Robert Cole begins first day on the job

a man standing at a podium in front of a tv
New Islamorada Village Manager Robert Cole addresses the council following contract approval at the March 12 meeting at Founders Park Community Center. JIM McCARTHY/Keys Weekly

Islamorada council members wasted no time in approving a contract for Robert Cole, the new village manager who was selected last month following a months-long search. Following a 5-0 vote at the March 12 council meeting, Cole’s first day on the job began the next day on March 13.

Per the contract, Cole will receive an annual $200,000 salary with no increases for 18 months. His salary can be adjusted from time-to-time, however, to account for cost-of-living adjustments which are consistent with changes to other village employees. 

As for housing, Cole will receive an allowance of $4,000 a month as part of the compensation package. He’ll also receive health insurance, retirement and three weeks vacation annually. Cole won’t get any relocation expenses, according to attorney Alison Smith. 

Under the agreement, the council will evaluate the village manager’s performance every 60 days until his anniversary date. After that, the council will conduct an annual evaluation on Cole’s performance within 30 days of his anniversary. The human resources department will be responsible for notifying council members and the village attorney at least 60 days prior to the anniversary date. 

Council members can evaluate Cole in written form, using a numerical rating system to assess attitude, judgment, ethics, attendance, execution of policy set by council, preparedness for meetings and communication with council, to name a few. Council members can choose to forgo the written evaluation and meet with Cole in person to discuss his performance. 

Cole’s contract with the village goes through March 13, 2025. Cole, who was in attendance for the March 12 meeting, subsequently thanked the council for having faith in selecting him as Islamorada’s next village manager. 

“I feel blessed to work in the gem of the Florida Keys, and I’m looking forward with great anticipation to seeing each of you and helping to advance the important goals and objectives we have to benefit the Islamorada community,” he said. 

Council members also approved changes to an agreement between the village and Monroe County for the services of Kimberly Matthews, who served as interim manager since January. The county director of strategic planning and libraries, Matthews will now act as an advisor for the village as Cole takes the reins as village manager. Matthews will stay with the village through April 5.

Matthews was slotted as the third interim manager for the village after the council voted 3-2 to not renew the contract of former manager Ted Yates last July. The county stepped in to assist the village last August by loaning several department heads to guide the council as they began a national search for a new manager.

Jim McCarthy
Jim McCarthy is one of the many who escaped the snow and frigid temperatures in Western New York. A former crime & court reporter and city editor for two Western New York newspapers, Jim has been honing his craft since he graduated from St. Bonaventure University in 2014. In his 5-plus years in the Keys, Jim has enjoyed connecting with the community. Jim is past president of the Key Largo Sunset Rotary Club. When he's not working, he's busy chasing his son, Lucas, around the house and enjoying time with family.