Orion180 Insurance Group Inc. (OIG) IPO Dates & Offering Details

424B4 1 orion180-424b4.htm 424B4 Document Filed Pursuant to Rule 424(b)(4) Registration No. 333-298453 Prospectus 20,000,000 Class A Common Stock This is the initial public offering of 20,000,000 shares of Class A common stock of Orion180 Insurance Group Inc. Prior to this offering, there has been no public market for our Class A common stock. The initial public offering price of our Class A common stock is $12.00 per share. Our Class A common stock has been approved for listing on the Nasdaq Global Select Market (“Nasdaq”) under the symbol “OIG.” We are an “emerging growth company” as that term is defined in the Jumpstart Our Business Startups Act of 2012, and, as such, have elected to comply with certain reduced public company reporting requirements for this registration statement and may do so in future filings. See “Prospectus summary—Implications of being an emerging growth company.” Upon the completion of this offering, we will have two classes of authorized common stock: Class A common stock and Class B common stock. The rights of the holders of Class A common stock and Class B common stock are identical, except with respect to voting, conversion, and transfer rights. Each share of Class A common stock is entitled to one vote. Each share of Class B common stock is entitled to ten votes and is convertible at any time, at the option of the holder, and mandatorily upon the occurrence of certain events, into one share of Class A common stock. Immediately following the completion of this offering, Kenneth Gregg, our Founder and Chief Executive Officer, will be the only holder of our Class B common stock, and will beneficially own 93.9% of the voting power of our outstanding capital stock (or 93.4% if the underwriters exercise their option to purchase additional shares of Class A common stock in full). As a result, Mr. Gregg will have the ability to exercise significant influence over the outcome of matters submitted to our shareholders for approval and, following this offering, we will become a “controlled company” as defined under the corporate governance rules of Nasdaq and will be exempt from certain corporate governance requirements of such rules. See “Management—Director independence and controlled company exemption.” Investing in our Class A common stock involves risks. See “ Risk factors ” beginning on page 27 to read about factors you should consider before purchasing shares of our Class A common stock. Neither the Securities and Exchange Commission (“SEC”) nor any state securities commission or regulatory authority has approved or disapproved of these securities or determined if this prospectus is truthful or complete. Any representation to the contrary is a criminal offense. Per share Total Initial public offering price $ 12.00 $ 240,000,000.00 Underwriting discounts and commissions (1) $ 0.78 $ 15,600,000 Proceeds to us, before expenses $ 11.22 $ 224,400,000 (1) See “Underwriting (Conflicts of Interest)” for a description of compensation to be paid to the underwriters. We have granted the underwriters an option for a period of 30 days from the date of this prospectus to purchase up to an additional 3,000,000 shares of our Class A common stock from us at the initial public offering price, less the underwriting discounts and commissions. The underwriters expect to deliver the shares of Class A common stock through the book-entry facilities of the Depository Trust Company on or about September 21, 2026. RBC Capital Markets UBS Investment Bank Raymond James Goldman Sachs & Co. LLC Deutsche Bank Securities Citizens Capital Markets Texas Capital Securities September 17, 2026 Table of contents Page About this prospectus ii Prospectus summary 1 The offering 20 Summary consolidated financial and other data 23 Risk factors 27 Forward-looking statements 74 Use of proceeds 76 Dividend policy 77 Common stock reclassification and C l ass B stock exchange 78 Capitalization 79 Dilution 80 Management's D iscussion and A nalysis of F inancial C ondition and R esults of O perations 82 Business 120 Regulation 146 Management 153 Executive and director compensation 159 Certain relationships and related party transactions 169 Principal shareholders 171 Description of capital stock 173 Shares eligible for future sale 184 Material U.S. federal income tax considerations to non-U.S. holders of our Class A Common Stock 187 Underwriting (Conflicts of Interest) 191 Legal matters 200 Experts 200 Where you can find more information 200 Index to financial statements F-1 Until October 12, 2026 (25 days after the date of this prospectus), all dealers that effect transactions in these securities, whether or not participating in this offering, may be required to deliver a prospectus. This is in addition to the dealer’s obligation to deliver a prospectus when acting as underwriters and with respect to their unsold allotments or subscriptions. i Table of Contents About this prospectus Market and industry data In this prospectus, we present certain market and industry data. This information is based on third-party sources which we believe to be reliable. We have not independently verified any third-party information. Forecasts and projections about our industry are based on historical market data, other publicly available information, our knowledge of our industry and assumptions based on such information and knowledge. These forecasts and projections have not been verified by any independent source. In addition, assumptions and estimates of our and our industry’s future performance are necessarily subject to a high degree of uncertainty and risk due to a variety of factors, including those described in “Risk factors.” These and other factors could cause future performance to differ materially from our assumptions and estimates. See “Forward-looking statements.” References to the industry average in this prospectus are based on management’s best assessment and estimates of industry norms and publicly available information. The sources of certain industry, market, and other data contained in this prospectus include: • Insurance Information Institute; • Library of Congress; and • S&P Global Market Intelligence. Trademarks and service marks Trade names, trademarks and service marks of other companies appearing in this prospectus are the property of their respective holders. Solely for convenience, the trademarks, service marks, and trade names are referred to in this prospectus without the SM and ® symbols, but such references are not intended to indicate, in any way, that the owner thereof will not assert, to the fullest extent under applicable law, such owner’s rights to their trademarks, service marks, and trade names. Non-GAAP financial measures This prospectus contains certain financial measures that are not presented in accordance with generally accepted accounting principles in the United States (“GAAP”). Under U.S. securities laws, these measures are called “non-GAAP financial measures.” We believe that certain non-GAAP financial measures provide investors in our Class A common stock with additional useful information in evaluating our performance. Our management uses these non-GAAP financial measures, in conjunction with GAAP financial measures, as an integral part of managing our business and to, among other things: (i) monitor and evaluate the performance of our business operations and financial performance; (ii) facilitate internal comparisons of the historical operating performance of our business operations; (iii) facilitate external comparisons of the results of our overall business to the historical operating performance of other companies that may have different capital structures and debt levels and different go-to-market models; (iv) review and assess the operating performance of our management team; (v) analyze and evaluate financial and strategic planning decisions regarding future operating investments; and (vi) plan for and prepare future annual operating budgets and determine appropriate levels of operating investments. These non-GAAP financial measures may be different than similarly titled measures used by other companies. These non-GAAP financial measures should not be considered in isolation from, or as substitutes for, financial information prepared in accordance with GAAP. There are limitations related to the use of these non-GAAP financial measures as compared to the most directly comparable GAAP financial measures. ii Table of Contents We use the following non-GAAP financial measures throughout this prospectus as defined below: • Consolidated adjusted EBITDA means earnings before interest, taxes, depreciation, amortization (i.e., software and loan), and non-recurring charges. • Consolidated adjusted EBITDA margin means consolidated adjusted EBITDA divided by total revenues. • Commission and fees revenue means total services segment revenue, less other services segment income. For a reconciliation of such measures to their mos