UPWK UPWORK, INC
Price Chart
Executive Summary
Upwork's CEO, CFO, and COO executed same-day open-market sales on May 18, totaling $404K, following the exercise of zero-strike derivatives. This cluster comes 13 days after a Q1 earnings miss and announced restructuring (24% workforce cut). The sales appear driven by option-exercise-related liquidity needs rather than a fresh negative signal, given the plan-like coordination and modest 0.04% of market cap.
Key Financial Metrics
Actionable Insight
The sales are modest relative to market cap and mechanically tied to option exercises — not a fresh bearish signal. The more salient event is the May 7 earnings/restructuring. Monitor for any Form 4 filings by the CEO/CFO showing further sales without a pending option exercise, which would be more concerning. No immediate action warranted.
Key Facts
- CEO Hayden Brown sold 22,546 shares at $8.66 for ~$195K
- CFO Erica Gessert sold 22,162 shares at $8.66 for ~$192K
- COO Kappus sold 1,905 shares at $8.66 for ~$17K
- All sales were preceded by same-day zero-strike derivative exercises by each insider
- Total open-market sales = $403,827 vs. market cap of $1.0B = 0.04% of market cap
- Last 30d prior insider activity: 3 sells totaling $404K — these sales more than double that volume
- Cluster occurs 13 days after Q1 earnings miss and restructuring announcement on May 7
Financial Impact
$403,827 in insider sales = 0.04% of market cap
Risk Factors
- Historical model calls on UPWK show 0% win rate at T+20, suggesting limited predictive power from filings alone
- Restructuring execution risk could pressure shares further if revenue trends worsen
- Further insider sales without derivative exercises would be a more bearish signal
Market Snapshot
Documents Analyzed
This report is based on 1 SEC document filed with EDGAR.
| Document | Accession Number |
|---|---|
| CLUSTER Data (Synthetic) | cluster-UPWK-1779308218583 |
Track record builds as more directional reports settle.
Filters
| Type | Now | ||||
|---|---|---|---|---|---|
|
Jun 8, 2026
1d ago
|
3
| $8.86 awaiting T+5 | awaiting T+5 | — | $8.82 (−0.45%) |
|
Jun 5, 2026
4d ago
|
8-K
| $8.73 awaiting T+5 | awaiting T+5 | — | $8.82 (+1.03%) |
|
May 20, 2026
20d ago
|
Insider Cluster
| $8.44 $8.82 | ▲ +4.50% | ▲ +2.65% | $8.82 (+4.50%) |
|
May 7, 2026
4w ago
|
8-K
| $8.82 $8.08 | ▲ +8.39% | ▲ +9.85% | $8.82 (+0.00%) |
|
Apr 23, 2026
6w ago
|
DEFA14A
| $10.48 $10.35 | ▼ −1.24% | ▼ −2.72% | $8.82 (−15.84%) |
|
Apr 14, 2026
8w ago
|
Press Release
| $11.30 $11.34 | ▲ +0.35% | ▼ −1.29% | $8.82 (−21.95%) |
|
Mar 18, 2026
12w ago
|
Insider Cluster
| $12.09 $11.32 | ▼ −6.37% | ▼ −5.65% | $8.82 (−27.05%) |
US Market Status
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