Schedulefly: The App for Staff Scheduling

Weston Aiken’s college job was stressful. Every Sunday, he was in charge of making the schedule for the employees at a restaurant in Wilmington, North Carolina. Things never seemed to go smoothly.

After spending hours piecing it together, he would post the finished schedule on the wall of the restaurant, only to be faced with disruptions. Keeping track of all the scheduling manually was a huge problem.

Business Ideas: An Online Schedule Maker

The solution that Aiken came up with? Schedulefly. Today the app helps restaurants and businesses everywhere make staff scheduling easier.

Employees log in to check their schedule and communicate with their team. If they need to make a switch with another employee, a manager takes care of it and approves it online.

Though Aiken carried the idea for Schedulefly in his head for years, it wasn’t until 2007 that it became a reality. That year, the company he was working for — First Research — was acquired by another, much larger company. This turn of events became the best thing that happened to Aiken. 

Starting a Business

Shortly after the acquisition, Aiken’s boss at First Research, Tyler Rullman, walked into his office to let him know he was leaving the business and was interested in the scheduling software that Aiken had written.

Aiken was ready for a change. “I was doing some web development for clients, and I would work on a project and hand it over, then I’d never see it again,” he recalls. “I wanted to do one for myself and build my own product.”

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That day, Aiken and Rullman agreed on sharing ownership of Schedulefly and officially started a business.

Creating an Online Schedule Maker: From Idea to Reality

In the beginning, Rullman got Schedulefly off the ground. He started an aggressive marketing campaign in which he emailed thousands of restaurants, set up new accounts, and answered questions during a free 30-day trial that the company offered to restaurants. “He was emailing so many restaurants that his provider shut his internet off because they labeled him as a spammer,” Aiken says.

Over the next six years, three more alumni from First Research joined Schedulefly. Wil Brawley came on board in 2008 to focus on sales, marketing, and building relationships with customers.

Charles Short signed on in 2010 to oversee Schedulefly’s hardware and network infrastructure. And Hank McCauley joined in 2013 to work with Aiken on software development and to oversee online billing and customer service.

In true digital enterprise style, they work toward a common goal while living in different cities. Aiken, Short, and McCauley live in Wilmington; Brawley lives in Charlotte; and Rullman is in Raleigh.

Schedulefly’s customer base has grown to nearly 7,000, and the pricing is simple. On average, the company's clients have 40 employees each, and “it’s $40 a month — about a dollar an individual,” Aiken says.

Aiken’s Advice for Starting a Business

Aiken cautions new entrepreneurs to be patient, as it takes a long time before most businesses can establish themselves. “It takes several years to get any traction at all,” he says. “Progress happens much slower than you might expect. I’d guess that’s true for most small businesses that are just getting started.”

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He also warns against throwing in the towel too soon. “It’s tough to work for several years without making any money — especially without investment,” Aiken says. “It’s hard when you have bills to pay and mouths to feed. It’s really easy to think, ‘Maybe I can start this later.’ It takes a long time [to start a business], and there’s a big opportunity cost to building a business during what may be a prime earning time of your career. But it’s so worth it.”

Aiken considers focus and patience to be important parts of getting Schedulefly off the ground. “I think that's the biggest reason for our success,” he says.

“The other reason is our team. We all bring something unique to the business, and we’re all after the same thing when it comes to our work and the time we want to spend with our families.”

Company Dynamics

Schedulefly’s entire staff works from home, which Aiken believes allows them to be diligent without sacrificing any part of their personal lives.

“The cool thing is that I can spend so much time with my kids during the early years of their life,” Aiken says. “I’m hoping when they grow up, that's what they’re gonna remember. I'm so fortunate to be around them so much.”

The company is in the growth phase, but Aiken, Rullman, Brawley, Short, and McCauley are doing it on their own terms, without bowing to external expectations. “We don’t have investors or other partners pressuring us to grow faster and do things we don’t enjoy,” Aiken notes.

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They focus on serving great independent restaurants to the exclusion of large chains. This is a strategy that Aiken says fits with their philosophy of giving the best to their customers while still being in control. “It’s still a giant market, and we’re able to offer [the independent restaurants] just what they need,” he says. “Right now we have almost 7,000 customers — I’d love to see that hit 10,000 one day.”