TAMPA — In January 2021, during her second week as chief executive of Hillsborough’s transportation agency, Adelee Le Grand met in a Ybor City conference room with senior employees excited for face time with the new boss.

But the mood shifted when Le Grand told the group they had a reputation for being “backstabbers” and would need to “earn her trust,” according to three people who attended.

Those comments set the tone for Le Grand’s tenure, the employees said. Dozens of senior staffers have been pushed out and key positions have been left unfilled while the agency teeters financially. Hundreds of pages of public records and interviews with 15 current and former employees, including chiefs and two of Le Grand’s former executive assistants, depict an atmosphere of fear and secrecy at the transit agency serving Florida’s fourth most populous county.

“We had such high hopes after so much transition. We thought we had a leader who was excited to work with us,” said Ruthie Reyes Burckard, whose career in management at Hillsborough Area Regional Transit Authority spanned almost two decades and 10 CEOs. “We were wrong.”

The accounts, from some speaking publicly for the first time, come as the agency undergoes an external probe into allegations of a toxic workplace and the double-dipping of a top employee who reported directly to Le Grand.

Le Grand declined to comment, saying it would be inappropriate to do so given the ongoing investigation but provided a written statement: “It is important that the investigation moves forward so that we can continue to focus on improving public transit services in Hillsborough County.” She has held the top job since the start of last year and is the highest-paid executive in the history of HART, earning $287,500 annually.

Vacancies and turnover have left some employees worried about the agency’s future and the public they serve, according to interviews and documents reviewed by the Tampa Bay Times.

A May audit of HART’s financial statements found the agency’s “absence of finance staff put a strain on the current personnel to complete their responsibilities in an accurate and timely manner,” according to accounting firm Cherry Bekaert.

Stretched thin, the staff made errors such as $361,000 in unreported federal expenditures and inventory being understated by approximately $159,000, according to the audit. Auditors found the staffing issue to constitute a “material weakness” of the agency. HART management said they agreed.

Chief financial officer Loretta Kirk wrote in early May that the agency was “aggressively recruiting to fill the vacant positions,” including a permanent CFO, a title she was holding temporarily.

More than four months later, Kirk remains CFO. Positions for a manager of accounting and a director of budgets and grants remain vacant.

Since late January 2021, Le Grand has been the only person listed under the “Executive Leadership” section of the agency’s “About” website page, according to internet archives.

“It boils down to a leader who doesn’t know how to lead,” said the agency’s former chief financial officer, Cyndy Stiglich, whom Le Grand terminated in February 2021.

The fiscal year 2022 adopted budget, the first produced under Le Grand’s leadership, is about a quarter the length of the budget for the previous year and does not include details such as a staff organization chart, an executive summary or a budget preparation calendar detailing key milestones from the year.

Under Le Grand, it’s unclear if proper hiring practices were followed.

The agency hired a new chief of staff last month, with a starting salary of $155,000 and a $7,000 signing bonus, according to public records. When asked where the position was advertised, who was interviewed for the position and who from HART served as interviewers, the agency listed the information as “unknown.” Records show one person interviewed for the job.

One of Le Grand’s first moves as CEO was to hire Teri Wright as the agency’s chief customer experience officer. Wright was the only candidate to have her video off during the remote interviews, according to Yolanda Jennings, Le Grand’s former executive assistant. “I found that odd,” Jennings said. “And her answers felt scripted.”

The Times requested records of the recruitment and hiring process for the position last month but has not received them.

Wright received a starting salary of $185,000 and left the agency making more than $200,000. Last month the Times reported she’d been simultaneously working for a public transit agency in New Orleans since April.

Confusion on personnel matters was by design, said Jennings, who worked for Le Grand from January to April 2021. Early in her role, Jennings said Le Grand chastised her for making and printing copies of HART’s organizational chart.

“Do not put this in writing,” Jennings recalled Le Grand telling her, adding she should use paper and pen to make alterations rather than anything digitally.

“She came in with an agenda that she wanted to get rid of people,” Jennings said. “She was always doing things to try to undermine her staff, looking for ways to build a case against them.”

Jennings said she grew so concerned by Le Grand’s efforts to erode morale that she filed a complaint with then-head of human resources Crystal Hundley, calling from her husband’s phone for fear of retaliation.

Nothing materialized, Jennings said. Before long, Hundley left. Hundley did not respond to repeated requests for comment.

It’s unclear how the agency’s second-highest-paid staff member, CFO Loretta Kirk, was hired.

When the Times requested Kirk’s personnel files a month ago, HART provided scant paperwork: a job description of the CFO and an email from HR noting the lack of documents. Absent was a job application, job offer or details of a compensation package.

When pressed, HART’s public records staff forwarded a message from HR: “Ms. Kirk originally came on board through a contract with a staffing agency on a part-time, temporary basis while we recruited to fill the vacant CFO position. An internal candidate was promoted to the position and Ms. Kirk was retained to help with the transition. That internal candidate resigned from the position two months after she was promoted.”

The Times still has not received Kirk’s contract detailing the nature of her work with the agency. She earns more than $204,000 per year, according to public records.

According to employees and public records, she lives near Cleveland, flying into Tampa for board and committee meetings. It remains unclear if the agency or Kirk is responsible for covering her airfare and hotel stays. The Times requested information on expenses, but HART hasn’t provided any.

When Hillsborough voters in November squashed a proposal that steered millions in tax revenue to HART, the four highest earners at the agency weren’t registered to vote in the state.

Kirk is registered in Ohio. Wright, no longer with the agency, is registered in Louisiana. Omar Alvarado, the agency’s chief delivery officer since June, is registered in New York, where he had been living before he received the job. Le Grand is registered in Georgia.

Le Grand received up to $50,000 to cover moving expenses and temporary housing to relocate from Atlanta to Tampa Bay. She submitted $2,119 in air travel and $48,180 in temporary housing relocation costs for reimbursement. That was more than twice what was paid to the previous chief executive, who also relocated from Atlanta.

Le Grand’s contract affords her a bi-weekly allowance up to $355.73 for “interim transportation such as taxis, Uber, Lyft and other rideshare companies.” She can use an agency vehicle but is “not entitled to any automobile allowance for any pay period” that she uses a HART vehicle.

Jennings told the Times that Le Grand had Jennings drive her using an agency vehicle so she wouldn’t lose her car allowance.

Four months into Le Grand’s tenure, an anonymous letter was sent to the board of directors. “HART is in crisis and nearing collapse. The blame for that condition lay squarely at the feet of Adelee Le Grand and Teri Wright,” said the letter, obtained through a public records request.

The letter said Le Grand and Wright had created a “hostile, abusive and highly unstable work environment,” driving away talented and dedicated staff. “You may read these words as nothing more than a disgruntled employee who is resistant to change, but I have it on good authority that mine is not the only plea for help.”

Mariella Smith, then a county commissioner and chair of the HART board, forwarded the email to Le Grand the next day.

“Change is hard. Some people would rather defend their current ways, and fight change, than work together on a new way forward,” Smith wrote in her email to Le Grand.

“...You have the confidence of your board. Take heart, carry on.”

Smith, who lost reelection in November, told the Times recently the agency had “devolved into a culture of finger-pointing,” and the board often received anonymous complaints about leadership in years past. “We needed to give her enough space to lead,” Smith said of Le Grand.

Hillsborough County Commissioner Pat Kemp, current chair of the HART board, declined to comment, saying she was advised by the agency’s general counsel not to comment given the external investigation underway.

The letter is one of a larger trove of complaints shared with the board about Le Grand, according to documents reviewed by the Times. A second anonymous letter was sent to David Smith, HART counsel, last April, accusing Le Grand of violating hiring policies, stifling collaboration, silencing employees and pushing out senior staff.

Former chief financial officer Cyndy Stiglich filed a complaint letter detailing similar behavior with board members after Le Grand terminated her one month into her time as CEO.

The letters echo sentiments raised again months later in an American Public Transit Association review of the agency in September 2021, first reported by Creative Loafing last week. Until then, board members and agency employees had not seen the review.

The complaints raised and the board’s lack of tangible response — until last month when they authorized an external investigation into allegations — left employees feeling isolated, according to interviews and documents reviewed by the Times.

Former chief financial officer Joanne Caceres said she witnessed firsthand the thinly stretched staffing mentioned in the May audit.

“‘We’re going to set you up for success,’” she said Le Grand would often tell her. “Little did I know, it was really for failure.”

Caceres resigned last December, after 10 weeks on the job. “No one from the board called to check in about what had happened, about the state of the agency,” she said. “Why?”

Under Le Grand’s leadership, 72 non-bargaining employees and 237 bargaining employees have left the agency, according to public records.

Amid growing dissent, a key talking point from Le Grand has been that change is difficult. “In making the tough decisions required to change the status quo, feathers will no doubt be ruffled,” she wrote last month in a memo to staff.

“When I started this job there was an acknowledgement that a lot needed to be addressed,” she said at a board meeting in early December, when she narrowly avoided suspension from the position during the ongoing external investigation. “It’s going to take several more years to delve in and really change the culture of an organization.”