Customer Success Lead

Job Description:

Customer Success Lead  

Reap · Full-time · Remote or Hybrid  

About Reap  

Reap is the AI platform built for skilled nursing facilities. We help operators automate the work that used to eat up their week - Medicaid case management, revenue cycle, compliance, and the back-office workflows that keep buildings running.

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We’re early, growing quickly, and working with some of the most respected operators in long-term care. Every new customer is a chance to prove that AI can actually change how this industry runs.  

Customer Success at Reap is highly hands-on. We work directly with operators every day to solve problems, improve workflows, and make sure customers get real value from the platform.  

The role  

We’re looking for someone to lead Customer Success at Reap while staying deeply involved in the day-to-day work. This is not a purely managerial role. You’ll spend time onboarding customers, handling escalations, improving support processes, working closely with product and engineering, and building strong relationships with operators across our customer base. You’ll help shape how Customer Success works at Reap as we grow, while also being one of the people customers rely on most directly.  

What you’ll do  

• Own customer onboarding and ongoing account management across a portfolio of facilities and multi-site operators.
• Act as a senior point of contact for customers, helping troubleshoot issues, drive adoption, and ensure customers are successful using Reap day to day.
• Work closely with product and engineering to communicate customer feedback, identify patterns, and improve the platform.
• Help build and improve customer support processes, onboarding workflows, documentation, and internal playbooks.
• Track customer health, adoption, renewals, and expansion opportunities.
• Support and mentor other team members as the Customer Success team grows.
• Help define the standard for how Reap communicates with and supports customers.  

What we’re looking for  

• 5+ years of experience in customer success, account management, implementation, or customer support within B2B SaaS.
• Experience working directly with customers in fast-moving environments where responsiveness and ownership matter.
• Healthcare experience is a strong plus, especially long-term care, post-acute care, RCM, or healthcare operations software.
• Strong communicator who is organized, proactive, and comfortable managing multiple customer conversations at once.
• Comfortable jumping between strategy and execution. You’re happy to be on a customer call, investigate an issue, improve a process, and help shape the long-term customer experience all in the same day.
• You stay calm under pressure and communicate clearly when things break or move quickly.  

Benefits  

Comprehensive benefits package included.