Scaling Leadership Development at CVS Health with Human-Led, AI-Assisted Coaching

CVS’s 10,000 mid-level managers are the company’s operational backbone. They oversee thousands of retail locations and support store-level leadership. They translate strategic vision into daily practice, driving the long-term success of the business. As the company pushes decision-making and accountability down, managers must be ready to own more.

Hudson Institute of Coaching

When CVS Health, the world’s second largest healthcare company, partnered with Hudson Institute of Coaching, they had a bold goal: develop thousands of mid-level managers into agile, future-ready leaders capable of driving transformation in a rapidly changing healthcare landscape.

The challenge was scale. With over 10,000 mid-level managers serving as the company’s operational backbone, CVS needed a development approach that was impactful, cost-effective, and adaptable to leaders’ busy schedules.

Hudson’s solution was Wiser — a leadership development platform blending proven coaching methodology with cutting-edge AI. At its heart is Ollie, an AI coaching assistant trained to prompt reflection, guide skill-building, and support managers in areas like delegation, accountability, and inclusive leadership.

How It Works

Over a few 6-week cycles, each participant learns and practices new leadership skills with the support of their human coach, the peers in their coaching group, and Ollie, the AI-coaching assistant.

  1. Kick-off: Group Coaching

    A human coach helps the group build connection, spark insight, and choose the skill they’ll focus on in this cycle.

  2. Week 1: Self-Observation

    Participants access the Wiser platform and complete two short AI coaching sessions with Ollie to reflect on their behavior.

  3. Weeks 2–5: Experimentation

    With Ollie, participants design and test real-world behavior experiments focused on their chosen skill.

  4. Week 6: Reframe & Build a Plan

    Ollie helps participants reframe their experience and prepare for their group coaching session.

  5. Close Cycle & Next Steps: Group Coaching

    Participants reunite to share learnings, stay accountable, and set the next skill—bridging into the next cycle.

By pairing Ollie’s on-demand, personalized coaching with human-led group sessions, CVS created a continuous development ecosystem. Early results are impressive:

100% of participants want to continue in the program.

93% tried leadership experiments they might not have attempted otherwise.

Every participant surfaced a lasting insight to carry forward.

The program is now expanding to hundreds — and soon thousands — of CVS leaders. The model delivers results at up to 50x less cost than traditional executive coaching, proving that high-quality leadership development can be both human-centered and scalable.

Read the full case study to explore how CVS and Hudson are redefining leadership development at scale.

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