Whippy

Customer Success Manager

• Own Net Revenue Retention
• Implement structured health scoring, renewal forecasting, and risk identification systems.
• Build frameworks that surface expansion signals early and reduce churn before it materializes.
• Define what “healthy account ownership” looks like across the team.
• Design and standardize onboarding frameworks and implementation workflows.
• Define solutioning guardrails to ensure AI agent configurations and automations are scalable and not fragile.
• Codify best practices for embedding Whippy into ATS and CRM environments.
• Ensure implementation quality holds up at scale across enterprise staffing customers.
• Identify where processes are breaking and redesign them.
• Manage and develop Customer Success Managers responsible for ongoing customer relationships.
• Set clear standards for account ownership, documentation quality, follow-through, and judgment.
• Review calls and provide direct feedback on execution quality and pushback discipline.
• Coach CSMs to balance flexibility with architectural integrity.
• Hold the team accountable to retention and expansion outcomes.
• Personally own a small portfolio of high-impact, complex accounts.
• Protect long-term solution design, guide renewal strategy, and ensure scalable implementation standards.
• Serve as the senior escalation point when architectural judgment or executive presence is required.
• Resolve escalations with structural fixes rather than short-term patches.
• Partner closely with Product and Engineering to surface patterns across customers.
• Translate customer complexity into structured feedback that informs product decisions.
• Build a Customer Success organization that operates independently from founder oversight.

Head of Customer Success

• Lead Customer Success Managers
• Manage and develop Customer Success Managers responsible for ongoing customer relationships.
• Set expectations for account ownership, cadence, documentation, and follow-through.
• Review account plans, notes, and activity to ensure consistent execution.
• Coach CSMs on identifying churn risk, expansion signals, and misaligned requests.
• Help CSMs improve how they push back, frame tradeoffs, and guide customers.
• Review calls and provide direct feedback on execution quality and decision-making.
• Ensure success plans, check-in cadences, and documentation are created and maintained.
• Identify where processes are breaking and fix them.
• Balance structure with flexibility as customer complexity grows.
• Join customer calls when needed for escalations, renewals, or strategic reviews.
• Support complex solutioning conversations without owning day-to-day execution.
• Ensure escalations are resolved with long-term outcomes in mind.
• Ensure CSMs are designing scalable workflows and AI agent configurations.
• Evaluate whether solutions will hold up at scale or create long-term issues.
• Know when to involve engineering versus adjusting process or configuration.

CSM Team Lead

Solutions Engineer

• Own post-sale delivery for enterprise customers from onboarding through long-term expansion
• Build deep understanding of customer goals, workflows, and operational context
• Act as the primary post-sale point of contact and trusted advisor
• Architect and deploy AI Recruiter implementations
• Design and configure AI agents (voice, chat, messaging)
• Build and optimize messaging workflows and automation
• Guide ATS/CRM integrations and data-driven workflows
• Translate business requirements into scalable system designs
• Run solutioning, optimization, and strategy calls independently
• Recommend phased approaches and tradeoffs
• Ensure strong adoption of initial AI Recruiter deployments
• Expand usage over time into additional AI agents and workflows
• Identify expansion opportunities through success, not forced selling
• Drive high net revenue retention through trust and outcomes
• Partner closely with product and engineering teams
• Share customer patterns, feedback, and best practices
• Help shape playbooks, templates, and scalable solutions

Customer Solutions Architect – Post-Sale, Enterprise

Operations

• Own and manage billing, payment, and contract operations
• Monitor billing systems for failed payments, overdue invoices, and expired payment methods
• Proactively follow up with customers regarding billing issues and outstanding balances
• Ensure billing information and payment methods are accurate and up to date
• Track customer contracts, payment schedules, and compliance
• Follow up with customers not honoring contract or payment terms
• Identify active accounts that are unpaid or past due and coordinate appropriate next steps
• Respond to customer requests for invoices, receipts, tax documentation, and billing confirmations
• Assist customers with billing questions and payment updates
• Resolve billing discrepancies clearly and professionally
• Maintain clear reporting on overdue balances, recovered revenue, and billing status
• Help document and improve internal billing and contract workflows

Head of Customer Success

CSM Team Lead

Customer Solutions Architect – Post-Sale, Enterprise

Billing & Operations Specialist