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Condensed Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
9 Months Ended
Oct. 31, 2020
Oct. 31, 2019
Operating activities    
Net loss $ (99,886) $ (80,463)
Adjustments to reconcile net loss to net cash used in operating activities:    
Depreciation and amortization 19,776 10,812
Amortization of deferred commissions 19,167 13,616
Stock-based compensation expense 81,453 80,296
Gain on property and equipment, and lease termination 0 (13,783)
Lease exit costs 7,828 0
Amortization of debt discount and issuance costs 2,762 0
Other 2,864 (1,463)
Changes in assets and liabilities:    
Trade and other receivables 52,783 36,627
Deferred commissions (32,811) (24,108)
Prepaid expenses and other current assets (220) (5,849)
Other noncurrent assets (3,421) 92
Accounts payable 6,676 2,655
Deferred revenue (71,387) (49,921)
Accrued expenses and other current liabilities (3,088) 10,410
Other noncurrent liabilities 6,308 17
Net cash used in operating activities (11,196) (21,062)
Investing activities    
Purchases of property, equipment and other (14,829) (14,250)
Purchase of marketable securities (294,220) (76,122)
Maturities of marketable securities 250,733 53,604
Proceeds from sale of marketable securities 1,100 511
Acquisitions, net of cash acquired (223,647) (75,238)
Other 0 (1,500)
Net cash used in investing activities (280,863) (112,995)
Financing activities    
Proceeds from issuance of convertible senior notes, net of issuance costs 558,998 0
Purchase of capped calls related to convertible senior notes (61,870) 0
Proceeds from initial public offering net of issuance costs, underwriters discounts and commissions, and concurrent private placement 0 319,972
Proceeds from Series F convertible preferred stock, net of issuance costs 0 69,848
Proceeds from revolving line of credit 43,000 0
Repayment of revolving line of credit (43,000) 0
Proceeds from exercise of stock options 57,724 16,451
Payments for employee taxes withheld upon vesting of restricted stock units 0 (15,592)
Proceeds from share purchase plan 17,828 0
Principal payments on capital leases (3,405) (2,505)
Repayment of debt assumed in acquisitions and other (6,445) (2,297)
Net cash provided by financing activities 562,830 385,877
Effect of exchange rate changes on cash and cash equivalents 51 (45)
Net increase in cash and cash equivalents 270,822 251,775
Cash and cash equivalents at beginning of period 226,866 44,876
Cash and cash equivalents at end of period 497,688 296,651
Supplemental disclosures of cash flow information    
Cash paid for interest 971 469
Cash paid for income taxes 667 1,208
Noncash investing and financing activities    
Other receivables related to stock option exercises 94 0
Vesting of early exercised stock options 0 453
Accrued unpaid issuance costs related to convertible senior notes 760 0
Accrued unpaid issuance costs related to initial public offering 0 400
Accrued unpaid purchase price related to acquisitions 0 2,729
Accrued unpaid capital expenditures $ 7,779 $ 6,573