Head of Customer Success – Operations

This is a fully remote position, open to applicants in United States.

📋 Description

• Personally onboard and assist each provider in the initial Alpha cohort — manage all incoming inquiries manually for the first 6–8 weeks to cultivate a profound understanding of the product and customer needs.

• Document and transcribe every provider call to create a structured question taxonomy that will serve as the cornerstone of the AI agent knowledge base.

• Manage the AI CS agent corpus: organize and synthesize rotating engineer inputs weekly, refine and publish the knowledge base, and assess agent responses for accuracy and PHI compliance.

• Be comfortable taking ownership of the AI agent corpus as a product artifact — this role encompasses content and systems ownership, not merely tooling decisions.

• Establish and document the PHI routing protocol before onboarding the first provider — clarify guidelines for routing to AI, routing to a human, and identifying cases that require immediate clinical escalation.

• Identify and onboard a licensed clinical consultant (LCSW, LPC, or LMFT) on retainer within 30–60 days post-launch to serve as the escalation pathway for critical clinical accuracy incidents.

• Develop the Nitro CS runbook, CE rotation handoff documentation, trust-repair scripts, and provider communication playbook — ensure documentation occurs in real-time, rather than retroactively.

• Own the long-term CS strategy: create the hiring and integration plan, team structure, metrics framework (CSAT, resolution rate, retention), and decisions regarding the CS tool stack.

• Share insights on best practices with the Customer Success Learning and Enablement team to align AI knowledge base strategies and protocols.

• Lead the evaluation of the AI CS agent platform in Week 4 and oversee its deployment in Weeks 6–8, utilizing the question taxonomy developed through direct provider engagement.

• Collaborate with the GTM / Growth Lead on referral generation, highlighting provider satisfaction signals and pinpointing optimal moments to request introductions.

• Ensure that all CS operations and provider interactions adhere strictly to HIPAA compliance, with heightened awareness of PHI management in the context of mental health documentation.

⛳️ Requirements

• 7–10 years of experience in customer success, including at least one role as the “first CS hire” or having built the function from the ground up at a SaaS company.

• Proven experience in hiring and developing a CS team — this is not a first-time leadership opportunity.

• Strong preference for healthcare-adjacent experience; a background in mental health or familiarity with clinical workflows is a significant advantage.

• PHI-fluent: possesses a clear understanding of HIPAA obligations in practice, including what can and cannot be communicated over various channels, and the distinction between clinical escalations and product support tickets.

• Player-coach mentality: genuinely motivated to work directly with customers in the first month and equally driven to build scalable systems in the sixth month.

• Comfortable taking ownership of the AI agent corpus as a product artifact — this requires a blend of content strategy and systems thinking, rather than just familiarity with tools.

• Experience with CS platforms, ticketing systems, and AI-assisted support tools; readiness to evaluate and select the appropriate stack from scratch.

• Excellent verbal and written communication skills, with a proven ability to navigate sensitive clinical or emotionally charged customer interactions with empathy and professionalism.

• Comfortable making judgment calls in uncertain situations, including routing decisions that intersect product support and clinical risk.

• Highly adept with AI tools in daily workflows — utilizes AI assistants, automation, and emerging capabilities as a fundamental aspect of operations, rather than an occasional shortcut; open to evaluating and adopting new tools as the landscape develops.

• Clear vision for AI-driven customer success transformation — understands how AI reshapes support operations, deflection strategies, and provider experiences, and can lead that transformation proactively; regards the AI agent corpus as a strategic asset rather than merely an IT project.

🏝️ Benefits

• Health insurance

• Wellness programs

• Employee Assistance Program

• Discount through Dell for work-from-home essentials

• Gympass for fitness access