Jesse Lipson on Reinventing Relationship Marketing for Small Businesses |Ep 1153

Summary

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Episode Overview

Podcast: The Digital Executive
Host: Brian, Coruzant Technologies
Guest: Jesse Lipson, Founder & CEO of Levitate
Episode Title: Jesse Lipson on Reinventing Relationship Marketing for Small Businesses | Ep 1153
Date: November 24, 2025

In this episode, Jesse Lipson shares insights on how Levitate is redefining relationship marketing for small businesses, especially in service- and relationship-driven industries like healthcare. The conversation dives into why authentic connections matter more than transactional marketing, the challenges small businesses (especially in healthcare) face, and how Levitate leverages a blend of software, services, and AI to help organizations nurture genuine relationships at scale.

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Key Discussion Points & Insights

Redefining Relationship Marketing

• Inspiration from Real Life:
  Jesse shares that Levitate’s inspiration came from observing his wife's consulting business. Despite heavy investments in traditional marketing automation tools, meaningful business was coming through authentic, personal connections rather than those systems.
  Quote:

  “It kind of occurred to me ... there's a whole segment of the economy that really operates more on word of mouth and referral and just doing a good job kind of keeping in touch authentically. But the suite of sales and marketing software out there was all built for ... mass blast transactional type businesses … not really built for the way that a lot of businesses actually try to keep in touch with their customers.” — Jesse Lipson [02:19]

• Targeting Relationship-Based Industries:
  Jesse notes a gap in existing sales and marketing platforms, which often target transactional or e-commerce-based models, leaving service-oriented and referral-based small businesses underserved. Levitate aims to fill this gap.

Challenges and Opportunities in Healthcare Communication

• Healthcare’s Unique Communication Challenges:
  With the platform now HIPAA-enabled, Levitate is providing value to healthcare small businesses (e.g., chiropractic and dental practices). Healthcare providers often lack the time and expertise for building an online presence and engaging consistently with patients via content and communication channels.
  Quote:

  “They really are experts at providing care to patients and not necessarily staying up to date on ... best practices for showing up in search engines and ... communicate high value content to their patients and just to the public in general.” — Jesse Lipson [04:34]

• Beyond Tools: The Need for Content & Strategy:
  Small businesses not only need automation tools but also guidance and support in content creation and communication strategy. Levitate’s approach integrates both.

Software Plus Services: A Holistic Approach

• Support Beyond Technology:
  Jesse highlights the importance of combining human support with software for small business success.
  Memorable Analogy:

  “It’s kind of like the workout plan for your business, where you know it’s good for you in the long term, but in the short term you don’t necessarily always have time for it.” — Jesse Lipson [07:06]

• Partnering for Success:
  Levitate meets with clients, prepares content calendars, and aligns communication strategies with business goals, taking tasks off the plates of already overburdened teams.

The Future of Relationship-Driven Software & the Role of AI

• Vision for AI in Relationship Marketing:
  Jesse is clear that Levitate uses AI to enhance, not replace, personal connection. AI’s role is to help remember and scale personalized outreach, not to automate away authenticity.
  Quote:

  “My goal was always to allow our customers to scale their personal outreach, not to use AI to replace it ... People have a pretty good radar for automated communications.” — Jesse Lipson [09:03]
  “To take the kind of personal outreach that you could normally do with just your closest friends and family and extend that to hundreds of people in your network—I do think AI has that ability … but not to replace the personal connection.” — Jesse Lipson [09:03]

• Human + Machine Synergy:
  The focus is on using technology to help businesses remember key facts (birthdays, hobbies, etc.) to deepen relationships, reinforcing that tech should empower—not distance—human connection.

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Notable Quotes & Memorable Moments

• “Keeping relationships at scale, that’s hard to do.” — Brian, Host [03:48]
• “First kind of resource that is critical is actually the human support ... We realized early on that if you just provide the software, that’s not necessarily enough ... it needs to be a software plus services approach.” — Jesse Lipson [07:06]
• “People have a pretty good radar for automated communications.” — Jesse Lipson [09:03]
• “Making them feel like you personally care goes so far in this business.” — Brian, Host [10:31]

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Timestamps for Important Segments

• [02:19] — Jesse explains the gap in traditional marketing tools and the inspiration for Levitate.
• [04:34] — Discussion of healthcare’s unique relationship-driven nature and challenges with patient communications.
• [07:06] — The necessity of software + services and how Levitate supports small businesses beyond just software.
• [09:03] — The future of AI in relationship marketing and Levitate’s philosophy on technology’s role in personalization.

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Conclusion

Jesse Lipson’s episode provides valuable, actionable insight into the evolving world of relationship marketing. Levitate’s model is tailored for authentic communication at scale—especially where personal connection forms the core of business success. The conversation emphasizes technology as a tool for empowerment rather than automation, with AI serving to bolster—not supplant—human relationships.

Listeners come away with an understanding of why relationship marketing matters, especially in sectors like healthcare, and how platforms like Levitate are positioned to help small businesses thrive in a tech-enabled, yet authentically personal, future.

Transcript

[A]

Foreign. Welcome to Coruscant Technologies, home of the Digital Executive Podcast. Do you work in emerging tech? Working on something innovative? Maybe an entrepreneur? Apply to be a guest at www.corazon.com brand welcome to the Digital Executive. Today's guest is Jesse Lipson. Jesse Lipson is the founder and CEO of Levitate, a SaaS 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 4 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 co working 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 North Carolina Tech Awards, further solidifying his reputation in North Carolina's tech ecosystem. Well, good afternoon Jesse. Welcome to the show.

[B]

Thanks for having me, Brian.

[A]

Absolutely my friend. I appreciate it. And you're hailing out of Raleigh, North Carolina today. I'm in Kansas City. We're just an hour apart, but still I appreciate it because you had to make the time to do this. So again, most thankful. And Jesse, let's jump into your first question here. Levitate's message is that authentic human connection beats transactional marketing. What gaps did you see in traditional email marketing, CRM or marketing automation tools that made you believe the market needed a new category centered on relationships rather than campaigns?

[B]

Yeah, the inspiration for me for Levitate came actually from my wife's business. She had a consulting firm, a 40 or 50 person consulting firm, and I noticed that even though she was spending thousands of dollars a month on Salesforce and marketing automation, that a lot of the business she was generating was coming from her operating completely outside of those systems and really just doing a good job keeping in touch with her network in a more personal, authentic way. And so it kind of occurred to me in my previous business, ShareFile, we had 70,000 customers and a lot of them were small businesses in professional services like accounting and legal and wealth Management. And I noticed that there's a whole segment of the economy that really operates more on word of mouth and referral and just doing a good job kind of keeping in touch authentically. But the suite of sales and marketing software out there was all built for kind of mass blast transactional type businesses selling sweatshirts and e commerce products or enterprise products. Not really built for the way that a lot of businesses actually try to keep in touch with their customers. So that was my goal, is to help these relationship based businesses keep in touch authentically, but do it at scale.

[A]

That's awesome. And it's hard to do that. And I like how you said keeping relationships at scale, that's hard to do. It's hard enough just to get a single authentic relationship created in nature. But I appreciate the backstory about your wife and the struggles she had and what you learned in your business as well. So I appreciate that. And Jesse recently moved into the healthcare space. And as healthcare is an innately service oriented, relationship driven industry, the platforms practitioners use to stay connected with their patients can make or break the patient practitioner relationship. Can you help our audience understand when communications platforms help organizations build personal connections at scale, they drive measurable value for both the patient and the organization.

[B]

Yeah, absolutely. So we did at Levitate, we just are HIPAA enabled now, so we are able to work with businesses. And in health care, initially we're targeting chiropractic firms and dental practices. But I think there's a couple challenges that happen in health care. First of all, in just general managing of online presence when it comes to both how you communicate with patients and potential patients through email, but also keeping a social media presence, website and blog, Google reviews. There's a lot of things to juggle for these small businesses in the world of healthcare. And I think they really are experts at providing care to patients and not necessarily staying up to date on what all the best practices are for showing up in search engines and having the time to actually write and communicate high value content to their patients and just to the public in general. And so that's the gap that we see is with a lot of small businesses which is just having a company that can not only and provide them with just the tools. There's a lot of tools out there where you can push a button and it'll blast out messages, but actually helping them create a content strategy that, that is thoughtful and write the content. We saw a big opportunity in the healthcare space for that.

[A]

That's pretty cool. And I really like that you're letting the Practitioners focus on their craft, which is patient care. That's what they went to school for, that's what they need to focus on while you and your platform allows them to manage that patient care while all the messaging is taken care and nurturing those relationships online. You mentioned social website messaging, all that. I think that's important. So appreciate that. And Jesse, healthcare providers face challenges of limited staff resources, growing competition and the need to balance efficiency with personalized communication. Finding the right communication tool that enables genuine relationship building while streamlining internal processes and operations is really critical for healthcare practitioners who are operating in an industry characterized by staffing challenges. Walk us through some tools that work with the organization to support their needs and can allow staff to allocate more time to that patient care. They.

[B]

Yeah, absolutely. Well, I think the first kind of resource that is critical is actually the human support. And so one of the things we realized early on as we were working with small businesses and helping with communication platform is that a lot of the analogy I use is doing this, keep in touch and being consistent with things like your social presence and blog articles. It's kind of like the workout plan for your business where you know it's good for you in the long term, but in the short term you don't necessarily always have time for it. And so we realized early on that if you just provide the software, that's not necessarily enough because like you said, healthcare practices are, they're short staffed. And so what we realized is it needs to be a software plus services approach. And so what we do is we actually will meet with clients and prepare a content calendar for them and consult with them on their business goals. So kind of providing the platform plus the services is kind of the winning combination because a lot of businesses just don't have the time to allocate so they need somebody to meet with them to kind of help help walk them through the process.

[A]

That's very cool. It's kind of like hand holding, right? Which is great because that you mentioned that software plus services approach where you've got the platform that can easily help scale nurture these relationships, but also you're there again to ensure that they're successful in that messaging and nurturing of those relationships while they can focus on their patient care. I really appreciate that. And Jesse, the big one, we always look ahead. If you look ahead maybe five to 10 years, what do you think the future holds for relationship driven software? Will AI make business communication more personal or maybe less personal? And where do you see levitate within that broader evolution yeah, it's a good question.

[B]

I think the interesting thing for us, I started the business back in the end of 2017 and we were actually called Levitate AI even back then, five years before ChatGPT. And so my vision was always to allow our customers to scale their personal outreach, not to use AI to replace it, because I think people have a pretty good radar for automated communications. And, and so my goal was, I think we all would love to do a better job remembering key facts about our business network and kids names and pets names and hobbies, and thoughtfully reaching out at the right time to folks. And so my goal is really to use AI to enhance the personal outreach that just tends to fall apart. I mean, we're all, we're all human and our brains can only hold so much information. And so to take the kind of personal outreach that you could normally do with your just your closest friends and family and extend that to hundreds of people in your network, I do think AI has the ability and potential to replace the personal connection, which is not what we're trying to do. And we don't think that's the right answer is to just blast out automated content using AI. It's really to use it as a tool that allows you to connect more and keep in touch with the people you want to as kind of an extension to your own brain.

[A]

Thank you. I think that's important. You did highlight that. How do we do a better job of remembering the little things, the important things about the customer? You know, you talked about birthdays, pets, whatever. But making them feel like you personally care goes so far in this business. But having the technology, the platform, leveraging AI to help remember all those things is so important and will only really make that relationship stronger when you have that human machine relationship as you support your customers. So I really appreciate that. And Jesse, it was such a pleasure having you on today and I look forward to speaking with you real soon.

[B]

Yeah, absolutely. My pleasure, Brian. Appreciate it.

[A]

Bye for now.