RALEIGH — What a year 2023 is shaping up to be for Levitate and founder Jesse Lipson.

Last month, Levitate shared its position as the 502nd fastest-growing private company on the INC. 5000 list citing 1170% growth in the last 3 years.

In April, the company raised nearly $14 million in an oversubscribed Series C round.

At the same time, they released their AI Assistant into a market rabid for AI tools, helping their customers write and edit emails and social media posts.

And just this week the company made an appearance as a finalist in two NC Tech Award categories: “FinTech/InsurTech” and “Software Solutions Company.”


Founded: 2017
Mission: To make the world a happier place by building more authentic relationships.
Product: “Happiness Platform”
Funding: ~$40 million raised between June 2019 and April 2023
Website: https://www.levitate.ai/

Yes, it’s been a strong year for the company that has had much success since its launch in 2017.

The story of Levitate starts with Jesse Lipson, but Lipson started long before Levitate. Lipson has had many roles. Co-founder and CEO of novelProjects. Founder and CEO of Sharefile. Founding partner at Raleigh Founded. Husband of the talented Brooks Bell. Board member at Yext and Green Places. And, of course, CEO and founder of Real Magic, the company behind Levitate. Lipson is also a finalist for NC Tech Awards “CEO of the Year.”

I spoke with Lipson about the current state of Levitate and got hints of exciting things to come. (Note: This interview has been edited for length and clarity.)

  • TechWire: You made the INC. 5000 list with the 502nd fastest-growing company, and you’re the 15th fastest-growing in NC. What part of that are you most proud of?

Jesse Lipson: I think being the 15th fastest-growing private company in North Carolina, and then also being the 66th fastest-growing software company. Yeah, I think those are both pretty cool. There are a lot of great companies in the state. We’ve also hit our 5,000th customer milestone.

  • Are there other AI plans in the works for you?

We’ve got a couple of things coming in this quarter around AI image suggestion. So if you write an email or a social media post, it will look through the text, figure out the relevant keywords, and then search our royalty-free library of images, videos, and gifs and suggest some images for that. And we have a big announcement planned later this month, so that’s coming as well.

  • Where are you getting your images and are any of them AI-generated?

We have a few partner companies: Pixabay, Giphy, and others that we’ve partnered and integrated with to pull into a library. In this new release, based on what clients have written, [the tool] essentially does the search of the library for you by figuring out what the right keywords are and suggesting some stuff. And you can scroll through and change the keywords or search you want.

We’re not doing [AI-generated images] right now. It’s still a little bit risky to generate the images with AI because you may get a person with seven fingers. It’s not quite commercially ready for our customers. It’s something we’re thinking about and experimenting with, but I think this is a good approach to be safe.

  • You raised a bunch of money in April. What was the round like and when will you do it again?

Raleigh software startup Levitate raises $13.75M from 60+ backers, joins AI race

Yeah. It’s been going really well. It was an interesting round that we did where we got a lot of local participation from entrepreneurs and business people. And so it’s been fun to give updates to this large group where there’s a lot of Triangle involvement, local interest on how we’re doing, and support from such a large group of smaller investors.

We don’t have any immediate fundraising plans. We have enough capital to do what we need to do and potentially never have to raise funds again, although you never know what might happen. But I’ve definitely enjoyed not thinking about fundraising for a while. It’s been a nice change of pace to be able to put that on the back burner.

  • Now you can be thinking about much more interesting things like hiring and new features. What are some of the positions that you’re hiring and the areas where you’re expanding?

Really across the board, but a lot of sales hires. We’re also hiring in customer support and success, account management, engineering, marketing. The biggest headcount is probably more on the sales side, but really, we’re hiring across the board, trying to scale every function. I think we’re up to about 180 employees now. We’re growing our headcount responsibly, but we’re definitely growing. By the end of the year, I think we’re probably going to be closer to the range of 200 people.

  • You also announced an integration with Wealthbox earlier this year. Have you been able to put that to use?

Raleigh data startup Levitate expands reach in financial communications sector

Yeah, so one of the things at Levitate that we really try to do is partner with as many systems-of-record as we can that our clients are using, just to streamline the process for them of being able to keep in touch, not having to manually upload spreadsheets, etc. And Wealthbox is getting more and more popular as a CRM system for financial advisors. It probably was our most requested integration at the time that we got it done. I think we’re probably into hundreds of customers that have taken advantage of the integration.

Another integration that we recently did was QuickBooks. We’re trying – every quarter, every year – to add more and more partners, more and more integrations because we want Levitate to be a system where eventually, almost no matter what industry you’re in, wherever your client data lives you can just very easily with a click of a button bring that in.

We’ll figure out who your clients are based on who you’ve invoiced and then figure out when you are working with them based on the dates of those invoices. Make it really easy to then reach out to them: “Hey, clients from three years ago, four years ago, let’s touch base.”

  • Anything else that you want to highlight?

Well, there is some new functionality that we’re really excited about. But we’re gonna be doing a big launch later in September.

Stay tuned, folks!