Cristina Apple Georgoulakis

I arrived at coaching through transition — both my own and others’. I first joined The Grand as part of the inaugural Career Transitions program while seven months pregnant and navigating big questions about work, identity, and purpose. What I found was a community that not only helped me step into my next chapter — from tech worker to venture capitalist — but also showed me the power of investing in yourself through connection. It was in that first Grand experience that I discovered my reason for being: to facilitate growth in people and organizations.

I was honored to be asked to support The Grand’s mission by coaching hundreds of members and helping design curriculum for leadership cohorts. I bring a systems lens and a focus on aligning profit, people, and purpose, with a coaching style that’s curious and candid — equal parts strategy and soul — so members leave with clarity and practical next steps.

I later became one of The Grand’s earliest institutional investors — a full-circle moment of giving back to a community that has given me so much. Together with Anita, I had the chance to spark conversations that evolved into The Grand Pursuit — a space for ambitious working moms to be real about the joys and disorientation of motherhood, and to reclaim their energy. It was a space I deeply needed and knew only The Grand could bring to life.Outside of The Grand, I’m an early-stage investor, former SaaS founder, aspiring seamstress, and lover of good design and a good belly laugh — drawing on years of experience building and scaling teams from the ground up.

At the heart of it all, my work is about asking the right questions, creating spaces for honest conversations, and helping people step into lives and careers that feel true to them.