Readily
AI Compliance Platform for Healthcare Organizations
🚀 Head of Customer Success
About the role
About Readily
30% of U.S. healthcare cost is administration. We’re fixing that.
Readily is building the compliance layer for every healthcare company. Billion-dollar insurers and health plans turn to Readily to analyze regulations, conduct audits, and automate compliance research with AI.
We’re the fastest-growing company in this space - tripling revenue QoQ. And we’re just getting started.
There’s an old Yorkshire saying: “Where there’s muck, there’s brass.” Healthcare compliance is messy. But in that mess lies an enormous opportunity. If you’re hungry to take ownership and build systems that matter, this is it.
About the Role
We’re hiring for a hands‑on Head of Customer Success to join our founding team and build the post‑sales function for our healthcare compliance AI platform. Rather than just maintaining accounts, you’ll own the entire post‑sale journey - from onboarding through renewals and expansion - ensuring our customers see measurable value from day one.
Your goal is to crack AI activation in healthcare enterprise - create a CS machine that feels consumer-simple. 1-month not 1-year implementations, 100% usage not 10%, lightning-fast time-to-value.
You’ll have founder‑level ownership: expect to design the strategy, stand up processes and tools, and partner directly with customers and product to shape our roadmap and playbooks.
What You’ll Do
- Stand up Customer Success from 0→1: playbooks for onboarding, adoption, QBRs, renewals.
- Own retention and growth: NRR/GRR, health scores, risk flags, expansion pipeline.
- Drive 1-month go-lives and 100% utilization with enterprise-ready onboarding and training.
- Close the loop with Product/Sales/Eng: turn customer signal into roadmap and wins.
- Hire and coach the team; stand up systems and dashboards (Salesforce/Gainsight) to forecast.
What We’re Looking For
- Builder 0→1: You’ve stood up CS playbooks and scaled them.
- Metric-owned: You live in NRR/GRR, churn, adoption/utilization, TTV - and move them.
- Hunger: High agency, a willingness to learn, and a drive to do whatever it takes
- Customer-obsessed: You earn executive trust and unblock complex enterprises fast.
- Intellectually humble: low ego, high curiosity, collaborative.
- Biased toward action: You act, you don't wait
Why Join Readily
- True founding-team ownership.
- Career-defining experience: ship products that rewrite how the industry works.
- Front-row to closing deals with billion-dollar enterprises
- Hyper-growth environment (3× QoQ — you’ll feel it).
- A real chance to fix healthcare’s most expensive problem with AI.
- Weekly pickleball 🏓 + a team that loves to win together.
📩 If you want true ownership and fix healthcare from its roots - we’d love to talk.
About Readily
30% of healthcare cost is administration - we’re trying to reduce that.
Readily is building the compliance layer for every healthcare company. Billion-dollar healthcare organizations turn to Readily to analyze regulations, conduct audits and automate research using AI. We’re the fastest growing company in this space and 3x our revenue QoQ.
There is an old Yorkshire saying: where there's muck, there's brass. We're looking for people who aren't afraid to get their hands dirty with healthcare compliance and hunger for ownership.
