144 ·Filed Jun 15, 2026

CWAN

Clearwater Analytics Holdings, Inc.
BEARISH
Impact 5/10
Horizondays Processed3mo ago SEC0001968582-26-000611
Form 144 — notice of proposed sale of securities
Actionable Insight ▼ Bearish

Monitor for actual sale execution on Form 4; a director selling ~$10.4M in a single block is notable and may signal lack of confidence. Given the 75% historical win rate on CWAN reports and recent institutional trimming, consider reducing exposure or hedging ahead of potential selling pressure.

DirectionBearish
Confidencemedium
Horizondays
Latest settled — T+5d ⚠ clustered
CWAN ▲ +1.24% at T+5d
SHORT call ✗ call lost -1.24% · α vs SPY -3.47% · entry $24.25 → $24.55
Next anchor: T+20d due 3mo ago
Latest observation: T+12 -0.59% FF3 residual α
Entry anchored
Jun 15, 03:59 PM ET
via exchange tick
T+1d
+0.04%
call -0.04% · α -1.29%
$24.26
settled 4mo ago
T+5d
+1.24%
call -1.24% · α -3.47%
$24.55
settled 3mo ago
T+20d
—
call — · α —
—
due 3mo ago
T+60d
—
call — · α —
—
due 22d ago

Price Chart

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Executive Summary

Director D. Scott Mackesy filed a Form 144 to sell 427,776 shares of Clearwater Analytics (CWAN) Class A Common Stock, with an estimated aggregate market value of approximately $10.4 million based on a filing date of June 15, 2026. The shares were acquired via compensation on November 2, 2020, and the sale is planned through J.P. Morgan Securities LLC. This is a large proposed sale by a director, representing about 0.06% of the $7.3B market cap, and comes amid mixed institutional activity and a 75% historical win rate on prior CWAN reports.

Key Facts

  • Director D. Scott Mackesy filed a Form 144 to sell 427,776 shares of CWAN Class A Common Stock.
  • Estimated aggregate market value of the proposed sale is approximately $10.4 million.
  • Shares were acquired via compensation on November 2, 2020.
  • Sale is planned through J.P. Morgan Securities LLC.
  • Filing date is June 15, 2026.
  • Market cap of CWAN is $7.3 billion.
  • Recent insider activity (30 days) includes 1 sell totaling $244K.
  • Institutional 13F shows top holders BlackRock ($669M) and Vanguard ($433M), with recent trimming and exits.

Financial Impact

Proposed sale of 427,776 shares valued at approximately $10.4 million, representing about 0.14% of outstanding shares (based on ~300M shares outstanding implied by $7.3B market cap and ~$24.35 stock price).

dilutioninsider selling

Risk Factors

  • Insider sale may signal reduced confidence in near-term prospects.
  • Large block sale could pressure stock price if executed quickly.
  • Institutional trimming and exits suggest cautious sentiment among large holders.

Market Snapshot

Exchange
NYSE
Sector
Services-Prepackaged Software
Analyst Consensus
47% bullish (15 analysts)

Investment Themes

Software & IT

Documents Analyzed

This report is based on 3 SEC documents filed with EDGAR.

DocumentAccession Number
144 Filing (Primary)0001968582-26-000611
Document: 0001968582-26-000611-index.html0001968582-26-000611
Document: 0001968582-26-000611.txt0001968582-26-000611
11 reports for CWAN
Performance horizon
100% Hit rate 3 of 3 directional calls best @ T+60▲ +3.83%Feb 24, 2026
Filters
Rows
Reports for CWAN — sortable, filterable
TypeNow
Jul 6, 2026
12w ago
15-12G
NEUTRAL ★ 3/10
$24.56 awaiting T+5awaiting T+5——
Jun 22, 2026
14w ago
8-K
NEUTRAL ★ 4/10
$24.53 $24.56▲ +0.12%▲ +0.58%—
Jun 17, 2026
15w ago
Insider Cluster
NEUTRAL ★ 3/10
$24.29 $24.56▲ +1.11%▲ +2.78%—
Jun 15, 2026
15w ago
144
NEUTRAL ★ 3/10
$24.25 $24.55▲ +1.24%▲ +3.47%—
Jun 15, 2026
15w ago
144
BEARISH ★ 5/10
$24.25 $24.55▼ −1.24%▼ −3.47%—
May 7, 2026
21w ago
8-K
NEUTRAL ★ 3/10
$24.35 $24.37▲ +0.08%▼ −1.38%—
Apr 15, 2026
24w ago
144
NEUTRAL ★ 3/10
$24.11 $24.18▲ +0.29%▼ −0.69%—
Apr 8, 2026
25w ago
DEFM14A
BULLISH ★ 8/10
$24.02 $24.04▲ +0.08%▼ −3.43%—
Apr 8, 2026
25w ago
Insider Cluster
BEARISH ★ 5/10
$24.02 $24.04▼ −0.08%▲ +3.43%—
Apr 1, 2026
26w ago
10-K/A
NEUTRAL ★ 3/10
$23.80 $24.00▲ +0.84%▼ −2.78%—
Showing 10 of 11

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