Job Details

Job Overview

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.

Qualifications

  • 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

Must-Have Requirements

  • 5+ years of experience in Customer Success, Account Management, or relevant experience in a SaaS environment
  • Proven track record of successfully managing and growing customer accounts in a high-growth startup
  • Experience working closely with product and engineering teams to influence product improvements based on customer feedback

Screening Questions

1. How many years of experience do you have in a customer success leadership role at a startup?
2. Can you describe your experience with scaling customer success teams in a high-growth environment?
3. Can you give an example of a time you effectively collaborated with product and sales teams to enhance the customer experience?
4. What intrigues you about Readily's mission and do you have a personal connection to the problem they're trying to solve?

About the Company

Company Overview

Company Size: 5-10 employees
Industry: Information Services
Specialties: Compliance Tools for Healthcare Organizations
Founded: 2023
Headquarters: San Francisco, CA
Total Funding: $500k+
LinkedIn: View Company Profile
Website: Visit Website

Our Mission

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

Company Culture

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.

Benefits

Retirement/401k
Health Insurance
Vision Insurance
Dental Insurance

Relocation & Sponsorship

Relocation Assistance
Visa Sponsorship

What you can expect

Growth

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.

Interview Process

Traditional 3 round interview process.

Companies to Source From

These companies are similar to our client. Candidates with experience at these companies are seen as a big plus.

Clausematchclausematch.com
Ascentregtechascentregtech.com
Regologyregology.com
Compliancecompliance.ai
Zangozango.ai
Complioncomplion.com
Protenusprotenus.com
Admiraloneadmiralone.cl

Additional Information

Additional Information

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.

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