Secrets of a Lasting EdTech Company

Cliff King walks us through four decades of grit, growth, and success in building something of enduring value for customers and a community.

INTERVIEW | by Victor Rivero

Cliff King of Skyward.pngIn the early years of the company, there were only a handful of employees, “so we all had to pitch in and do a little bit of everything,” remembers Cliff King, the CEO of Skyward, the Wisconsin-based software company founded four years before Mark Zuckerberg was born and when Jimmy Carter was still president. The 580-employee firm specializes in K-12 school management and municipality management technologies, including Student Management, Human Resources, and Financial Management.

“Some of us were coding software, answering phones, making sales calls, and even going to schools and districts to install software and train end users,” he recalls.

Many of those early employees are still with Skyward today “and we all remember what it is like to be on the front lines with customers. One of our base philosophies is to treat others the way we want others to treat us.” This philosophy has been a cornerstone of their success.

Your company has a unique history, and is older than most edtech companies.

Skyward Logo.jpgCliff: Skyward has been around since 1980 and our first customer, Merrill Area Public School District, right here in Wisconsin, is still a customer after all these years.

That’s something we’re very proud of.

Even though we’ve been around for a long time, the company is well positioned for many more years of growth and success.

In March of 2016, you moved to your new world headquarters in Stevens Point, Wisconsin.

Yes, and In November of 2016 we announced our new Qmlativ platform which is receiving great reviews from customers.

Even though we’ve been around for a long time, the company is well positioned for many more years of growth and success.

Most recently, we reached a major milestone by partnering with our 2,000th customer. This was extra exciting because that customer happens to be Orange County Public Schools, which is the fourth largest district in Florida and the tenth largest in the United States.

What values persisted through the years? How is Skyward 2017 the same as the 1980 company?

CREDIT Skyward 01.pngCliff: Edtech is a fleeting industry. In the past 37 years, many companies burst on the scene only to vanish just as quickly because they made the mistake of thinking that a software product was all that mattered.

We’ve always done things a bit differently.

We’re always striving to make our software the absolute best it can be. Beyond that, we provide the kind of service and support we would expect to receive ourselves, which creates a better experience for our customers.

Our founder Jim King always said we needed to make our software products easy enough for our mother to use them.

We continue to emphasize this in our product development.

An easy-to-use software product is essential for success.

When we create software, our best resource has always been our customers. We are not the experts – our customers are – and we find that listening to their concerns goes a long way in creating our innovative products based on their needs.

As we move forward, we will continue to listen to our customers’ needs.

Thus far, these two strategies have been an effective way to deliver the software tools that school districts need to do their jobs efficiently.

When did it become apparent there was a need for what you provide? What is the history on that?

Cliff: When my brother Jim and his wife Jean started the company on September 1, 1980, they never dreamed the company would become what it is today.

Jim was an entrepreneur and wanted to be his own boss rather than work for someone else. His initial goal was focused around developing software for the new mini-computer market that emerged in the late 1970s.

Jim was an entrepreneur and wanted to be his own boss rather than work for someone else.

Our first school district customer was Merrill Area Public Schools (MAPS) in November of 1981. They were looking for a software package to calculate salary negotiations compensation costs for their district.

Up until that time, they did this all by hand and it took several days for them to complete the calculation. In addition to taking a lot of time, the potential for errors was quite high.

In late 1981, I became the first full-time employee of Jim King and Associates, as the company was known back then.

We created the Personnel Salary Negotiations software product according to the specifications that Merrill gave us and we had a functional product in January of 1982.

When we first heard about this project for MAPS, we also learned that there were 50 other school districts in the state that used the same type of computer. We saw an opportunity to capitalize on our programming efforts with our Salary Negotiations product.

At the time, we assumed that all school districts operated the same way.

Once we completed it, we sent out an invitation to all 50 schools to come see our new Salary Negotiations product that we had developed. We had high hopes that all 50 schools would attend.

Unfortunately, only three districts attended the demonstration.

We did the demonstration by running several different salary negotiations packages, tweaking just a few of the salary and benefit parameters that were part of the current salary package that MAPS had offered. Within 15 minutes, we had calculated all three packages with 100% accuracy in the cost estimates of each of the plans.

Interestingly, the plan that all three districts thought would be the costliest turned out to be the least expensive.

Needless to say, MAPS was very pleased that their district had a computer program to address bargaining with all of their unions and the three schools that were there all purchased the software.

Once we began to implement the software at each of the schools, we quickly found out that not all school districts work the same. We needed to create a parameter file to control how the software would work at each district.

To this day, we have one version of our software product that all of our current 2,000 customers use to run our ERP and SIS software products.

After we created the Salary Negotiations software product, we begin hearing about other needs that our customers had when it came to software.

We created a report writing system that allowed districts to easily run reports from their accounting system and budget for next year. We kept adding customers for both products and then the state of Wisconsin went from a cash-based accounting system to an accrual-based accounting system that included finance and payroll.

All the districts that had an accounting system would need to upgrade their current cash-based accounting products for an accrual-based accounting system.

CREDIT Skyward 02.pngWith the success that we were having with Wisconsin school districts, we announced that we would develop an accounting software system to meet the new requirement of the state of Wisconsin. Once we created our accounting software, other districts within the state were interested in our new product because it was less expensive, easy to use, and allowed the district to do more with less.

After we created the accounting system, our customers kept coming up with other systems that they needed so we would listen to what they needed and create software products that met their needs.

In 1984, Jim King and Associates became School Administration Software, Inc.

As you can imagine, that name was a mouthful and our customers referred to us as SASI. This was how we continued to grow the company in Wisconsin during the early 1980s.

In the late 80s, we started to get interest in our software products via word-of-mouth testimonials that our customers would share with their contacts outside of Wisconsin. As a result, we gained customers in both Minnesota and Illinois.

Throughout our company’s history, we continued to grow our business using this same philosophy.

We officially became Skyward in 1994.

As I mentioned earlier, when we were School Administration Software, Inc., our customers referred to us as SASI and we began using this acronym in some of our marketing materials. We received a letter from one of our competitors stating that SASI was too close to their trademarked name and we needed to change the name of the company.

Rather than employ a marketing firm for this, Jim decided to hold a contest amongst all employees to create a new name for the company. He had a couple of limitations that he wanted in the new name, one of which was that it could not be longer than 10 characters or 2 syllables. He offered $1,000 to the employee who submitted the winning name.

Our nephew knew that Jim had the nickname Sky King when he worked at the Schlitz Brewing Company.

Sky King was also an early 1960s television series I used to enjoy as a child about a pilot who used a plane to solve day-to-day issues.

With this knowledge, our nephew went to all the sources he could find to help him come up with a new name for the company that would be close to Sky King.

Jim chose Skyward and my nephew received $1,000.

Today, our software products are used in more than 2,000 school districts by over 7 million students. All our customers use the software built on a single set of source code to operate more efficiently and to create the Federal and State reports they need to receive their funding.

Today, our software products are used in more than 2,000 school districts by over 7 million students.

We provide all of this functionality without necessitating a dedicated programming staff to support it. It becomes an easy decision for a school district to select our product versus any of our competitors.

Any district not using our software on our secure cloud-hosted environment is spending more money than necessary to meet their administrative software needs.

What key lessons have you learned over the years as a company?

Cliff: Probably the biggest lesson we’ve learned is to listen to our customers.

Competitors come and go and we do pay attention to what they are doing with their products.

But we’ve always felt that if we listen to our customers and respond to their needs first and foremost, everything else will take care of itself.

It sounds simple and it’s a bit of a cliché, but we always try to treat our customers like we want others to treat us and that really comes down to listening to them and providing them with opportunities to give us input on our products and services.

Will it be 40 years in 2020? Anything planned for that?

Cliff: We have not really talked about that yet, but we will start planning our 40th anniversary celebration sometime next year.

How has your company impacted your local community and drawn and developed talent locally?

CREDIT Skyward 03.pngCliff: This could probably be a separate article all by itself.

Skyward currently has more than 580 employees and the population of Stevens Point is about 26,000.

We work very closely with the University of Wisconsin-Stevens Point (UWSP), Mid-State Technical College (MSTC), and even the local K-12 schools to help educate local students about careers in technology and job opportunities available right here in their backyard.

Skyward currently has more than 580 employees and the population of Stevens Point is about 26,000.

I also chair the Central Wisconsin IT Alliance (CWITA) which brings local business leaders together to promote our area for careers in IT or computer science.

Lastly, we have an incredible internship program through UWSP and MSTC and this has provided a great pipeline for talent for not only our IT and developer positions, but nearly all areas of the company.

How has Skyward stayed young; in other words, kept up with the times – regarding technology, philosophy, business model?

Cliff: Our philosophy is to hire interns, recent graduates, and seasoned professionals and teach them the Skyward way of doing things. Most employees who work here enjoy our culture so much that they choose to stay.

Our company promotes from within, giving all employees a clear vision of what they need to accomplish to earn more responsibility and compensation.

When you are growing as we are, we are always looking for the newest technology to ensure our product continues to meet our customers’ needs. We view that as an advantage and our culture here is very open so even the employees who are at the very beginning of their careers are encouraged to share their ideas.

In 2017, a young professional networking company in Milwaukee, Wisconsin recognized our company as one of the top 10 places to work in Wisconsin for young professionals.

What is your perspective on the explosion of edtech companies and activity in the last 3 to 5 years?

Cliff: I’ve always believed that competition is a good thing.

Education leaders are smart.

They do their homework before they implement new products and solutions, so the companies that are providing good value will thrive and the ones that aren’t won’t.

In the last few years, there’s been an increase in the amount of private equity money pouring into edtech and that can actually hurt competition as the big companies swallow up the smaller ones.

Education leaders are smart. They do their homework before they implement new products and solutions, so the companies that are providing good value will thrive and the ones that aren’t won’t.

We view that as a positive for us because we feel we can always give our customers a better experience than they’ll get from a vendor that’s going to change owners and leadership every few years.

What do you believe is the state of education these days?

Cliff: I get a little frustrated with all the doom-and-gloom articles I read about education.

The educators I meet at our user conferences and other events are some of the most dedicated and passionate people I have ever met.

They have so much on their plates and so many more things to deal with than the educators had when I was in school.

Making sure our children and grandchildren are receiving a good education is the most important job in the world. We always try to remember that and hope we are doing our part by delivering tools that will make their lives a little easier.

CREDIT Skyward bldg.pngWhy is it so important that Skyward and other companies in education continue to flourish?

Cliff: Nothing is more important to the future of our country and our communities than education. Today’s kids will be the leaders of tomorrow.

Teaching is a difficult and often thankless job so it’s important that edtech companies do everything they can to make the lives of educators easier and give them the tools they need to help them do their jobs more effectively.

We need to do everything we can to make sure that our best educators stay in the classrooms and district offices because that is where they can make the biggest impact on kids’ lives.

What do you believe is the role of technology in education? What makes you say that?

Cliff: Technology needs to make things easier for educators.

It needs to be easy to use and it needs to save them time and hopefully also save districts money.

Educators are like everybody else today in that they are all being asked to do more with fewer resources.

Edtech companies that create solutions that do that will stand the test of time.

Educators are like everybody else today in that they are all being asked to do more with fewer resources. Edtech companies that create solutions that do that will stand the test of time.

I see a lot of products in our space that are impressive on the surface but don’t have much substance when you strip away the fluff. If it’s not making things easier for teachers and office staff, you can bet it won’t be around for very long.

Victor Rivero is the Editor-in-Chief of EdTech Digest. Write to:


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