Executive Director, Customer Success Operations

About the Role

The Director of CS Operations is the operational engine behind Health
100’s Customer Success organization. While Customer Program Owners focus outward on building customer relationships and driving outcomes, you focus inward on building the operational framework that lets the whole team operate consistently and scale. You will design processes, metrics, and tooling to support Health
100 operations and own operationally complex functions such as release coordination across multiple product lines at the intersection of CS, Engineering, and Product teams.

Design and run the cadences that keep CS leadership informed and aligned: team reviews, portfolio health reporting, executive governance, and commitment tracking. Maintain a clear, current view of every customer across all phases; keep the CS team’s organizational memory up to date; provide CS leadership with the visibility they need to make resourcing, escalation, and prioritization decisions.

Serve as the operational bridge between CS and Health
100’s product release processes. Translate customer-facing decisions into the scheduling and execution artifacts that Engineering and Deployment teams need. Build and maintain working relationships with each product’s release leads, aggregate relationships to give CS leadership a single coherent multi‑product view of release activity and risk, and surface conflicts between customer timelines and product release calendars early to resolve them before they become customer issues.

Build playbooks that make CS repeatable: implementation kickoffs, release activations, business review preparation, escalation handling, go‑live, and steady‑state operations. Own the CS tech stack—customer relationship management, documentation, project tracking, and reporting—and make these tools work for the team. Identify duplicated efforts among CPOs and turn them into shared, standardized approaches.

• Customer Program Owners – the customer‑facing team you enable.
• Technical Account Management – the inward and outward technical engines that support the client.
• Product Release leads – your counterparts for coordinating customer activation across Health
  100’s product lines.
• Product Deployment teams – execution partners for implementation across the customer base.
• Customer Insights – close collaboration on defining and instrumenting the metrics that reflect CS and customer health.
• CS Leadership and SVP – you produce portfolio visibility and governance reporting that enables top‑level decisions.

• 15+ years of experience in CS Operations or a similar operational function in enterprise software.
• Demonstrated experience building or scaling operational infrastructure, including playbooks, metrics frameworks, and tooling in a CS or post‑sales organization.
• Fluency in enterprise software release and deployment mechanics: release trains, change management, configuration management, release cadences.
• Structured, systematic thinker who documents decisions and builds repeatable processes.
• Strong cross‑functional coordination ability with Engineering, Product, Release Management, and Deployment.
• Data fluency: defining what to measure, interpreting operational metrics, and translating data into actionable CS leadership visibility.

• Healthcare IT, pharmacy technology, or enterprise technology background.
• Prior experience standing up a Customer Success Ops function or significantly expanding one during rapid customer growth.
• Familiarity with multi‑product organizational models with separate release practices and matrix reporting relationships.
• Experience with configuration management principles and tooling in complex enterprise deployments.

The typical pay range for this role is: $ - $. This represents the base annual salary; the actual offer depends on experience, education, geography, and other factors. The position is eligible for a bonus, commission, short‑term incentive program, and a company equity award program.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. Benefits include medical, dental, and vision coverage; paid time off; retirement savings options; wellness programs; and other resources based on eligibility.

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.