WAY Waystar Holding Corp. Insider Trading

Director Heidi Miller purchases 7,200 shares of WAY at $26.25; stock now $26.58, down 39.2% from 52-week high

Director Heidi Miller initiated a position in Waystar with a purchase of 7,200 shares at $26.25 on March 2, 2026, establishing her first holding in the company. The purchase occurs as the stock trades 39.2% below its 52-week high of $43.69 and has declined 24.5% over the past 90 days, creating a backdrop of significant downward price momentum. Miller's cross-ticker track record shows 2 prior open-market sales with a 0.00% well-timed rate, indicating her historical sells did not precede gains—though this cross-ticker pattern provides limited predictive value for timing at Waystar specifically. Waystar's fundamentals remain intact with revenue of $268.7M, net income of $30.6M, annual revenue growth of 16.5%, and a P/E of 21.10, suggesting operational stability despite the recent stock decline.

Chief Business Officer Eric Sinclair sells 40,225 shares (40.2K) of WAY at $30.08; stock down 34.9% from 52-week high of $45.35.

Sinclair III Eric L., Chief Business Officer, sold 40,225 shares at $30.08 on 2026-01-20, reducing his holdings by 40,225 shares from 515,051 to 474,826 shares (-7.8% reduction). The stock is currently trading at $29.51, down 34.9% from its 52-week high of $45.35, and has declined 24.3% over the 90-day period. While Waystar maintains strong near-term growth with annual revenue growth of +19.3% and a $268.7M quarterly revenue base, the company operates at a net loss on a full-year basis and carries a trailing P/E of 50.88, indicating elevated valuation relative to current earnings. The executive's partial sale during a period of significant stock price deterioration occurs against the backdrop of fundamentally unprofitable operations, leaving open questions about both the sustainability of revenue growth and confidence in the valuation trajectory.

CEO Matthew J. Hawkins sold 25,000 shares of WAY at $38.08 across 2 transactions for $951,976.16

Matthew J. Hawkins, Chief Executive Officer of Waystar Holding Corp., executed 2 separate sales totaling 25,000 shares for $951,976.16 on September 22–23, 2025, reducing his holdings from 742,474 to 717,474 shares. The sales occurred at $38.08 per share, which was above the current price of $37.04, meaning the CEO sold into strength relative to the immediate market. His cross-ticker track record shows a 90-day well-timed rate of 60.00%, but this performance reflects 12 prior sells across multiple tickers; at Waystar specifically, his 5 prior trades show 3 measurable 90-day outcomes, all negative (ranging from -6.8% to -8.0%), suggesting an inconsistency between his broader timing success and his WAY-specific sell outcomes. The company trades at a P/E of 75.59 on the back of $270.7M quarterly revenue and $32.2M net income, yet was unprofitable on a full-year basis, creating a tension between growth momentum (+19.3% annual revenue growth) and valuation risk.

CPP Investment Board sold 5,938,773 shares (5.94M) of WAY at $39.21 on 2025-09-12, reducing stake by -23.8% to 19.03M shares; $232.9M transaction.

Canada Pension Plan Investment Board, a 10% owner, sold 5,938,773 shares for $232,859,289.33, a material reduction in stake size. The timing warrants attention: prior same-ticker history shows 3 of 3 prior sales by this insider were well-timed at the 90-day mark, and the cross-ticker track record reflects an 80.00% well-timed rate on sells—meaningfully better than random. The current stock price of $38.25 sits -15.7% from the 52-week high, and notably, the company was unprofitable over its most recent full fiscal year despite showing +19.3% annual revenue growth, a pattern that typically precedes volatility. This large block sale by an institutional 10% holder at a price ($39.21) above current levels may signal perception of near-term downside risk, consistent with this insider's demonstrated pattern of executing sells ahead of subsequent declines.

Bain Capital Investors LLC (10% owner) sold 4,295,139 shares of WAY at $39.21 for $168.4M on 2025-09-12, reducing stake by 24.5%.

Bain Capital liquidated nearly a quarter of its Waystar holding, offloading 4,295,139 shares at $39.21. The 24.5% reduction in position size represents a material reallocation by a significant 10% shareholder, with proceeds of $168.4M. At the same-ticker level, Bain's prior three WAY sales (Feb 2025, May 2025 ×2) showed mixed 90-day outcomes: two of three were well-timed against subsequent declines. The current $38.25 price sits 15.7% below the 52-week high but 6.0% above the 30-day moving average. Waystar's valuation backdrop shows a 78.06 P/E, elevated revenue growth of +19.3% year-over-year, yet full-year profitability remains negative despite positive recent quarterly earnings of $32.2M on $270.7M revenue—a composition that may warrant scrutiny of underlying earnings sustainability at this valuation multiple.

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.

Derby LuxCo sells 7,766,088 shares of WAY for $304.5M at $39.21; reduces stake 23.8% to 24.88M shares

Derby LuxCo, a 10% owner, executed a substantial sale of 7,766,088 shares (7.77M shares) at $39.21 on 2025-09-12, generating $304,508,310.48 in proceeds and reducing holdings by 23.8% to 24,879,437 shares (24.88M shares). The transaction occurred at a price $0.96 above the current market price of $38.25, placing the sale near recent highs within the 52-week range of $26.39–$45.35. Notably, Derby LuxCo's prior three sales at WAY (2025-05-20, 2025-05-16, and 2025-02-24) all displayed well-timed execution at the 90-day mark, with negative subsequent returns of -3.0%, -5.0%, and -3.4% respectively, suggesting a consistent pattern of selling into strength and before declines. The company's elevated P/E of 78.06 against full-year unprofitability and recent quarterly profitability raises valuation concerns, and the timing of this large-block liquidation by a major shareholder at recent peaks warrants investor attention as to the broader growth narrative supporting the stock's 19.3% annual revenue growth.

CFO Oreskovich sells 16,666 shares (16.7K) of WAY at $40.49; stock now $38.35; prior 5 WAY sales showed 0% well-timed outcomes at 90 days.

Oreskovich sold 16,666 shares at $40.49 on 2025-09-10, reducing his holdings by 4.5% to 354,512 shares, with a total transaction value of $674,848.01. The stock has since declined 15.4% from its 52-week high and trades at $38.35 today—below the sale price. However, timing cannot be reliably attributed: his prior 5 trades at WAY showed a 0% well-timed rate at the 90-day mark, meaning none of those sales preceded declines; in fact, average 90-day returns after his WAY sells were positive (ranging from +0.4% to +9.8%), indicating the stock generally rose after his exits. The broader technical context shows mixed signals: the stock surged 10.9% over 30 days but declined 1.5% over 90 days. The company's fundamentals remain tension-laden—strong Q revenue of $270.7M with 19.3% annual growth, but a P/E of 78.27 is elevated and the company was unprofitable on a full-year basis despite recent quarterly profitability.

CTO Bridge T. Craig sells 85,000 WAY shares at $40.06 (down 10.7% from 52-week high); holdings drop to 583.4K shares from 668.4K

Bridge T. Craig, Chief Transformation Officer, sold 85,000 shares on 2025-09-08 at $40.06, reducing his holdings by 12.7%. His prior trades at Waystar show a well-timed pattern: a 2025-02-26 sale preceded a 90-day decline of 7.2%, aligning with his cross-ticker track record where 100.00% of sells were well-timed. The current sale price sits 10.7% below the 52-week high of $45.35, and over 30 days the stock is up 17.5%, suggesting he sold into recent strength. Fundamentals remain mixed—the company posted $270.7M quarterly revenue (+19.3% annual growth) and $32.2M net income, but carried negative full-year net income with a steep P/E of 82.65—warranting close monitoring to assess whether the insider's historical sell-timing edge continues at this ticker.

CEO Matthew J. Hawkins sold 46,667 shares of WAY at $34.66; stock now -23.8% from 52-week high amid premium valuation.

CEO Matthew J. Hawkins sold 46,667 shares (5.8% of his pre-transaction holdings) at $34.66 on 2025-08-12, reducing his position from 810,798 to 764,131 shares. The stock has declined 23.8% from its 52-week high of $45.35 and is currently trading at $34.58, down 7.6% over 30 days and 12.5% over 90 days. Hawkins has completed five sales at WAY in recent weeks (May 22–August 12), collectively moving shares during a period of sustained downward price movement. Against his cross-ticker track record showing a 33.33% well-timed rate on 11 prior sells, his WAY-specific timing has not measured favorably, with 4 measurable same-ticker sales posting negative 30-day returns (-2.1%, -2.2%, -3.7%) or flat performance. The company's fundamentals present a paradox: strong revenue growth of 19.3% and profitable quarterly results ($32.2M net income in the latest quarter), yet the full fiscal year was unprofitable and the stock trades at a P/E of 70.57 against a $6.0B market cap, suggesting elevated valuation relative to earnings power despite operational progress.