A high-ranking finance official is leaving Oakland as the city struggles to patch a projected $115 million shortfall.

As of Nov. 22, Sherry Jackson will no longer be employed by Oakland, city officials confirmed. Jackson is Oakland’s revenue and tax administrator. She oversees a bureau within the Finance Department that is responsible for collecting hundreds of millions of dollars in taxes from residents, businesses, and property owners.

It’s unclear why Jackson is leaving. The Oaklandside tried to reach Jackson through multiple calls and emails. She did not respond to our interview requests.

Jackson’s departure comes at a bleak time for Oakland. 

On Tuesday, Finance Department staff warned the City Council that Oakland faces a projected $115 million hole in the general purpose fund at the end of the fiscal year. The city must make substantial budget cuts before Dec. 31, which will likely include painful cuts to police and fire. The council must also approve deeper, permanent cuts to address a structural deficit that is expected to exceed $280 million across the next two-year budget cycle from July 2025 through June 2027.

The main cause of the shortfall in the general fund is overspending by the police and fire departments and the delayed sale of the city’s stake in the Coliseum. But city staff have also warned that Oakland may not be collecting all the tax revenue it’s owed.  

Earlier this year, the Finance Department reported that thousands of businesses have failed to pay taxes since 2021, leaving behind as much as $34 million. Senior staff in the Finance Department blamed the ransomware attack in 2023 for delaying the process for notifying businesses about delinquent taxes. Finance workers have shared detailed memos with the council about this issue but also struggled to provide a total for the number of businesses that were delinquent on payments over three years.

The city’s unions, which face possible furloughs and layoffs, have been sounding the alarm about what they say are problems in the revenue management bureau for over a year. 

In December 2023, several members of IFPTE Local 21 who work in the bureau sent a letter to City Administrator Johnson requesting a meeting to discuss “wide-ranging problems and issues caused by Sherry Jackson’s inability and unwillingness to perform her duties as the Revenue and Tax Administrator.” The letter-writers claimed that Jackson wasn’t performing her duties and that this was jeopardizing the collection of $118 million in business tax revenues.  

IFPTE did not respond to interview requests. 

Members of the union met with city officials at the end of 2023 to discuss tax collection issues. But the city officials who could answer detailed questions did not attend the meeting, according to an unfair practice charge filed several months later by IFPTE Local 21, which represents workers in the revenue bureau. The charge accused Oakland’s Director of Finance Erin Roseman of violating the collective bargaining agreement by failing to confer with the unions about financial plans that could affect the workforce.

The city contested the unfair practice charge, arguing that it responded in a timely fashion to every information request unless it was unduly burdensome or unavailable. IFPTE withdrew the charge after Oakland officials provided the union with the documents it sought.

Over the summer, a group of workers in the Revenue Management Bureau signed a petition to Mayor Sheng Thao, City Administrator Johnson, and the City Council declaring no confidence in Jackson’s leadership and asking the city administrator to intervene.

“Sherry Jackson has repeatedly failed to plan, organize, manage, and direct through subordinate supervisors the work of the Revenue Bureau,” the petition claimed.

Oakland’s handling of its budget problems were further complicated last week with the accidental release of a financial report that warned the city is facing bankruptcy if it doesn’t take corrective measures. The city quickly took that report down and replaced it with one that did not use terms like “Chapter 9” and “insolvency.” The city administration told The Oaklandside that “no employee has been disciplined or fired in connection with the Q1 report or its publication.”

Oakland has seen improvements in some of its revenue collection. Earlier this year, the city anticipated it would collect $115 million for fiscal year 2023-2024, or 7.6% less money than it budgeted for from business tax. But last month the Finance Department reported that it did better than expected, collecting $123.5 million. For the current fiscal year, 2023-2024, the city anticipates it will actually collect more than it budgeted for.