Immediately after Verizon announced its acquisition of Yahoo’s core operations, Dan Rosensweig’s phone lit up. 

“I’ve heard from dozens and dozens of former Yahoo employees,” Rosensweig told BNN in an interview. “I think there’s a little bit of melancholy about all of this.” 

Rosensweig, who served as Yahoo’s chief operating officer between 2002 and 2007, acknowledges the competitive landscape has been tough on his former employer. Still, like thousands of so-called Yahoos, he was hoping for another end to this storyline. “I think people were holding out hope for a different outcome, where the company could be a standalone brand.”

As reports of Verizon’s imminent purchase surfaced over the weekend, many former Yahoos expressed their sadness, including LinkedIn CEO Jeff Weiner. On Sunday, Weiner (who spent more than seven years as an executive with Yahoo) tweeted, “End of an era, but hopefully not end of an internet icon. Yahoo meant a lot to me & many others.” 

At its peak in 2008, Yahoo employed approximately 15,200 people. With recent layoffs, the workforce has been slimmed down to roughly 8,800.  In an interview with BNN Monday, former Yahoo CEO Ross Levinsohn said more cuts could be coming. “Under most circumstances, I don’t see a way that you don’t reduce the workforce fairly substantially.”

In 2012, Levinsohn was in the running to take Yahoo’s top job on a permanent basis. The board ultimately selected Marissa Mayer, a long-time Google executive, whose ambitious growth strategy failed to move the needle. Yahoo generated nearly US$5 billion in revenue last year, virtually identical to its annual revenue in 2012.

“The company is ultimately selling – if you extract real estate and patents – for something like US$3.8-$4 billion, which is less than one times its revenue,” Levinsohn told BNN. “So, for an iconic brand like Yahoo to have fallen this far, it’s certainly disappointing as a former employee.”

Levinson does see a big opportunity for Yahoo’s brand to find new relevance under Verizon’s leadership, with help from leaders like AOL CEO Tim Armstrong. But given Yahoo’s strong culture, Rosensweig says execution could be tricky. “When you have to deal with three different companies, three different cultures, two different coasts … there’s going to be a lot of work to do.”