About Mary Rapaport

After years inside corporate America building teams that could actually think and not just execute, Mary kept running into the same pattern: smart people, fast environments, and just enough pressure to keep real thinking on the sidelines. She worked with major brands to align capabilities to strategy and push beyond surface-level problem solving… and still watched leaders unintentionally hold onto the thinking, stepping in, connecting the dots, and moving things forward while everyone else stayed in execution mode. Not on purpose. Just habit.

That’s when it clicked. The issue isn’t a lack of intelligence or ambition.  It’s that THINKING often gets concentrated at the top. So Mary built The Strategic Playground to flip that dynamic. It’s a refreshingly practical, slightly irreverent, actually enjoyable way to help teams step into strategic thinking themselves right in the middle of their real work.

No jargon. No waiting. No “we’ll take this offline for leadership.” Mary believes strategic thinking belongs in the middle of the work. Not locked in a senior meeting somewhere else. Strategic thinking shows up in better questions, clearer thinking, and more people jumping in with ideas that actually move things forward. 

Mary’s on a mission to democratize strategic thinking—so it’s not something a few people own, but something teams do together. Because work gets a lot more interesting, a lot more effective, and a lot more FUN when everyone’s invited to think.

Experience & Expertise

✔ 20+ years experience in leadership development

✔ Strategic learning & capability design expert

✔ Works with global teams and organizations

✔ Focused on real-world business impact