Jesse Lipson Podcast Transcript
Jesse Lipson joins host Brian Thomas on The Digital Executive Podcast.
Brian Thomas: Welcome to Coruzant Technologies Home of The Digital Executive Podcast.
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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 yet 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 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 North Carolina Tech Awards. Further solidifying his reputation in North Carolina’s tech ecosystem.
Well, good afternoon, Jesse. Welcome to the show.
Jesse Lipson: Thanks for having me, Brian.
Brian Thomas: 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, I’m most thankful. And Jesse, let’s jump into your first question here.
Levitates 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?
Jesse Lipson: 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 share file. 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 a 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, 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.
Brian Thomas: That’s awesome. And it’s hard to do that. And I like how you said, keeping your relationships at scale that’s hard to do. It’s hard enough just to get a single authentic relationship created and nurtured.
But I appreciate the backstory about your wife and the struggle she had and, and what you learned in your business as well. So, I appreciate that. And Jesse recently moved into a healthcare space. And as healthcare is an innately service oriented, relationship driven industry. The platforms practitioner uses 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
Jesse Lipson: Yeah, absolutely. So, we did at Levitate, we just are HIPAA enabled now, so we are able to work with businesses and in healthcare.
Initially we’re targeting chiropractic firms and, and, uh, dental practices, but I think there’s a couple of challenges that happen in healthcare. First of all, 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 and 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, their patients and, and just to the, the public in general.
And so that’s the gap that we see is. With a lot of these, a lot of small businesses, which is just having a company that can not only 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 is thoughtful and write the content.
We saw a big opportunity in the healthcare space for that.
Brian Thomas: That’s pretty cool. And I, I really like that you are. Let 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 of and nurturing those relationships online. You mentioned social website messaging, all that. I think that’s important, so I 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 characteristic, as 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.
Jesse Lipson: Yeah, absolutely. Well, I think the first kind of resource that is critical is actually human support. And so, one of the things we realized early on as we were working with, 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. ’cause like you said health 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, we’ll 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.
Brian Thomas: That’s very cool. It’s kind of like handholding, 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 relation driven, relationship driven software? Will AI make business communication more personal or maybe less personal? And where do you see Levitate within the broader evolution?
Jesse Lipson: Yeah, it’s a good question. 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 Chat GPT. 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 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, 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 too.
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.
Brian Thomas: Thank you. And 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, in this business, as 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. Yeah, and Jesse, it was such a pleasure having you on today and I look forward to speaking with you real soon.
Jesse Lipson: Yeah, absolutely. My pleasure, Brian. I appreciate it.
Brian Thomas: Bye for now.
Jesse Lipson Podcast Transcript. Listen to the audio on the guest’s Podcast Page.
