Head of Customer Success
Whippy
full-time
Posted on:
Location Type: Remote
Location: Anywhere in the World
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Job Level
About the role
- 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.
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.
Benefits
- Competitive salary
- Flexible work hours
- Professional development budget
- Home office setup allowance
- Global team events
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
customer success managementretention metricschurn reductionexpansion metricsonboarding frameworksworkflow standardsintegrationsAPIsautomationsSaaS implementations
Soft Skills
systems thinkingdirect feedbackaccountabilityexecutive presencecoachingjudgmentflexibilitycommunicationleadershipproblem-solving