As the liberal group Democracy for America approached insolvency following the midterm elections, staffers faced a related problem: their CEO, Yvette Simpson, was on vacation at a vineyard in California.

Weeks earlier Simpson had told two members of the development team that $320,000 needed to be raised for DFA to make it through the year, according to two former employees. But as the group’s dire financial state started to become clear to staff, she attended a leadership training paid for by the organization and a personal multi-day sommelier education course in Napa Valley, according to five former employees.

“Is this heaven? No, but it’s pretty close!” Simpson posted on Instagram while there. Eventually, she held an all-staff Zoom call while in Napa, in which she announced that DFA was running out of cash, according to an audio recording.

“We didn’t get major donations as we expected last month so we ended up using $100,000 from our reserve just to cover expenses,” she said. “If I were you, I would be looking for another job. … I want every member of this team to go out into the marketplace to see if they can get another job just in case.”

Though DFA was in deep trouble before Simpson left for California, her lack of substantial outreach to donors and her personal time away at that critical juncture was the culmination of the organization’s demise, according to the five former employees and a staffer’s contemporaneous notes and documents from inside DFA. She resigned on Dec. 7 as CEO and all non-leadership staffers were laid off the same day without any severance.

And last week, POLITICO reported that DFA was about to shut down while its separate 501(c)4 nonprofit would stay afloat.

It was an ignoble sendoff of a group that was once a major arm of the progressive movement. DFA was started in the wake of Howard Dean’s unsuccessful 2004 presidential campaign. The group harnessed his progressive supporters and the anti-Iraq War movement’s momentum to support like-minded candidates across the country. It leaned on small-dollar fundraising to aggressively back progressives in competitive primaries. And in recent years, it expanded its focus to include secretary of state and attorney general races, ranked choice voting, student debt relief and Medicare for All.

But in a progressive ecosystem where groups have become more narrowly focused on issue advocacy or specific electoral tasks — such as candidate recruitment or voter protection — DFA has struggled. Dean left the organization after he became chair of the DNC in 2005 but continued to occasionally advise DFA from 2009 until 2016. He called the demise of DFA “sad” in a brief interview but declined to elaborate.

“DFA left it all on the field this year to stop the red wave and win critical elections up and down the ballot across the country. As DFA heads into the next cycle in this difficult fundraising environment, the decision was made to wind down the PAC by the end of the year,” said DFA special adviser Charles Chamberlain. “The DFA Advocacy Fund will continue its work for the foreseeable future focused on election reforms like ranked choice voting and the National Popular Vote Interstate Compact.” Simpson is still on the board of that fund, according to a person familiar with the matter, but it’s unclear whether she will remain in that position in the longer term.

Simpson declined an interview request beyond calling the reporting “unsubstantiated.” Instead, she pointed POLITICO to her resignation statement that she posted on Twitter. Jim Dean, the group’s former chair and the brother of Howard Dean, privately defended her from her critics on staff, according to an internal office communication obtained by POLITICO. Jim Dean, who did not return a request for comment, said at the time Simpson was transparent about the group’s financial difficulties and that the problems DFA faced were not unique to her stewardship.

DFA has been hurt this year by a host of other issues that extend beyond Simpson’s management. The lack of a chair has hampered fundraising, as has email becoming a less effective way to raise money for progressive groups. Donor fatigue has also led some contributors to scale back their giving to PACs in favor of donating to specific candidates.

And some former staffers praised aspects of Simpson’s performance: They credited her with embracing a diverse range of candidates and her detailed knowledge of grassroots organizing.

But according to internal memos and Slack messages reviewed by POLITICO, 10 employees at DFA pinned much of the blame for its demise over the past several months on Simpson.

“[A]s we understand it, no effort was made by you to meet or call with donors” for the first three weeks of November, the entire non-leadership staff of 10 people wrote in a memo to her a few days before she resigned. “You should know that your staff no longer has confidence in your ability to lead this organization. We feel you should have spent more time with donors and that we should have had a clearer understanding of the budget and an earlier warning of things going in the wrong direction.”

A former president pro tempore of Cincinnati’s city council, Simpson became CEO of DFA in early 2019 after getting hand-picked by Jim Dean and Chamberlain, who was then the executive director.

She was chosen as part of a “new generation of bold, visionary progressive leaders,” Jim Dean said in a statement at the time, and made history as DFA’s first Black leader. In 2017, Dean had visited Cincinnati to help get out the vote for Simpson’s unsuccessful mayoral campaign and was impressed with her energy and her campaign team.

But while Simpson was skilled in electoral politics and field organizing, she struggled, those five former employees said, in cultivating donors. That 2018 cycle, the organization raised $6.9 million and spent $7.6 million, according to OpenSecrets.org. Four years later, DFA raised almost half of that, $3.6 million, and spent $3.8 million.

“She had said [raising money] is not something she liked to do, but it’s also your job as CEO to fundraise and she didn’t want to do it,” one former employee said. “She preferred to be on the ground with candidates and knocking on doors.”

Simpson’s leadership, three of the five former employees said, was also complicated by the fact that she held other jobs. She started working as a real estate agent in June and is also an employment and business lawyer at a Cleveland-based law firm and a political contributor to ABC News, according to her LinkedIn profile. Those former employees said that Simpson’s other jobs took her attention away from DFA’s fundraising needs. The former staffers were granted anonymity to protect their future career prospects.

The organization’s two main revenue sources had long been its email program and call time with donors. But “Yvette [had] just stopped doing call time,” one of the former employees said. Those former employees, who had access to Simpson’s calendar, said she only did eight hours of fundraising calls between the beginning of October and Nov. 22 of this year.

As DFA’s financial state worsened, Simpson told development staffers that Jim Dean and Chamberlain were going to help make calls to raise money. But one of the five former employees, a development staffer, later learned that this might not be so. During a call, Chamberlain explained he and Dean had not agreed to do so “and were not fully informed about the gravity of the situation and shortage of funds in [the] reserve account,” according to notes taken at the time by the staffer.

At a staff meeting on Nov. 11, Simpson did not discuss fundraising except for stating she didn’t want DFA to do any of it around the Georgia runoff, according to the notes by the former employee. But as cash reserve of the organization continued to dwindle, one employee confronted Simpson about DFA’s financial situation during a meeting on Nov. 21 with campaign staff. She responded by saying the development team was not letting her do call time with donors, according to the former employee, who disputed the notion she was not allowed to do so.

Later in November, Simpson attended a leadership training seminar in California paid for by DFA from the Rockwood Leadership Institute. She then went on vacation to attend the multi-day sommelier education course in Napa Valley. On November 30, she organized an all-staff Zoom, but, according to DFA staffers, showed up a half hour late. On the call, she said November had been “a very tough month.”

“I can’t guarantee on Jan. 1st that I’m going to have the resources to pay everybody on this team,” she stated on the call in an audio recording obtained by POLITICO.

Simpson went on to note that the absence of a chair for the organization was hurting the fundraising situation and that she had recently met with several prospective chairs and had an offer out. But she couldn’t guarantee that there would be enough money to pay the person and admitted that she had not told the prospective chair about how bad the organization’s finances were.

“I didn’t feel comfortable sharing that,” she said.

Simpson also said that she was talking to several progressive movement organizations about a merger and had gotten some interest but she didn’t know “if the conversations happened fast enough.”

The meeting got heated when staffers asked why she hadn’t told all of them earlier about how DFA was teetering. “I apologize if it was not early enough,” she said, conceding that she was “not a perfect leader” and “sometimes transparency can be dangerous.”

“Here’s what I’m prepared for 100 percent: You can and should attack my leadership if you think I’m doing a horrible job. You can and you should,” she said, adding that the critique of her being absent was “fair.” But she said she wouldn’t respond to questions in the Zoom chat about why she had taken a personal vacation as the organization stood on the brink of collapse.

The next day, the non-leadership staff wrote a two-and-a-half page memo to Simpson where they upbraided her for not doing more to save DFA.

“As CEO, we expected you were in tune with the pulse of the staff, but during yesterday’s meeting, it was clear that you were not,” they wrote in the memo obtained by POLITICO.

Simpson never replied. But Jim Dean wrote a few hours later in a Slack message to staff, obtained by POLITICO, that their “pointing fingers” in the memo was “really disappointing” and that he felt that he had “just read a memo from DC consultant[s] explaining why the campaign they were running lost.” He noted it was “not the first time DFA has been in challenging circumstances, financial or otherwise.” Simpson, he insisted, had “been very transparent about DFA’s financial circumstances which is for everyone’s benefit.”

Admonishing the memo writers, he also said neither he nor his brother or Chamberlain would be coming in to run DFA or solve its financial woes.

Six days later, Simpson was gone.

Holly Otterbein contributed to this article.