[Remote] Director, Enterprise Customer Success

Note: The job is a remote job and is open to candidates in USA. Sword Health is pioneering AI Care, a new approach to healthcare designed for medical reasoning and real-time treatment. They are seeking a Director of Enterprise Customer Success to lead a team serving enterprise clients, focusing on retention and expansion outcomes while building executive-level relationships.

Responsibilities

• Own retention and expansion outcomes across your portfolio: you create, advance, and close renewal and expansion opportunities
• Lead a team of Enterprise CSMs to the highest performance standards, coaching continuously and acting decisively when someone is not meeting the bar
• Build and sustain executive-level relationships with employer buyers, including C-suite, VP Benefits, total rewards leaders, and benefits consultants
• Drive cross-functional collaboration with GMs, Product, Implementation, Finance, and RevOps to deliver measurable client outcomes and resolve issues without escalation dependency
• Own QBR and ABR execution: every account has a current value story and a renewal readiness plan well ahead of milestone dates

Skills

• Prior people leadership: you have set high performance standards, developed talent, and made hard calls when someone is not meeting the bar
• Commercial accountability mindset: you measure yourself by retention and expansion outcomes
• Strong analytical and critical thinking foundation: you reason from facts and data, synthesize clearly, and communicate with brevity in writing and in conversation
• High initiative and sound judgment: you identify what matters, act without waiting to be directed, and build influence across functions to get things done
• Experience working with or within the self-insured employer or benefits ecosystem
• AI fluency is a core expectation at Sword Health. Every candidate is assessed against our three-level framework — be ready to share real examples of how AI is already part of how you work

Benefits

• Comprehensive health, dental and vision insurance*
• Life and AD&D Insurance*
• Financial advisory services*
• Supplemental Insurance Benefits (Accident, Hospital and Critical Illness)*
• Health Savings Account*
• Equity shares*
• Discretionary PTO plan*
• Parental leave*
• 401(k)
• Flexible working hours
• Remote-first company
• Paid company holidays
• Free digital therapist for you and your family
• *Eligibility: Full-time employees regularly working 25+ hours per week

Company Overview