We are seeking an accomplished Vice President, Data & AI to lead our enterprise-wide data capabilities and accelerate our transformation into a data-powered organization. This executive leader will oversee all functions across Data Engineering, Data Science, AI/ML Engineering, Analytics, and Business Intelligence, driving a unified strategy that enables trusted insights, scalable platforms, and innovative AI solutions.
This is a high-impact leadership role responsible for defining our data vision, elevating technical excellence, and partnering across product, technology, clinical, operations, finance, and go-to-market teams. Healthcare industry experience is beneficial but not required, while deep expertise in building world-class data platforms, teams, and capabilities is essential.
What You’ll Do
Strategic Leadership & Vision
- Develop and drive the enterprise data strategy aligned with company goals and long-term product and technology roadmaps.
- Establish a clear vision for data quality, governance, interoperability, and responsible AI practices.
- Evangelize a data-driven culture across the organization, ensuring teams can access actionable and trustworthy insights.
Team & Organizational Leadership
- Lead, mentor, and scale high-performing teams across data engineering, machine learning engineering, data science, and analytics.
- Foster a culture of innovation, collaboration, experimentation, and continuous improvement.
- Build talent pipelines and capabilities that support both rapid innovation and reliable enterprise infrastructure.
Data Platform & Engineering
- Own the architecture, delivery, and operation of modern, scalable data platforms—including data lakes, warehouses, streaming pipelines, and ML infrastructure.
- Implement best-in-class engineering practices (CI/CD, observability, automation, performance optimization).
- Ensure data availability, security, and quality to meet business, regulatory, and compliance needs.
AI, ML, and Advanced Analytics
- Lead the development and deployment of AI/ML models, predictive analytics, and intelligent automation solutions.
- Partner with product and engineering teams to embed data-driven and AI-powered capabilities into our products and experiences.
- Create a repeatable and secure ML lifecycle—model development, validation, deployment, monitoring, and governance.
Analytics & Insights
- Oversee enterprise analytics, reporting, self-service capabilities, and executive dashboards.
- Partner with business leaders to translate data into actionable insights that improve outcomes, efficiency, and customer experience.
- Ensure consistency of definitions, metrics, and KPIs across the organization.
Operational Excellence
- Manage budgets, vendor relationships, technology choices, and long-term investment plans.
- Champion responsible use of AI, data privacy, compliance, and ethical data practices.
- Implement processes that ensure reliability, scalability, and strong performance across all data services.
Who You Are
Required Qualifications
- 12+ years of progressive experience in data engineering, analytics, data science, or ML/AI, with at least 5 years in senior leadership roles.
- Demonstrated success building and scaling modern cloud-based data platforms and high-performance technical teams.
- Deep expertise in data architecture, distributed systems, ML engineering, and advanced analytics.
- Proven ability to partner with executives and cross-functional teams to drive strategic decision-making.
- Experience owning enterprise data strategies and delivering measurable business impact.
Preferred Qualifications
- Healthcare or other highly regulated industry experience (nice to have, not required).
- Experience with responsible AI frameworks, data governance, and privacy-by-design principles.
- Track record of integrating AI and analytics into customer-facing products and services.
- Strong communication and storytelling skills—able to translate complex technical concepts into clear business value.
What You Bring
- A visionary mindset combined with pragmatic execution.
- A passion for building modern data ecosystems and leveraging AI/ML to reshape product and business outcomes.
- A commitment to developing people, elevating capabilities, and fostering a high-trust, high-performance culture.
- An entrepreneurial spirit, comfort with ambiguity, and the ability to scale systems, teams, and processes rapidly.
Who we are
Transcarent and Accolade have come together to create the One Place for Health and Care, the leading personalized health and care experience that delivers unmatched choice, quality, and outcomes. Transcarent’s AI-powered WayFinding, comprehensive Care Experiences – Cancer Care, Surgery Care, Weight – and Pharmacy Benefits offerings combined with Accolade’s health advocacy, expert medical opinion, and primary care, allows us to meet people wherever they are on their health and care journey. Together, more than 20 million people have access to the combined company’s offerings. Employers, health plans, and leading point solutions rely on us to provide trusted information, increase access, and deliver care.
We are looking for teammates to join us in building our company, culture, and Member experience who:
- Put people first, and make decisions with the Member’s best interests in mind
- Are active learners, constantly looking to improve and grow
- Are driven by our mission to measurably improve health and care each day
- Bring the energy needed to transform health and care, and move and adapt rapidly
- Are laser focused on delivering results for Members, and proactively problem solving to get there
Total Rewards
Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s 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.
Our benefits and perks programs include, but are not limited to:
- Competitive medical, dental, and vision coverage
- Competitive 401(k) Plan with a generous company match
- Flexible Time Off/Paid Time Off, 12 paid holidays
- Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance
- Mental Health and Wellness benefits
Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out!
Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences.
Top Skills
What We Do
Transcarent is a health and care experience company that makes it easy to get the high-quality, affordable health and care that everyone and their families deserve – where and when they want it, on their terms. Transcarent puts health consumers back in charge by directly connecting them with an integrated ecosystem of high-value providers and health solutions, providing transparent information, and offering trusted guidance – in as little as 60 seconds, 24/7/365, from the palm of their hand, often at no cost to Members and at a lower cost to their employer. Transcarent takes accountability for results – offering at-risk pricing models and transparent impact reporting to align incentives towards measurably better experience, better health, and lower costs.
