Skyward/2025/FY/Annual report
| Document info | |
|---|---|
| Organization | Skyward |
| Year | 2025 |
| Period | FY |
| Period label | FY25 |
| Document type | Annual report |
| Document name | Skyward Specialty Insurance Group 2025 Form 10-K |
| Publication date | 2026-03-02 |
| Language | English |
| Source | Original URL |
This article presents Skyward's FY 2025 annual report — the cover and primary financial statements from its SEC Form 10-K.
Cover
| USD ($) | 12 Months Ended | ||
|---|---|---|---|
| — | Dec. 31, 2025 | Feb. 26, 2026 | Jun. 30, 2025 |
| Cover [Abstract] | — | — | — |
| Document Type | 10-K | — | — |
| Document Annual Report | true | — | — |
| Document Period End Date | Dec. 31, 2025 | — | — |
| Current Fiscal Year End Date | --12-31 | — | — |
| Document Transition Report | false | — | — |
| Entity File Number | 001-41591 | — | — |
| Entity Registrant Name | SKYWARD SPECIALTY INSURANCE GROUP, INC. | — | — |
| Entity Incorporation, State or Country Code | DE | — | — |
| Entity Tax Identification Number | 14-1957288 | — | — |
| Entity Address, Address Line One | 800 Gessner Road | — | — |
| Entity Address, Address Line Two | Suite 600 | — | — |
| Entity Address, City or Town | Houston | — | — |
| Entity Address, State or Province | TX | — | — |
| Entity Address, Postal Zip Code | 77024-4284 | — | — |
| City Area Code | 713 | — | — |
| Local Phone Number | 935-4800 | — | — |
| Title of 12(b) Security | Common stock, par value $0.01 | — | — |
| Trading Symbol | SKWD | — | — |
| Security Exchange Name | NASDAQ | — | — |
| Entity Well-known Seasoned Issuer | No | — | — |
| Entity Voluntary Filers | No | — | — |
| Entity Current Reporting Status | No | — | — |
| Entity Interactive Data Current | Yes | — | — |
| Entity Filer Category | Large Accelerated Filer | — | — |
| Entity Small Business | false | — | — |
| Entity Emerging Growth Company | false | — | — |
| ICFR Auditor Attestation Flag | true | — | — |
| Document Financial Statement Error Correction [Flag] | false | — | — |
| Entity Shell Company | false | — | — |
| Entity Public Float | — | — | $ 2,165,161,643 |
| Entity Common Stock, Shares Outstanding | — | 44,467,084 | — |
| Documents Incorporated by Reference | Portions of the Registrant’s Proxy Statement relating to the 2026 annual meeting of stockholders (the “2026 Proxy Statement”), which will be filed within 120 days of December 31, 2025, are incorporated by reference into Part III of this Form 10-K. | — | — |
| Entity Central Index Key | 0001519449 | — | — |
| Amendment Flag | false | — | — |
| Document Fiscal Year Focus | 2025 | — | — |
| Document Fiscal Period Focus | FY | — | — |
Audit Information
| 12 Months Ended | |
|---|---|
| — | Dec. 31, 2025 |
| Audit Information [Abstract] | — |
| Auditor Name | Ernst & Young LLP |
| Auditor Location | Houston, Texas |
| Auditor Firm ID | 42 |
Consolidated balance sheets
| USD ($) $ in Thousands | Dec. 31, 2025 | Dec. 31, 2024 |
|---|---|---|
| Investments: | — | — |
| Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $7,000 and $0, respectively) (amortized cost of $1,848,755 and $1,320,266, respectively) | $ 1,856,303 | $ 1,292,218 |
| Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $468 and $243, respectively) | 32,822 | 39,153 |
| Equity securities, at fair value | 1,174 | 106,254 |
| Mortgage loans, at fair value | 9,902 | 26,490 |
| Equity method investments | 77,365 | 98,594 |
| Other long-term investments | 58,650 | 33,182 |
| Short-term investments, at fair value | 264,299 | 274,929 |
| Total investments | 2,300,515 | 1,870,820 |
| Cash and cash equivalents | 168,544 | 121,603 |
| Restricted cash | 30,570 | 35,922 |
| Premiums receivable, net | 544,217 | 321,641 |
| Reinsurance recoverables, net | 1,119,880 | 857,876 |
| Ceded unearned premium | 238,948 | 203,901 |
| Deferred policy acquisition costs | 136,100 | 113,183 |
| Deferred income taxes | 27,865 | 30,486 |
| Goodwill and intangible assets, net | 88,040 | 87,348 |
| Other assets | 137,173 | 86,698 |
| Total assets | 4,791,852 | 3,729,478 |
| Liabilities: | — | — |
| Reserves for losses and loss adjustment expenses | 2,318,894 | 1,782,383 |
| Unearned premiums | 774,035 | 637,185 |
| Deferred ceding commission | 46,453 | 40,434 |
| Reinsurance and premium payables | 279,888 | 177,070 |
| Funds held for others | 128,003 | 102,665 |
| Accounts payable and accrued liabilities | 115,034 | 76,206 |
| Carrying Value | 100,411 | 100,000 |
| Subordinated debt, net of debt issuance costs | 19,569 | 19,536 |
| Total liabilities | 3,782,287 | 2,935,479 |
| Stockholders’ equity | — | — |
| Common stock, $0.01 par value, 500,000,000 shares authorized, 40,511,222 and 40,127,908 shares issued and outstanding, respectively | 405 | 401 |
| Additional paid-in capital | 730,555 | 718,598 |
| Accumulated other comprehensive income (loss) | 11,457 | -22,120 |
| Retained earnings | 267,148 | 97,120 |
| Total stockholders’ equity | 1,009,565 | 793,999 |
| Total liabilities and stockholders’ equity | $ 4,791,852 | $ 3,729,478 |
Consolidated balance sheets (parenthetical)
| USD ($) $ in Thousands | Dec. 31, 2025 | Dec. 31, 2024 |
|---|---|---|
| Statement of Financial Position [Abstract] | — | — |
| Available-for-sale allowance for credit losses | $ 7,000 | $ 0 |
| Amortized cost | 1,848,755 | 1,320,266 |
| Allowance for credit losses | $ 468 | $ 243 |
| Common stock, par value (in dollar per share) | $ 0.01 | $ 0.01 |
| Common stock, shares authorized (in shares) | 500,000,000 | 500,000,000 |
| Common stock, shares issued (in shares) | 40,511,222 | 40,127,908 |
| Common stock, shares outstanding (in shares) | 40,511,222 | 40,127,908 |
Consolidated statements of operations and comprehensive income
| USD ($) $ in Thousands | 12 Months Ended | ||
|---|---|---|---|
| — | Dec. 31, 2025 | Dec. 31, 2024 | Dec. 31, 2023 |
| Revenues: | — | — | — |
| Net earned premiums | $ 1,304,505 | $ 1,056,722 | $ 829,143 |
| Commission and fee income | 6,855 | 6,703 | 6,064 |
| Net investment income | 83,619 | 80,600 | 40,340 |
| Net investment gains | 22,149 | 6,342 | 11,054 |
| Other loss | -587 | -167 | -632 |
| Total revenues | 1,416,541 | 1,150,200 | 885,969 |
| Expenses: | — | — | — |
| Losses and loss adjustment expenses | 795,022 | 669,809 | 515,237 |
| Underwriting, acquisition and insurance expenses | 377,359 | 311,757 | 243,444 |
| Transaction costs | 14,019 | 0 | 0 |
| Interest expense | 7,919 | 9,496 | 10,024 |
| Amortization expense | 1,636 | 2,007 | 1,798 |
| Other expenses | 4,162 | 4,392 | 5,364 |
| Total expenses | 1,200,117 | 997,461 | 775,867 |
| Income before income taxes | 216,424 | 152,739 | 110,102 |
| Income tax expense | 46,396 | 33,911 | 24,118 |
| Net income | 170,028 | 118,828 | 85,984 |
| Net income attributable to participating securities | 0 | 0 | 1,677 |
| Net income attributable to common stockholders | 170,028 | 118,828 | 84,307 |
| Comprehensive income | — | — | — |
| Net income | 170,028 | 118,828 | 85,984 |
| Unrealized gains and losses on investments: | — | — | — |
| Net change in unrealized gains on investments, net of tax | 33,092 | 9,792 | 25,516 |
| Reclassification adjustment for gains (losses) on securities no longer held, net of tax | 485 | -8,959 | -4,984 |
| Total other comprehensive income | 33,577 | 833 | 20,532 |
| Comprehensive income | $ 203,605 | $ 119,661 | $ 106,516 |
| Per share data: | — | — | — |
| Basic earnings per share (in dollar per share) | $ 4.21 | $ 2.97 | $ 2.34 |
| Diluted earnings per share (in dollar per share) | $ 4.07 | $ 2.87 | $ 2.24 |
| Weighted-average common shares outstanding | — | — | — |
| Basic (in shares) | 40,407,310 | 40,056,475 | 36,031,907 |
| Diluted (in shares) | 41,808,046 | 41,377,460 | 38,317,534 |
Consolidated statements of stockholders’ equity
| USD ($) $ in Thousands | Total | Preferred stocks: | Common stock: | Treasury stock: | Additional paid-in capital: | Stock notes receivable: | Accumulated other comprehensive income (loss): | Retained earnings (accumulated deficit): | Retained earnings (accumulated deficit): Period of adoption, adjustment |
|---|---|---|---|---|---|---|---|---|---|
| Preferred shares balance at beginning of period (in shares) at Dec. 31, 2022 | — | 1,969,660 | — | — | — | — | — | — | — |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Preferred stock conversion to common shares (in shares) | — | -1,969,660 | 16,305,113 | — | — | — | — | — | — |
| Preferred shares balance at ending of period (in shares) at Dec. 31, 2023 | — | 0 | — | — | — | — | — | — | — |
| Common shares balance at beginning of period (in shares) at Dec. 31, 2022 | — | — | 16,599,666 | — | — | — | — | — | — |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Issuance of shares (in shares) | — | — | 6,958,977 | — | — | — | — | — | — |
| Common shares balance at ending of period (in shares) at Dec. 31, 2023 | — | — | 39,863,756 | — | — | — | — | — | — |
| Stockholders' equity beginning balance at Dec. 31, 2022 | — | $ 20 | $ 168 | $ (2) | $ 577,289 | $ (6,911) | $ (43,485) | $ (105,417) | $ (2,275) |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Preferred stock conversion to common shares | — | -20 | 161 | 2 | -143 | — | — | — | — |
| Issuance of common stock/Employee equity transactions | — | — | 22 | — | 9,213 | 1,349 | — | — | — |
| Proceeds from equity offerings, net | — | — | 48 | — | 124,496 | — | — | — | — |
| Other comprehensive income, net of tax | $ 20,532 | — | — | — | — | — | 20,532 | — | — |
| Net income | 85,984 | — | — | — | — | — | — | 85,984 | — |
| Stockholders' equity ending balance at Dec. 31, 2023 | $ 661,031 | $ 0 | $ 399 | 0 | 710,855 | -5,562 | -22,953 | -21,708 | 0 |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Preferred stock conversion to common shares (in shares) | — | 0 | 0 | — | — | — | — | — | — |
| Preferred shares balance at ending of period (in shares) at Dec. 31, 2024 | — | 0 | — | — | — | — | — | — | — |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Issuance of shares (in shares) | — | — | 264,152 | — | — | — | — | — | — |
| Common shares balance at ending of period (in shares) at Dec. 31, 2024 | 40,127,908 | — | 40,127,908 | — | — | — | — | — | — |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Preferred stock conversion to common shares | — | $ 0 | $ 0 | 0 | 0 | — | — | — | — |
| Issuance of common stock/Employee equity transactions | — | — | 2 | — | 7,743 | 5,562 | — | — | — |
| Proceeds from equity offerings, net | — | — | 0 | — | 0 | — | — | — | — |
| Other comprehensive income, net of tax | $ 833 | — | — | — | — | — | 833 | — | — |
| Net income | 118,828 | — | — | — | — | — | — | 118,828 | — |
| Stockholders' equity ending balance at Dec. 31, 2024 | $ 793,999 | $ 0 | $ 401 | 0 | 718,598 | 0 | -22,120 | 97,120 | $ 0 |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Preferred stock conversion to common shares (in shares) | — | 0 | 0 | — | — | — | — | — | — |
| Preferred shares balance at ending of period (in shares) at Dec. 31, 2025 | — | 0 | — | — | — | — | — | — | — |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Issuance of shares (in shares) | — | — | 383,314 | — | — | — | — | — | — |
| Common shares balance at ending of period (in shares) at Dec. 31, 2025 | 40,511,222 | — | 40,511,222 | — | — | — | — | — | — |
| Increase (Decrease) in Stockholders' Equity [Roll Forward] | — | — | — | — | — | — | — | — | — |
| Preferred stock conversion to common shares | — | $ 0 | $ 0 | 0 | 0 | — | — | — | — |
| Issuance of common stock/Employee equity transactions | — | — | 4 | — | 11,957 | 0 | — | — | — |
| Proceeds from equity offerings, net | — | — | 0 | — | 0 | — | — | — | — |
| Other comprehensive income, net of tax | $ 33,577 | — | — | — | — | — | 33,577 | — | — |
| Net income | 170,028 | — | — | — | — | — | — | 170,028 | — |
| Stockholders' equity ending balance at Dec. 31, 2025 | $ 1,009,565 | $ 0 | $ 405 | $ 0 | $ 730,555 | $ 0 | $ 11,457 | $ 267,148 | — |
Consolidated statements of cash flows
| USD ($) $ in Thousands | 12 Months Ended | ||
|---|---|---|---|
| — | Dec. 31, 2025 | Dec. 31, 2024 | Dec. 31, 2023 |
| Cash flows from operating activities: | — | — | — |
| Net income | $ 170,028 | $ 118,828 | $ 85,984 |
| Net investment (gains) losses | -22,149 | -6,342 | -11,054 |
| Depreciation and amortization expense | 3,535 | 3,358 | 3,891 |
| Stock-based compensation expense | 11,960 | 9,395 | 8,525 |
| Undistributed earnings (loss) from long-term investments | 10,122 | -6,252 | 6,730 |
| Net change in fair value of derivatives | -34,857 | 0 | 0 |
| Deferred income tax, net | -6,397 | -8,708 | 9,383 |
| Premiums receivable, net | -222,576 | -142,406 | -40,020 |
| Reinsurance recoverables, net | -262,004 | -261,542 | -17,270 |
| Ceded unearned premium | -35,047 | -17,780 | -28,476 |
| Deferred policy acquisition costs | -22,917 | -21,228 | -23,017 |
| Federal income taxes | 1,797 | 4,500 | -1,892 |
| Losses and loss adjustment expenses | 536,511 | 467,882 | 172,744 |
| Unearned premiums | 136,850 | 84,653 | 110,023 |
| Deferred ceding commission | 6,019 | 3,377 | 7,208 |
| Reinsurance and premium payables | 102,818 | 26,914 | 36,460 |
| Funds held for others | 25,338 | 44,077 | 21,730 |
| Accounts payable and accrued liabilities | 37,032 | 19,177 | 2,285 |
| Other, net | -27,987 | -12,788 | -5,047 |
| Net cash provided by operating activities | 408,076 | 305,115 | 338,187 |
| Cash flows from investing activities: | — | — | — |
| Purchase of fixed maturity securities, available-for-sale | -910,039 | -617,606 | -459,672 |
| Purchase of illiquid investments | 0 | -75 | -1,675 |
| Purchase of equity securities | -13,213 | -14,077 | -26,009 |
| Purchase of equity method investments and other long-term investments | -6,814 | -32,173 | 0 |
| Purchase of intangible assets and goodwill | -2,000 | 0 | -50 |
| Investment in direct and indirect loans | 19,674 | 27,480 | 2,984 |
| Purchase of property and equipment | -5,454 | -4,224 | -3,108 |
| Proceeds from the sales of fixed maturity securities, available-for-sale | 198,195 | 217,468 | 26,626 |
| Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale | 183,951 | 122,694 | 48,957 |
| Maturities, calls and paydowns of fixed maturity securities held-to-maturity | 4,357 | 6,015 | 11,444 |
| Proceeds from the sales of equity securities | 126,738 | 37,534 | 40,201 |
| Sales of and distributions from equity method and other long-term investments | 11,902 | 14,073 | 3,572 |
| Change in short-term investments | 10,626 | -4,799 | -149,068 |
| Change in receivable/payable for securities | 11,928 | 34 | 76 |
| Cash provided by deposit accounting | 3,251 | 3,962 | 11,913 |
| Net cash used in investment activities | -366,898 | -243,694 | -493,809 |
| Cash flows from financing activities: | — | — | — |
| Employee share purchases | 0 | 0 | 1,350 |
| Repayment of stock notes receivable | 0 | 5,562 | 0 |
| Proceeds from long term borrowings | 43,411 | 107,000 | 50,000 |
| Payments on long term borrowings and trust preferred | -43,000 | -116,794 | -50,000 |
| Proceeds from initial public offering | 0 | 0 | 129,597 |
| Net cash provided by (used in) financing activities | 411 | -4,232 | 130,947 |
| Net increase (decrease) in cash and cash equivalents and restricted cash | 41,589 | 57,189 | -24,675 |
| Cash and cash equivalents and restricted cash at beginning of period | 157,525 | 100,336 | 125,011 |
| Cash and cash equivalents and restricted cash at end of period | 199,114 | 157,525 | 100,336 |
| Supplemental disclosure of cash flow information: | — | — | — |
| Cash paid for interest | $ 6,149 | $ 8,573 | $ 10,667 |