Editor’s note: Startup Spotlight is an exclusive feature from WRAL TechWire that brings attention to emerging entrepreneurial companies across the Triangle and North Carolina. These spotlight stories also are a regular part of our Startup Monday lineup.


RALEIGHReal Magic, the startup launched by Triangle serial entrepreneur Jesse Lipson, recently rolled out a new sales team product called Coffee, and added $6 million in new capital to its coffers. That brings its total raised to $26 million since 2017.

Lipson, who joined investors in this latest round, is one of the Triangle’s big success stories and homegrown talents.

After graduating from Duke University in 2000, the self-taught engineer became a full-time entrepreneur at 23. Later, he launched Sharefile, a file transfer service that he grew to four million users in six years and sold to Citrix in 2011.

Real Magic is his fourth company. Its first product, aptly called Levitate, is a “keep-in-touch” marketing platform that helps businesses grow.

WRAL TechWire’s Chantal Allam had the chance to pose a few questions to him. Here’s what he had to say:

  • Talk to us about the launch of your new sales team product, Coffee. How did you come up with the idea? And why now?

Like a lot of great product ideas, the idea for Coffee came from pain points that we felt as a growing company trying to optimize our sales process. We couldn’t find a solution that met our needs, so we decided to build it on the Levitate platform. Originally, we were not planning on selling Coffee and just wanted to keep it for ourselves, but we were so happy with how the software turned out, we decided to share it with the world.

  • How does the product work exactly?

Coffee is designed to make the lives of salespeople easier and more fun by showing the best leads for them to be reaching out to at any given time, and also gamifying the process of sales by letting them earn points for different activities they complete throughout the day and competing (in a friendly way) with their team members. We integrate directly with the CRM (customer relationship management system) so sales reps never have to enter data in multiple places.

  • What’s the story behind its name?

There’s a famous line from the movie “Glengarry Glen Ross” that “Coffee is for closers,” so that’s what inspired the name. It also doesn’t hurt that most people have a very positive association with the word coffee.

WRAL TechWire photo

Real Magic founder Jesse Lipson.

  • What has the response been like so far?

I just landed back in Raleigh after attending the HubSpot Inbound conference in Boston, where we launched the product on Tuesday. The early response to Coffee has been fantastic. The feedback we’re getting is that the gamification and ease of use of Coffee is very unique and something that folks are very excited about.

  • You’ve also raised an additional $6 million. That brings your total funding raised to date to $26 million. Why did you decide to raise these funds now? How do you plan to spend it?

With the launch of Coffee, Real Magic is now a multi-product company. We raised additional funding to help us continue to innovate on Levitate and Coffee as well as build out our sales and marketing team to help show the world how great both products are.

  • Can you give us a sense of Real Magic’s revenue growth? When you sold ShareFile, it had about 100 employees and was worth in the $10 to $15 million-revenue range. How does Real Magic compare to that?

Real Magic is pretty close to the revenue that ShareFile was back when the company was acquired by Citrix in 2011. Thanks to our venture capital investment, we’ve been able to cross $10 million in revenue a lot more quickly than we did back at ShareFile.

Raleigh startup Real Magic raises $6M, launches sales team product; founder Jesse Lipson is among investors

  • Compared to ShareFile, how does it feel this time around scaling a company?

It’s a very different world this time around. First, ShareFile was very early in the software-as-a-service space. These days, there are thousands of software products competing for attention. On the other hand, this time around, customers are very comfortable with adopting web-based software. Back in the day, many customers were afraid to let other companies store their data and they were not comfortable using software in a web browser.

The other major difference is obviously the pandemic. Half of Real Magic’s company history has occurred during the pandemic. A big part of scaling Real Magic has involved navigating all of the turbulence in the outside world, whereas with ShareFile I spent the vast majority of my time just thinking about the internal aspects of scaling the business.

  • Any partnerships in the pipeline?

For the Coffee product, we are deeply integrating with HubSpot’s CRM product and are looking forward to working with HubSpot’s partners and customers.

  • What’s Real Magic’s current employee count? Are you hiring? If so, how are you planning to expand your team?

We have a little bit less than 150 employees right now. We are hiring in just about all areas of the business, with a special focus on expanding our sales team.

  • Post pandemic, what is Real Magic’s policy when it comes to workers in the office? Are you fully remote, hybrid or in-office only? Where do you see this all going, and what’s your take on this shifting landscape?

We are hybrid, but our policy varies based on role and tenure with the company. I’m a big believer that hybrid will be the path forward for most companies in the long term.

  • Looking ahead, where to from here? Any plans to exit anytime soon?

No plans to exit anytime soon. We have a big market opportunity, a great team, an awesome culture, and I have fun coming into work (just about) every day. Why change that?