Head of Customer Success

About Medsender Medical practices run on paperwork. Referrals still arrive by fax, and patients wait while staff retype what a machine already knows. Medsender exists to take that work off their plate. Our mission is to automate administrative work for healthcare providers so patients get the care they need faster. We started with fax, the unglamorous protocol that still carries most of the documents moving between practices. That wedge became a platform. Today Medsender reads and routes the documents flowing into a practice, writes what it finds back into the EHR, and works the referrals that come out of them, and MAIRA, our voice AI, picks up the phone calls a front desk never gets to. Thousands of providers in all fifty states run on it, and in the past year it saved them more than 2 million hours. We're a lean team backed by Ballast Point Partners, and we've made the Inc. 5000 two years running. Healthcare is one of the few places left where good software changes what a workday feels like for the people doing the work, and most of that work is still undone. If you want real ownership and a short distance between your decision and its effect, we'd like to talk. Why this role, now Our customers expand. Net revenue retention is comfortably above 100%, and practices that start with one product buy the next. As we continue to scale, every dollar that churns has to be replaced by a new logo before we grow. Today success, implementation, and support each do good work and each report separately. No one owns the arc from signed contract to renewal, no one owns the churn number, and no one can tell you from a dashboard which accounts are at risk next quarter. This is the hire that fixes that. You will own customer success, implementation, and support, and you will carry gross and net retention as your number. What you'll own Retention. Diagnose where churn concentrates: practice size, EHR, product line, onboarding cohort, tenure. Build the health scoring and account coverage model that surfaces risk early. Move the GRR number and be able to say why it moved. Expansion. Protect the expansion motion that works today and make it systematic: which products follow which, when to introduce them, and who makes the ask. Partner with sales on hand-offs for expansion deals large enough to need an AE. Time to value. Implementation runs well today under a strong director. Your job is to make it measurable, set a time-to-value target by segment, and connect onboarding quality to first-year retention so we can see which shortcuts cost us later. Support that scales sub-linearly. Own responsiveness and quality, and build the deflection layer: documentation, in-product guidance, and AI-assisted triage. Headcount should not scale one-for-one with customers. The customer journey. Define the stages from contract to renewal, put an owner on each hand-off, and make the customer experience one company rather than three teams. The voice of the customer. Get what customers actually do, not what they ask for, into product on a predictable rhythm. Supply the references and performance data our analyst relations and case study programs need. The team. You inherit a Director of Implementation, a Customer Success Lead, an Implementation Specialist, and a Support Specialist. Assess, develop, and structure the team for a book that doubles. Hire as the book grows. What success looks like 90 days. You know the book account by account. You have a churn diagnosis with numbers behind it, a point of view on team structure and staffing, and the three metrics we should run on. 6 months. Health scoring live and trusted by sales and leadership. A documented journey with owners at each stage. A time-to-value baseline by segment. First changes to onboarding or coverage shipped, with a hypothesis about what they will do to GRR. 12 months. GRR measurably up. NRR held or better. A team that is clearly structured and growing. Customer insight reaching product on a cadence they rely on. What we're looking for 7+ years in customer success or customer operations, including 3+ years managing across more than one function. Has owned a gross retention number and moved it. Can name the rate they inherited, where it went, and what they changed. Has run or worked alongside implementation closely enough to know what a bad onboarding looks like six months later. Operates at SMB scale: a book of hundreds of accounts with small ACVs, where coverage is a model and not a named-account list. Hands-on with CRM and customer data. Builds the first version of health scoring themselves. A manager who develops people and makes hard calls about structure. Healthcare or health-tech strongly preferred: practice workflows, EHR integrations, HIPAA. Nice to have AI-enabled products and setting customer expectations around them. Support tooling and deflection at scale. Has carried an expansion quota or managed people who did. HubSpot experience. Logistics Location: Remote US or New York. Reports to the CEO. Benefits: Health, dental, and vision. Unlimited PTO, and people use it. Regular company offsites. #J-18808-Ljbffr