Five9 (1F9) Risk Analysis

The market price of our common stock has been volatile in the past and may fluctuate significantly in the future in response to numerous factors, many of which are beyond our control. During the twelve months ended December 31, 2025, the sale price per share of our common stock ranged from a low of $17.71 to a high of $49.90. Factors that may contribute to continuing volatility in the price of our common stock include: - actual or anticipated fluctuations or declines in our operating results;- the impact of adverse economic conditions, including the impact of macroeconomic challenges, global tariff increases and potential future increases and announcements regarding same, continued inflation, uncertainty regarding consumer spending, high interest rates, fluctuations in currency rates, the impact of current and potential global conflicts, or other factors;- loss of customers or a reduction, or slower growth, in subscriptions or features subscribed to by our existing customers;- the financial projections we provide to the public, any changes in these projections, our failure to meet these projections, or our failure to exceed these projections by amounts or percentages expected by our investors and analysts;- changes in our board of directors or management;- failure of securities analysts to initiate or maintain coverage of our company, changes in financial estimates by any securities analysts who follow our company, or our failure to meet these estimates or the expectations of investors;- ratings changes by any securities analysts who follow our company;- sales of our common stock (or securities that convert into our common stock) by us or sales by our significant stockholders, or the public announcement of same;- the assessment of our business or position in our market published in research and other reports;- announcements by us or our competitors of significant product or technical innovations, financings, acquisitions, strategic partnerships, joint ventures or capital commitments;- entry into the market by new competitors, or the introduction of new products or the generation of new sales by us or our competitors;- changes in operating performance and stock market valuations of other technology companies generally, or those in the software as a service industry in particular;- price and volume fluctuations in the overall stock market, including as a result of trends in the U.S. or global economy;- lawsuits threatened or filed against us;- security breaches or incidents impacting us or our customers or their customers and security breaches of companies that provide solutions similar to our solution, which could negatively impact our industry as a whole;- actions, threats or public statements by activist stockholders;- legislation or regulation of our business, the business of our customers, the internet and/or contact centers;- new entrants into and consolidations of the contact center market, including the transition by providers of legacy on-premises contact center systems to cloud solutions and the continued advancement of AI solutions;- acquisitions by us or our competitors, and our ability to effectively integrate and achieve the desired benefits from acquisitions by us;- the perceived or real impact of events that harm our competitors;- loss of key personnel;- developments with respect to patents or proprietary rights; and - other events or factors, including those resulting from war, incidents of terrorism or responses to these events, which would be unrelated to our business and industry, and outside of our control. In addition, stock markets have experienced extreme price and volume fluctuations that have affected and continue to affect the market prices of equity securities of many technology companies, particularly in connection with the continued macroeconomic challenges, global tariff increases and potential future increases and announcements regarding same, continued inflation, uncertainty regarding consumer spending, high interest rates, fluctuations in currency rates, and the current and potential global conflicts. Stock prices of many technology companies have recently declined, including in some cases in a manner unrelated or disproportionate to the operating performance of those companies. These and other factors may disproportionately impact the trading price of our common stock. In the past, stockholders have instituted securities class action litigation following periods of volatility. If we were to become involved in such securities litigation, it could subject us to substantial costs, divert resources and the attention of management from our business and harm our business, results of operations, financial condition, reputation and cash flows.

The trading market for our common stock depends in part on the research and reports that securities or industry analysts publish about us or our business, our industry, our market and our competitors. We do not have any control over these analysts. If one or more of the analysts who cover us downgrade our shares or change their opinion of our shares or our business, our share price would likely decline. If one or more of these analysts cease coverage of our company or fail to regularly publish reports on us, we could lose visibility in financial markets or our industry market, which could cause our share price or trading volume to decline.

In October 2025, our Board of Directors authorized a share repurchase program, or the 2025 Repurchase Program, for the repurchase of shares of our common stock, in an aggregate amount up to $150.0 million, which 2025 Repurchase Program expires on December 31, 2027. As part of the 2025 Repurchase Program, in November 2025, we entered into an accelerated share repurchase, or ASR, program under which we repurchased $50.0 million of our common stock. This program was completed on February 2, 2026. As of December 31, 2025, $100.0 million remained available under the 2025 Repurchase Program. There can be no assurances that we will continue to repurchase shares under the current authorization. Future share repurchase activity under our current authorization, if any, could cause the price of our common stock to be higher than it otherwise would be and could potentially reduce the market liquidity for our stock. Although share repurchases are intended to enhance long-term stockholder value, there is no assurance they will do so because the market price of our common stock may decline below the levels at which we repurchased shares and short-term stock price fluctuations could reduce the effectiveness of the repurchases. Repurchasing common stock reduces the amount of cash we have available to fund capital expenditures, interest payments, debt retirements, acquisitions, additional share repurchases, investments in strategic initiatives and other operating requirements and we may fail to realize the anticipated benefits of share repurchases.

The market price of shares of our common stock and our 2029 convertible senior notes could decline as a result of substantial sales of our common stock, particularly sales by our directors, executive officers and significant stockholders or the perception in the market that holders of a large number of shares intend to sell their shares. The future registration of shares of our common stock may cause our stock price and the price of our 2029 convertible senior notes to decline, even before such shares are actually sold in the market. We have registered shares of common stock that we may issue under our employee equity incentive plans. These shares can be sold freely in the public market upon issuance. We are unable to predict the effect that sales, or the perception that our shares may be available for sale, will have on the prevailing market price of our common stock.

Provisions in our amended and restated certificate of incorporation and amended and restated bylaws may have the effect of delaying or preventing a change in control, changes in our Board or management, and other governance changes. Our amended and restated certificate of incorporation and amended and restated bylaws: - provide that our board of directors is classified into three classes of directors (the "classified board provisions");- provide that stockholders may remove directors only for cause;- provide that the authorized number of directors may be changed only by resolution of the board of directors;- provide that all vacancies, including newly created directorships, may, except as otherwise required by law, be filled by the affirmative vote of a majority of directors then in office, even if less than a quorum;- provide that our stockholders may not take action by written consent, and may only take action at annual or special meetings of our stockholders;- provide that stockholders seeking to present proposals before a meeting of stockholders or to nominate candidates for election as directors at a meeting of stockholders must provide notice in writing in a timely manner, and also specify requirements as to the form and content of a stockholder's notice;- restrict the forum for certain litigation against us to Delaware;- restrict the forum for complaints asserting a cause of action under the Securities Act to the federal district courts;- do not provide for cumulative voting rights (therefore allowing the holders of a majority of the shares of common stock entitled to vote in any election of directors to elect all of the directors standing for election);- provide that special meetings of our stockholders may be called only by the chairman of the board, our chief executive officer or the board of directors pursuant to a resolution adopted by a majority of the total number of authorized directors; and - provide that stockholders will be permitted to amend our amended and restated bylaws and certain parts of our amended and restated certificate of incorporation only upon receiving at least 662/3% of the votes entitled to be cast by holders of all outstanding shares then entitled to vote generally in the election of directors, voting together as a single class (the "supermajority approval provisions"). In July 2025, our board of directors announced its intent to approve and recommend to our stockholders that they approve at our 2026 annual meeting of stockholders (i) the phased removal of the classified board provisions (which, upon the completion of such declassification, will also result in our directors being able to be removed without cause under Delaware law) and (ii) the removal of the supermajority approval provisions effective at the close of our 2027 annual meeting. To the extent that our stockholders vote for the removal of such provisions, and upon the effectiveness of such changes, we would have a decreased ability to delay or prevent a change in control, changes in our Board or other governance changes. However, even if such provisions are no longer effective, the remaining provisions described above may frustrate or prevent a change in control, or any attempts by our stockholders to replace or remove our current board or management or change aspects of our corporate governance. In addition, because we are incorporated in Delaware, we are governed by the provisions of Section 203 of the Delaware General Corporation Law, which generally prohibits a Delaware corporation from engaging in any of a broad range of business combinations with any "interested" stockholder for a period of three years following the date on which the stockholder became an "interested" stockholder. The existence of these provisions could negatively affect the price of our common stock and limit opportunities for you to realize value in a corporate transaction.