Role Summary

Are you a systems thinker who takes pride in building the infrastructure that makes customer success organizations run — and keeps them running at scale? AdvancedMD is entering a defining chapter. We are building a CS function that can support both our established enterprise motion and a new product-led offering launching this year. The Sr. Leader, Customer Success Operations will lead the function that makes both motions work — owning the technology stack, data infrastructure, playbooks, and reporting that our CS organization depends on every day.

This is a builder's role. You will inherit a function that needs to be rebuilt from the ground up, with the mandate, support, and autonomy to do it. You will report directly to the Chief Customer Officer and work closely with Product, Finance, Sales, Marketing, and Engineering on a regular basis. This role is equal parts strategy and execution — you will be expected to set the direction and see it through.

If you enjoy designing systems that scale, turning customer data into clear operational decisions, and building the operating rhythm that keeps a CS team focused on the right outcomes, we'd love to meet you.

Essential Job Duties:

CS Infrastructure & Tooling

• • Evaluate, select, and implement the CS technology stack — owning vendor relationships, contract negotiations, and ensuring every tool maps to a specific moment in the customer journey. AI-powered capabilities should be a deliberate part of the evaluation, not an afterthought
  • Own the customer journey map and ensure the tools we use remove friction from that journey and produce reliable, consistent data
  • Partner with Product, Finance, Sales, Marketing, and Engineering to share customer data across the organization — this role is the connective tissue between CS and the rest of the business

Reporting & Analytics

• • Build and own the at-risk account reporting process — tiered health scoring, early warning signals, and the weekly cadence that keeps the CS team focused on the right accounts
  • Own the metrics that go up to the CCO, CFO, and Board — GRR, NRR, churn by segment, NPS, and time-to-value — and ensure they are accurate, consistent, and tell a clear story
  • Identify patterns in churn and expansion data and implement changes to address them — don't just surface the problem, fix it

Process & Playbook Design

• • Design and operationalize CS playbooks across the customer lifecycle — onboarding, adoption, renewal, and escalation
  • Design the framework for digital touch workflows and consult with CS leaders on how to implement them — you set the standard for how we engage customers at scale, they execute it
  • Build the operating rhythm for the CS team: QBRs, account reviews, escalation protocols, and capacity modeling
  • Partner with the implementation team to continuously reduce time-to-value — identifying opportunities to automate steps in the process, leverage AI to personalize and accelerate onboarding, decrease dependency on live training through self-serve resources, and get customers to productive use faster

Team Leadership

• • Lead and develop a small but growing CS Ops team
  • Build a culture of rigor, accountability, and continuous improvement
  • Act as a thought partner to the CCO on organizational design, headcount planning, and CS strategy

What You'll Need to Get the Job Done:

• 10+ years in Customer Success or a related function — with at least 3–4 years in an Ops-specific leadership role
• Background in B2B SaaS; healthcare IT experience is a plus but not required
• Hands-on experience evaluating and implementing CS platforms and a track record of building a technology stack that actually gets used
• Proven track record building reporting infrastructure from scratch in high-growth or PE-backed environments
• You think in systems — you see how data flows, where it breaks, and how to fix it
• You know how to construct a customer journey map and use it as a practical tool — not just a slide in a deck
• You have a clear point of view on how AI can improve CS operations — and you've either already applied it or are ready to
• You can move between a Board-ready summary and a SQL query in the same afternoon
• You are direct, organized, and comfortable operating with limited resources
• You hold the line on data quality and process consistency even when it's inconvenient
• You communicate clearly with non-technical stakeholders and don't hide behind complexity

What Will Make us LOVE You

• You've built a CS Ops function from scratch before — and have the scars, playbooks, and wins to prove it
• You obsess over the customer journey and naturally translate operational data into decisions that improve it
• You can build a clean Board-ready deck yourself — not just direct others to do it — and you hold the bar high for every number that goes up the chain
• You have a genuine passion for healthcare technology and an intuitive understanding of what drives churn and expansion in medical practice environments
• You've worked in both high-growth and scaled CS environments and know how to adapt your operating model to match where the business is
• You bring data to life — turning health scores, cohort trends, and churn signals into clear, actionable priorities that the CS team can act on
• You lead with clarity and calm in ambiguous environments, and the teams around you — from Product to Sales to the C-suite — trust you as a true operational partner

Life at AdvancedMD: The BURST Way to Be - Learn more about our Company culture.

• Be Intentional – We act with clarity, focus, and purpose in everything we do.
• Urgency with Purpose – We move fast on what matters and deliver meaningful results.
• Respect Always – We lead with integrity, value every voice, and build each other up.
• Strive for Greatness – We set high standards, embrace innovation, and never stop improving.
• Together with Clients – We collaborate deeply, build trusted partnerships, and win as one team.