How Jason Blessing Slipped Out Of Larry Ellison's Grasp Twice

Jason BlessingPlex Systems CEO Jason Blessing

Photo: LinkedIn/Jason Blessing

Jason Blessing is the brand-new CEO of a hot enterprise startup, Plex Systems, but it was a strange road that got him here.Plex Systems offers enterprise resource planning software to manufacturers, competing with Oracle, SAP, and Infor.

It’s based in a suburb of Detroit, Auburn Hills, in Blessing’s home state of Michigan. Plex poached Blessing after it scored a $30 million investment from Accel Partners in December.

Not only did they offer him the CEO title—his dream job—but the company is near his beloved alma mater University of Michigan, where he can finally use his football season tickets.

“I will take those to the grave with me,” he told Business Insider.

To get here, Blessing had to escape the clutches of Oracle, twice.

Blessing was a vice president running PeopleSoft’s consulting business when Oracle launched the nastiest hostile takeover in software history. At one point, Oracle CEO Larry Ellison even jokingly threatened to shoot PeopleSoft’s CEO.

Oracle won the battle and in 2004 Blessing was surprised to find his new employer was “good for me.”

“Oracle gave PeopleSoft employees great opportunities,” he said.

He went on to run a big regional consulting operation for Oracle.

But he left in two years later to join Taleo, a startup lead by ex-PeopleSoft alum Mike Gregoire.

Blessing ran product development starting with six employees and growing his team to 580 before Oracle came calling again.

Gregoire was no fan of Oracle or Larry Ellison. He described the hostile takeover as “18 months of continuous bombardment.”

But for $1.9 billion, he sold to Oracle anyway.

So Blessing was again an Oracle employee.

A few months later, Plex Systems called “out of the blue” and offered him his second escape.

A happy ending.

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