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Insider Cluster (2 insiders) ·Filed Mar 18, 2026

UPWK

UPWORK, INC
NEUTRAL
Impact 4/10
Horizondays Processed7mo ago
Insider cluster: 2 insiders, $435K total
Actionable Insight • Neutral

Monitor for additional selling in the next 30 days — while this level of selling is modest (0.034% of $1.5B market cap), coordinated transactions by top executives may signal reduced conviction, though they remain within typical ranges for post-exercise sales.

DirectionNeutral
Confidencehigh
Horizondays
Final — all horizons settled through T+60d
UPWK ▼ -30.02% at T+60d
NEUTRAL call -30.02% · α vs SPY -41.55% · entry $12.09 → $8.46
Entry = T+0 close
Mar 17, 2026
via day close
T+1d
-6.12%
call -6.12% · α -5.85%
$11.35
settled 7mo ago
T+5d
-6.37%
call -6.37% · α -5.65%
$11.32
settled 7mo ago
T+20d
-8.52%
call -8.52% · α -14.57%
$11.06
settled 7mo ago
T+60d
-30.02%
call -30.02% · α -41.55%
$8.46
settled 5mo ago

Price Chart

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Executive Summary

Upwork executives executed a cluster of insider transactions over seven days, including open-market sales totaling $515K by the CEO and GM of Marketplace. The majority of transactions were non-cash derivative exercises with no direct economic impact.

Key Financial Metrics

Direction
selling
Total Value
$515.3K
Insiders
2

Key Facts

  • CEO Hayden Brown sold $292,344 worth of shares in open-market transactions on March 18, 2026.
  • GM Dave Bottoms sold $222,957 worth of shares across two open-market sales on March 18 and 19, 2026.
  • Total open-market sales in the cluster amount to $515,301.
  • Multiple derivative exercises (totaling 63,426 shares) were conducted at $0 cost, representing non-cash events (code M).
  • No open-market purchases were made; all sales were direct dispositions.

Financial Impact

$515,301 in total open-market share sales over 7 days

insider ownershipshare countmarket sentiment

Risk Factors

  • Perception of insider pessimism due to CEO and GM selling shares concurrently.
  • Potential for increased selling pressure if more executives follow suit.

Market Snapshot

Exchange
Nasdaq

Investment Themes

Software & IT

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

DocumentAccession Number
CONTEXT: Insider Cluster Data (7 trades, 7d window)cluster-UPWK-1774039845013
12 reports for UPWK
Performance horizon
75% Hit rate @ T+20 3 of 4 directional calls Went positive at some point 4 of 4 best @ T+5▲ +8.39%May 7, 2026
Filters
Rows
Reports for UPWK — sortable, filterable
TypeNow
Sep 22, 2026
5w ago
Insider Cluster
BEARISH ★ 5/10
$8.18 $8.75▼ −6.97%▼ −6.28%$9.07 (−10.88%)
Aug 20, 2026
9w ago
Insider Cluster
BEARISH ★ 5/10
$8.61 $8.37▲ +2.79%▲ +3.80%$9.07 (−5.34%)
Aug 10, 2026
11w ago
Press Release
BEARISH ★ 6/10
$8.36 $8.24▲ +1.44%▲ +0.38%$9.07 (−8.49%)
Jul 16, 2026
14w ago
8-K
NEUTRAL ★ 2/10
$9.06 $8.49▼ −6.35%▼ −10.79%$9.07 (+0.11%)
Jun 23, 2026
18w ago
8-K
NEUTRAL ★ 4/10
$8.22 $8.96▲ +9.00%▲ +7.07%$9.07 (+10.34%)
Jun 8, 2026
20w ago
3
NEUTRAL ★ 1/10
$8.82 $8.87▲ +0.57%▼ −0.88%$9.07 (+2.83%)
Jun 5, 2026
20w ago
8-K
NEUTRAL ★ 2/10
$8.76 $8.86▲ +1.14%▼ −0.72%$9.07 (+3.54%)
May 20, 2026
22w ago
Insider Cluster
NEUTRAL ★ 3/10
$8.44 $7.86▼ −6.93%▼ −7.26%$9.07 (+7.46%)
May 7, 2026
24w ago
8-K
BEARISH ★ 7/10
$8.82 $8.76▲ +0.68%▲ +0.70%$9.07 (−2.83%)
Apr 23, 2026
26w ago
DEFA14A
NEUTRAL ★ 2/10
$10.48 $8.66▼ −17.37%▼ −22.00%$9.07 (−13.45%)
Showing 10 of 12

US Market Status

Market Closed — Opens in 9h 28m

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Report published Mar 20, 2026