Here come the cons.
1. The product, or expedia.com. It is really subpar. They lack many features that are common online. For one, they don't have a shopping cart on the site, meaning if you want to make multiple purchase, you would have to go through the shopping funnel multiple times. For another, they don't support free form search. You would have to pick the type of item you want to buy, and then enter the location you are going, and date. You cannot just enter "flight from Boston to London" like you can on google.
2. The competition. With google rolling out it's own travel product and directing traffic directly to hotel or flight carrier site and bypassing Expedia, I just don't see how Expedia can compete. Plus, Expedia lack a strong value proposition to persuade visitors to book on expedia.com instead of hotel or carrier site. Why book on expedia.com when I can just book on fourseasons.com?
3. The pandemic. It's Fall 2021 already and the coronavirus is still around, at least in United States. As long as the pandemic is still around or people still fear it, Expedia will never recover.
4. Employees. While most are friendly and professional, there are just too many people in the company, and frankly, some are really incompetent. This might have changed now since Peter Kern has been downsizing the company, laying off employees, merging teams, and selling off assets. On the other hand, some so called managers or directors are just not smart enough. My first manager was great, smart, dedicated, gave me room to work on stuff. My last manager was just totally a low person, does not know the business well, have no idea in the area she's responsible for, and was rude and disrespectful. And she was promoted by her manager, who is another incompetent person that cannot even speak English well.
5. Compensation. If you've heard Expedia pays low, it is true. My next job after Expedia pays me substantially higher. Substantially! This has a negative impact on talent acquisition and retention as well. Over the years I've seen so many ex-colleagues going to amzn, msft, fb, and other companies. I rarely see folks coming to Expedia from those companies. People don't consider Expedia as a tier one tech company because Expedia just does not pay tier one money.