VP, Customer Success & Retention

6 hours, 48 minutes ago
Full-time
Lead
Customer and Technical Support
HealthJoy

HealthJoy

HealthJoy simplifies healthcare with a platform connecting employees to care, offering access to doctors, concierges, and insurance experts. Centralizing benefits, saving costs, and increasing satisfaction, HealthJoy's mobile app guides users to the ri...

Insurance
251-1K
Founded 2014
$108M raised

Description

  • Own net revenue retention, gross retention, and the renewal calendar for the customer portfolio.
  • Drive expansion, upsell pipeline management, and product adoption across live accounts.
  • Lead the AI-native transformation of Customer Success, including agentic workflows and lifecycle automation.
  • Partner with Data, Product, and RevOps to maintain reliable data foundations and operational workflows.
  • Run Customer Success operations out of Salesforce as the system of record for forecasting, opportunities, and account health.
  • Own broker-advocacy retention efforts by equipping brokers with renewal narratives, benchmarks, and ROI proof.
  • Serve as the senior client-facing leader for QBRs, business reviews, escalations, on-site visits, and incident communications.
  • Own the Customer Advisory Board and Voice of Customer program and bring insights back to the business.
  • Lead, manage, and develop the Customer Success team, including CS managers and CSMs.
  • Monitor retention, expansion, and engagement metrics and turn insights into action.

Requirements

  • 8+ years of experience in Customer Success, account management, or a commercial retention role, including team leadership.
  • Experience owning a retention or net revenue retention number.
  • Revenue-first mindset focused on retention, expansion, and net revenue retention.
  • AI-native mindset, with strong interest in building and iterating on AI-augmented or agentic workflows.
  • Hands-on experience designing AI-augmented or agentic processes is a strong plus.
  • Commercial and cross-functional fluency with Sales, Marketing, RevOps, Data, Product, and Legal.
  • Comfort working with Salesforce, pulling your own metrics, and using data to drive decisions.
  • Comfort with ambiguity and building new processes from scratch.
  • Executive presence and strong communication skills across CSMs, clients, and executive stakeholders.
  • Healthcare or benefits experience is preferred.

Benefits

  • Base salary plus commissions.
  • Additional cash incentives may be available, including annual bonus targets or other variable incentives.
  • Medical, dental, and vision insurance.
  • HSA contribution match.
  • Stock options for eligible roles.
  • 401(k) match.
  • Paid parental leave.
  • Company-sponsored short-term and long-term disability coverage.
  • Flexible PTO.
  • Remote-first work environment, with preference for Tampa Bay-based candidates for certain roles.

Interested in this position?

Apply directly on the company website

Apply Now

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