Facetime: Kevin O'Reilly

Interview by Courtney Brockman ’17

Growing up in Montana, Kevin O’Reilly worked jobs ranging from retail to trail maintenance. But wherever he worked, he seemed to encounter endless shift-scheduling frustrations. So he decided to create a better way to communicate with colleagues than through Post-it notes.

And Orbital Shift was born.

After graduating from UM in 2009 with master’s degrees in computer science and business administration, O’Reilly built the time-saving staff management web and mobile platform from scratch.

Orbital Shift – which allows managers and employees to create and view schedules, track hours, cover shifts, request time off and send out reminders – serves hotels, food co-ops, resorts and even Grizzly Athletics. It now has thousands of users and more than 150 business clients across the country and the globe.

“We’re really proud to be from Montana, creating a product that we can sell outside of the state,” O’Reilly says.

O’Reilly talked to the Montanan about the growing startup, which tripled from three to nine employees in the past year.

You serve people as far away as South Africa. How does that work? The power of the web is amazing. So while we may sleep, it’s working 24 hours around the clock. On other sides of the globe, people might be looking for workforce management needs or staff scheduling or time clock or employee communication. We’ve had people sign up in South Africa, we’ve had people sign up in the U.K., we’ve had people sign up in Canada, which is a bit closer, and then as far away as the Philippines. It’s pretty incredible just overnight how fast, once you put yourself out there on the web, you’re really moving yourself up to a global market nowadays.

How does it feel to have developed this from the ground up? Kind of surreal sometimes. It’s hard to believe we’ve been in business for eight years. We started from the ground up and bootstrapped things. Looking back on it now, there’s such different challenges we tackle today then we tackled then. As your company grows, there’s just new hurdles and obstacles. And it’s still exciting. It’s still fun. I think that’s one of the neat things about technology and not just that problem-solving mindset, like, “Hey, here are the challenges we help with today,” but helping prepare for what a business may face in the future.

What has been UM’s role? While I was getting my MBA, Cameron Lawrence was a person I had studied under and was a great mentor, and he’s a professor in the business school. He became an investor in our company in the last year, which is really awesome. It’s really humbling to think that somebody you’re taking a class from believes enough in what you’re doing that one day they even invest in your company.

With UM athletics, I was able to come in and make a pitch to them. We were able to help with some events and things, like when they had the Paul McCartney concert a couple of years ago. They used our software to help schedule their staffing needs for the concert.

How do you think being in Missoula has helped your business grow? I think being in a university town, first of all, is great just for access to education and evolving technologies. I’m so grateful that the University stays on the cutting edge in the business school on the newest things that people need to be trained for to go out into the workforce, and [I like] having a lot of opportunity for giving back and internships and working with students and really wanting to help them better their resumes. I also think there’s a really cool tech community here. Just getting a chance to chat with each other or run into each other in the community and share notes on how we can help each other – there’s a real sincere interest in that. It’s not ultimately competitive, as it’s more nurturing and supportive.

What is one lesson you’ve learned? In the early stages of building a product, everybody is so scared of “It’s not ready yet” or “It’s not perfect enough.” And a lot of that’s in our heads. The fastest way you can prototype something is to get someone’s honest feedback about it. And not be ashamed to say, “Don’t worry about hurting my feelings. I just need to know your honest thoughts, so I can make this better.” Getting into a test market is really critical, because you can spend way too long in development, and maybe you’re developing the wrong thing. Let the market speak to you.

Do you have any advice for future entrepreneurs? Nothing matters until you get a stranger to pay you for it. Your friends and family love you, and they want the best for you. But they might not be the best ones to give you that honest, truthful feedback. It’s OK if you make a mistake. It’s one of the reasons I love this statement here: “Experiment. Fail. Learn. Repeat.” Failure’s not the end, unless you want it to be. Failure’s just a milestone, and the more you realize it’s a repeatable process in the approach you take to things, then I think your businesses have a better chance to succeed.