Vanessa Jupe
Vanessa Jupe is a founder and advocate for investing in women. She is the founder and CEO of Leva, a company built around supporting working parenthood — one of life's most common inflection points — and the host and researcher behind 101 Ways Out, a research-led storytelling project documenting the "Great Exit" from corporate life. Her career includes senior leadership roles at Clearcover, H&R Block, and USAA, spanning digital products, insurtech, and financial services.
On Grand Slam Journey, Vanessa draws on her own journeys through career, culture, and parenthood to explore how we navigate life's transitions — from starting new roles to raising kids in an AI-shaped world. She highlights the power of curiosity, celebrating small wins, and asking simple questions to unlock growth through change.