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Director of Customer Success - Healthcare

United States, Brooklyn, New York 140000.00 - 180000.00 USD / Year · Job Posted February 18, 2026
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Job Description

This is a build-and-own role with real stakes. You will step into active, high-impact customer relationships from day one. You’ll work directly with the founders and partner closely with Sales, Product/Engineering, and Marketing.

Job Responsibility

  • Own Outcomes for Our Most Strategic Customers: Make Flip the most impactful tool in our customers’ tech stack by delivering clear business outcomes and ROI
  • Ensure our reference list grows as fast as our customer list
  • Build trusted, executive-level relationships across stakeholders — becoming our customers’ favorite partner
  • Travel frequently to meet customers in person and deepen partnerships
  • Lead the Full Customer Lifecycle: Partner with Sales to support late-stage evaluations and close complex deals
  • Lead onboarding and implementation through the full lifetime of the customer relationship
  • Go above and beyond to solve edge cases, test scenarios, and deliver outcomes customers didn’t think were possible
  • Be a Deep Product & Domain Expert: Master Flip’s platform quickly (Ecommerce/Retail or Healthcare)
  • Unpack customer problems beyond surface symptoms to uncover root causes
  • Translate customer needs into actionable feedback that shapes product strategy and roadmap
  • Build & Scale a World-Class CS Organization: Initially operate as a senior IC for ~6 months while setting the standard
  • Hire, mentor, and scale a high-performing CS team as the business grows
  • Build scalable systems, processes, and operating rhythms without losing quality
  • Act as a player-coach who raises the bar for execution, ownership, and culture
  • Partner Across the Business: Collaborate with Product to ship customer-driven improvements
  • Work with Marketing to turn customers into advocates and community leaders
  • Use data and storytelling to show impact, performance, and ROI

Requirements

  • 10+ years of experience leading Customer Success for a B2B software company
  • Proven experience scaling CS from early customers to hundreds of accounts
  • A track record managing complex, high-stakes, business-critical relationships — and the ability to articulate exactly how you navigated the hardest moments
  • Strong executive communication skills with customers and internal stakeholders
  • Deep ownership mentality — you see problems as yours to solve
  • Player-coach mindset with a passion for developing exceptional teams
  • Obsession with customer experience and delivering outcomes

Nice to have

  • Experience building CS processes in both startup and enterprise environments
  • Passion for storytelling, references, and customer community building
  • Experience at an early-stage Healthtech company (Series A–C)
  • Familiarity with EHR/PM integrations (Epic, Athena, Experity, eClinicalWorks, etc.)
  • Knowledge of healthcare data standards (HL7, FHIR, HIPAA)
  • Understanding of payer/provider dynamics and patient experience workflows

What we offer

  • Comprehensive healthcare
  • Unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
  • Bonus and/or commission as well as equity, in accordance with company policy, and subject to board approval

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