Senior Lead of Retention Operations

Workiva Inc.

1d•Hybrid

About The Position

The Senior Lead of Retention Operations is a high-impact role responsible for the strategic architecture and horizontal execution of Workiva’s retention and save programs. This role serves as the primary Subject Matter Expert (SME) for the churn and downsell lifecycle, possessing the authority to re-architect retention methodologies and "independently determine processes" that improve operational effectiveness. At Workiva, you’ll bring technology to market that executives, boards, and regulators depend on. The work you do here helps organizations navigate uncertainty, maintain trust, and make decisions that stand up to scrutiny. If you’re energized by meaningful challenges, inspired by collaborative teams, and motivated to help organizations turn uncertainty into advantage, we’d love to meet you.

Requirements

8+ years of experience in Renewal Operations, Revenue Operations, or a related field within a B2B SaaS environment
Undergraduate degree or equivalent combination of experience and education in a related field
Proven track record of protecting renewal revenue by designing programmatic risk-mitigation logic (AI or rule-based) and leading horizontal initiatives across cross-functional teams
Expert-level proficiency in Salesforce, Gainsight, and Excel/Google Sheets (Power Query, modeling) to manage workflows, health scoring, and complex data visualization
Deep understanding of value-based pricing models with a demonstrated ability to simplify complex processes and present strategic findings to senior stakeholders

Nice To Haves

Experience with churn prediction modeling or customer health analytics
Familiarity with CPQ tools (e.g., Salesforce CPQ, DealHub) and their integration with renewal workflows
Exposure to revenue recognition standards (ASC 606) and their implications on deal structure
Experience in a high-growth SaaS company with complex, multi-product subscription offerings
Salesforce Administrator or Gainsight certification is a plus

Responsibilities

Serve as the primary owner of the end-to-end churn and attrition framework, developing processes and standards to improve operating effectiveness
Lead the design of internal risk-mitigation tools and AI decisioning apps while monitoring renewal pipelines to forecast and protect recurring revenue
Act as the operational hub by monitoring retention process health and coordinating cross-functional teams to ensure save plays are executed at a high standard
Build formal networks across Sales, CS, and Finance to resolve complex risks and iterate on playbooks based on win/loss performance analysis
Manage a book of complex renewal risks, using independent judgment and advanced data synthesis (Salesforce/Gainsight) to secure at-risk revenue
Maintain accountability for churn process performance, evaluating program success rates to pivot strategies in alignment with long-term business goals
Partner with the Deal Desk to architect renewals involving expansion, multi-year commitments, and discounting guardrails to maximize retention
Provide operational analysis and pricing recommendations for non-standard renewals, downsells, and complex contract restructurings
Serve as the primary resource for Sales and CS on the solution-based pricing framework, ensuring consistent application across all transactions
Analyze pricing outcomes to identify opportunities for improved packaging or bundling while guiding field teams through pricing complexities
Manage Salesforce and Gainsight workflows to maintain data hygiene, track customer health scores, and build dashboards for operational visibility
Utilize expert Excel capabilities to build sophisticated renewal forecasting tools, scenario analyses, and ad-hoc reporting