Director of Customer Support

About Sana Benefits: Founded in 2017, Sana is an innovative health plan solution built for small and midsize businesses—designed around our integrated primary care service, Sana Care. We believe healthcare in the US is simply too hard, and we fight to create an experience that feels genuinely easy when members need to access care. Operating as a fully remote-first and distributed team across the U.S. since day one, Sana values curiosity, ownership, and velocity to reshape how healthcare works from the inside out.

Position Overview

We are looking for a passionate, data-driven, and empathetic Director of Customer Support to lead our global support operations to the next level. In this high-impact leadership role reporting directly to the VP of Operations, you will own the end-to-end member and provider care experience. You will balance sophisticated multi-channel operations (managing thousands of chat, voice, and email tickets weekly) with automated AI/LLM support tool integrations to drive scalable workflows. Your success will be directly measured through customer satisfaction (CSAT) indices, SLA outperformance, and cost-to-serve financial target management.

Key Responsibilities

• Strategic & Operational Leadership: Author the comprehensive business plan for member and provider experience tracks, forecasting workforce schedules and implementing scalable, multi-channel customer care toolsets.
• AI & Support Automation Strategy: Lead the technical implementation of AI-driven tools and LLM features to automate routine ticket paths, maximize self-service rates, and prioritize white-glove human touchpoints.
• Team Cultivation & Development: Manage and scale an elite squad of Customer Support Managers, Member Advocates, and Workforce Management (WFM) Analysts. Ensure ongoing career growth via regular 1:1 coaching.
• Performance & SLA Management: Enforce rigorous team accountability for corporate OKRs, SLAs, and performance metrics—specifically optimizing CSAT scores, chat first response times, and call answer rates.
• Data Analysis & Root Cause Tracking: Analyze complex interaction telemetry to find structural trends, address escalation roots, and distribute actionable data insights to cross-functional Product, Engineering, and Claims squads.
• Cross-Functional Partnership: Act as a critical operational liaison across Care Navigation, Case Management, Claims auditing, Network Development, and Customer Success to build frictionless member workflows.

Required Skills & Qualifications

• 6+ years of verified professional leadership experience directing customer service operations, with a distinct preference for fast-growth health, wellness, digital healthtech, or medical benefits environments.
• Deep, authority-level technical mastery over the full Zendesk enterprise product suite, including macro configuration, triggering logic, and workflow optimizations.
• Demonstrated tracking background leveraging AI/LLM integrations to scale high-volume support portals systematically.
• Exceptional analytical rigor, with a proven ability to process daily and weekly operations dashboards, pinpoint leakage trends, and convert raw data into scalable processes.
• Strong background in Workforce Management (WFM) principles, quality assurance models, and onboarding program engineering.
• Outstanding emotional intelligence (EQ) and change management communication mechanics, capable of clarifying the structural "why" behind transitions alongside technical and non-technical staff.
• Location Context: 100% remote-first workspace infrastructure support open to qualified customer care executives based anywhere within the United States.

What We Offer

• Targeted Cash Compensation Bracket: $133,450 – $157,000 USD per annum (Plus lucrative startup equity stock options; final offer calibration maps directly against individual qualification checks and interview performance).
• Comprehensive medical, dental, and vision insurance packages providing 100% company-paid employee coverage plans.
• Flexible vacation guidelines backed by a healthy, authentic remote company culture of systematically utilizing time off.
• Corporate 401(k) retirement plan with an active company match feature, alongside flexible FSA and HSA setups.
• Generous paid parental leave, short-term and long-term disability, and company-sponsored life insurance.
• One-time home office setup stipend combined with an ongoing learning and professional development budget.
• Paid one-month sabbatical credit after five years of continuous service.
• Streamlined candidate application parsing and step tracking handled transparently via integrated Lever ATS systems.