Why Do I Feel Like I’m Cheating on Upwork?

A few days ago, Upwork’s Board of Directors received a letter from one of their key investors, Engine Capital.

The letter was fairly critical of Upwork and raised concerns such as:

• A lack of strategic clarity and focus
• Ineffective execution
• Poor capital allocation
• A revolving management team
• Board oversight issues
• Underperformance

You can read more about that letter, and Upwork’s response, in an article I put together [here].

But as I covered the story, I felt a mix of emotions.

At first, I felt a bit defensive.

After all, Upwork was my first freelance “love.” It’s the platform that changed my life when I joined back in 2017. It helped launch a long, successful freelance career.

But after diving deeper, I couldn’t help but agree with many of Engine Capital’s points.

“We believe the company has a great deal of potential that is unfortunately not being realized. This is due to Upwork’s lack of strategic clarity and focus [and] ineffective execution…,” the letter reads in part.