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Company profile

Upwork, Inc Insider Trading

UPWK

Every SEC Form 4 insider trading filing for Upwork, Inc (UPWK) since April 2023 — open-market buys and sells by directors and officers, option exercises, and cluster activity, updated as each filing is reported to the SEC. Why 2023?

Exchange
Nasdaq
Sector
Services-Computer Processing & Data Preparation
CIK
0001627475
Filings
162
Insiders
17
Last filing
2026-08-18
SEC EDGAR ↗Yahoo Finance ↗Finviz ↗Stock Analysis ↗

Activity summary

No insider transactions in the last 30 days. The most recent was on August 18, 2026, when Erica Gessert bought 37,500 shares. 162 filings from 17 insiders are on record below.

Three year balance

Buy and sell value by quarter, Q4 23 to Q3 26. Upwork, Inc insiders were net sellers in every quarter shown.

PurchasesSales
Q4 23Q1 24Q2 24Q3 24Q4 24Q1 25$13.6MQ2 25Q3 25Q4 25Q1 26Q2 26Q3 26

Bars below the rule are sales, above are purchases. Largest quarter on the chart is $13.6M.

90 day insight

Over the last 90 days, Upwork, Inc insiders bought $0 (14 transactions) and sold $410K (4 transactions).

  • Most active insider: Hayden Brown with 8 transactions totaling $617K.
  • Largest single sale: $421K by Hayden Brown on Aug 18, 2026.
  • 20% of recent sales were pre-scheduled 10b5-1 trades — typically less informative than open-market activity.

Activity skews bullish — buys outpace sales.

Insider Transactions

Sourced from SEC EDGAR Form 4 filings. Updated hourly.

DateInsiderCompanyTypeSharesPriceValueReturn
Aug 18, 2026Erica GessertUPWK
Option Exercise
37,500——-3.5% 1m
Aug 18, 2026Erica GessertUPWK
Option Exercise
8,524——-3.5% 1m
Aug 18, 2026Erica GessertUPWK
Sale
22,844$8.43$192K-3.5% 1m
Aug 18, 2026Erica GessertUPWK
Option Exercise
37,500——-3.5% 1m
Aug 18, 2026Erica GessertUPWK
Option Exercise
8,524——-3.5% 1m

45 more transactions hidden

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Top insiders

By total value filed.

Hayden BrownPresident & CEO5 filings−$1.4M
Erica GessertChief Financial Officer2 filings−$267K
Anthony Ray KappusGM & Chief Operating Officer2 filings−$22K
Sabrina MekhalfaChief Accounting Officer1 filing−$10K

Institutional Ownership

Top 13F-HR holders of Upwork, Inc as of 2026-06-30

↓ decreasing
Total reported AUM
$330.8M
QoQ change
-70.8%
Reporting period
2026-06-30
#1
BlackRock, Inc.
CIK 0002012383
$113.1M
13.5M shares
#2
State Street Corp
CIK 0000093751
$43.4M
5.2M shares
#3
BlackRock, Inc.
CIK 0002012383
$33.4M
4.0M shares

Data source: quarterly 13F-HR filings — institutional holders report positions within 45 days of quarter end. Joined with insider activity above — see who's loading up institutionally while insiders are trading. Full 13F-HR API →

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Form4API, StockholmNot affiliated with the SEC or EDGAR. Data sourced from public EDGAR filings. Not investment advice.

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