Success, including goal setting, capacity modeling, and performance tracking Facilitate stakeholder alignment across CS leadership, Sales Strategy & Operations, and other GTM functions Conduct research and analysis on org design, operating model options, and industry best practices to inform transformation decisions Use SQL, G-Suite, and BI tools to support ad hoc quantitative analysis in service of strategic projects and pilot evaluations Track and synthesize outcomes of pilot programs and process changes to inform go/no-go and scale decisions Coordinate quantitative and qualitative inputs from stakeholders into cohesive project recommendations Identify business improvement opportunities through analysis of process, tooling, and organizational data Apply deepening functional expertise and upcoming technologies, including AI, to deliver both routine and non-routine work with increasing autonomy Select and optimize technical tools and potential AI solutions to improve productivity, streamline workflows, and solve complex problems Evaluate and adopt AI-enabled capabilities to boost efficiency while fostering a culture of continuous learning, peer support, and knowledge sharing within the team