Director of Customer Success

Sword Health is shifting healthcare from human-first to AI-first through its AI Care platform, making world-class healthcare available anytime, anywhere, while significantly reducing costs for payers, self-insured employers, national health systems, and other healthcare organizations. Sword began by reinventing pain care with AI at its core, and has since expanded into women’s health, movement health, and more recently mental health. Since 2020, more than 700,000 members across three continents have completed 10 million AI sessions, helping Sword's 1,000+ enterprise clients avoid over $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies and over 44 patents, Sword Health has raised more than $500 million from leading investors, including Khosla Ventures, General Catalyst, Transformation Capital, and Founders Fund. Learn more at www.swordhealth.com.

Sword Health is seeking a Director of Customer Success to lead and scale our enterprise Customer Success function, ensuring our customers realize measurable clinical and economic outcomes from Sword’s AI Care platform. This is a senior enterprise leadership role with direct accountability for customer outcomes, responsible for owning post-sale success across a portfolio of complex enterprise customers while evolving the strategy, operating model, and playbooks that support long-term retention, expansion, and advocacy.

As a Director, you will balance hands-on customer leadership with team development and cross-functional influence, helping shape how Sword delivers world-class, AI-first healthcare at scale. Accountable for gross retention, net revenue retention, and expansion outcomes across a portfolio of complex enterprise customers, in close partnership with Sales and Commercial leadership.Define and scale Sword’s enterprise Customer Success operating model, including customer segmentation, coverage ratios, capacity planning, and success motions aligned to growth targets.

You will be a key leader within Sword’s Customer Success organization, managing and mentoring a team of Customer Success Managers while partnering closely with Sales, Implementation, Marketing, Product, Clinical, and Data teams. This role reports into Customer Success leadership and plays a critical role in aligning customer outcomes with Sword’s broader commercial and clinical strategy. This role manages and scales a team of approximately 6–10 Enterprise Customer Success Managers, with responsibility for performance, development, and succession planning.

What you’ll be doing:

• Lead the end-to-end customer lifecycle for a portfolio of enterprise clients, with clear ownership of retention, adoption, time-to-value, and expansion readiness.
• Build and maintain trusted, executive-level relationships with customer stakeholders, including C-suite leaders, benefits teams, and external partners.
• Own and evolve Sword’s enterprise customer success motion, including implementation best practices, engagement strategies, QBR frameworks, and success metrics.
• Manage and mentor a team of Customer Success Managers, providing coaching, performance feedback, and career development support.
• Partner closely with Sales to ensure seamless handoffs, account planning, renewals, and expansion opportunities.
• Provide executive oversight and orchestration for complex customer implementations, partnering closely with Implementation leadership to ensure on-time, on-value delivery.
• Deliver quantifiable and qualitative insights to customers through reporting, regular business reviews, and strategic recommendations.
• Develop and oversee client account plans, including opportunity sizing, success milestones, and investment recommendations.
• Advocate for customer needs internally, influencing Product, Clinical, and Operations teams to address pain points and improve customer outcomes.
• Own strategic initiatives within the Customer Success organization, continuously refining playbooks, processes, and tooling as the business scales.
• Own and report on key Customer Success metrics including gross retention, net revenue retention, engagement, adoption, and expansion pipeline influenced.

What you need to have:

• 8+ years of experience in enterprise customer success, account management, or related roles, with demonstrated progression into leadership.
• Experience managing and developing high-performing Customer Success teams.
• Strong background working with enterprise customers, ideally within digital health, healthcare technology, SaaS, or the benefits ecosystem.
• Experience supporting Fortune 1000 or similarly complex, multi-stakeholder enterprise customers, ideally across multi-year contracts and multi-geo deployments.
• Proven ability to influence executive stakeholders and navigate complex, multi-threaded customer relationships.
• Exceptional communication, storytelling, and analytical skills, with the ability to translate data into strategic insights.
• Strong program and project management capabilities, with experience managing multiple customers and initiatives simultaneously.
• Comfort operating in fast-paced, ambiguous, high-growth environments.

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.

USD 187,810 - 295,130 a year

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.