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Unaudited Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
6 Months Ended
Jun. 30, 2022
Jun. 30, 2021
Operating Activities:    
Net loss $ (65,702) $ (47,731)
Adjustments to reconcile net loss to net cash and cash equivalents provided by operating activities, net of acquisitions    
Depreciation and amortization 27,063 21,736
Stock-based compensation 126,868 75,856
Loss on early extinguishment of 2022 Convertible Notes   3,088
Repayment of 2022 Convertible Notes attributable to the debt discount   (13,028)
Gain on strategic investments (4,200) (1,022)
Benefit from deferred income taxes (398) (1,120)
Amortization of debt discount and issuance costs 1,017 12,512
(Accretion) amortization of bond discount (150) 1,670
Unrealized currency translation 1,980 280
Changes in assets and liabilities    
Accounts receivable (14,349) 8,944
Prepaid expenses and other assets (21,911) (7,694)
Deferred commission expense (13,744) (16,402)
Right-of-use assets 13,447 18,547
Accounts payable 8,960 (1,269)
Accrued expenses and other liabilities 23,089 15,533
Operating lease liabilities (11,330) (18,374)
Deferred revenue 52,506 49,365
Net cash and cash equivalents provided by operating activities 123,146 100,891
Investing Activities:    
Purchases of investments (864,063) (654,063)
Maturities of investments 625,378 596,602
Sale of investments 124,998  
Purchases of property and equipment (18,272) (10,746)
Purchases of intangible assets (10,000)  
Acquisition of a business, net of cash acquired   (16,810)
Purchases of strategic investments (13,873) (6,202)
Equity method investment (250) (3,100)
Capitalization of software development costs (19,931) (16,421)
Net cash and cash equivalents used in investing activities (176,013) (110,740)
Financing Activities:    
Proceeds from settlement of Convertible Note Hedges related to the 2022 Convertible Notes 60,483 725
Payment for settlement of 2022 convertible notes (79,807) (45,409)
Repayment of 2025 Convertible Notes attributable to the principal (1,619)  
Employee taxes paid related to the net share settlement of stock-based awards (7,764) (6,913)
Proceeds related to the issuance of common stock under stock plans 19,699 24,868
Net cash and cash equivalents used in financing activities (9,008) (26,729)
Effect of exchange rate changes on cash, cash equivalents, and restricted cash (9,474) (3,209)
Net increase in cash, cash equivalents and restricted cash (71,349) (39,787)
Cash, cash equivalents and restricted cash, beginning of period 380,042 381,152
Cash, cash equivalents and restricted cash, end of period 308,693 341,365
Supplemental cash flow disclosure:    
Cash paid for interest 881 948
Cash paid for income taxes 2,824 4,198
Right-of-use assets obtained in exchange for operating lease liabilities 4,673 3,767
Non-cash investing and financing activities:    
Issuance of common stock for repayment of 2022 Convertible Notes   209,859
Capital expenditures incurred but not yet paid 3,271 219
Asset retirement obligations $ 1,161 $ 71