Jon Roskill began his career at a now-defunct computer hardware company in Boston in the late 1980s. In 1993, Roskill’s wife was offered a position at the University of Washington School of Medicine, so he got in touch with a friend at “a small software company called Microsoft” for a job. The rest, as they say, is history.


Jon Roskill, CEO of Acumatica. Photo courtesy Acumatica.

“Three weeks later, we were moving across the country,” Roskill said. “We came out thinking we would be here for a three- or four-year stint, and here we are 25 years later.”

Today, Roskill is the CEO of Acumatica, a Bellevue-based company founded in 2008 that offers cloud-based business-management software. The company recently moved to Bellevue from Kirkland in search of space to accommodate its growing number of employees. Acumatica also operates offices elsewhere across the United States, as well as in Canada, Russia, Asia, and Mexico.

A marketing man at heart, Roskill learned how to stretch his sales skills as a member of the Boys & Girls Clubs’ board of governors. “I was very uncomfortable approaching people for donations, and you have to figure out your sweet spot and that’s true in nonprofit and it’s true in the business,” he said.

Roskill took a minute to share some of his wealth of knowledge with 425 Business, highlighting the importance of understanding the details, and keeping control over your career.

Understand all the facets of the business. “I am not a career salesperson, and yet understanding the detail around setting sales quotas is super important. It’s one of those things that if you get it wrong one way, you end up with upset salespeople, and the other way you’re not maximizing the value for the company. It’s a very important discipline.”

Prove them wrong. “Several times early in my career I had people tell me flat out that they didn’t think I could do the job. For me, it’s just the ultimate challenge to step up and prove them wrong. Don’t let people tell you what you can’t do, because they don’t really know you and what you’re ready to step up and go for.”

Don’t let your job hold back your career. “I’m very much a product person, and I really wanted to get back to being connected to a product. At that point, at Microsoft, I was too senior in my role to be able to move back into a product group. It was time for me to leave the nest and find my own product element outside the company.”

This article originally appeared in the March 2016 issue of “425 Business.”