Matthew J. Hawkins

CEO Matthew J. Hawkins sells 70,000 WAY shares for $1,613,976.12 via scheduled 10b5-1 plan

Matthew J. Hawkins, CEO of Waystar Holding Corp., executed 2 separate sales totaling 70,000 shares for $1,613,976.12 on 2026-07-15 and 2026-07-16 at blended average price $23.06, pursuant to a pre-arranged 10b5-1 trading plan adopted on 2026-03-13. His non-derivative holdings declined from 996,816 shares to 926,816 shares (-7.0%), while maintaining significant derivative holdings of 1,435,238 and 1,398,337 stock options. The current stock price of $22.27 is -46.3% from the 52-week high of $41.47, yet the CEO's prior sells at this ticker have yielded mixed results: his 5 prior WAY transactions showed 90-day returns ranging from -13.8% to +4.2%, with 4 of 5 yielding negative 90-day outcomes. This scheduled divestiture occurs as the company reports strong fundamentals (revenue $313,874,000.00, net income $43,283,000.00, annual growth +16.5%, P/E 33.74), and the stock has rebounded +22.0% over 30 days despite remaining significantly depressed from its 52-week peak.

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.

Waystar CEO Matthew Hawkins sells 46,667 shares at $34.66 under 10b5-1 plan adopted 2024-11-22

Matthew J. Hawkins, Chief Executive Officer, sold 46,667 shares of Waystar Holding Corp. at $34.66 on 2025-08-12 for a total value of $1,617,580.89, reducing his holdings from 810,798 shares to 764,131 shares. This transaction was executed under a pre-arranged 10b5-1 trading plan adopted on 2024-11-22, meaning the sale was scheduled in advance rather than discretionary. The sale represents a 5.8% reduction in his post-transaction holdings, which is consistent with a systematic disposition under a previously established plan rather than a reactive market decision.

CEO Matthew J. Hawkins sold 46,667 shares at $38.26, reducing stake by 5.8% to 764,131 shares; stock now -17.1% from 52-week high.

Matthew J. Hawkins, Chief Executive Officer of Waystar Holding Corp., executed a sale of 46,667 shares at $38.26 on 2025-07-15, with total transaction value of $1,785,540.09. His post-transaction holdings of 764,131 shares represent a net reduction of 46,667 shares, or -5.8% versus pre-transaction holdings of 810,798 shares. The sale occurred when WAY traded at $38.26; the stock has since declined to $37.59 (current price), trading -17.1% from its 52-week high of $45.35 and down 3.0% over the past 30 days. At the same ticker, Hawkins has executed five prior open-market sales: on 2025-06-05 (30d return -2.1%), 2025-05-27 (30d return +0.6%), 2025-05-23 (30d return -2.2%), 2025-05-22 (30d return -3.7%), and 2025-05-13 (30d return +0.3%). Across all his open-market activity spanning multiple tickers, his track record shows 10 prior sells with an average 90-day return of +8.4% and a well-timed rate of 0.00% (meaning none of his prior sales preceded a stock decline). The company's latest-quarter fundamentals show revenue of $256,435,000.00 and net income of $29,269,000.00, with annual revenue growth of +19.3%, yet the company posted negative full-year net income on a full-fiscal-year basis. The P/E multiple of 250.60 reflects significant valuation compression relative to current profitability.

CEO Hawkins sells 59,836 shares of WAY at $40.18; fifth sale in nine days amid elevated valuation (P/E 274.40)

Matthew J. Hawkins, CEO of Waystar Holding Corp., executed a sale of 59,836 shares at $40.18 on 2025-06-05, reducing his holdings by 7.3% to 764,131 shares. This sale is the fifth transaction by Hawkins at WAY in nine calendar days (2025-05-13 through 2025-06-05), representing a sustained pattern of liquidation in a compressed timeframe. Waystar trades at an elevated P/E of 274.40 against quarterly revenue of $256.4M and net income of $29.3M, though the company remains unprofitable on a full-year basis. The current price of $41.16 sits 9.2% below the 52-week high of $45.35. Without scheduled trade plan disclosures in the filing, the frequency and timing of these sales merit investor attention to whether they reflect portfolio management at a stretched valuation or signal internal sentiment regarding near-term trajectory.

CEO Matthew Hawkins sells 340,164 shares of WAY for $13,179,048.39 across 3 trades; reduces stake by 30.8%

Matthew Hawkins, Chief Executive Officer of Waystar, executed 3 separate sales totaling 340,164 shares for $13,179,048.39 between May 22–27, 2025, at prices ranging from $38.53 to $39.15. His post-transaction holding of 764,131 shares represents a 30.8% reduction from 1,104,295 shares, a material reduction in his equity stake. The company carries a P/E ratio of 260.67 despite posting annual revenue growth of +19.3% and quarterly net income of $29,269,000, though full-year net income was negative. At the current price of $39.10, the stock is -13.8% from its 52-week high of $45.35 but +5.6% over the prior 30 days, creating ambiguous directional signals. His prior 5 trades at WAY (3 measurable outcomes through April 2025) showed positive 30-day returns ranging from +4.9% to +10.9%, though 90-day outcomes remain unmeasured for the April trades and beyond.

CEO Matthew J. Hawkins sold 46,667 shares at $38.97 avg for $1.8M; retains 764.1K shares

Matthew J. Hawkins, CEO of Waystar, executed 2 separate sales totaling 46,667 shares for $1,818,656.66, reducing holdings by 5.8% to 764.1K shares. His prior trades at WAY show mixed near-term execution: recent April sells have posted 30-day returns of +10.9% and +9.0%, while March sales were smaller at +4.9% and +2.5%, suggesting post-sale price appreciation rather than downside prediction. The company's fundamentals are mixed—strong 19.3% annual revenue growth and positive net income of $29,269,000 in the latest quarter contrast with a historically unprofitable full fiscal year and an elevated P/E of 263.33. The current stock price of $39.50 sits 12.9% below its 52-week high of $45.35, having declined 11.6% over 90 days despite an 8.0% 30-day rebound, reflecting recent volatility in the name.

CEO Hawkins sells 46,667 shares across 2 transactions for $1,696,729.98 on 2025-04-10, reducing stake to 500,000 shares.

Matthew J. Hawkins, CEO of Waystar Holding Corp., executed two separate sales totaling 46,667 shares for $1,696,729.98, reducing his holdings from 546,667 to 500,000 shares (-8.5% of pre-transaction holdings). The sales occurred at $36.09 and $36.72, slightly below the current price of $36.58. While his cross-ticker track record shows prior sells with an average 30-day return of +3.7%, this lacks predictive power for WAY specifically; his two prior sales at WAY (on 2025-03-13) are not yet measurable at the 90-day mark. The company reported annual revenue growth of +19.3% and a $240.1M quarterly revenue base, but remains unprofitable on a full-year basis. The sale represents a material reduction in insider ownership but does not contradict the company's growth trajectory or recent operational metrics.

WAY CEO Hawkins sells 46,655 shares at $35.54 on 2025-03-13, reducing stake by 8.5% to 500,000 shares.

Matthew J. Hawkins, Chief Executive Officer of Waystar, executed 2 separate sales totaling 46,655 shares for $1,658,645.64 on March 13, 2025, at a blended average price of $35.55. This represents an 8.5% reduction in his post-transaction holdings to 500,000 shares. The sale occurred when the stock was trading at $35.54–$36.36, well below the 52-week high of $45.35 (currently -19.6% from that peak and -16.6% over the past 30 days). While the company shows positive quarterly revenue of $240,112,000.00 and annual revenue growth of +19.3%, it remains unprofitable on a full-year basis, creating a backdrop of execution risk despite strong top-line growth. The timing of the sale amid recent price deterioration warrants investor attention to whether the CEO's assessment of near-term prospects differs from public guidance.