Manager, Customer Success

Parachute Health is transforming post-acute care as the leading digital ordering platform for medical equipment and supplies. As the Manager of Customer Success, you will lead a team of customer success managers, mentor them, and manage a portfolio of high-value accounts while collaborating closely with the VP of Customer Success.

Responsibilities:

• 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
• 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
• 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
• 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

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
• 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