Director, Enterprise Customer Success

AI Proficiency at Sword Health

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.

Explorer (Level 1) — Uses AI daily to boost personal productivity

Builder (Level 2) — Creates workflows and tools that elevate the whole team

Integrator (Level 3) — Embeds AI into products and processes at scale

Every hire must demonstrate at least Level 1. The expected level will vary depending on the seniority of the role.

What you’ll be doing:

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.

What you need to have:

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.

To ensure you feel good solving a big Human problem, we offer:

A stimulating, fast-paced environment with lots of room for creativity.

A bright future at a promising high-tech startup company.

Career development and growth, with a competitive salary.

The opportunity to work with a talented team and to add real value to an innovative solution with the potential to change the future of healthcare.

A flexible environment where you can control your hours (remotely) with unlimited vacation.

Access to our health and well-being program (digital therapist sessions).

Remote or Hybrid work policy.

To get to know more about our Tech Stack, check here .