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Insider Cluster (3 insiders) ·Filed Sep 25, 2026

PINS

PINTEREST, INC.
BEARISH
Impact 5/10
Horizonweeks Processed1mo ago
Insider cluster: 3 insiders, $1.7M total
Actionable Insight ▼ Bearish

The combination of a director/10% owner and CFO selling open-market shares in the same week, after derivative conversions, suggests a coordinated reduction. Monitor for any upcoming earnings or material news that could explain the timing. The $18.20-$18.61 price range is a key level to watch for further insider activity.

DirectionBearish
Confidencemedium
Horizonweeks
Latest settled — T+20d ⚠ clustered
PINS ▲ +15.32% at T+20d
SHORT call ✗ call lost -15.32% · α vs SPY -15.35% · entry $18.41 → $21.23
Next anchor: T+60d in 8w
Entry = T+0 close
Sep 25, 2026
via day close
T+1d
+0.71%
call -0.71% · α -0.89%
$18.54
settled 29d ago
T+5d
+8.96%
call -8.96% · α -7.76%
$20.06
settled 25d ago
T+20d
+15.32%
call -15.32% · α -15.35%
$21.23
settled 4d ago
T+60d
Pending
in 8w

Price Chart

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Executive Summary

Multiple PINS insiders, including a director/10% owner and the CFO, sold shares in open-market transactions totaling $1.66M over a 7-day window. The sales follow a pattern of derivative conversions and tax-withholding events, but the open-market component is notable for its size and seniority. At a $326M market cap, the $1.66M represents ~0.5% of market cap, a modest but not trivial signal. The cluster is mixed with non-cash conversions and tax-withholding, but the open-market sales by a director and CFO carry weight.

Key Financial Metrics

Direction
selling
Total Value
$1.7M
Insiders
3

Key Facts

  • Director/10% owner Benjamin Silbermann sold 46,875 shares at $18.21 on 2026-09-23 for $853K
  • CFO Julia Brau Donnelly sold 29,500 shares at $18.61 on 2026-09-24 for $550K
  • Chief Legal & Bus Affairs Officer Walcott Wanjiku Juanita sold 14,103 shares at $18.21 on 2026-09-23 for $257K
  • Total open-market sales: ~$1.66M, representing ~0.5% of market cap
  • Multiple insiders also had tax-withholding transactions on 2026-09-20, indicating vesting events
  • Silbermann also converted derivatives (non-cash) on 2026-09-22 and 2026-09-23

Financial Impact

Open-market sales of ~$1.66M by director/10% owner and CFO, representing ~0.5% of market cap

insider ownershipmarket sentiment

Risk Factors

  • Insider selling by senior executives and a director may signal lack of confidence in near-term prospects
  • The sales follow vesting/tax events, which could be liquidity-driven, but the open-market component by multiple senior insiders is unusual
  • No 10b5-1 plan indicated for these sales, increasing the information content

Investment Themes

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-PINS-1790367621561
34 reports for PINS
Performance horizon
100% Hit rate @ T+20 3 of 3 directional calls Went positive at some point 5 of 5 best @ T+20▲ +21.18%Aug 19, 2026
Filters
Rows
Reports for PINS — sortable, filterable
TypeNow
Oct 23, 2026
3d ago
Institutional Cluster
NEUTRAL ★ 3/10
$22.32awaiting T+20—$22.32 (−0.00%)
Oct 21, 2026
5d ago
Insider Cluster
NEUTRAL ★ 3/10
$22.93awaiting T+20—$22.32 (−2.66%)
Oct 21, 2026
5d ago
Insider Cluster
BEARISH ★ 4/10
$22.93awaiting T+20—$22.32 (+2.66%)
Oct 20, 2026
6d ago
144
NEUTRAL ★ 2/10
$22.95awaiting T+20—$22.32 (−2.75%)
Oct 15, 2026
11d ago
8-K
NEUTRAL ★ 4/10
$21.91awaiting T+20—$22.32 (+1.87%)
Oct 14, 2026
12d ago
144
NEUTRAL ★ 2/10
$22.71awaiting T+20—$22.32 (−1.72%)
Oct 13, 2026
13d ago
144
NEUTRAL ★ 3/10
$21.76awaiting T+20—$22.32 (+2.57%)
Oct 7, 2026
19d ago
144
NEUTRAL ★ 3/10
$20.53awaiting T+20—$22.32 (+8.72%)
Oct 6, 2026
20d ago
144
NEUTRAL ★ 3/10
$20.31awaiting T+20—$22.32 (+9.90%)
Oct 6, 2026
20d ago
144
NEUTRAL ★ 2/10
$20.31awaiting T+20—$22.32 (+9.90%)
Showing 10 of 34

US Market Status

Market Closed — Opens Wed (13h 1m)

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Report published Sep 25, 2026