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Milwaukee election shakeup triggers doubts about whether new leader is ready to run 2024 vote

City officials defend their decision to replace an experienced chief after staff members air concerns.

A woman wearing a gray suit works at a machine in a room with a man standing near an orange brick wall in the background.
Milwaukee Election Commission then-Deputy Director Paulina Gutierrez prepares to export absentee ballot election results from a tabulator on April 2, 2024. (Alexander Shur / Votebeat)

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Update, May 23, 2024: This article has been updated to note the terms of an employment contract for former executive director Claire Woodall’s new role.

Several members of Milwaukee’s election staff have voiced concerns to the mayor’s office about the inexperience of the new leader chosen to replace the Election Commission’s recently ousted executive director, two people close to the matter told Votebeat.

The new head, Paulina Gutiérrez, became deputy director of the commission in 2023 and had worked in several other positions in city and state government before that. But during her tenure at the commission, she has not worked a federal general election.

In addition to staff members raising concerns in a meeting with the mayor’s chief of staff and Gutiérrez herself, two employees wrote letters to the mayor’s office noting their doubts about whether she is equipped to lead the commission during a critical time in Wisconsin’s largest city, said a person close to the commission who requested anonymity to avoid professional consequences.

The concerns sprang from Mayor Cavalier Johnson’s surprise move not to reappoint Claire Woodall, who has been with the commission for about a decade and executive director since 2020. Woodall told Votebeat that she was ousted because she was quoted in a recent news article criticizing election staff over a ballot error. A spokesperson for the mayor said there was more to it but declined to be more specific.

The mayor’s office didn’t directly address multiple Votebeat questions about the mayor’s selection process, and Gutiérrez declined to answer Votebeat’s questions.

City officials maintain the mayor made the right choice appointing Gutiérrez.

“Paulina’s integrity and capabilities are ideally suited to this position,” Johnson said in a statement announcing her appointment. “She will lead the office at an important juncture when public scrutiny of the work of the department will be extremely high. I have confidence in her, and I will make certain the department has the resources it needs to fulfill its duties.”

In April, in her role as deputy director, Gutiérrez managed the city’s central count facility, where election officials count absentee ballots. Before joining the commission, Gutiérrez spent over a decade working with public safety professionals in leadership roles at the Wisconsin Department of Corrections, City of Milwaukee Department of Administration, the city’s Fire & Police Commission and Marquette Law School, according to her bio on the website of Milwaukee’s Harbor District, of which Gutiérrez is a board member.

The city council has to act on her appointment by June, but Gutiérrez is running the office in the meantime, mayoral spokesperson Jeff Fleming said.

Amid the shake-up, Fleming said Woodall would be back to fill a temporary position at the election commission that city staff said would address the “acute need to capitalize upon the expertise and knowledge transfer of outgoing staff.”

Mayoral staff told the commission of the leadership change in early May but has since done little to address election staff concerns, one person close to the commission said.

The transition is happening just six months ahead of the 2024 presidential election, a contest that will put Milwaukee under scrutiny from election observers as it processes hundreds of thousands of ballots, likely late into the night on Election Day or the next morning.

Elections in the Democratic stronghold are already under a microscope, especially because of its practice of counting absentee ballots in a single location. That sometimes leads to a late upload of voting results that reflect a larger proportion of Democratic voters. In that environment, the slightest error — or even a perceived error — can trigger speculation or suspicion of election malfeasance.

Amid unprecedented turnover among election officials nationwide, election offices are dealing with mistakes occurring at the hands of inexperienced administrators. A Votebeat review in Pennsylvania, for example, found election errors often linked to administrators with little election experience.

Errors are typically rare, even with inexperienced election officials, said UCLA assistant political science professor Dan Thompson, who studies election administration.

But “even if election turnover doesn’t lead to errors or problems noticeable to the public,” he said, “it can make the process of running an election much less pleasant and much more stressful.”

The Milwaukee Election Commission, with about 10 full-time staff at any given point, is responsible for administering elections in the city. The staff sends out ballots, manages polling sites, processes absentee ballots and helps troubleshoot election issues that voters face.

Gutiérrez will have help to run election, mayor’s office says

The uproar over Gutiérrez began the day her appointment was announced to staff. In a meeting with the mayor’s chief of staff, several election commission staff questioned her ability to lead the organization, citing her lack of election experience, two people familiar with the discussions told Votebeat. In front of Gutiérrez, one person asked Johnson’s chief of staff, Nick DeSiato, what to do if commission staff didn’t have confidence in Gutiérrez’s ability to run elections, they said.

The following day, two staff members sent letters to the mayor’s office outlining their concerns, one person said. Votebeat requested copies of the letters through a public-records request two weeks ago, but the mayor’s office hasn’t provided them.

One person close to the commission said Johnson met with the staff last week, and emphasized that he had already made his decision.

The mayor’s staff has talked to multiple people experienced with elections who are ready to help Gutiérrez, Fleming told Votebeat.

Gutiérrez “is well acquainted with the process; there are others in the office who have extensive experience; and, the mayor has assured her that resources from both inside and outside city government will be available to support her work,” he said.

Fleming declined to respond to concerns voiced by people not speaking on the record to Votebeat and wouldn’t discuss whether other candidates were considered for the position. He disputed the notion that Gutiérrez lacked election leadership experience.

In a May 5 email to staff, Gutiérrez acknowledged that changing leadership can be an uncertain and demanding experience.

“It is not lost on me that Claire’s wealth of knowledge and understanding of elections is extensive, and her insight in elections that she carries can only be cultivated through years of experience,” she wrote. “I am building a network of people with experience in elections to support our efforts in this upcoming critical election year. I am also connecting with other jurisdictions and election leaders to assist in my transition.”

She added that she planned one-on-one meetings with employees.

Gutiérrez declined to address Votebeat questions about staff concerns over her preparedness. She didn’t respond to emails seeking comment until after Votebeat tried to contact her in person several days later.

A Votebeat reporter who went to the commission office to speak with Gutiérrez in person was told by staff members that she wasn’t there. But then the reporter was alerted by two other people that she was in her office, watching live video of the reporter through a lobby camera feed.

Asked about that, Gutiérrez said two days later: “I regret the miscommunication. My intention was to convey to you that I was not available, not that I wasn’t there.”

“Out of respect for the confirmation process, I’m not engaging media at this time,” she later said.

Ann Jacobs, a Democratic member of the Wisconsin Elections Commission, said elections aren’t about one person.

“Elections are based on the systems and organization and the people who make it happen,” she said. “Milwaukee has some really good systems in place, and I’m certain she’s going to be able to step in and accomplish what she needs to accomplish.”

Jacobs said she recognized Gutiérrez’s competence and organization when Gutiérrez ran the city’s central count in April.

“I have every confidence she’s got the ability to do the job,” Jacobs said.

Claire Woodall will have temporary role at the commission

One of the people slated to help Gutiérrez through the transition is her predecessor, Woodall, who has worked at the commission since 2013, except for a brief break in 2019 to serve as Cedarburg’s clerk.

“There’s no one who would say that she was not extremely capable at running elections,” Fleming said, adding that Woodall “administered elections in Milwaukee with integrity, accuracy, and dedication.”

Woodall faced questions this year over an error in which more than 220 Milwaukee residents received absentee ballots for the incorrect ward. Much of the criticism came after Woodall told the Milwaukee Journal Sentinel, about the commission’s mistake, “I can’t express how frustrating and infuriating it is that it just seems like there was no critical thinking involved or communication.”

Woodall had to rebuild trust and strengthen morale after that comment went public, she told Votebeat shortly after her removal.

“I regretted being that forthright … but also don’t feel like I can skirt details or sidestep questions in my line of work,” she said. “Folks didn’t follow procedure, and I was extremely frustrated when I uncovered that.”

Woodall said the comment to the newspaper was the sole reason Milwaukee officials cited for not reappointing her. Fleming disputed that.

“There were multiple … non-operational issues, management issues that were of significant concern,” he said, declining to elaborate.

On May 10, after commission staff raised their concerns about Gutiérrez with the mayor’s office, staff at the city’s employment office outlined a temporary associate director position at the commission to support the transition.

Woodall and Fleming told Votebeat she would fill that role, which lasts between May and August.

Under a separation agreement between Woodall and the city that also temporarily extends her time with the election commission, Woodall can’t contact commission staff to discuss the election process, and must forward staff who contact her about elections to Gutierrez; is heavily limited in what she can tell the media; and must work from a remote location. The agreement also holds that the mayor’s office and Woodall, who both have been limited in their comments to the public about this situation, cannot disparage each other.

The agreement, however, states that in her continued time with the commission, Woodall “shall not perform any task in the conduct of any elections for the City of Milwaukee,” directly referencing the language of a recently passed constitutional amendment limiting outside election assistance.

“I am dedicated to a smooth and successful transition of leadership and will remain available to support Paulina and the staff in the coming months,” Woodall said. “Regardless of who leads, it is the collective expertise and remarkable teamwork of 9 others that has ensured transparent, accurate, accessible elections in Milwaukee.”

Alexander Shur is a reporter for Votebeat based in Wisconsin. Contact Alexander at

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