What Happened?
Shares of online work marketplace Upwork (NASDAQ: UPWK) fell 4.3% in the afternoon session after 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.
The shares closed the day at $19.31, down 3.8% from previous close.
The stock market overreacts to news, and big price drops can present good opportunities to buy high-quality stocks. 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 4 days ago when the stock gained 4.4% on the news that investors scooped up equities, shaking off the initial concerns inferred from the Fed's dot plot, with tech stocks leading the charge.
As a reminder, the Federal Reserve cut its benchmark interest rate by 25 basis points the previous day and signaled that more reductions could come before year-end and beyond. Initially when the cut was announced and Fed Chair Powell held his press conference, there was a pullback in the market as the Fed's "dot plot" revealed that only one cut was likely for 2026. This was below the three cuts that had been priced into the markets. This was the first interest rate cut of 2025, a move investors had widely anticipated. In response to the decision, stocks rose significantly, positioning major indexes like the S&P 500 and Nasdaq to open at record levels.
The Fed's decision was influenced by signs of a weakening labor market. Lower interest rates are generally seen as positive for stocks because they reduce borrowing costs for businesses and make fixed-income investments like bonds less attractive by comparison, driving capital into the equity market. While Fed Chair Powell noted the path forward has risks, the prospect of looser monetary policy has fueled optimism on Wall Street.
Upwork is up 17.8% since the beginning of the year, and at $19.33 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 $1,227.
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