Senior Lead of Retention Operations

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.

What You'll Do

Revenue Protection & Renewal Safeguarding

• Architect Retention Methodology: Serve as the primary owner of the end-to-end churn and attrition framework, developing processes and standards to improve operating effectiveness

• Drive AI & Revenue Innovation: Lead the design of internal risk-mitigation tools and AI decisioning apps while monitoring renewal pipelines to forecast and protect recurring revenue

Operational Health and Save Play Execution

• Process & Pipeline Management: 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

• Cross-Functional Strategy: Build formal networks across Sales, CS, and Finance to resolve complex risks and iterate on playbooks based on win/loss performance analysis

Revenue Preservation & Expert Analysis

• Expert Risk Mitigation: Manage a book of complex renewal risks, using independent judgment and advanced data synthesis (Salesforce/Gainsight) to secure at-risk revenue

• Outcome Optimization: Maintain accountability for churn process performance, evaluating program success rates to pivot strategies in alignment with long-term business goals

Deal Architecture & Collaboration

• Strategic Deal Structuring: Partner with the Deal Desk to architect renewals involving expansion, multi-year commitments, and discounting guardrails to maximize retention

• Negotiation Support: Provide operational analysis and pricing recommendations for non-standard renewals, downsells, and complex contract restructurings

Solution-Based Pricing Model Execution

• Pricing Subject Matter Expertise: Serve as the primary resource for Sales and CS on the solution-based pricing framework, ensuring consistent application across all transactions

• Optimization & Guidance: Analyze pricing outcomes to identify opportunities for improved packaging or bundling while guiding field teams through pricing complexities

Systems & Analytics (Salesforce, Gainsight, Excel)

• Platform Mastery: Manage Salesforce and Gainsight workflows to maintain data hygiene, track customer health scores, and build dashboards for operational visibility

• Advanced Modeling: Utilize expert Excel capabilities to build sophisticated renewal forecasting tools, scenario analyses, and ad-hoc reporting

What You'll Need

Minimum Qualifications

• 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.

Preferred Qualifications

• 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

Travel Requirements & Working Conditions

• Up to 10% Travel

• Reliable internet access for any period of time working remotely, not in a Workiva office

How You'll Be Rewarded

A discretionary bonus typically paid annually

Restricted Stock Units granted at time of hire

401(k) match and comprehensive employee benefits package

The salary range represents the low and high end of the salary range for this job in the US. Minimums and maximums may vary based on location. The actual salary offer will carefully consider a wide range of factors, including your skills, qualifications, experience and other relevant factors.

Why Join Workiva

Workiva is the platform designed to bring confidence, control, and a competitive edge to the world's most complex organizations. Our AI-powered platform unifies finance, risk, and sustainability on a single, secure foundation-ensuring data is trusted, traceable, and ready to act on. With an unbroken path from source to output, leaders gain confidence in their numbers, visibility into current and emerging risks, and the ability to move with speed and precision in a constantly changing world.

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.

Employment decisions are made without regard to age, race, creed, color, religion, sex, national origin, ancestry, disability status, veteran status, sexual orientation, gender identity or expression, genetic information, marital status, citizenship status or any other protected characteristic.

Workiva is committed to working with and providing reasonable accommodations to applicants with disabilities. To request assistance with the application process, please email talentacquisition@workiva.com.

Workiva employees are required to undergo comprehensive security and privacy training tailored to their roles, ensuring adherence to company policies and regulatory standards.

Workiva supports employees in working where they work best - either from an office or remotely from any location within their country of employment.