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CONSOLIDATED STATEMENTS OF CASH FLOWS - USD ($)
$ in Thousands
12 Months Ended
Dec. 31, 2022
Dec. 31, 2021
Dec. 31, 2020
Cash flows from operating activities      
Net loss $ (879,166) $ (376,250) $ (82,996)
Adjustments to reconcile net loss to net cash (used in) provided by operating activities:      
Depreciation and amortization 246,561 125,292 75,612
Share-based compensation 386,009 357,965 189,600
Unrealized loss (gain) on investments 203,483 14,611 (80,988)
Asset write-down and other charges 305,351 0 0
Amortization of deferred and prepaid sales commission costs 115,184 74,165 47,207
Amortization of debt discount and issuance costs 4,468 64,063 49,031
Loss on early extinguishment of debt 0 1,736 13,284
Repayment of convertible senior notes attributable to debt discount 0 (10,131) (35,020)
Reduction of operating lease right-of-use assets 19,907 18,025 15,712
Provision for bad debt 9,367 8,132 5,936
Other 4,327 809 (2,941)
Changes in assets and liabilities:      
Accounts receivable (87,843) (64,940) (51,980)
Deferred and prepaid sales commission costs (235,869) (178,358) (274,908)
Prepaid expenses and other assets 3,812 9,111 (20,612)
Accounts payable (6,166) 17,852 21,916
Accrued and other liabilities 89,473 74,517 76,467
Deferred revenue 33,275 34,227 34,851
Operating lease liabilities (20,868) (18,675) (15,362)
Net cash provided by (used in) operating activities 191,305 152,151 (35,191)
Cash flows from investing activities      
Purchases of property and equipment (32,713) (28,959) (43,618)
Capitalized internal-use software (53,730) (43,692) (38,113)
Purchases of intangible assets and long-term investments (3,990) (324,178) (25,955)
Proceeds from sale of marketable equity investments 3,223 0 0
Net cash used in investing activities (87,210) (396,829) (107,686)
Cash flows from financing activities      
Proceeds from issuance of convertible senior notes, net of issuance costs 0 0 1,627,177
Payments for repurchase or redemption of convertible senior notes 0 (333,632) (1,086,268)
Payments for capped calls and transaction costs 0 0 (102,695)
Proceeds from series A convertible preferred stock, net of issuance costs 0 199,449 0
Payments for repurchase of common stock (99,793) 0 0
Proceeds from issuance of stock in connection with stock plans 15,855 36,721 41,230
Payments for taxes related to net share settlement of equity awards (7,598) (21,549) (36,717)
Repayment of financing obligations (4,815) (4,160) (1,489)
Payment for contingent consideration (1,867) (3,880) (3,648)
Net cash provided by (used in) financing activities (98,218) (127,051) 437,590
Effect of exchange rate changes (3,055) (962) 1,534
Net increase (decrease) in cash, cash equivalents, and restricted cash 2,822 (372,691) 296,247
Cash, cash equivalents, and restricted cash      
Beginning of period 267,162 639,853 343,606
End of period 269,984 267,162 639,853
Supplemental disclosure of cash flow data:      
Cash paid for interest 347 309 220
Cash paid for income taxes, net of refunds 3,726 1,388 870
Non-cash investing and financing activities      
Common stock issued for acquisition of intangible assets 0 302,600 0
Contingent consideration not paid 0 50,000 0
Equipment and capitalized internal-use software purchased and unpaid at period end 6,808 7,343 7,926
Cash held for future indemnity claims and other potential future payments 0 0 197
Equipment acquired under financing obligations $ 0 $ 6,898 $ 4,694