Why Strategic Plans Stall at Implementation and How to Ensure They Don’t

How Vail Mountain School Used the MoonshotOS School Operating System to Bring the Strategy to Life
A conversation with Steve Bileca, Head of School at Vail Mountain School

Wednesday, February 11, 2026, 2 pm ET

Register today!

Steve Bileca, Head of School at Vail Mountain School, on Turning a Strategic Plan Into Day-to-Day Leadership Work

Vail Mountain School has a thoughtfully designed and clear strategic plan, Learning Elevated, and a leadership team deeply committed to making it work.

Like many schools, the plan was approved, expectations were high, and the harder question quickly surfaced: how do you actually implement strategy without it stalling or overwhelming the leadership team?

What they didn’t have was a shared way to consistently move that plan forward.

In this session, Steve Bileca, Head of School, Vail Mountain School, will share how his leadership team used the MoonshotOS School Operating System to fix that execution gap by:

  • Take a long-term strategic plan and make it executable each and every week.

  • Translate strategy into clear priorities and 90-day sprints

  • Reworking weekly leadership meetings so the most important strategic work moves forward week to week, instead of getting lost in everything else

Steve Bileca, Head of School, Vail Mountain School

Hear from:

Steve Bileca, Head of School, Vail Mountain School

Who is this for?

  • Heads of school and senior leaders responsible for executing a strategic plan.

  • Especially those who already have a plan and are feeling the pressure to make it work.

If your school has a strategy and you’re feeling the weight of making it work, join the conversation.

A Conversation About Strategy Execution

Peter Baron with Steve Bileca, Head of School at Vail Mountain School

Ready to talk about what comes after the strategic plan?