Dye & Durham Ltd. DND-T has dumped its chief executive officer after board changes that put one-time chairman Tyler Proud effectively in command of the embattled company’s direction.

The move came two weeks after D&D’s outgoing chairman Alan Hibben called the brother of former CEO Matt Proud unfit to lead the company, adding to what has become a protracted Bay Street soap opera.

The Toronto legal software business said late Tuesday that CEO George Tsivin was “no longer serving as chief executive officer” and would be replaced on an interim basis by a board committee chaired by Tyler.

Tyler was D&D chairman before it went public in mid-2020. His private holding company OneMove Capital controls about 8 per cent of the stock.

He was one of a group of shareholders that grew disaffected by the company’s governance and his brother Matt’s leadership after a debt-fuelled acquisition binge. Those investors supported an activist campaign led by New York’s Engine Capital in 2024 that forced Matt’s exit from the company and a board overhaul. Tyler was also involved in the hiring of Mr. Tsivin.

2025: Another board overhaul caps off year of chaos for beleaguered Dye & Durham

But the Engine board failed to deliver quick changes as promised, results disappointed and the company was hit with a cease-trading order after it was late filing audited financial statements last year.

Tyler turned on the Engine-led board last fall with a proxy challenge. That prompted the departure of Engine founder Arnaud Ajdler and the appointment of several directors Tyler had proposed, including OneMove’s chief financial officer, Wendy Cheah. He also soured on Mr. Tsivin.

Despite their prior differences, Matt’s holding company, Plantro, which owns 15 per cent of the stock, supported his brother’s return to the board in May, replacing Ms. Cheah, three sources familiar with the matter said. (Plantro made several offers for D&D last year before entering into a standstill agreement.)

Newly appointed D&D chair Mary Filippelli and Angela Zhang, who both joined the board this year, are also on the CEO committee.

D&D said in an e-mailed statement “recent changes to management reflect a renewed focus on the company moving forward with greater discipline and a commitment to delivering results. The company is confident it has the right governance in place at the board to ensure it is acting in the best interests of all stakeholders.”

Dye & Durham names Mary Filippelli as new board chair

The change comes two weeks after Bay Street veteran Mr. Hibben resigned as chairman and from the board with a blistering letter that criticized the directors and Tyler.

In the letter, obtained by The Globe and Mail, Mr. Hibben wrote that he had made a “substantial mistake” last fall in largely accepting OneMove’s board slate “and did not do enough to protect the company from the foreseeable consequences of an inadequately scrutinized governance reset.”

Mr. Hibben, who declined to comment, wrote that the board’s decision to allow Tyler to become a director is “further evidence of a pattern of decision-making that falls short of the seriousness this company requires. More than that, I do not consider Tyler Proud fit and proper, in the public-company sense, to serve as a director of this company.”

Tyler did not respond to a request for comment.

Former D&D director and chief financial officer Ronnie Wahi, criticized Tyler in an interview, saying he was “exerting a disproportionate amount of influence over the company that is not aligned with the larger shareholder interest.” He further said Tyler was “instrumental or aligned with some of the company’s decline since Engine Capital govt involved.”

Mr. Wahi said D&D needed someone with “historic knowledge and experience” as CEO, suggesting Matt as an option.

The latest changes follow two recent setbacks. D&D reported in May that revenue in the third quarter ended March 31 dropped by 11.8 per cent to $91.2-million, compared with the same period a year earlier. Cash flows from operations fell by more than 50 per cent. Operating earnings fell 19 per cent.

Meanwhile, the board has quietly shelved a sales process for the whole company after receiving two preliminary bids earlier this year, the sources said. D&D’s stock price is down 60 per cent this year, closing Wednesday at $1.61. It traded in the $40s in 2021 and above $20 in 2024.

The Globe and Mail is not identifying the unnamed sources as they are not authorized to discuss the matters.

D&D is still considering offers for its financial services unit and the “strategic process remains ongoing,” the company said Tuesday.

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