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Condensed Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
6 Months Ended
Jul. 31, 2020
Jul. 31, 2019
Operating activities    
Net loss $ (67,727) $ (40,843)
Adjustments to reconcile net loss to net cash provided by (used in) operating activities:    
Depreciation and amortization 11,790 6,718
Amortization of deferred commissions 12,433 8,687
Stock-based compensation expense 56,438 43,141
Impairment (gain) on property and equipment, and lease termination 0 (13,783)
Lease exit costs 7,634 0
Other 1,813 (560)
Changes in assets and liabilities:    
Trade and other receivables 63,310 50,224
Deferred commissions (19,983) (15,785)
Prepaid expenses and other current assets (2,214) (7,405)
Other noncurrent assets (1,404) (36)
Accounts payable (2,912) 1,832
Deferred revenue (57,766) (39,198)
Accrued expenses and other current liabilities (4,295) 4,245
Other noncurrent liabilities 6,574 121
Net cash provided by (used in) operating activities 3,691 (2,642)
Investing activities    
Purchases of property, equipment and other (9,774) (5,234)
Purchase of marketable securities (139,196) (76,122)
Maturities of marketable securities 133,473 23,125
Proceeds from sale of marketable securities 1,100 511
Acquisitions, net of cash acquired (80,372) (19,540)
Net cash used in investing activities (94,769) (77,260)
Financing activities    
Proceeds from initial public offering net of issuance costs, underwriters discounts and commissions, and concurrent private placement 0 320,392
Proceeds from Series F convertible preferred stock, net of issuance costs 0 69,848
Proceeds from revolving line of credit 43,000 0
Proceeds from exercise of stock options 41,032 13,018
Proceeds from share purchase plan 10,267 0
Principal payments on capital leases (2,117) (1,469)
Repayment of debt assumed in acquisitions and other (2,139) (2,297)
Net cash provided by financing activities 90,043 399,492
Effect of exchange rate changes on cash and cash equivalents (49) (47)
Net (decrease) increase in cash and cash equivalents (1,084) 319,543
Cash and cash equivalents at beginning of period 226,866 44,876
Cash and cash equivalents at end of period 225,782 364,419
Supplemental disclosures of cash flow information    
Cash paid for interest 652 265
Cash paid for income taxes 656 806
Noncash investing and financing activities    
Other receivables related to stock option exercises 1 0
Vesting of early exercised stock options 0 392
Accrued unpaid issuance costs related to initial public offering 0 690
Accrued unpaid capital expenditures $ 2,111 $ 5,809