Jennings likely to leave Portland by November

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City Manager Jon Jennings is expected to leave the city Nov. 1 for a position in Clearwater, Florida, creating an unexpectedly urgent need for Portland to find an interim replacement.

Jennings, who has been Portland’s sometimes embattled manager since 2015, was named the next manager of the Florida city last week and will start work there Nov. 8.

Jon Jennings
Portland City Manager Jon Jennings.

Mayor Kate Snyder said once the City Council became aware Jennings was looking for a new job she adopted the mindset that “anything was possible.” While the hope had been Jennings would provide notice of 90 days, or even 120 days, she said she wasn’t surprised Clearwater was in a hurry after that city’s longtime manager died.

She said Portland’s goal will be to name an interim manager at the first council meeting in October, so that person would have time to work with Jennings before he leaves.

The council is slated to hold a workshop Thursday, Sept. 16, on how it will hire a new manager.

“My intention is that we name an interim sooner rather than later,” Snyder said.

The city recently hired a new assistant city manager, Anne McGuire, who began work on Aug. 30.

Several city councilors have said they would like to see an interim manager promoted from within the existing administration to ensure the person selected is up to speed with the city’s affairs while a search is conducted for the next permanent manager.

Snyder said the council will have more clarity after the Sept. 16 workshop, but said most councilors have agreed there is no reason to delay the search.

“I don’t make decisions unilaterally,” she said. “The manager is an employee of the full Council. We will navigate that process.”

The council held an Aug. 30 workshop to discuss replacing Jennings, who was expected to leave when his contract expires in July 2022. Councilors were divided on the best course of action, with some supporting finding an interim while also conducting a search for a long-term manager, while others favored delaying a search for the long-term replacement.

Some councilors expressed concerns about the candidates the city could attract without knowing what will come from the Charter Commission, which could recommend providing the city manager with less authority.

That workshop was scheduled before Jennings became a finalist for the Florida job, with councilors unaware he would possibly leave Portland before his contract expired.

Under his agreement with Clearwater, Jennings will be paid $230,000 annually to manage the city of approximately 115,000 people. In Portland, which has 66,600 residents, Jennings’ annual salary was almost $180,000.  

He will also be paid up to $35,000 in moving costs by Clearwater.

Unlike his employment in Portland, which was under a pair of three-year contracts, Jennings’ Florida contract will be in effect “until terminated” by the city or by him.