Whippy is hiring a Head of Customer Success to own Net Revenue Retention, customer architecture, and the performance of our Customer Success team. You will lead and elevate our CSM team while designing the systems, standards, and guardrails that ensure scalable solutioning across all customer accounts.
What You'll Do
- Own Net Revenue Retention across the entire customer base.
- Implement structured health scoring, renewal forecasting, and risk identification systems.
- Build frameworks that surface expansion signals early and reduce churn.
- 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.
- 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.
- Define when issues require engineering involvement versus process adjustment.
- Partner closely with Product and Engineering to surface patterns across customers.
- Translate customer complexity into structured feedback that informs product decisions.
- Ensure Customer Success and Product remain tightly aligned as complexity grows.
- Build a Customer Success organization that operates independently from founder oversight.
- Create systems that allow leadership to focus on product and growth rather than daily account decisions.
What We're Looking For
- 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.
Work Mode
This is a remote position.
Whippy is an equal opportunity employer.
