Head of Customer Success

Medsender

. Own customer success, implementation, and support .

Posted 10/13/2026full-timeRemote • New York • United States, CanadaLead💰 $155,000 - $190,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in customer success management, focusing on retention metrics, implementation processes, and team development. Proficient in building health scoring models and enhancing customer journeys within the healthcare or health-tech sectors.

Highest-signal resume keywords

Customer Success ManagementGross Retention ImprovementImplementation OversightPeople ManagementHealthcare Experience

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Health Scoring DevelopmentCustomer Data AnalysisRetention Metrics ManagementOnboarding Process OptimizationExpansion Strategy Systematization

Soft Skills

Organizational Decision-MakingTeam DevelopmentCustomer Insight Integration

Tools & Technologies

CRM SystemsAI-Enabled ProductsSupport Tooling

Industry Keywords

HealthcareHealth-TechEHR IntegrationsHIPAA ComplianceSMB Scale Operations

About the role

Key responsibilities & impact

Own customer success, implementation, and support
Carry gross and net retention as the primary metrics
Diagnose churn by practice size, EHR, product line, onboarding cohort, and tenure
Build health scoring and account coverage models
Systematize expansion motions and partner with sales on expansion hand-offs
Make implementation measurable and establish time-to-value targets by segment
Connect onboarding quality to first-year retention
Own support responsiveness and quality
Build documentation, in-product guidance, and AI-assisted triage to scale support
Define the customer journey from contract to renewal and assign ownership at each hand-off
Bring customer insights into product on a predictable cadence
Supply references and performance data for analyst relations and case studies
Assess, develop, and structure the team for a doubling book of business
Hire as the customer book grows
Report to the CEO

Requirements

What you’ll need

7+ years in customer success or customer operations
3+ years managing across more than one function
Experience owning and improving a gross retention number
Experience running or closely partnering with implementation
Experience operating at SMB scale with hundreds of accounts and small ACVs
Hands-on CRM and customer data experience
Ability to build the first version of health scoring
People management and organizational-structure decision-making experience
Healthcare or health-tech experience strongly preferred, including practice workflows, EHR integrations, and HIPAA
Experience with AI-enabled products and setting customer expectations around them nice to have
Support tooling and deflection at scale nice to have
Expansion quota or management experience nice to have
HubSpot experience nice to have
Must reside in the US or Canada; application asks about US work sponsorship

Benefits

Comp & perks

Health, dental, and vision
Unlimited PTO
Regular company offsites
Equity
Bonus