David T. Bottoms, who serves as General Manager, Marketplace at Upwork Inc. (NASDAQ: UPWK), completed a series of stock transactions on March 18 and March 19, 2026, involving both the sale of common shares and the receipt of shares from vested restricted stock units (RSUs).
According to the filings, Bottoms sold a total of 18,575 shares across the two days for an aggregate proceeds figure of approximately $222,957. On March 18, Bottoms disposed of 11,575 shares in multiple transactions at prices that ranged from $12.13 to $12.52 per share, generating roughly $142,509. The following day, March 19, he sold an additional 7,000 shares at prices between $11.33 and $11.72 per share, totaling about $80,448.
Also recorded on March 18, Bottoms exercised RSUs to acquire 20,908 shares of Upwork common stock. The exercise comprised three tranches of shares: 8,980 shares, 6,024 shares and 5,904 shares. Each RSU represents a contingent right to receive one share of the issuer's common stock, and the filings note these vesting events and subsequent transactions.
The filings clarify the nature of the sales tied to the RSU vesting. A portion of the shares were sold to satisfy tax withholding obligations under the issuer's equity incentive plans - a "sell to cover" mechanism required by the company. The reporting specifies that these sales to cover taxes were not discretionary trades by Bottoms but were mandated by the issuer's election under its equity plans. The reported prices for the sales are presented as weighted average prices, and the reporting person has committed to provide detailed information on the number of shares sold at each separate price within the stated ranges to the issuer, any security holder, or Securities and Exchange Commission staff upon written request.
Both blocks of sale transactions were effected pursuant to a Rule 10b5-1 plan that the reporting person adopted on May 30, 2025. The first set of disposals on March 18 were recorded with prices ranging from $12.13 to $12.52 per share, inclusive. The March 19 sales were recorded with prices ranging from $11.33 to $11.72 per share, inclusive. The filings reiterate the weighted-average-price reporting convention and the undertaking to provide more granular pricing details on request.
The RSU vesting schedules described in the filings are as follows: one set of RSUs vests in equal quarterly installments over four years beginning December 18, 2022; another set vests in equal quarterly installments over four years beginning June 18, 2024; and a third set vests in equal quarterly installments over four years beginning June 18, 2025. Each of these vesting schedules is conditioned on the reporting person's continued employment with the issuer on each vesting date.
These transactions coincide with several corporate developments and financial metrics disclosed for Upwork. The company's shares are trading close to their 52-week low of $11.13, with the stock at $11.28 at the time of the report - a decline of 43% over the past six months. Despite that recent weakness, analysis by InvestingPro referenced in the filings suggests the stock may be undervalued, with a Fair Value assessment indicating potential upside. The company is also reported to have a gross profit margin of 78% and to hold more cash than debt.
Upwork's recent corporate and financial actions are also documented. The company reported fourth-quarter 2025 results with revenue and adjusted EBITDA coming in at or slightly above the high end of its prior guidance. In response to recent performance, two analysts made adjustments to their price targets: Goldman Sachs reduced its target to $27 while maintaining a Buy rating, and UBS cut its target to $23 while also keeping a Buy rating.
On the capital-allocation front, Upwork announced a new $300 million share repurchase program, which raises the total authorized repurchases to $600 million since November 2023. The company frames this program as part of its efforts to enhance shareholder value.
On leadership, the filings note that Bottoms has reached a resignation agreement with Upwork, effective through April 3. Under the terms of that agreement, Mr. Bottoms will receive a lump-sum payment equal to twelve months of his base salary.
Investors seeking deeper research on Upwork can access comprehensive Pro Research Reports that include Upwork and more than 1,400 other U.S. equities, according to the information in the filings.
These filings collectively disclose the mechanics of the trades, the relationship of the sales to RSU vesting and tax withholding requirements, the employment-conditional vesting schedules, and the corporate context of Upwork's financial results, analyst target moves, share repurchase activity and executive transition arrangements.