It was an offer he couldn't refuse.
And it was for a reason she understands.
On Tuesday, Sudbury Public Schools Superintendent Dr. Anne Wilson said the offer made to Dees, despite it being a lateral move and to a smaller school, included a significant bump in salary. And the chance to offer his family a more financially secure life was something she understood.
"It's a financial opportunity he couldn't pass up," she said. "The salaries in Wellesley are much higher than in Sudbury. He'll make 25 percent more than here. It's a huge jump in pay."
Wilson, who is in her first year as superintendent, said she does not believe in holding people back from better opportunities, but admitted Dees' leaving would be a personal and professional loss.
"From my personal experience with Jeff this year and form what I've heard from others, he's done a wonderful job at Loring," she said. "He created a great community. I'm feeling the loss personally. But when someone is able to provide for their family financially, it's difficult not to wish them well."
Wellesley Public Schools Superintendent Bella Wong said she was overjoyed when Dees accepted the position.
"We’re thrilled he’s decided to come to Wellesley," Wong said. "The school committee is ecstatic, as well."
Wong said many things stood out about Dees during the interview process, which made offering him the position an easy decision.
"He clearly is an experienced educator," she said. "He brings a lot of positive energy. What we picked up is he has that certain magic with kids and staff. He has a lot of motivational and inspirational energy. He seems very kid oriented and respectful of other professionals."
Wong said Dees is taking over a school that is in great shape academically and hopes he can lead it toward continued success.
"He's coming into an established school," she said. "We hope Jeff takes the school forward and sustains its quality."
Wilson said the process to find a replacement for Dees is already in motion, but that because of the timing it might be difficult to find the right person quickly.
"We're going to post the position this week, see what candidates we get and make a determination," she said. "We'll have an interview team for the initial interview made up of staff, parents and administrators. I'll then take feedback to name a finalist."
Should a finalist be named, that person would then visit the district, hold a forum for parents and staff, and visit classrooms with student leaders.
With April vacation scheduled for next week, Wilson said interviews might not begin until May.
"If we can't find a finalist, we'll appoint an interim principal, someone who may be retired with experience, someone with a good track record to help us through next year. Then in the fall, we'll advertise again and hopefully find a better pool of candidates."
This is the second time in the past year Loring has lost an educator to the Wellesley school system.
Wilson hopes this isn't a recurring situation.
"The unfortunate thing is principal salaries are lower here ... so are teacher, support staff and central office salaries," Wilson said. "I'm worried to lose people in all roles. When money comes into play it makes a difference. When you have to support a family and you're offered another $25,000, that's significant and can be frustrating. Until salaries become more competitive (in Sudbury), it will continue to be a concern. It's not the best situation."
Dees declined comment for the story.