In this episode of The Digital Executive, host Brian Thomas sits down with Jesse Lipson, founder and CEO of Levitate, a relationship marketing platform helping small businesses build genuine, human connections at scale. A seasoned entrepreneur, Jesse previously founded ShareFile, growing it to millions of users before its acquisition by Citrix, and has since become a key leader in North Carolina’s tech ecosystem. Jesse shares the inspiration behind Levitate—observing firsthand how traditional CRMs and marketing automation tools fall short for relationship-driven businesses. Instead of mass-blast, transactional communication, he saw a need for a platform built around authentic, personal outreach—the kind that drives referrals, trust, and long-term loyalty. He discusses Levitate’s recent expansion into healthcare, where providers face unique challenges: limited staff, increasing competition, and the delicate balance between efficiency and personalized patient communication. Jesse explains how Levitate’s software-plus-services model helps practices stay top-of-mind with patients, maintain a strong online presence, and offload time-consuming content creation so practitioners can focus on care. Looking ahead, Jesse explores how AI will shape the future of relationship-driven software. Rather than replacing personal connection, he believes AI should enhance it—helping professionals remember meaningful details, reach out at the right moments, and scale genuine communication without losing the human touch. If you liked what you heard today, please leave us a review - Apple or Spotify. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.