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September 01, 2020 1:41pm
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Why Upwork (UPWK) Stock Is Trading Up Today

UPWK Cover Image

What Happened?

Shares of online work marketplace Upwork (NASDAQ: UPWK) jumped 3.9% in the afternoon session after analyst firm UBS raised its price target on the company to $21 from $16, citing signs of a business turnaround. 

While keeping a Neutral rating on the shares, UBS noted that Upwork was nearing a key turning point in its Gross Services Volume (GSV) after five straight quarters of declines. GSV measures the total sales flowing through its freelance platform. The investment firm saw that falling web traffic was slowing and that the annual spending per buyer showed continued improvement. This potential stabilization in sales was viewed as a major milestone that could help blunt the narrative that Artificial Intelligence is a headwind for the company. Based on these trends, UBS improved its forecast to show flat GSV for the second half of 2025, up from its prior projection of a 1-2% drop.

After the initial pop the shares cooled down to $19.79, up 2.5% from previous close.

Is now the time to buy Upwork? Access our full analysis report here, it’s free.

What Is The Market Telling Us

Upwork’s shares are very volatile and have had 20 moves greater than 5% over the last year. In that context, today’s move indicates the market considers this news meaningful but not something that would fundamentally change its perception of the business.

The previous big move we wrote about was about 23 hours ago when the stock dropped 4.3% on the news that the stock's negative momentum continued as the company's President and CEO, Hayden Brown, disclosed a significant sale of company stock. 

According to filings with the SEC, Brown sold shares worth approximately $1.57 million. The transactions occurred on September 17 and 18. While insider selling can sometimes worry investors about a company's outlook, it was noted that these sales were made under a pre-arranged trading plan, known as a Rule 10b5-1 plan. This type of plan allows company insiders to set up a schedule for selling stocks in advance, which can help avoid accusations of trading on non-public information. Despite the sale being pre-planned, a large transaction by a top executive can still create downward pressure on a stock as it increases the number of shares available on the market.

Upwork is up 20.6% since the beginning of the year, and at $19.79 per share, it is trading close to its 52-week high of $20.07 from September 2025. Investors who bought $1,000 worth of Upwork’s shares 5 years ago would now be looking at an investment worth $1,251.

Today’s young investors won’t have read the timeless lessons in Gorilla Game: Picking Winners In High Technology because it was written more than 20 years ago when Microsoft and Apple were first establishing their supremacy. But if we apply the same principles, then enterprise software stocks leveraging their own generative AI capabilities may well be the Gorillas of the future. So, in that spirit, we are excited to present our Special Free Report on a profitable, fast-growing enterprise software stock that is already riding the automation wave and looking to catch the generative AI next.

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