2026 Speakers
Kip Hollister
Keynote Speaker
The Hollister Group, Owner & Founder
Kip has been practicing authentic and self-aware leadership for over 35 years as Owner & Founder of The Hollister Group. Her passion to help leaders discover the possibility, inner knowing, and worthiness that resides within them drew her to launch the Cultures division.
Kip's innovation shines through as the mastermind behind the proprietary REAL™ Results program designed to assist organizations led by people-centric leaders in developing effective teams, maximizing individual contributions, and fostering work cultures that encourage sustainable creativity and impact.
Beyond her executive role, Kip is renowned as an energy activator and keynote speaker, distinguishing herself with an engaging conversational style that prioritizes being with people, rather than talking at them. Emphasizing the essence of being human first, Kip tailors each engagement uniquely, drawing from the collective wisdom of the group to awaken individuals to their true, vulnerable, and authentic selves.
Angela Pitter
Keynote Speaker
Angela Pitter is the Founder & CEO of LiveWire Collaborative, where she helps leaders close the visibility gap between the reputation they’ve earned and what AI-powered search can actually see. A 25-year global technology veteran with degrees in Computer Engineering and Administration from Boston University, Angela brings systems thinking, executive strategy, and plainspoken storytelling to one of the biggest business questions of the AI era: who gets found, trusted, and recommended?
Angela’s own reinvention began with an unexpected run for public office, where digital storytelling became the bridge between a message and a community. Since founding LiveWire Collaborative in 2012, she has helped organizations including Harvard’s Houghton Library, Meet Boston, Redgate, and mission-driven teams strengthen their digital presence, executive visibility, and AI-era positioning — work she brought to the TEDxRoxbury stage in 2026 with “AI and Digital Erasure: The New Redlining We’re Not Talking About.”
Named a Commonwealth Heroine and one of the 50 Most Influential Business People of Color, Angela also serves as Board Chair of the Charles River Regional Chamber. She doesn’t talk about AI as theory — she helps leaders understand where visibility breaks down, why it matters, and how to stay discoverable before opportunity passes them by.
