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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
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