UNDERWRITING
Under the terms and subject to the conditions in an underwriting agreement dated the date of this prospectus supplement, Morgan
Stanley & Co. LLC has agreed to purchase, and we have agreed to sell to Morgan Stanley & Co. LLC, 5,100,000 shares of Class A common stock.
Morgan Stanley & Co. LLC is referred to herein as the underwriter. The underwriter is offering the shares of Class A
common stock subject to their acceptance of the shares from us and subject to prior sale. The underwriting agreement provides that the obligations of the underwriter to pay for and accept delivery of the shares of Class A common stock offered
by this prospectus supplement are subject to the approval of certain legal matters by its counsel and to certain other conditions. The underwriter is obligated to take and pay for all of the shares of Class A common stock offered by this
prospectus supplement if any such shares are taken. However, the underwriter is not required to take or pay for the shares covered by the underwriters option to purchase additional shares of Class A common stock described below.
The underwriter is purchasing the shares of Class A common stock from us at a price of
$ per share, which will result in approximately $ aggregate proceeds to us, before deducting expenses.
The underwriter proposes to offer the shares of Class A common stock for sale from time to time in one or more transactions on the NYSE, in the over-the-counter market, through negotiated transactions or otherwise at market prices prevailing at the
time of sale, at prices related to prevailing market prices or at negotiated prices, subject to receipt of acceptance by it and subject to their right to reject any order in whole or in part. The underwriter may effect such transactions by selling
the shares of Class A common stock to or through dealers, and such dealers may receive compensation in the form of discounts, concessions or commissions from the purchasers of shares of Class A common stock for whom they may act as agents or to whom
they may sell as principal. The difference between the price at which the underwriter purchases shares of Class A common stock and the prices at which the underwriter resells such shares of Class A common stock may be deemed underwriting
compensation.
We have granted to the underwriter an option, exercisable for 30 days from the date of this prospectus supplement, to
purchase up to 765,000 of additional shares of Class A common stock at the public offering price listed on the cover page of this prospectus supplement. To the extent the option is exercised, the underwriter will become obligated, subject to
certain conditions, to purchase these additional shares of Class A common stock.
The estimated offering expenses payable by us,
exclusive of the underwriting discounts and commissions, are approximately $ . We have agreed to reimburse the underwriter for an estimated $25,000 of
expenses relating to clearance of this offering with the Financial Industry Regulatory Authority.
Our Class A common stock is listed
on the NYSE under the symbol CHWY. On September 15, 2020, the closing price of our Class A common stock as reported on the NYSE was $54.11.
We and the underwriter have agreed to indemnify each other against certain liabilities, including liabilities under the Securities Act.
Lock-Up Agreements
We, all of our directors and officers and certain of our other stockholders (including PetSmart) have agreed that for a period of 60 days from
the date of this prospectus supplement, neither we nor they will, subject to certain exceptions, without the prior written consent of Morgan Stanley & Co. LLC, (i) offer, pledge, sell, contract to sell, sell any option or contract to
purchase, purchase any option or contract to sell, grant any option, right or warrant to purchase, lend or otherwise transfer or dispose of, directly or indirectly, any shares of our Class A common stock or Class B common stock
(collectively, the Stock), or any securities convertible into or exercisable or exchangeable for Stock, or publicly disclose the intention to make any offer, sale, pledge,
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