When Vice Media named Nancy Dubuque as its new CEO in 2018, her contract hinted at one of her assignments. Sell ​​the company — which at the time was a darling of the media industry — and it could cash in on a sizable stock bonus, according to a copy of the contract obtained by The New York Times.

So far, this has not been achieved. On Friday, Ms. Dubuque said she was leaving Vice, which investors expect is worth much less than it was before she took over.

Just a month ago, Mrs. Dubuque announced that the company was for sale. No deal has materialized yet.

Its unexpected departure — its last on Friday — and Vice’s struggles in recent years, highlight the flagging fortunes of a group of digital media companies not so long ago talked about as the future of the industry.

Vice, hailed as a new media giant at the height of its staggering $5.7 billion valuation, has been coveted by some early backers, including Disney. The company has accumulated debt and is now expected to sell for well below this high valuation.

A person familiar with the sale process said that bids for Vice were due soon, and she would likely sell the company within the next 60 days.

Other major digital media companies, such as BuzzFeed and Vox Media, have had similar setbacks. Investor enthusiasm waned as these companies struggled to live up to some of their loftiest ambitions, digital advertising increasingly turned to tech giants like Alphabet and Meta, and legacy media companies began to focus on catching up with streaming giants like Netflix.

“The market is back to basics,” said Keith Hernandez, a former BuzzFeed CEO and co-founder of digital advisory firm Launch Angle. Potential and promise have given way to profit margin and efficiency. Sexy just does not sell. “

In a note to employees Friday, Ms. Dubuque said that although Vice faced business headwinds, the company had become less reliant on advertising during her tenure and had made great strides to become more financially independent.

She also noted other improvements under her leadership, including creating a more inclusive work environment. Ms. Dubuque joined Vice shortly after investigations into the company’s culture, including by The Times, revealed incidents of sexual harassment against women who work for the company.

“I know that you are among the most flexible, creative, and determined talents in business, and that your future is bright and hopeful,” Ms. Dubuque wrote in her email. “Remember what I am trying to remind you of, and this is to appreciate your progress.”

Contacted by phone on Friday, she declined to comment further.

In a statement, Vice’s board of directors said Ms. Dubuque joined the company during a critical period and “positioned the company for long-term success,” adding that Vice will soon announce new leadership for the company.

The deputy refused to comment on the board’s deliberations.

Ms. Dubuque replaced Vice founder Shane Smith, who struck a string of deals that sent the company’s valuation higher than ever but left it with onerous financial obligations to its increasingly anxious investors, who were eager to get out.

There was a major point of tension at the beginning of Ms. Dubuque’s appointment.

In March 2018, Vice’s board met by telephone in private session to choose its new CEO, according to a copy of the meeting minutes obtained by The Times and two people familiar with the board’s deliberations. Mr. Smith, a board member, told the other directors that leaks to the press are forcing the company to speed up some of its decisions.

Additionally, Kevin Mayer, a board member who was then a high-ranking Disney executive, expressed frustration that he was unaware of Ms. Dubuque’s potential hiring until it was in the final stages. Disney had ownership stakes in Vice and A&E Networks, where Ms. Dubuc was CEO.

Nevertheless, the board approved Ms. Dubuque’s appointment, expressing optimism that an experienced executive with Ms. Dubuque’s proven track record could address Vice’s cultural issues and improve its financial performance prior to a potential sale. Mr. Meyer, who was outraged, abstained.

As part of her contract, Ms. Dubuc was awarded tens of thousands of shares in Vice, according to the transcript of her contract. Since the company is private, selling shares can be a stressful process. It will be easier to get shares if the company is sold or goes public. Stock grants are a common incentive offered to employees in startup companies. Ms. Dubuque also earned an annual salary of over $1.5 million and a huge signing bonus, according to a copy of her contract.

In the years since Ms. Dubuque joined the company, the company has struggled to reach sustainable profitability. Last year, the company missed its $700 million revenue target by nearly $100 million. Many of Vice’s biggest backers, including Disney and A&E Networks, no longer expect to turn a profit on the investments they’ve made in the company.

In an interview last month about plans to sell some or all of the company, Ms. Dubuque said Vice would break even in 2023.

In an interview at the time, she said the company was having serious problems when it arrived, stating that it was “unclear if the company could survive”.