Vice President, Customer Success

About the Role

We are seeking a Vice President, Customer Success to lead our most strategic customer partnerships and accelerate the adoption and impact of AI across healthcare. This executive will sit at the intersection of healthcare, AI, enterprise transformation, and customer growth. The mandate is to help leading healthcare organizations move beyond AI experimentation and deployment to achieve sustained adoption, transformed workflows, and measurable business and healthcare outcomes.

The ideal leader brings deep experience with complex healthcare enterprises, credibility with C-suite executives, strong commercial instincts, and the ability to translate emerging AI capabilities into practical solutions at scale.

Responsibilities

• Enterprise AI Transformation
  • Develop AI transformation strategies with health systems, health plans, employers, life sciences organizations, and other healthcare enterprises.
  • Identify and prioritize high-value AI use cases and guide customers from pilots to enterprise-scale adoption.
  • Advise customers on workflow integration, change management, governance, and responsible AI implementation.
  • Establish clear measures of clinical, operational, financial, and workforce impact.
• Strategic Customer Leadership
  • Own executive relationships with our most strategic customers and serve as a trusted advisor to CEOs, CIOs, CMIOs, CFOs, COOs, and other senior leaders.
  • Develop multi-year transformation roadmaps aligned to customer priorities.
  • Lead executive business reviews centered on adoption, outcomes, ROI, and future opportunities.
  • Navigate complex stakeholder environments and position the company as a strategic transformation partner.
• Growth & Value Realization
  • Own retention, expansion, and strategic account growth.
  • Partner with Sales on account strategy, renewals, and expansion opportunities.
  • Define and track adoption, utilization, time-to-value, ROI, and business outcomes.
  • Identify barriers to adoption and lead interventions to accelerate value realization.
  • Turn successful AI deployments into broader, long-term enterprise partnerships.
• Product & Organizational Leadership
  • Translate customer needs and market insights into priorities for Product, Engineering, and AI teams.
  • Build and lead a high-performing enterprise Customer Success organization.
  • Establish scalable operating models, segmentation, KPIs, forecasting, and customer transformation playbooks.
  • Build a culture of customer obsession, commercial accountability, and technical fluency.

How Success Will Be Measured

Success will be measured by enterprise AI adoption, customer outcomes, retention, expansion, time-to-value, ROI, strategic account growth, executive engagement, and customer advocacy.

Requirements

• 12+ years in enterprise technology, healthcare technology, SaaS, consulting, Customer Success, strategic accounts, or digital transformation.
• 5+ years leading enterprise customers or Customer Success organizations at a senior level.
• Deep experience with large, complex healthcare organizations and C-suite stakeholders.
• Demonstrated success scaling AI, analytics, automation, SaaS, or digital transformation solutions.
• Strong understanding of generative AI and the organizational changes required to drive enterprise adoption.
• Proven track record of driving retention, expansion, and strategic customer growth.
• Strong commercial and financial acumen with exceptional executive communication skills.
• Ability to translate complex technology into clear business, clinical, and operational value.
• Experience building high-performing teams and scalable operating models.

About the Company

Transcarent is the One Place for Health and Careᵀᴹ, bringing medical, pharmacy, and point solutions together with the WayFindingᵀᴹ experience, the first and only generative AI-powered health and care platform for health consumers. Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences – Cancer Care, Surgery Care, and Weight Health – to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members.

Company Values

• People First: We prioritize our Members, clients, and each other in every decision.
• Care: Every decision starts with improving health and care for our Members.
• Resilience: We push boundaries and take the uncharted path to change an industry.
• Results: We take ownership, solve with speed, and deliver for our people and each other.
• Humble and Human: We lead with humility, bring fun to tough moments, and go further together.

Benefits

• Competitive medical, dental, and vision coverage.
• Competitive 401(k) Plan with a generous company match.
• Flexible Time Off/Paid Time Off, 13 paid holidays.
• Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance.
• Mental Health and Wellness benefits.

Pay

Individual compensation packages are based on factors unique to each candidate, including primary work location and an evaluation of skills, experience, market demands, and internal equity. Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options.