Insider Cluster (3 insiders) ·Filed May 27, 2026

UPST

Upstart Holdings, Inc.
NEUTRAL
Impact 2/10
Horizondays Processed4mo ago
Insider cluster: 3 insiders, $0.4M total
Actionable Insight • Neutral

This cluster is too small to warrant a directional trade. The $449K in sales is noise relative to UPST's $2.9B market cap and is offset by $6.4M in insider purchases over the past 30 days. Monitor for any material corporate events (earnings, guidance, capital raise) that could explain a shift in insider behavior, but no action is warranted from this filing alone.

DirectionNeutral
Confidencehigh
Horizondays
Final — all horizons settled through T+60d
UPST ▼ -7.31% at T+60d
NEUTRAL call ✗ call lost -7.31% · α vs SPY -9.05% · entry $32.69 → $30.30
Entry anchored
May 27, 2026
via day open
T+1d
+3.37%
call +3.37% · α +3.13%
$33.79
settled 4mo ago
T+5d
-1.28%
call -1.28% · α -1.60%
$32.27
settled 4mo ago
T+20d
+2.97%
call +2.97% · α +6.11%
$33.66
settled 3mo ago
T+60d
-7.31%
call -7.31% · α -9.05%
$30.30
settled 6w ago

Price Chart

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Executive Summary

Three UPST insiders, including the Chief Legal Officer and President of Capital & Enterprise, sold a total of ~$449K in open-market sales over a 7-day window. The dollar value is ~0.015% of market cap — trivial relative to the $2.9B company. The cluster is small, non-CEO, and likely driven by routine portfolio diversification or vesting-related liquidity, not a coordinated bearish signal.

Key Financial Metrics

Direction
selling
Total Value
$449.0K
Insiders
3

Key Facts

  • Three insiders sold a total of ~$449K in open-market sales from May 19–26, 2026.
  • Sales include CLO Scott Darling ($191K), President Sanjay Datta ($230K), and officer Natalia Mirgorodskaya ($28K).
  • Total sales represent ~0.015% of UPST's $2.9B market cap — well below the 0.1% materiality threshold.
  • No insider purchases were reported in the cluster window.
  • Recent 30-day insider activity shows $6.4M in buys vs $560K in sells, indicating net bullish insider positioning over the longer term.

Financial Impact

~$449K in insider sales, ~0.015% of market cap

Risk Factors

  • Insider sales could accelerate if a material negative catalyst emerges, but this cluster does not indicate one.
  • The cluster's small size and lack of CEO participation limit its informational value.

Market Snapshot

Exchange
Nasdaq
Sector
Finance Services
Analyst Consensus
62% bullish (21 analysts)

Investment Themes

Artificial IntelligenceFintech & Payments

Documents Analyzed

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

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-UPST-1779914271367
12 reports for UPST
Performance horizon
100% Hit rate 4 of 4 directional calls best @ T+20▲ +13.11%Aug 21, 2026
Filters
Rows
Reports for UPST — sortable, filterable
TypeNow
Sep 10, 2026
21d ago
Insider Cluster
MIXED ★ 5/10
$25.59 $25.00▼ −2.31%▼ −2.08%$22.81 (−10.86%)
Aug 27, 2026
5w ago
Insider Cluster
NEUTRAL ★ 3/10
$29.08 $28.05▼ −3.54%▼ −3.65%$22.81 (−21.56%)
Aug 21, 2026
5w ago
Insider Cluster
BEARISH ★ 4/10
$29.89 $28.68▲ +4.05%▲ +4.52%$22.81 (+23.69%)
Aug 19, 2026
6w ago
Insider Cluster
NEUTRAL ★ 2/10
$30.60 $30.47▼ −0.42%▼ −0.04%$22.81 (−25.46%)
May 27, 2026
18w ago
Insider Cluster
NEUTRAL ★ 2/10
$32.69 $32.27▼ −1.28%▼ −1.60%$22.81 (−30.22%)
May 20, 2026
19w ago
144
NEUTRAL ★ 2/10
$28.85 $32.69▲ +13.31%▲ +11.71%$22.81 (−20.94%)
May 19, 2026
19w ago
8-K
NEUTRAL ★ 3/10
$28.08 $30.45▲ +8.44%▲ +6.19%$22.81 (−18.77%)
May 18, 2026
19w ago
Insider Cluster
BULLISH ★ 6/10
$28.08 $30.45▲ +8.44%▲ +6.19%$22.81 (−18.77%)
May 15, 2026
19w ago
144
NEUTRAL ★ 2/10
$27.94 $30.62▲ +9.59%▲ +7.97%$22.81 (−18.36%)
May 7, 2026
21w ago
Insider Cluster
BULLISH ★ 6/10
$29.00 $29.71▲ +2.45%▲ +0.15%$22.81 (−21.34%)
Showing 10 of 12

US Market Status

Market Closed — Opens Mon (65h 25m)

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Report published May 27, 2026