Cheles had previously announced his plan to retire from the Office of Administration IT Services, citing personal reasons and calling his work with Missouri an ideal career "capstone."
Under Cheles, the state sought a program of increased efficiency, focusing on spending, increased worker productivity, and a plan to break down the siloed nature of state leadership to advance a more unified governance approach.
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Speaking with Government Technology, Cheles said that entering state government for the first time had presented its own unique set of challenges.
"There are some very significant differences between government and the private sector," he said. "The whole procurement process and RFPs and bidding was completely different than what I was able to do in the private sector. I had far more leverage in business than I had in government to put together a good deal," he said.
Cheles said he sought to shift norms around vendor relationships and procurements, looking to optimize those relationships. "I hope I opened people's eyes to [the idea] that you constantly have to look for value," he said.
Cheles also focused on increasing worker pay by leveraging increased productivity. To do this, he launched a large workforce training program that resulted in staff logging around 2,800 more hours of training than when he first started.
"I set a goal that 5 percent of their hours I wanted spent on training and I made it clear that supervisors that get in the way of training aren't doing their jobs," he said.
Cheles also focused on fostering a more unified approach to governance through increased communication.
"This was an extremely siloed organization. We had people within their own departments not talking to each other," he said. "I finally put my foot down and said we're not going to be that type of organization. I expect people to talk."
It is unclear who will immediately replace Cheles, said Angel Hughes, assistant to the CIO. However, Cheles commented that it seemed the state was nearing a decision.
"I have not been part of the process," he said. "What I do hear is that they're 'close,' that it's an outside hire and that they either have made an offer or are close to finalizing one."