CEO-Affiliated Trust Files to Sell $41M of Sezzle Stock
SEZL has more than doubled off its 52-week low of $49.5.
Summary
A trust affiliated with CEO Charles Youakim filed to sell 350,000 Sezzle shares worth approximately $41 million, the largest insider sale filing in the past 90 days.
Key Events · Ownership and Investor Activity · SEZL
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CEO-Affiliated Trust Files $41M Sale
Charles G. Youakim 2020 Irrevocable GST Trust filed a Form 144 to sell 350,000 shares worth approximately $41.0 million, with an approximate sale date of October 9, 2026.
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Largest Insider Sale in 90 Days
This filing is materially larger than prior insider sales — CFO Brading Dickson sold $1.95M and President Paul Paradis sold $3.63M in July, and director Brehm Kyle M. filed to sell just 1,000 shares in August.
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Follows CEO Ownership Drop
The sale comes after CEO Charles Youakim's beneficial ownership fell to 39.6% in September following a divorce decree that removed 1.5M trust shares from his holdings.
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Shares Acquired as Gift in 2020
The trust acquired the 350,000 shares as a gift from Charles G. Youakim on March 20, 2020, with the donor having acquired them on January 4, 2016.
Analysis · SEZL · Trade & Services
A trust affiliated with CEO Charles Youakim filed a Form 144 to sell 350,000 shares worth approximately $41 million. This is a significant sale — roughly 1% of the company's outstanding shares — and comes just weeks after Youakim's beneficial ownership dropped to 39.6% following a divorce decree. The trust acquired the shares as a gift from Youakim in 2020, and this is the first time this entity has filed to sell. While the sale is from an affiliate rather than Youakim directly, the size and timing make it notable for investors.
How filings like this one have moved
In the 30 days to Oct 9, 2026, 28.2% of the 1631 measured filings Wiseek scored 7 moved their stock by 5% or more by the next session's close. The median move was -0.49%. These are measured outcomes after filings of this importance, not a forecast for this one.
Measured one observation per ticker per day, after exclusions. Current figures: Filing Impact Tracker · open dataset
At the time of this filing, SEZL was trading at $129.00 on NASDAQ in the Trade & Services sector, with a market capitalization of approximately $4.3B. The 52-week trading range was $49.50 to $195.71. This filing was assessed with negative market sentiment and an importance score of 7 out of 10.