Intern to CEO: A Page from the Skyward History Book

#District Stories

Caroline Gilchrist

by Caroline Gilchrist

Caroline Gilchrist Skyward Storyteller

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Scott Glinski’s “Skyward” Journey

Scott Glinski’s career didn’t begin by scouring the jobs section of the newspaper. There were no inky fingers, no highlighted "help wanted" ads—just the smell of sunscreen and gasoline mingling in the air.

Every summer, Scott’s family spent weeks on the Mississippi River, boating and enjoying the sunshine with family friends Walter and Alice Panko. But this year—1986—was a bit different than the others. This year, Walter and Alice had brought their grandson, Jerry King, on vacation with them. It was the first time Scott had met Jerry, so they made conversation about what they had in common: a love for boats. As the end of their vacation neared, Walter told Scott that his son-in-law, Jerry’s father, had recently started an educational software business. He encouraged Scott to apply.

Scott still had a year of schooling left—he was enrolled in a two-year program at Midstate Technical College in Stevens Point—but he ultimately decided to take Walter’s advice. He submitted an application, and in December Scott was called in for an interview at Skyward, which was at the time called School Administration Software, Inc., or SASI (“sassy”). Not long later, Scott became the company’s seventeenth employee: an intern in the IT department.

But Scott couldn’t start right away. SASI had completely outgrown its office space, and there just wasn’t room for him. In April 1987, when SASI had settled into its first company-owned building, Scott made his start. His role? Installing computers for school districts that purchased SASI’s software and demonstrating how to use them. Upon his graduation in May, the work turned full time.

SASI was growing at a rapid pace. By October 1987, SASI had about 80 Wisconsin district customers and a few in Minnesota. Hoping to increase business in Minnesota, owner Jim King approached Scott and asked if he would be willing to move across state lines to help open the company’s first branch office. Never one to turn down an opportunity for growth, Scott agreed.

In St. Cloud, Scott initially did a lot of the same technical work he did in Wisconsin, but soon he began studying the product itself. He became involved in the student records area of customer service—and as there weren’t many IT professionals in school districts back then, his services were both needed and appreciated. With a background in customer service, he next began assisting in sales. “We were a small company,” Scott reflects today. “We all wore a lot of hats.”

Over time, Scott’s hat collection grew, and he swapped out some old hats for new ones. In 1990, Scott moved from Minnesota down to Bloomington, Illinois, and became branch manager of another brand-new office. He moved back to the corporate office in 1998—now with a wife and two small children—as vice president of operations. He was then promoted to chief operations officer. In addition to being responsible for day-to-day operations, he oversaw a group of programmers; this gave him further experience and helped round out his skillset.

From there, he went on to become the vice president of sales and marketing. Next up? President of the company from 2008 through 2018, where he got to oversee the construction of Skyward’s new 900-person-capacity world headquarters.

In 2019, Scott became the company’s chief executive officer.

Happy Nostalgia

After over 30 years with the company, there are bound to be a lot of great memories. But a few stand out in Scott’s mind.

One such memory took place in the late ‘80s when Scott was working in Minnesota. At the time, SASI could sell its student information system in Minnesota, but not its finance/HR system; the company first needed the state’s approval. The school district of Staples loved the product and consequently agreed to partner with SASI throughout the approval process.

“I can remember working with the business manager there, Bob Hammon,” Scott recalls. “He and I had some extremely late nights working through the system to get certified. On several occasions, it would get to be ten or eleven o’clock, and I wasn’t planning on spending the night there. I didn’t have a hotel and I lived about three hours away, and Bob would invite me over to his house. I would go to his house at midnight or one in the morning and sleep in the spare bedroom. His wife would make us breakfast, and we’d head back to the office. He was just one of those customers; without Bob believing in Skyward and helping us through that certification, I don’t know where we’d be today in the state of Minnesota.”

Scott’s funniest memory? That took place in Little Falls, Minnesota, where Skyward achieved its first wide-area network multi-entity system. Once again, Scott was working late nights.

“One night it got to be about two in the morning,” Scott remembers. “I didn’t feel like driving home just to get back up in the morning again, so I lay down in the computer room. I woke up at about five in the morning, and I went downstairs to the cafeteria to get something out of the vending machine. As I went around the corner, the superintendent—who had come in early that day to get some work done—was coming the other way. It was dark, and we were both scared. We both went, ‘Who are you?!’ He said, ‘I’m the superintendent!’ and I said, ‘I work for Skyward; I’m here working on your computer system!’”

Laughing, Scott adds, “That was just one of those funny moments.”

"You’re Never Done Learning”

With experience comes wisdom.

Scott has done what many people strive to do—climb the corporate ladder from the very bottom to the very top. Having stood on that ladder, pulling himself up rung by rung, he understands what it takes. And he knows what to share with other people who share this dream.

“You really need to be passionate about what you do,” he explains. “You need to prove yourself, and you have to be patient. Opportunities will come along. And you will make mistakes, but you learn from the mistakes. You’re never done learning.”

Through it all, Scott says, it’s important to keep in perspective what your work is all about. “First and foremost, it’s about taking care of our customers’ needs with our product.” To that end, success is measured by more than financial growth. “It’s incredible how many friendships are built with our customers.”

A Witness to Change

In his thirty-plus years with Skyward, Scott Glinski has seen firsthand the transformation of a small, “sassy” start-up to a firmly established and respected company. Its customer base has spread not only across the country, but across the world. The number of employees has skyrocketed to nearly 700—including Scott’s own children, Emily and Nathan. And that young boy who shared his love of boats, Jerry King, has become Skyward’s chairman of the board.

Scott has faced his fair share of challenges—but rather than wearing him down, those challenges have strengthened him. They’ve made him better fit for leadership. And lead he does, always aiming upwards, always striving to bring a better experience to customers and employees alike.