Enterprise Customer Success Manager

Flossy
United States
RemoteCareer-pivot friendly

Who this role is best for

Geared toward experienced professionals comfortable with managing complex client implementations and cross-functional collaboration, with a focus on appointment-based industries in the US.

Best fit for

  • Candidates with 4–8 years of enterprise customer success or operations experience in multi-location businesses
    — “4–8 years’ experience in enterprise customer success, implementation, management consulting, or operations at a multi-location business”
  • Individuals who can translate operational data into business outcomes and influence product development
    — “Channel your on-the-ground insights into Flossy’s product roadmap”
  • Professionals with a track record of driving account expansion and identifying upsell opportunities
    — “Drive account growth. Uncover new needs and opportunities, aligning them with additional Flossy solutions”

Things to consider

  • This role demands a hands-on approach with technical configuration and integration tasks
    — “Technical skills to configure software, understand system integrations”
  • Strong emphasis on building trust and relationships across all client levels
    — “Build relationships across all client levels—from front-desk managers to executive leadership”

How to stand out

  • Highlight experience in managing full client journeys from contract to expansion
    — “Lead the customer journey. Own every phase—from contract signature through implementation”
  • Emphasize past success in identifying and securing upsell opportunities
    — “Develop the case for upsells and expansions, frequently identifying these ahead of the sales team”
  • Showcase ability to collaborate with engineering and product teams on solutions
    — “Work directly with product and engineering to tailor agent solutions”
Pace · SteadyCollaboration · HighAutonomy · MediumDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • lead customer journey from contract signing through implementation and expansion
  • analyze client data and identify business drivers
  • deploy AI agents and demonstrate ROI
  • drive account growth and uncover new opportunities
Typical background
enterprise customer success, implementation, management consulting, or operations at a multi-location business

Skills & requirements

Required

Enterprise Customer SuccessProject ManagementAnalytical SkillsCommercial AcumenTechnical SkillsHands-on Approach

Preferred

Dental, Medspa, Veterinary, Wellness, Or Other Appointment-based Industries Experience

Stack & domain

Project ManagementData AnalysisSql-like AnalysisAI AgentsSystem IntegrationsCommercial AcumenROI ThinkingPresentation SkillsDentalMedspaVeterinaryWellness

About the role

Original posting from Flossy via Ashby

ABOUT THE ROLE

As an Enterprise Customer Success Manager at Flossy, you will take full ownership of a portfolio of our largest clients, guiding them from contract signing through implementation, renewal, and expansion. Think of yourself as the general manager for each client's business—partnering deeply to drive outcomes, not just offering advice. You'll immerse yourself in each client's operations to deploy Flossy AI agents, drive key metrics, and demonstrate clear, measurable ROI.

WHAT YOU'LL DO

  • Lead the customer journey. Own every phase—from contract signature through implementation, KPI validation, go-live, and ongoing expansion. Manage plans, timelines, stakeholders, and results.
  • Gain deep business insights. Analyze client data such as call volume, booking rates, scheduling, cancellations, revenue per location, marketing spend, and staffing. Identify business drivers and uncover areas of lost opportunity.
  • Deliver measurable ROI. Deploy our AI agents against core business drivers. Collaborate on defining success metrics, track progress at every location, and build ROI cases that secure broader adoption.
  • Drive account growth. Uncover new needs and opportunities, aligning them with additional Flossy solutions. Develop the case for upsells and expansions, frequently identifying these ahead of the sales team.
  • Collaborate cross-functionally. Work directly with product and engineering to tailor agent solutions—configuring call scoring, scheduling logic, scripts, integrations, and reporting. Channel your on-the-ground insights into Flossy’s product roadmap.
  • Act as a trusted advisor. Build relationships across all client levels—from front-desk managers to executive leadership. Lead engaging weekly sessions and business reviews that clients value and attend.

REQUIREMENTS

  • 4–8 years’ experience in enterprise customer success, implementation, management consulting, or operations at a multi-location business. PE portfolio experience preferred.
  • Strong analytical skills and data fluency. Proficient with spreadsheets and SQL-like analysis, able to turn operational data into actionable business stories.
  • Proven project management capability—adept at managing multiple complex rollouts simultaneously without losing detail.
  • Commercial acumen; you think in terms of ROI, payback, and growth, and are confident presenting business cases to executives.
  • Technical skills to configure software, understand system integrations (i.e., practice-management, CRMs, phone systems), and partner effectively with engineers.
  • Hands-on approach—eager to drive real change, not just make recommendations.
  • Experience in dental, medspa, veterinary, wellness, or other appointment-based industries is a strong advantage.

WHY FLOSSY?

Flossy builds AI agents for the appointment economy. Our technology answers calls, coaches front-desk teams, fills schedules, and drives significant revenue impact for multi-location businesses in dental, medspa, veterinary, and massage sectors. We partner with leading brands and measure our success by their tangible ROI.

As part of our fast-growing team, you will directly influence some of the fastest-scaling multi-location brands nationwide. You’ll collaborate closely with our founders and have a clear path to leadership as we expand our customer success organization.

Source: Flossy careers (Ashby)

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