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Associate Director, AI Transformation and Strategy - Remote - 2298013

Dovetail Health

Dovetail Health

Software Engineering, Data Science
Washington, DC, USA · San Francisco, CA, USA · Eden Prairie, MN, USA · New York, NY, USA · Boston, MA, USA
USD 110,200-188,800 / year + Equity
Posted on Aug 7, 2025

Optum is a global organization that delivers care, aided by technology to help millions of people live healthier lives. The work you do with our team will directly improve health outcomes by connecting people with the care, pharmacy benefits, data and resources they need to feel their best. Here, you will find a culture guided by inclusion, talented peers, comprehensive benefits and career development opportunities. Come make an impact on the communities we serve as you help us advance health optimization on a global scale. Join us to start Caring. Connecting. Growing together.

The AI Transformation and Strategy team, led by our Chief AI Transformation and Strategy Officer, owns the development of our enterprise AI strategy and modernization agenda. Our small but highly empowered team drives high-impact AI initiatives to deliver significant value to our business and those we serve.

As the Associate Director of AI Transformation and Strategy, you’ll support our Senior Director, AI Transformation and Strategy. You’ll help the team advance our mission by developing exec-level content, project managing major initiatives, and delivering high impact strategic analyses. You’ll also collaborate with internal business and technology stakeholders to develop AI/ML strategies for key opportunities across UnitedHealth Group businesses, including UnitedHealthcare, Optum Financial, Optum Health, Optum Insight, and Optum Rx.

You will have the flexibility to work remotely* as you take on some tough challenges.

Primary Responsibilities:

  • Enterprise Strategy
    • Collaborate with internal business and technology stakeholders to define and execute an AI strategy that aligns with UnitedHealth Group’s business goals, regulatory requirements, and healthcare industry trends
    • Conduct research on market trends, the competitive landscape, and emerging AI technologies to identify opportunities for improved healthcare quality and outcomes, commercialization, and greater operational efficiency
    • Generate written analyses, primarily in the form of slide decks and memos, to make the business case, quantify value, evaluate options, and present strategic recommendations for the use and development of AI within UHG
    • Support strategic investment decisions and execution strategies for AI initiatives, ensuring alignment with UHG’s business and quality objectives
    • Encourage a culture of AI literacy across the organization, enabling business leaders to leverage AI for strategic decision-making
    • Ensure consistency in internal and external communications used to describe AI applications at UHG
  • Corporate Development and Partnerships
    • Support AI-related corporate development strategy, including identifying and evaluating acquisition and partnership targets
    • Facilitate strategic partnerships with AI technology providers, startups, research institutions, and industry partners
    • Create integration plans for acquired AI technologies, ensuring seamless alignment with existing platforms and business units
  • Implementation and Execution
    • Drive stakeholder alignment across business, operations, and technology to ensure AI engagements are set up to deliver measurable outcomes, receive cross-functional support, and minimize business disruption
    • Define and track KPIs of AI implementations to monitor progress, measure success, and project manage delivery
  • Product Strategy
    • Collaborate with UHG’s AI, product, and engineering teams to define the vision, roadmap, and execution strategy for AI-powered products and solutions within UHG
    • Ensure best practices leveraged for AI use case identification, model development, and output validation to maintain compliance with healthcare regulations (HIPAA, CMS, etc.)
    • Develop frameworks for measuring AI value and ROI, ensuring alignment with business KPIs, quality standards, and key timelines
    • Reinforce responsible AI practices, including bias mitigation, transparency, and fairness in all AI builds and implementations

You’ll be rewarded and recognized for your performance in an environment that will challenge you and give you clear direction on what it takes to succeed in your role as well as provide development for other roles you may be interested in.

Required Qualifications:

  • 5+ years of professional experience
  • 3+ years of experience in strategy, including the development of strategic recommendations for large organizations and/or complex use cases
  • 3+ years of experience working in healthcare and/or on healthcare projects
  • 3+ years of experience in project management, including 2+ years of leading high impact initiatives
  • 2+ years of experience supporting senior leaders, including the creation of rigorous analyses and executive-level slide decks and memos
  • 2+ years of experience collaborating directly with executives and/or senior stakeholders
  • Proven to be a self-starter who is excited to take on open-ended projects and run with time-sensitive, high priority asks
  • Proven excellent oral and written communication skills

Preferred Qualifications:

  • 2+ years of experience in consulting
  • Experience with AI/ML products and strategy
  • Working knowledge of UnitedHealthcare, Optum and/or UHG businesses
  • Demonstrated expertise in healthcare, especially in provider or payor space

*All employees working remotely will be required to adhere to UnitedHealth Group’s Telecommuter Policy

Pay is based on several factors including but not limited to local labor markets, education, work experience, certifications, etc. In addition to your salary, we offer benefits such as, a comprehensive benefits package, incentive and recognition programs, equity stock purchase and 401k contribution (all benefits are subject to eligibility requirements). No matter where or when you begin a career with us, you’ll find a far-reaching choice of benefits and incentives. The salary for this role will range from $110,200 to $188,800 annually based on full-time employment. We comply with all minimum wage laws as applicable.

At UnitedHealth Group, our mission is to help people live healthier lives and make the health system work better for everyone. We believe everyone–of every race, gender, sexuality, age, location and income–deserves the opportunity to live their healthiest life. Today, however, there are still far too many barriers to good health which are disproportionately experienced by people of color, historically marginalized groups and those with lower incomes. We are committed to mitigating our impact on the environment and enabling and delivering equitable care that addresses health disparities and improves health outcomes — an enterprise priority reflected in our mission.

UnitedHealth Group is an Equal Employment Opportunity employer under applicable law and qualified applicants will receive consideration for employment without regard to race, national origin, religion, age, color, sex, sexual orientation, gender identity, disability, or protected veteran status, or any other characteristic protected by local, state, or federal laws, rules, or regulations.

UnitedHealth Group is a drug – free workplace. Candidates are required to pass a drug test before beginning employment.