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Ryan Specialty Holdings, Inc. insider Patrick G. Ryan, serving as trustee of the Ryan Stock Option Trust, reported acquiring a call option obligation covering 287,646 underlying shares of Class A common stock at a $43.63 per-share purchase price for the issuer. The trust is obligated to sell shares to the company from time to time through September 9, 2036 as employees exercise related Executive Chairman stock options that vest in equal annual installments on October 1, 2029, 2030 and 2031. On August 4, 2026, 287,646 shares of Class A common stock were transferred into the trust in an exempt internal transaction under Rule 16a-13.
Ryan Specialty Holdings reported that EVP & CHRO Michael Conklin received a grant of 22,920 Executive Chairman stock options on August 4, 2026. The options have a $43.63 exercise price, expire on August 4, 2036, and vest in three equal installments on October 1, 2029, 2030 and 2031. Following the award, he holds 22,920 derivative securities directly. The options are exercisable on a 1-for-1 basis into Class A common stock, and the grant was approved by the compensation and governance committee for purposes of Rule 16(b)(3).
Ryan Specialty Holdings, Inc. granted Co-President and COO Stephen Patrick Keogh an Executive Chairman Stock Option covering 22,920 shares of Class A common stock at an exercise price of $43.63 per share. The options vest in three equal installments on October 1, 2029, 2030 and 2031, are exercisable 1-for-1 into Class A common stock, and expire on August 4, 2036.
Ryan Specialty Holdings reported higher revenue but mixed profitability for the quarter and six months ended June 30, 2026. Total revenue for the quarter rose to $916.647 million from $855.170 million, driven by net commissions and fees across Wholesale Brokerage, Binding Authority, and Underwriting Management. Quarterly net income declined to $108.381 million from $124.705 million, and net income attributable to Ryan Specialty fell to $42.315 million, with diluted EPS at $0.33 versus $0.38 a year earlier.
For the first half of 2026, revenue increased to $1.711 billion from $1.545 billion, and net income attributable to Ryan Specialty rose to $59.961 million from $24.334 million, lifting diluted EPS to $0.45. Operating cash flows were $125.618 million, down from $210.760 million. Total assets reached $11.967 billion, supported by large fiduciary balances, while total debt increased to $3.633 billion, including a $1.7 billion term loan, $1.6 billion of senior secured notes, and higher revolving borrowings.
The company repurchased and retired 9.1 million Class A shares for $300.2 million and paid $0.13 per share in quarterly dividends on Class A stock. A multi‑year Empower restructuring program is underway, with expected total costs of $160.0 million through 2028 and anticipated annual savings of about $80.0 million in 2029; related expenses of $37.9 million, including a $12.0 million software impairment, were recognized in the first half of 2026.
Ryan Specialty Holdings, Inc. announced that it issued a press release on July 30, 2026 reporting its results of operations for the second quarter ended June 30, 2026.
On the same date, the board of directors declared a regular quarterly dividend of $0.13 per share on the outstanding Class A common stock, payable on August 25, 2026 to stockholders of record as of the close of business on August 11, 2026. The company also stated that comments about future dividends, restructuring activities and expected cost savings are forward-looking statements and subject to significant risks and uncertainties.
Ryan Specialty Holdings, Inc. reported that Chief Financial Officer Janice M. Hamilton had Restricted LLC Units of New Ryan Specialty, LLC vest and, at the issuer’s option, settle into 5,821 shares of Class A common stock on July 22, 2026. In connection with this settlement, 1,706 shares at $40.89 per share were delivered or withheld to pay the exercise price or tax liability by delivering or withholding securities. Following this event, Hamilton directly holds 40,747 Restricted LLC Units under the July 22, 2021 grant.
Ryan Specialty Holdings director Anthony J. Kuczinski bought a total of 3,000 shares of the company’s Class A Common Stock in open-market purchases on June 11 and 12, 2026. He paid weighted average prices of $34.83 and $35.77 per share across multiple trades.
Following these purchases, Kuczinski directly owns 13,072 shares of Ryan Specialty. The filing notes that each day’s reported price is a weighted average, with individual trade prices ranging from $34.56 to $35.06 on June 11 and $35.57 to $35.94 on June 12.
Ryan Specialty Holdings director John W. Rogers Jr. bought 7,500 shares of Class A Common Stock in an open-market purchase at a weighted average price of $35.1643 per share. The trades occurred in multiple transactions between $35.15 and $35.165. He now directly holds 117,933 shares.
Ryan Specialty Holdings Executive Chairman Patrick G. Ryan, a more than 10% owner, indirectly bought 120,000 shares of Class A Common Stock in an open-market purchase. The weighted average price was $32.4978 per share, with individual trades ranging from $32.24 to $32.62.
The shares were acquired through living trusts where Ryan and his spouse serve as co-trustees. Following the purchase, trusts for his benefit held 13,817,859 Class A shares, and additional family trusts held 55,475 shares, all reported as indirect ownership.
Ryan Specialty Holdings, Inc. Chief Financial Officer Janice M. Hamilton reported an open-market purchase of Class A Common Stock. She bought 6,300 shares on June 3, 2026 at a weighted average price of $31.7925 per share, through multiple trades between $31.17 and $32.13. Following this transaction, she directly owns 14,574 shares of Class A Common Stock.