Head of Customer Success

This range is provided by Readily. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$110,000.00 / yr - $200,000.00 / yr

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.

Responsibilities

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.

Requirements

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

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