Remote Manager, Customer Success

Parachute Health is transforming post-acute care as the leading digital ordering platform for medical equipment and supplies. We connect major health systems, health plans, and suppliers to help patients get the life-saving products they need at home. Since launching, we've connected 300,000+ clinicians and 3,000+ supplier locations across all 50 states and helped 15M+ patients. What started as a DME ePrescribing tool has become the order management platform of choice for home medical equipment. Join our team and make a difference in patient care. About the Role As the Manager of Customer Success, you'll sit between the VP of Customer Success and the broader CSM team. You'll carry your own portfolio of accounts — weighted toward complex, high-value customers — while also serving as a mentor, escalation resource, and operational partner for newer CSMs across enterprise, mid-market, and SMB segments. You'll help the VP build a high-performing team by translating strategy into day-to-day coaching, playbook execution, and process consistency. This is the right role for someone who loves the craft of customer success, is genuinely energized by developing others, and wants to grow into CS leadership without stepping fully out of customer-facing work. What You'll Do Team Development & Coaching Serve as the primary day-to-day mentor for newer CSMs — providing guidance on account strategy, difficult customer conversations, renewal negotiations, and escalation handling. Manage and mentor a team of up to 5 CSM direct reports Conduct regular 1:1s or structured coaching sessions with developing CSMs to review account health, pipeline, and growth opportunities. Review and provide feedback on BR decks, account plans, and customer communications before they go out to help newer CSMs level up their craft. Support onboarding of new CS team members — sharing institutional knowledge, walking through playbooks, and helping them ramp quickly on both the platform and the HME/home health industry. Identify skill gaps across the team and work with the VP to design targeted development plans or training resources. Model what great looks like — in discovery conversations, renewal calls, stakeholder navigation, and internal advocacy for customers. VP Support & Team Operations Act as a strategic thought partner to the VP of Customer Success, helping translate team goals into executable plans and holding the team accountable to key metrics. Own or co-own the development and maintenance of core CS playbooks — onboarding, EBR, renewal, risk, and expansion — ensuring they reflect current best practices and are consistently applied. Help maintain visibility into team-wide account health, surfacing patterns, risks, and opportunities to the VP before they become problems. Step in to cover accounts or lead key customer interactions when CSMs are unavailable or when a situation requires a more senior presence. Lead team meetings, deal reviews, or account health check-ins in partnership with or in place of the VP as needed. Contribute to hiring by participating in interviews, evaluating CS candidates, and helping define what the team needs at each level. Own Account Portfolio Carry a focused portfolio of accounts — typically the more complex, strategically sensitive, or at-risk customers that benefit from a senior CSM's attention. Develop and execute account plans, lead EBRs, drive adoption, and own renewal and expansion outcomes for your accounts. Serve as an escalation point for high-stakes customer situations across the broader team, jumping in to stabilize relationships and develop resolution plans. Bring lessons from your own accounts back to the team — using real examples to illustrate what good account management looks like in practice. Maintain accurate account data in HubSpot and CS tooling, and hold the team to the same standard. Process & Playbook Development Partner with the VP to identify gaps in how the CS team operates and build or refine the systems, templates, and workflows that close them. Document and institutionalize best practices so that tribal knowledge becomes team-wide capability. Evaluate CS tooling and make recommendations for improvements that help the team scale — health scoring models, automation, reporting dashboards, and more. Collaborate with Sales, Implementation, Product, and Support to ensure cross-functional handoffs and workflows are well-defined and consistently executed. What We're Looking For Requirements 5+ years of experience in Customer Success, with a track record of strong performance managing complex or enterprise-level accounts. 3+ years of management experience Prior experience mentoring, coaching, or informally leading other CSMs — even without a formal management title. Deep knowledge of the HME, DME, or home health industry — you can credibly advise a newer CSM on how to handle a billing-related escalation at a large DME provider or navigate a health system's procurement process. Strong commercial instincts: you understand what drives retention and expansion, and you can help others see and act on those signals in their own accounts. Excellent judgment in high-stakes situations — you stay calm when accounts are at risk, communicate clearly with customers and internal teams, and develop plans that actually work. A natural teacher and communicator: you can explain the why behind a strategy, not just the what. Organized and process-minded — you see the value in playbooks and documentation and can build them without it feeling like a chore. Proficiency with HubSpot or similar CRM and CS tooling. Bachelor's degree in Business, Healthcare Administration, or a related field — or equivalent experience. Strongly Preferred Experience at a SaaS company serving the post-acute, home health, or HME/DME market. Formal or informal experience leading CS team initiatives — playbook development, onboarding programs, deal review processes, or similar. Familiarity with CS platforms such as Gainsight, ChurnZero, or Totango and an understanding of how to use health scoring data at a team level. Prior exposure to building or scaling a CS function in a growth-stage company, where the playbook was still being written. Experience partnering directly with a VP or Director of CS in a senior IC or lead capacity. 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) $100,000-$150,000 Base + Commission California job applicants may access the Notice of Collection of Personal Information and Privacy Policy with information and rights required by the California Privacy Rights Act (CPRA) the link here . We are proud to be an equal opportunity employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth related medical conditions and lactation), gender identity or gender expression (including transgender status), sexual orientation, marital status, military service and veteran status, disability, genetic information, or any other characteristic protected by applicable federal, state, or local laws and ordinances. This role is not eligible for employer visa sponsorship. Applicants must be legally authorized to work in the United States at the time of application and for the duration of employment. The Company does not sponsor employment authorization for this position.