Enterprise Customer Success Manager

Parachute Health$130K — $160K *
US-AnywhereRemote in United States
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in Customer Success, Account Management, or strategic consulting
  • 2+ years managing enterprise or complex accounts
  • Direct experience with health systems, DME/HME providers, or similar environments
  • Ability to influence senior stakeholders in large organizations
  • Proven track record of retaining and expanding accounts
  • Experience navigating complex account structures
  • Excellent executive communication skills

Responsibilities

  • Own a portfolio of enterprise accounts as the primary post-sale contact
  • Develop multi-year Account Plans to align customer goals with platform capabilities
  • Navigate complex organizational structures to maintain stakeholder alignment
  • Lead Executive Business Reviews, presenting strategic recommendations
  • Drive product adoption across complex workflows
  • Identify adoption gaps and collaborate with teams to address them
  • Manage renewal cycles and mitigate churn risk for enterprise accounts

Benefits

  • Comprehensive Medical, Dental, and Vision Coverage
  • Employer HSA Contribution
  • 401(k) Retirement Plan
  • Equity Incentive Plan
  • Annual Company-Wide Bonus opportunity of up to 15%
  • Remote-First culture with office and co-working reimbursement
  • Flexible Vacation Policy
  • Summer Fridays with additional days off
  • Home Office and Wellness Stipend
  • Monthly Internet Stipend
  • Annual Learning and Development Stipend
Full Job Description
About the Role

As an Enterprise Customer Success Manager, you will own the post-sale relationship for a focused portfolio of high-value, high-complexity customers. These are large-scale DME/HME operators that require a more consultative, operationally sophisticated approach than a typical SaaS CSM role. You will serve as a strategic advisor, a trusted operational partner, and the internal champion for your accounts.

This role requires fluency in healthcare operations, supply chain, or HME workflows, and the ability to navigate large, matrixed organizations with multiple buying and influencing stakeholders.
What You'll Do

Account Ownership & Strategic Leadership
  • Own a focused portfolio of enterprise accounts, serving as the primary post-sale point of contact for stakeholders from the C-suite to frontline operations.
  • Develop and execute multi-year Account Plans that map customer goals to platform capabilities and drive measurable business outcomes.
  • Navigate complex organizational structures - including multi-site health systems, regional DME branches, and national chains - to maintain alignment across all key stakeholders.
  • Lead Executive Business Reviews (EBRs), presenting ROI data, adoption trends, strategic recommendations, and forward-looking roadmap alignment.
  • Build deep relationships with VP- and C-level executives, clinical operations leaders, procurement, IT, and billing/revenue cycle stakeholders.

Adoption & Value Realization
  • Drive product adoption across complex, multi-workflow environments - including intake, order management, billing, and compliance workflows common in HME/DME and health system settings.
  • Develop customized success plans tied to each customer's operational KPIs (e.g., order cycle time, denial rates, utilization, patient satisfaction).
  • Proactively identify adoption gaps and work cross-functionally with Implementation, Product, and Support to close them.
  • Lead onboarding handoffs with the Implementation team and ensure enterprise customers reach time-to-value milestones defined during the sales process.

Retention & Commercial Expansion
  • Own renewal cycles for enterprise accounts, with full accountability for gross retention and net revenue retention targets.
  • Proactively identify and mitigate churn risk through health scoring, stakeholder mapping, and early intervention playbooks.
  • Identify, develop, and partner with Sales to close expansion opportunities - including additional product lines, new locations, and deeper workflow integrations.
  • Build strong internal champions and multi-threaded relationships to protect against single-point-of-contact risk in large accounts.

Cross-Functional Collaboration
  • Act as the voice of the customer internally, synthesizing enterprise feedback into actionable input for the Product roadmap.
  • Partner with Product, Support, and Implementation to resolve complex issues that span multiple systems or workflows.
  • Collaborate with Marketing to develop case studies, ROI narratives, and customer advocacy content featuring enterprise wins.
  • Maintain accurate, detailed account data in HubSpot and CS tooling - including health scores, stakeholder maps, risk flags, and expansion pipeline.
What We're Looking For

Requirements
  • 5+ years of experience in Customer Success, Account Management, or a strategic consulting role - with at least 2 years managing enterprise or complex accounts.
  • Direct experience working with health systems, DME/HME providers, home health organizations, or similar complex healthcare operations environments.
  • Demonstrated ability to manage and influence senior stakeholders (VP, C-suite) in large, matrixed organizations.
  • Strong business acumen with the ability to connect platform capabilities to operational and financial outcomes meaningful to healthcare operators.
  • Proven track record of owning renewal and expansion targets in a commercially accountable CSM role.
  • Experience navigating complex account structures with multiple sites, divisions, or business units.
  • Excellent executive communication skills - comfortable leading high-stakes QBRs, presenting ROI analyses, and navigating difficult renewal conversations.
  • Proficiency with CRM and CS tooling (HubSpot experience a plus).
  • Bachelor's degree in Business, Healthcare Administration, or a related field - or equivalent professional experience.

Strongly Preferred
  • Familiarity with HME/DME-specific workflows: intake and order management, Medicare/Medicaid billing, prior authorization, resupply programs, and compliance requirements.
  • Experience with health system procurement processes, IT governance, and clinical change management.
  • Previous experience at a SaaS company serving the post-acute, home health, or healthcare supply chain market.
  • Knowledge of payer dynamics, revenue cycle considerations, and regulatory factors (HIPAA, CMS guidelines) that affect enterprise health operators.
Benefits
  • Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums
  • Employer HSA Contribution: Company-funded contributions to your Health Savings Account
  • 401(k) Retirement Plan
  • Equity Incentive Plan
  • Annual Company-Wide Bonus: Opportunity for up to 15% bonus based on company performance
  • Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces
  • Flexible Vacation Policy
  • Summer Fridays: 5 additional Fridays off during the summer (separate from PTO)
  • Home Office and Wellness Stipend
  • Monthly Internet Stipend
  • Annual Learning and Development Stipend
Base Salary Band (based on experience and level)

$130,000 - $160,000 Base + Commission

About Parachute Health

Parachute Health is a healthcare technology company that provides a platform for ordering and delivering medical equipment. The company's platform enables healthcare providers to order medical equipment and supplies for their patients, and then have those items delivered directly to the patient's home. Parachute Health's platform is designed to streamline the medical equipment ordering process and improve patient outcomes. The company was founded in 2015 and is headquartered in New York, New York.
Learn more about Parachute Health
Size
50 employees
Industry
Net Income
-$5 million
Founded
2015
5 Year Trend
+30%
Revenue
$10 million

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