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CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - USD ($)
$ in Thousands
9 Months Ended
Sep. 30, 2020
Sep. 30, 2019
Cash flows from operating activities    
Net loss $ (81,169) $ (28,350)
Adjustments to reconcile net loss to net cash provided by operating activities:    
Depreciation and amortization 53,563 26,060
Share-based compensation 137,410 71,690
Amortization of deferred and prepaid sales commission costs 33,060 21,189
Amortization of debt discount and issuance costs 32,613 15,149
Loss on early extinguishment of debt 12,323 0
Repayment of convertible senior notes attributable to debt discount (32,640) 0
Reduction of operating lease right-of-use assets 11,478 10,166
Unrealized gain and other related costs on investments (41,453) 0
Foreign currency remeasurement (gain) loss 63 61
Provision for bad debt 3,909 2,339
Deferred income taxes (267) (632)
Tax benefit from release of valuation allowance 0 (3,210)
Other 203 1,925
Changes in assets and liabilities:    
Accounts receivable (27,502) (24,845)
Deferred and prepaid sales commission costs (183,745) (51,467)
Prepaid expenses and other current assets (14,613) (8,125)
Other assets 322 400
Accounts payable 5,180 10,626
Accrued liabilities 41,530 22,432
Deferred revenue 20,128 16,632
Operating lease liabilities (11,019) (10,507)
Other liabilities 7,919 (525)
Net cash (used in) provided by operating activities (32,707) 71,008
Cash flows from investing activities    
Purchases of property and equipment (33,992) (21,355)
Capitalized internal-use software (28,049) (11,472)
Cash paid for business combination, net of cash acquired 0 (27,870)
Net cash used in investing activities (62,041) (60,697)
Cash flows from financing activities    
Proceeds from issuance of convertible senior notes, net of issuance costs 1,627,209 0
Payments for 2023 convertible senior notes partial repurchase (1,019,813) 0
Payments for capped calls and transaction costs (102,695) 0
Proceeds from issuance of stock in connection with stock plans 24,123 17,590
Payments for taxes related to net share settlement of equity awards (27,698) (10,244)
Payment for contingent consideration for business acquisition (3,548) 0
Repayment of financing obligations (1,215) (943)
Net cash provided by financing activities 496,363 6,403
Effect of exchange rate changes 337 (380)
Net increase (decrease) in cash, cash equivalents and restricted cash 401,952 16,334
Cash, cash equivalents and restricted cash    
Beginning of period 343,606 566,329
End of period 745,558 582,663
Supplemental disclosure of cash flow data    
Cash paid for interest 190 189
Cash paid for income taxes, net of refunds 512 718
Non-cash investing and financing activities    
Cash held for future indemnity claims and other potential future payments 0 7,148
Equipment and capitalized internal-use software purchased and unpaid at period end $ 7,879 $ 4,861