Director, Customer Success

Director, Customer Success

Remote
Employment Type: Full-Time | Management

About Nsight Health:

Nsight Health is transforming how care is delivered through Remote Patient Monitoring (RPM), Chronic Care Management (CCM), and Behavioral Health Integration (BHI). We empower healthcare providers to manage chronic conditions using real-time data, AI-enabled technology, and 24/7 clinical support. Our HIPAA-compliant platform connects patients and care teams nationwide—improving outcomes, adherence, and peace of mind. Join a fast-growing, mission-driven team that blends healthcare and technology to make a measurable difference in people’s lives.

Nsight Health — Where Technology Meets Compassion.

Position Summary:
We are seeking a Director of Customer Success who is equal parts operator, coach, and strategic leader. This is not a relationship management role — it is a performance leadership role.

Reporting directly to the VP of Customer Success, you will own the day-to-day execution of our CSM team, serve as the strategic architect of the CSL program, and be the first escalation lever when high-value accounts are at risk. You will manage a team of CSMs and Senior CSMs and partner closely with the CSL Manager.

The right person for this role has already built something. You have managed teams, owned retention numbers, and made hard calls. You move toward difficult conversations, you think in systems, and you actively use AI tools to multiply your team's output — not as a curiosity, but as a daily practice.

AI Fluency Requirement - Non-Negotiable
Nsight Health is an AI-first organization. Every member of our leadership and operations team is expected to actively use AI tools in their day-to-day work - not as a novelty, but as a core productivity multiplier. This role requires genuine curiosity about AI, comfort experimenting with tools like Claude, ChatGPT, and workflow automation platforms, and the judgment to know when AI helps and when it doesn't. If AI makes you uncomfortable, this is not the right role.


Key Responsibilities:

CSM Team Leadership & Day-to-Day Management

• 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, ChatGPT, CRM automation) to build smarter coaching workflows, flag at-risk accounts earlier, and automate manual overhead.

Retention, Growth & Account Oversight

• 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.

CSL Program Strategy & Oversight

• 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.

• Drive program refinement initiatives that make the CSL model more scalable, efficient, and performance-oriented over time.

Performance Management & Operations

• Monitor and report on team-level KPIs: CSM retention rates, renewal conversion, health scores, enrollment pacing, and escalation metrics.

• Identify recurring issues as symptoms of structural gaps — build plans to address root causes at the system level, not case by case.

• 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.

VP Partnership & Cross-Functional Collaboration

• Partner closely with the VP of Customer Success on CS strategy, capacity modeling, compensation frameworks, and team development roadmaps.

• Collaborate cross-functionally with Sales, Implementation, Clinical, Finance, and CS Ops to eliminate interdepartmental friction.

• 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.
  
  
  

The Impact You’ll Make:

• Performance Leader: You will transform a growing CSM team into a high-performance retention engine driving measurable improvements in gross revenue, retention health scores, and expansion revenue across 400+ clinics.

• Patient Outcome Accelerator: By reducing churn and deepening clinic engagement You directly enable more patients to benefit from RPM, CCM, and BHI programs, keeping underserved populations connected to life-changing care.

• AI Pioneer: You will build the most efficient CS organization in digital health by embedding AI-powered workflows into every layer of team operations, from health scoring to QBR prep to escalation triage

• System Architect: You will design playbooks, operating rhythms, and CS infrastructure that outlast any individual contributor, building a foundation that scales as Nsight reaches its next 100,000 patients.

Qualifications
Required:

• 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 (HubSpot, 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.

Preferred:

• Healthcare, RPM, CCM, or value-based care experience is a meaningful differentiator.

• Experience in a high-growth SaaS environment with a complex, multi-program product suite.

• Background building or scaling a Clinical Success Liaison (CSL) or field-facing CS program.

• Certifications in CS methodology (Gainsight PX, HubSpot, or equivalent).

Compensation & Benefits

• Competitive base pay: $125,000 – $155,000 annually.

Additional Compensation:

• Performance-Based Bonus: Eligible for an annual bonus based on company and individual performance.

Benefits Include:

• PTO

• Medical, Dental, Vision, and supplemental insurance options

• 401(k) Plan with 3.5% Company Match

• Company-provided equipment

Join Our Mission-Driven Team
At Nsight Health, you'll be part of a fast-growing organization that sits at the intersection of healthcare, technology, and compassion. We're looking for people who care deeply about improving patient lives and building the future of connected care.

Our team culture is collaborative, agile, and purpose-driven. Every role, from clinical operations and customer success to marketing, technology, and leadership, directly contributes to improving how healthcare organizations care for their patients.