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CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - USD ($)
$ in Millions
3 Months Ended
Apr. 30, 2020
Apr. 30, 2019
Operating activities:    
Net income (loss) $ 66.5 $ (24.2)
Adjustments to reconcile net income (loss) to net cash provided by operating activities:    
Depreciation, amortization and accretion 30.0 32.7
Stock-based compensation expense 98.2 75.2
Deferred income taxes 3.5 24.4
Restructuring and other exit costs, net 0.0 0.2
Other operating activities 32.7 15.3
Changes in operating assets and liabilities    
Accounts receivable 295.5 206.2
Prepaid expenses and other assets (47.5) 11.4
Accounts payable and other liabilities (154.6) (172.6)
Deferred revenue (1.1) 62.2
Accrued income taxes 4.1 (9.6)
Net cash provided by operating activities 327.3 221.2
Investing activities:    
Purchases of marketable securities (11.0) (19.8)
Sales of marketable securities 0.0 4.6
Capital expenditures (19.9) (14.7)
Purchases of developed technologies (3.6) 0.0
Other investing activities (43.5) 0.7
Net cash used in investing activities (78.0) (29.2)
Financing activities:    
Proceeds from issuance of common stock, net of issuance costs 56.8 46.9
Taxes paid related to net share settlement of equity awards (32.5) (25.8)
Repurchases of common stock (202.0) (88.5)
Repayment of debt (450.0) (125.0)
Other financing activities (2.5) 0.0
Net cash used in financing activities (630.2) (192.4)
Effect of exchange rate changes on cash and cash equivalents (4.1) (2.4)
Net decrease in cash and cash equivalents (385.0) (2.8)
Cash and cash equivalents at beginning of period 1,774.7 886.0
Cash and cash equivalents at end of period 1,389.7 883.2
Non-cash financing activities:    
Fair value of common stock issued to settle liability-classified restricted stock units $ 28.7 $ 0.0