UPWORK, INC·4

May 20, 4:15 PM ET

Brown Hayden 4

4 · UPWORK, INC · Filed May 20, 2026

Research Summary

AI-generated summary of this filing

Updated

Upwork CEO Hayden Brown Sells 72,546 Shares, Exercises RSUs

What Happened Hayden Brown (President & CEO, Director) had multiple equity transactions reported for May 18, 2026. He converted/vested a total of 46,822 shares from derivative awards (RSUs) and simultaneously had those shares withheld to satisfy tax withholding obligations (net settlement). Separately, he sold 22,546 shares at a weighted average price of $8.66 (proceeds $195,325) and 50,000 shares at a weighted average price of $8.57 (proceeds $428,475), for total gross proceeds of approximately $623,800. The filing also notes a purchase of 1,544 shares under the company’s employee stock purchase plan on May 14, 2026.

Key Details

  • Transaction date: May 18, 2026 (filed May 20, 2026) — filing appears timely.
  • Open-market sales: 22,546 shares @ $8.66 (WA price; range per filing $8.57–$8.73) = $195,325; 50,000 shares @ $8.57 (WA price; range $8.10–$8.79) = $428,475. Total ≈ $623,800.
  • Derivative conversions: 14,850 + 18,334 + 13,638 = 46,822 shares converted; same amounts reported as disposed at $0.00 to satisfy tax withholding (sell-to-cover).
  • One sale was effected under a Rule 10b5-1 trading plan (adopted Nov 19, 2025).
  • RSU definition and vesting: Each RSU equals one share (F1); various RSU vesting schedules noted in the filing (F7–F9).
  • Shares owned after the transactions are not specified in this summary filing.

Context

  • The "M" code indicates exercise/conversion of derivatives (here, RSUs converting to common shares). The $0.00 dispositions reflect shares withheld or surrendered to cover taxes (a mandatory, non-discretionary sell-to-cover), not a market sale for cash.
  • The open-market sales were (at least in part) pre-arranged (10b5-1), meaning they followed a pre-set plan rather than ad hoc insider timing.
  • For retail investors: purchases can signal conviction, while routine tax-withhold or plan-driven sales are less informative about insider sentiment. This filing is primarily routine vesting and plan-based selling rather than a straightforward discretionary sale.

Insider Transaction Report

Form 4
Period: 2026-05-18
Brown Hayden
DirectorPresident & CEO
Transactions
  • Exercise/Conversion

    Common Stock

    [F1][F2]
    2026-05-18+14,850815,126 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-05-18+18,334833,460 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-05-18+13,638847,098 total
  • Sale

    Common Stock

    [F3][F4]
    2026-05-18$8.66/sh22,546$195,325824,552 total
  • Sale

    Common Stock

    [F5][F6]
    2026-05-18$8.57/sh50,000$428,475774,552 total
  • Exercise/Conversion

    Restricted Stock Units

    [F1][F7]
    2026-05-1814,85044,550 total
    Common Stock (14,850 underlying)
  • Exercise/Conversion

    Restricted Stock Units

    [F1][F8]
    2026-05-1818,33455,000 total
    Common Stock (18,334 underlying)
  • Exercise/Conversion

    Restricted Stock Units

    [F1][F9]
    2026-05-1813,638204,583 total
    Common Stock (13,638 underlying)
Footnotes (9)
  • [F1]Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
  • [F2]Reflects 1,544 shares acquired under the Issuer's employee stock purchase plan on May 14, 2026.
  • [F3]Represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs listed in Table II. This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a "sell to cover" transaction and does not represent a discretionary trade by the Reporting Person.
  • [F4]The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $8.57 to $8.73 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon written request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
  • [F5]This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on November 19, 2025.
  • [F6]The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $8.10 to $8.79 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon written request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
  • [F7]The RSUs vest 25% on February 18, 2024, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date.
  • [F8]The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
  • [F9]The RSUs vest in equal quarterly installments over four years beginning on May 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
Signature
/s/ Jacob McQuown, Attorney-in-Fact|2026-05-20

Documents

1 file
  • 4
    primarydocument.xmlPrimary

    PRIMARY DOCUMENT