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CONSOLIDATED STATEMENTS OF CASH FLOWS - USD ($)
$ in Thousands
 12 Months Ended
Dec. 31, 2023
Dec. 31, 2022
Dec. 31, 2021
Cash flows from operating activities:      
Net loss $ (149,260) $ (124,717) $ (146,334)
Adjustments to reconcile net loss to net cash provided by operating activities:      
Depreciation and amortization 45,939 41,038 33,501
Amortization of debt discount and issuance costs 4,138 4,085 3,982
Stock-based compensation expense 108,081 119,902 102,579
Impairment of long-lived assets 30,784 0 0
Change in fair value of derivative assets 15,511 0 0
Deferred income taxes (5,624) (1,440) 466
Induced conversion expense 53,889 0 2,740
Other 469 (200) 1,920
Changes in assets and liabilities:      
Accounts receivable (14,021) (9,050) (25,475)
Deferred contract acquisition and fulfillment costs (18,534) (15,910) (22,526)
Prepaid expenses and other assets (4,125) (2,231) (3,355)
Accounts payable 5,449 7,977 (2,077)
Accrued expenses 2,422 3,741 19,205
Deferred revenue 30,472 52,516 85,562
Other liabilities (1,312) 2,493 3,729
Net cash provided by operating activities 104,278 78,204 53,917
Cash flows from investing activities:      
Business acquisitions, net of cash acquired (34,841) 0 (358,420)
Purchases of property and equipment (4,366) (20,382) (9,010)
Capitalization of internal-use software (15,878) (17,145) (9,854)
Purchases of investments (276,829) (122,765) (93,092)
Sales and maturities of investments 150,450 121,304 147,998
Other investments 2,710 (1,000) (3,000)
Net cash used in investing activities (178,754) (39,988) (325,378)
Cash flows from financing activities:      
Proceeds from issuance of convertible senior notes, net of issuance costs of $7,909 and $14,976 for the years ended December 31, 2023 and 2021, respectively 292,091 0 585,024
Purchase of capped calls related to convertible senior notes (36,570) 0 (76,020)
Payment of debt issuance costs 0 (71) (300)
Payments for redemption, repurchase and conversion of convertible senior notes (199,998) (12) (230,000)
Payments related to business acquisitions (2,250) (300) (12,118)
Proceeds from capped calls settlement 17,518 0 0
Taxes paid related to net share settlement of equity awards (5,570) (7,462) (16,044)
Proceeds from employee stock purchase plan 11,323 11,943 9,276
Proceeds from stock option exercises 3,053 3,318 4,315
Net cash provided by financing activities 79,597 7,416 264,133
Effect of exchange rate changes on cash ,cash equivalents and restricted cash 1,202 (2,845) (1,272)
Net increase (decrease) in cash, cash equivalents and restricted cash 6,323 42,787 (8,600)
Cash, cash equivalents and restricted cash, beginning of period 207,804 165,017 173,617
Cash, cash equivalents and restricted cash, end of period 214,127 207,804 165,017
Supplemental cash flow information:      
Cash paid for interest on convertible senior notes 4,605 6,675 7,345
Cash paid for income taxes, net of refunds 1,624 1,571 3,305
Reconciliation of cash, cash equivalents and restricted cash:      
Cash and cash equivalents 213,629 207,287 164,582
Restricted cash included in prepaid expenses and other assets 498 517 435
Total cash, cash equivalents and restricted cash $ 214,127 $ 207,804 $ 165,017