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Condensed Consolidated Statements of Cash Flows - USD ($)
$ in Thousands
6 Months Ended
Jul. 31, 2019
Jul. 31, 2018
[1]
Cash flows from operating activities:    
Net loss $ (94,946) $ (65,169)
Adjustments to reconcile net loss to net cash provided by (used in) operating activities:    
Stock-based compensation 53,959 32,357
Depreciation, amortization and accretion 7,916 3,699
Amortization of debt discount and issuance costs 8,113 6,413
Amortization of deferred commissions 13,192 9,613
Deferred income taxes (3,057) (1,575)
Non-cash charitable contributions 652 1,008
Other 84 18
Changes in operating assets and liabilities:    
Accounts receivable 4,459 (7,240)
Deferred commissions (21,372) (14,240)
Prepaid expenses and other assets 1,534 622
Operating lease right-of-use assets 6,189 7,540
Accounts payable 1,368 767
Accrued compensation 4,717 498
Accrued expenses and other liabilities 1,304 2,061
Operating lease liabilities (159) (4,554)
Deferred revenue 36,175 26,811
Net cash provided by (used in) operating activities 20,128 (1,371)
Cash flows from investing activities:    
Capitalization of internal-use software costs (1,330) (1,725)
Purchases of property and equipment (9,917) (9,790)
Purchases of securities available for sale and other (237,693) (320,018)
Proceeds from maturities of securities available for sale 136,344 79,500
Proceeds from sales of securities available for sale and other 17,329 0
Purchases of intangible assets (8,500) 0
Payments for business acquisition, net of cash acquired (44,223) (15,638)
Net cash used in investing activities (147,990) (267,671)
Cash flows from financing activities:    
Proceeds from issuance of convertible senior notes, net of issuance costs 0 334,980
Purchase of convertible senior notes hedge 0 (80,040)
Proceeds from issuance of warrants related to convertible notes 0 52,440
Proceeds from stock option exercises, net of repurchases 27,453 21,055
Proceeds from shares issued in connection with employee stock purchase plan 9,005 6,654
Other, net (126) (206)
Net cash provided by financing activities 36,332 334,883
Effects of changes in foreign currency exchange rates on cash, cash equivalents and restricted cash (1,187) (632)
Net increase (decrease) in cash, cash equivalents and restricted cash (92,717) 65,209
Cash, cash equivalents and restricted cash at beginning of period 311,215 136,233
Cash, cash equivalents and restricted cash at end of period 218,498 201,442
Supplementary cash flow disclosure:    
Interest 431 0
Income taxes 654 0
Vesting of early exercised common stock options 370 459
Common stock issued as charitable contribution 652 1,008
Operating lease right-of-use assets exchanged for lease obligations 1,665 125,526
Property and equipment acquired through tenant improvement allowance 0 22,237
Property and equipment and other accrued but not yet paid 602 605
Bonus settled through the issuance of common stock 2,809 0
Reconciliation of cash, cash equivalents and restricted cash within the condensed consolidated balance sheets to the amounts shown in the condensed consolidated statements of cash flows above:    
Total cash, cash equivalents and restricted cash $ 311,215 $ 136,233
[1]
Adjusted for adoption of ASC 842, Leases. See Note 2.