On this episode of The Innovative Agency Podcast, Sharon Toerek welcomes Jesse Lipson, Founder of Levitate and a seasoned technology entrepreneur, for an insightful conversation about staying genuinely connected in a world overflowing with automation.

Agency leaders know relationships drive growth, referrals, and long-term client trust. But, meaningful outreach often gets buried beneath deadlines, deliverables, and the daily scramble of running the business. Jesse Lipson saw this firsthand through his wife's agency experience, and it ultimately inspired him to build Levitate to be a platform designed to help professionals strengthen relationships at scale without sacrificing authenticity.

Jesse shares how agencies can use "keep in touch" systems to create more personalized communication, deepen trust with clients and prospects, and finally make relationship-building a consistent business practice instead of an afterthought.

If you want to use technology to strengthen relationships, this conversation offers a practical and refreshing perspective on what authentic outreach should look like in the AI era.

What you will learn in this episode:

• Why most agencies struggle to keep in touch with important contacts (and what that's costing them)

• The gap between transactional marketing tools and the deeply personal connections that actually drive referrals

• How technology and AI can augment, not replace, authentic outreach for agencies and their clients

• Why relying solely on automated messaging risks eroding trust

• How AI agents might soon revolutionize the way agencies stay top-of-mind

• The power, and the payoff, of long-term relationship building, even when it feels like a slow burn

Bio

Jesse Lipson is the Founder and CEO of Levitate, a SaS relationship marketing platform on a mission to help small businesses build authentic, human connections at scale. He previously founded ShareFile in 2005, bootstrapping it to over four million users and a $93 million acquisition by Citrix in 2011, where he later served as Corporate Vice President and General Manager of Citrix Cloud Services.

A self-taught software developer, Jesse launched his first company at age 23 and earned a philosophy degree from Duke University. He co-founded Raleigh Founded, a coworking community for entrepreneurs, and started Levitate through his holding company Real Magic. In 2023, he led a successful Series C raise of approximately $14 million, scaling Levitate to more than 4,000 small business customers nationwide. In addition to his role at Levitate, Jesse serves as an independent director at Yext and is on the board of Green Places, reinforcing his leadership in both technology and community-driven ventures. He was also named Tech CEO of the Year at the 2023 NC TECH Awards, further solidifying his reputation in North Carolina's tech ecosystem.

A lifelong entrepreneur with a passion for creativity and community, Jesse lives in Raleigh, North Carolina, with his wife, fellow entrepreneur Brooks Bell, and their dog Cecil.

Resources:

• Website: https://www.levitate.ai/

• LinkedIn Personal: https://www.linkedin.com/in/jesse-lipson-625195/

• LinkedIn Business: https://www.linkedin.com/company/real-magic/

• Instagram: https://www.instagram.com/levitateai/