The simultaneous open-market sales by both the CEO and COO without a disclosed trading plan is a bearish signal. Monitor upcoming earnings or any material corporate event that may have prompted the sales.
Price Chart
Executive Summary
Two top executives at Upwork (CEO and COO) sold a combined $588K in open-market shares on the same day, September 18, 2026, at $8.45 per share. This is a material insider cluster sale by the two most senior officers, representing approximately 0.18% of the company's market cap, and is bearish given the lack of 10b5-1 plan indication and the coordinated timing.
Key Financial Metrics
Key Facts
- CEO Brown Hayden sold 23,900 shares for $202K on 2026-09-18
- COO Anthony Ray Kappus sold 45,700 shares for $386K on 2026-09-18
- Total insider sales: $588K at $8.45/share
- Both sales were open-market (code S) with no 10b5-1 plan indicated
- Sales occurred on the same day, suggesting coordinated or event-driven timing
Financial Impact
$588K in insider sales, approximately 0.18% of market cap
Risk Factors
- Insider sales may be part of pre-arranged 10b5-1 plans not disclosed in the filing
- Sales could be for personal diversification or tax planning, not informational
- Stock price may not react immediately if the market views the dollar amount as routine
Investment Themes
Documents Analyzed
This report is based on 1 SEC document filed with EDGAR.
| Document | Accession Number |
|---|---|
| CLUSTER Data (Synthetic) | cluster-UPWK-1790144688861 |
Filters
| Type | Now | ||||
|---|---|---|---|---|---|
Sep 22, 2026 5w ago | Insider Cluster | $8.18 $8.75 | ▼ −6.97% | ▼ −6.28% | $9.51 (−16.26%) |
Aug 20, 2026 9w ago | Insider Cluster | $8.61 $8.37 | ▲ +2.79% | ▲ +3.80% | $9.51 (−10.45%) |
Aug 10, 2026 11w ago | Press Release | $8.36 $8.24 | ▲ +1.44% | ▲ +0.38% | $9.51 (−13.76%) |
Jul 16, 2026 14w ago | 8-K | $9.06 $8.49 | ▼ −6.35% | ▼ −10.79% | $9.51 (+4.97%) |
Jun 23, 2026 17w ago | 8-K | $8.22 $8.96 | ▲ +9.00% | ▲ +7.07% | $9.51 (+15.69%) |
Jun 8, 2026 20w ago | 3 | $8.82 $8.87 | ▲ +0.57% | ▼ −0.88% | $9.51 (+7.82%) |
Jun 5, 2026 20w ago | 8-K | $8.76 $8.86 | ▲ +1.14% | ▼ −0.72% | $9.51 (+8.56%) |
May 20, 2026 22w ago | Insider Cluster | $8.44 $7.86 | ▼ −6.93% | ▼ −7.26% | $9.51 (+12.68%) |
May 7, 2026 24w ago | 8-K | $8.82 $8.76 | ▲ +0.68% | ▲ +0.70% | $9.51 (−7.82%) |
Apr 23, 2026 26w ago | DEFA14A | $10.48 $8.66 | ▼ −17.37% | ▼ −22.00% | $9.51 (−9.26%) |
US Market Status
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