Uber Technologies (NYSE:UBER) investors have a fresh reason to watch insider activity. CEO Dara Khosrowshahi bought 141,000 Uber shares on September 10, 2026, spending about US$10.01 million in an open-market purchase. And he is not the only senior Uber executive buying. Just six days earlier, Uber President and Chief Operating Officer Andrew Macdonald bought 70,000 shares worth about US$5.31 million. Together, the two executives made roughly US$15.31 million in open-market purchases of UBER stock within less than a week.
Uber CEO Buys 141,000 Shares
According to an SEC Form 4 filed on September 10, Khosrowshahi purchased 141,000 Uber shares at a weighted average price of US$70.9642. That puts the total value of the transaction at approximately US$10.01 million.
The shares were purchased at prices ranging from US$70.73 to US$71.18. The filing lists the transaction code as “P,” confirming it was a purchase rather than a stock award. (sec.gov)
After the transaction, Khosrowshahi directly owned 1,367,100 Uber shares.
Before the purchase, he held about 1.226 million shares, meaning the transaction increased his direct position by roughly 11.5%. A US$10 million purchase by a sitting CEO is significant on its own. But another recent transaction makes the insider-buying story even more interesting.
Uber’s COO Also Bought Millions
On September 4, Uber President and COO Andrew Macdonald bought 70,000 shares.
The purchase was split into two transactions:
- 54,325 shares at a weighted average price of US$75.6526
- 15,675 shares at a weighted average price of US$76.4425
The combined value was approximately US$5.31 million. After the purchases, Macdonald directly owned 426,320 Uber shares. The SEC filing also lists these transactions as purchases. (sec.gov)
Combined, Khosrowshahi and Macdonald made about US$15.31 million in open-market purchases within six days.
Why Does This Matter?
Insider buying does not guarantee that a stock will rise. However, investors often pay attention when senior executives voluntarily increase their exposure to their own company.
In this case, the buying involves both Uber’s CEO and COO, and the purchases are large enough to stand out. The timing is also notable because Uber’s underlying business continues to grow.
In the second quarter of 2026, Uber reported gross bookings of US$58.0 billion, up 24% year over year on a reported basis. Revenue rose 12% to US$14.2 billion, while trips increased 18% to 3.9 billion.
Uber also reported US$2.8 billion in adjusted EBITDA and US$2.8 billion in free cash flow. Trailing 12-month free cash flow exceeded US$10 billion for the first time in the company’s history. (investor.uber.com)
What Should Investors Watch?
The biggest long-term question remains autonomous driving. Robotaxis could change the ride-hailing industry and create both opportunities and risks for Uber.
Investors should watch whether Uber can continue growing bookings and free cash flow while expanding its autonomous vehicle partnerships. Any further insider buying would also make the recent activity more notable.
Bottom Line
Uber’s latest insider activity is worth watching. CEO Dara Khosrowshahi bought about US$10.01 million of UBER stock, while President and COO Andrew Macdonald bought about US$5.31 million just six days earlier.
Together, the two senior executives made approximately US$15.31 million in open-market purchases. That does not guarantee UBER stock will move higher.
But with Uber still growing revenue, bookings and free cash flow, the fact that two of its most senior executives are buying millions of dollars of stock gives investors another reason to keep the company on their radar.
