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EdgarHawk

Moskowitz Paul G

Director

Director 10% Owner
3 filings analyzed · 1 company · Latest 2025-09-16

Companies

Company Buys Sells Direction
Waystar Holding Corp. WAY 0 7 Net selling

Activity

September 2025
high
Sell
4,295,139 shares
$168,412,400
Significance 7/10

Director Paul G Moskowitz sold 4,295,139 shares of WAY at $39.21 on 2025-09-12 for $168,412,400.19, reducing holdings by 24.5%.

Moskowitz divested a substantial 4,295,139 shares (24.5% of his pre-transaction holdings) at $39.21, raising $168,412,400.19. The sale occurred when WAY trades at $38.25, down 15.7% from its 52-week high of $45.35, suggesting he sold above the current market level. His same-ticker history at WAY shows 2 of 3 prior sells were well-timed at the 90-day mark, indicating a pattern of selling before subsequent declines. The company carries a notably elevated P/E of 78.06 against positive near-term fundamentals (19.3% annual revenue growth, $32.2M quarterly net income), though it was unprofitable on a full-year basis, warranting investor attention to whether this large director reduction reflects confidence in valuation or concern about forward momentum.

May 2025
high
Sell
3,464,090 shares
$129,522,325
Significance 6/10

Director Paul G Moskowitz sold 3,464,090 shares for $129,522,325.10 across 2 transactions on WAY, reducing holdings by 16.1%.

Paul G Moskowitz, a director at Waystar, executed 2 separate sales totaling 3,464,090 shares for $129,522,325.10 (blended average $37.39 per share) on 2025-05-16 and 2025-05-20, reducing his post-transaction holdings to 18,055,049 shares from 21,519,139 shares—a net reduction of 16.1%. The sales occurred at prices modestly below the current market price of $39.65 and well below the 52-week high of $45.35, suggesting execution during a period of relative stability. Waystar's fundamentals present a mixed picture: the company achieved strong revenue growth of 19.3% year-over-year with $256,435,000.00 in latest-quarter revenue and positive net income of $29,269,000.00 in that quarter, yet reported negative full-year net income in its most recent fiscal year. The elevated P/E of 264.33 reflects valuation stress despite the growth narrative. Moskowitz's cross-ticker track record shows limited selling history (1 prior sell with a 30-day return of -2.4%), providing minimal precedent for assessing timing precision at this ticker; his single prior WAY transaction (a February 2025 sell) has not yet reached a measurable 90-day outcome.

February 2025
high
Sell
5,652,689 shares
$218,193,795
Significance 7/10

Director Paul G Moskowitz sells 5,652,689 shares of WAY for $218.2M, reducing stake by 20.6% to 21.75M shares

Director Paul G Moskowitz sold 5,652,689 shares at $38.60 on 2025-02-24, generating $218,193,795.40 in proceeds and reducing his holdings from 27,407,225 shares to 21,754,536 shares. The sale occurred while the stock was trading 6.6% below its 52-week high of $45.35, and represents a substantial 20.6% reduction in his pre-transaction position. The company showed strong quarterly revenue of $240,112,000.00 with annual growth of 19.3%, but remains unprofitable on a full-year basis despite generating $5,413,000.00 in the latest quarter net income. The magnitude and structuring of this transaction—a material reduction in a director's personal stake—warrant attention to whether this reflects a shift in insider positioning or capital allocation strategy at a company still establishing profitability momentum.

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