Lead and scale the enterprise Customer Success function, focusing on retention, adoption, and expansion for complex enterprise customers. Manage a team, develop strategies, and foster executive relationships to ensure successful healthcare outcomes.
At Sword, we’re building AI to heal billions and unlock humanity’s full potential. In doing so, we’re pioneering AI Care, a fundamentally new approach to healthcare built for medical reasoning, safety, and real-time treatment, not generic technology applied after the fact. As both a clinical-centric frontier AI lab and an applied AI platform, Sword is reimagining how care is delivered at scale, removing traditional barriers like appointments, waiting rooms, and stigma so more people can access the care they need—and ultimately get back to lives lived in full.
Since 2020, Sword has expanded across physical therapy, women’s health, cardiometabolic, and mental health, and is now moving beyond the session to a fully AI-native, 24/7 care program that brings physical activity, therapeutic exercise, psychotherapy, nutrition, and behavior change into one connected experience. More than 700,000 members across three continents have completed over 10 million AI sessions, helping 1,000+ enterprise clients avoid more than $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies, 44+ patents, and more than $500 million raised from leading investors including Khosla Ventures, General Catalyst, and Founders Fund, Sword is defining a new standard for healthcare.
Since 2020, Sword has expanded across physical therapy, women’s health, cardiometabolic, and mental health, and is now moving beyond the session to a fully AI-native, 24/7 care program that brings physical activity, therapeutic exercise, psychotherapy, nutrition, and behavior change into one connected experience. More than 700,000 members across three continents have completed over 10 million AI sessions, helping 1,000+ enterprise clients avoid more than $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies, 44+ patents, and more than $500 million raised from leading investors including Khosla Ventures, General Catalyst, and Founders Fund, Sword is defining a new standard for healthcare.
Sword Health is seeking a Director of Enterprise Customer Success to own post-sale outcomes across a portfolio of enterprise clients and lead the team that serves them. A peer to Sword's existing Enterprise CS leadership, this Director carries full accountability for GRR, NRR, and client advocacy across complex, multi-stakeholder enterprise accounts. The right candidate brings commercial depth, strong people leadership, and he ability to translate clinical program performance into durable business partnerships.
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
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.
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.
*This range includes base, variable and equity.
These compensation bands are just the starting point. Once someone joins and proves they’re outlier talent, we adjust quickly to ensure their compensation aligns with their impact.
Our job titles may span more than one career level. Actual pay is determined by skills, qualifications, experience, location, market demand, and other factors. Compensation details listed in this posting reflect the base salary and any potential variable, bonus or sales incentives, and the Company’s estimation of the value of private company stock options, if applicable. The pay range is subject to change, future value of company stock options is not guaranteed, and compensation may be modified in the future. In addition to our total compensation, Sword offers a number of benefits as listed below.
US - Sword Benefits & Perks:
• 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
Note: Applicants must have a legal right to work in the United States, and immigration or work visa sponsorship will not be provided.
SWORD Health, which includes SWORD Health, Inc. and Sword Health Professionals (consisting of Sword Health Care Providers, P.A., SWORD Health Care Providers of NJ, P.C., SWORD Health Care Physical Therapy Providers of CA, P.C.*) complies with applicable Federal and State civil rights laws and does not discriminate on the basis of Age, Ancestry, Color, Citizenship, Gender, Gender expression, Gender identity, Gender information, Marital status, Medical condition, National origin, Physical or mental disability, Pregnancy, Race, Religion, Caste, Sexual orientation, and Veteran status.
Similar Jobs
Consumer Web • Fintech
Lead strategy and execution for enterprise demand customer success and distribution partners. Manage a team to ensure private marketplaces drive engagement, conversions, and long-term growth. Partner with Product, Marketing, and Sales to expand footprints, build CS playbooks, onboard enterprise customers, and translate audience engagement data into ROI-driven growth opportunities.
Healthtech • Software • Telehealth
Lead a team of Client Success Senior Managers and Managers for enterprise RCM accounts, develop scalable client management frameworks, drive adoption and measurable outcomes, serve as executive escalation, partner cross-functionally to reduce churn and improve service delivery, and represent customer voice in strategic initiatives.
Top Skills:
Excel
Database
The Director of Client Services leads a team of Account Managers, driving client retention and growth through coaching, strategic insight, and data-driven decision-making while collaborating across departments.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
