Director, Customer Success

Responsibilities

• Directly manage, coach, and develop a team of Senior CSMs and CSMs — serving as their primary manager for all operational matters, escalations, and performance accountability.
• Conduct regular 1:1s focused on account health, pipeline visibility, and professional development; deliver end-of-year performance reviews and goal-setting.
• Own low-level and mid-level escalations; step in directly on at-risk accounts and model best-in-class de-escalation and relationship recovery.
• Lead PIP, hiring, and offboarding decisions at the CSM level without requiring executive approval for operational decisions.
• Identify individual skill gaps and design targeted coaching plans; build and refine playbooks that elevate team capability and execution consistency.
• Leverage AI tools (Claude, Chat GPT, CRM automation) to build smarter coaching workflows, flag at-risk accounts earlier, and automate manual overhead.
• Own team-level retention and expansion outcomes across the entire CSM portfolio — accountable for the number, not just the activity.
• Refine and enforce playbooks for upsell, cross-sell, renewals, and de-escalation to ensure consistent execution across the CSM team.
• Maintain active visibility into high-value and strategically critical accounts; build trusted relationships with clinical, operational, and executive stakeholders.
• Partner with Sales and Implementation leadership to ensure smooth handoffs and a seamless customer journey from onboarding through long-term retention.
• Use AI-powered health score modeling and CRM data signals to detect churn risk before it materializes.
• Partner with the CSL Manager on program-level strategy: enrollment forecasting, site-level capacity planning, and CSL deployment decisions.
• Collaborate with Sales and Implementation to sequence new site deployments, ensure proper CSL staffing, and set each new site up for successful enrollment ramp.
• Define program performance benchmarks and hold the CSL Manager accountable to monthly and quarterly targets; identify structural gaps and build corrective plans.
• Monitor and report on team-level KPIs: CSM retention rates, renewal conversion, health scores, enrollment pacing, and escalation metrics.
• Design and implement scalable processes, templates, and workflows that improve team efficiency and customer experience consistency.
• Build and own AI-augmented reporting workflows that surface portfolio risk to leadership without requiring manual data assembly.
• Partner closely with the VP of Customer Success on CS strategy, capacity modeling, compensation frameworks, and team development roadmaps.
• Represent the CS team perspective in cross-functional discussions; translate team performance into clear, data-backed narratives for leadership.
• Surface people, process, and tooling gaps proactively to the VP before they become material risks.

Requirements

• 7+ years of progressive experience in Customer Success or client services, with at least 3 years in a direct people management role.
• Demonstrated track record of owning team-level retention and expansion outcomes in B2B, healthcare, or managed services.
• Proven ability to coach and develop CS professionals across multiple levels — from early-career to senior individual contributors.
• Experience building or refining scalable playbooks, operating rhythms, and CS infrastructure in a high-growth environment.
• Strong proficiency with CRM and CS tooling (Hub Spot, Salesforce, Gainsight, or equivalent) — you manage by data, not gut feel.
• Hands-on experience with AI tools in a professional CS context — not exploration, but active daily use with measurable output.
• Excellent communication, facilitation, and executive presentation skills.
• Experience working cross-functionally with Sales, Implementation, Clinical, or Finance in a matrixed organization.
• Bachelor\'s or Master\'s degree in Business, Management, or Healthcare Administration preferred.
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