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DENTON – It was announced at the Tuesday, February 3 Caroline County Board of Education meeting that Dr. Tara Downes, the current Assistant Superintendent of CCPS, has accepted a position with the Maryland State Department of Education and will be leaving CCPS effective May 1, 2026. Superintendent Dr. Derek Simmons explained that he is taking the opportunity of Dr. Downes’s departure to restructure the titles, roles, and responsibilities of the highest CCPS officials.
“When change comes, you can learn to embrace change and look at opportunities when they present themselves. And with this change, and I am instituting a new organizational chart,” Dr. Simmons said, “we're reorganizing the system a little bit…We have different needs now than we did three years ago.” Under this new system, the position of Assistant Superintendent of Instruction is morphing into a title of Chief Academic Officer. Dr. Simmons explained that this will allow the officeholder to better focus solely on instructional administration.
“It will still be aligned with the work, with the blueprint. But there's a lot of other things that Dr. Downes got pulled into as the number two in the district that she was very capable to handle very well, but we're going to take the opportunity to take that academic position and focus it a little bit more on just academics,” he said, “With that, the school system does need a clear number two, and I'm a firm believer that we have a plan in place.”
Dr. Simmons explained that CCPS would be carving out a new title in the chart for this second-in-command: a Deputy Superintendent. “The Deputy is somebody who will be relied on to be pulled into absolutely everything that I am and to be able to pick up and move our system forward if something were to happen, but also to give me that extra level over top of all the divisions.” Dr. Simmons clarified that CCPS is not adding positions, “just reorganizing the chart.”
“There is a clear choice for me as Superintendent, and that clear choice that I'm recommending to the Board tonight is Dr. Rob Willoughby to be appointed from his current position as Director of Administrative Services into the Deputy Superintendent role.”
Dr. Willoughby got his start as a social studies teacher for CCPS in 2002, after coincidentily being mentored by Dr. Simmons. Over the years he has also served in school administration at Lockerman Middle, North Caroline High, and Colonel Richardson Middle, before serving in various roles at the Board office.
“I'll be honest, a lot of the foundational work that we've been able to do over the last few years in my role as Superintendent would not have been possible without Rob's knowledge, his skill, his understanding, his ability to be flexible and to navigate all of the waters associated with things in the administrative office, in the HR office, understanding enough about instruction to help us when we have those big things that we're working through, and even having touch points in pretty much anything you can think of in the state,” Dr. Simmons said, “I can't think of a better person to work with me closely over the next remainder of my contract.”
After assuring Dr. Willoughby’s wife and two young children approved of his promotion, the Board voted unanimously to follow Dr. Simmons’ recommendation.
“Thank you for your support…I'm honored,” Dr. Willoughby said. He will take over the Deputy Superintendent position effective May 1 after Dr. Downes moves into her new role with MSDE. The Chief Academic Officer position is currently vacant.
