Vice President, AI Transformation

We are looking for  a visionary and execution-oriented Vice President, AI Transformation to lead enterprise-wide AI strategy and drive measurable business impact across our organization. As a late-stage, high-growth health technology company, we are focused on advancing AI from promising initiatives to scaled, value-generating capabilities across the organization.

Reporting to the CTO, this leader will operate at the intersection of technology, product, operations, clinical, finance, and data, ensuring AI initiatives deliver measurable ROI while maintaining regulatory compliance, security, and ethical AI standards. They will define and execute the company’s AI transformation roadmap

Please note that this is a hybrid role based in New York City or San Francisco, with an expectation to be in office 2-3 days a week.

What you’ll do:

• Define and execute a multi-year enterprise AI transformation strategy aligned to company growth objectives.
• Identify and prioritize high-impact AI opportunities across operations, customer support, sales, marketing, finance, HR, and engineering.
• Establish and operationalize an enterprise AI governance model, including pilot sequencing, scaling, and rollout.
• Lead AI-driven automation initiatives to improve efficiency through copilots, workflow automation, and intelligent orchestration.
• Develop and implement ROI frameworks to evaluate and prioritize AI investments based on measurable business value.
• Partner with Product and Engineering to embed AI capabilities into member and provider-facing products.
• Drive experimentation with generative and predictive AI to unlock new capabilities and competitive differentiation.
• Lead enterprise-wide AI adoption, including building AI literacy programs and enabling cross-functional teams.
• Establish centers of excellence and scalable frameworks to support AI enablement across the organization.
• Partner with Data and Engineering to build scalable AI infrastructure, including MLOps, model lifecycle management, and vendor strategy.

What success looks like: 

• Measurable reduction in operating expenses through AI-driven automation.
• Improved operational cycle times (e.g., onboarding, support resolution etc).
• Increased enterprise productivity metrics.
• AI embedded in core products driving measurable user and revenue impact.
• Clear AI governance and responsible AI framework implemented company-wide.
• Strong adoption and AI fluency across functions.

What you’ll bring:

• 12+ years of experience in technology, data, AI, or digital transformation roles.
• 5+ years of executive leadership experience driving enterprise-scale AI initiatives.
• Proven track record of deploying AI solutions that deliver measurable business impact, including cost savings or productivity gains.
• Experience operating in high-growth, late-stage startup or scaled technology company environments.
• Experience working in regulated industries, with healthcare experience strongly preferred.
• Deep understanding of generative AI, LLM applications, agentic systems, machine learning lifecycle, MLOps, and automation frameworks.
• Strong ability to evaluate technical architectures and translate them into clear business outcomes.
• Demonstrated ability to lead cross-functional initiatives across Product, Engineering, Clinical, and Operations teams.
• Strong financial acumen with a data-driven approach to decision-making and ROI evaluation.
• Proven ability to drive organizational change and foster adoption of AI-first ways of working.

Nice to have:

• Experience building or scaling AI platforms in a healthcare or digital health environment.
• Familiarity with enterprise AI governance, risk, and ethical AI frameworks.
• Experience leading AI centers of excellence or enterprise-wide enablement programs.

The target base salary range for this position is $287,500 - $332,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Databaseat minimum to ensure competitive and fair pay. 

Benefits provided by Spring Health:

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medicalaccounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals. 
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access toWellhub,  which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.