Remote (Global)

Whippy is hiring a Head of Customer Success

Responsibilities

  • Own Net Revenue Retention
  • Architect Customer Success Systems
  • Lead and Elevate the CSM Team
  • Strategic Account Ownership
  • Own Escalation Structure
  • Cross Functional Alignment
  • Reduce Founder Dependency

Requirements

  • Experience building or scaling Customer Success at a high-growth B2B SaaS company.
  • Direct ownership of retention, churn reduction, or expansion metrics.
  • Experience managing and elevating Customer Success Managers.
  • Strong systems thinking and comfort designing onboarding frameworks and workflow standards.
  • Experience working with integrations, APIs, automations, or complex SaaS implementations.
  • Ability to evaluate solution architecture without being an engineer.
  • Comfort giving direct feedback and holding teams accountable.
  • Executive presence with U.S.-based enterprise customers.
  • Bias toward structured execution, scalable systems, and long-term retention.

Nice to Have

  • Experience working with staffing, workforce, or ATS platforms.
  • Experience building Customer Success operations from early stage to scale.
  • Background in Technical Account Management, Solutions Architecture, or Customer Success Operations.

Team

Structure: Customer Success function that is structured, scalable, and independent from founder oversight.

Additional Information

  • Must overlap with U.S. Eastern Time while supporting U.S.-based customers.
Required Skills
Customer Success ManagementTeam LeadershipCustomer Relationship ManagementStrategic PlanningCustomer OnboardingAccount ManagementCross-functional CollaborationData AnalysisCustomer AdvocacyProcess ImprovementStakeholder Management
About company
Whippy
Whippy is leading the way in AI-powered business communication, helping companies replace manual workflows with intelligent AI agents across voice, chat, and messaging. We work closely with enterprise staffing and workforce organizations, embedding AI agents and automation directly into their ATS and CRM systems.
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Job Details
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Posted 4 months ago