The leader of the higher ed technology company named Symplicity is now learning a valuable business lesson: Cheating is never the answer to solving business problems.

He may have plenty of of time to reflect on lessons learned, too.

Inside Higher Ed’s Cory Weinberg files this report:

During the summer of 2010, Symplicity Corporation knew it wasn’t keeping up with the competition.

Trying to stand out in the small world of technology companies that supply colleges with software to track student disciplinary cases, Symplicity CEO Ariel Manuel Friedler noticed more colleges and universities picking its main competitor, Maxient, because its software “feels like a website,” he emailed to employees. “We are bleeding … we have lost close to a dozen [clients] this year.”

To win back colleges, Symplicity’s top leader and two other employees hacked their way into Maxient’s servers to stock up on the competitor’s product design, new features and software layout.

“Desperate times call for desperate measures,” Friedler told the chief technology officer, Alok Dhir, in a message, according to court documents.

That wasn’t the first or last time that Friedler and other workers at Symplicity gained illegal access to competitors’ software and client list. In January 2010, he texted Dhir that he was trying to hide his IP address to “get into a competitor’s shit.”

After a four-year federal investigation, Friedler, 36, now faces up to five years in prison after pleading guilty last week to conspiring between 2007 and 2011 to hack into the computer systems of two competitors, Maxient and Pave Systems Inc.

Friedler last week also left the company he founded 18 years ago as a sophomore at Northwestern University and issued a mea culpa last week, saying he “let my competitiveness get the best of me and I crossed a line.”

He will be sentenced by a U.S. district judge on Aug. 1.

The depth of the scandal is almost unheard-of in the higher education technology market – and may just be the start of a larger dispute.

Maxient officials are now mulling civil action against the company after initially raising concerns with federal officials four years ago that when it traced unauthorized log-ins to its network from Symplicity’s headquarters in Arlington, Va.

Symplicity, Maxient and their competitors “derive their competitive edge from the design and features of the system, which they consider proprietary and confidential,” according to court documents. Maxient lost at least $217,097 because of Friedler’s conspiracy, according to the plea agreement filed last week.