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CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS - USD ($)
$ in Millions
9 Months Ended
Oct. 31, 2019
Oct. 31, 2018
Operating activities:    
Net income (loss) $ 82.7 $ (145.5)
Adjustments to reconcile net income (loss) to net cash provided by operating activities:    
Depreciation, amortization and accretion 96.4 69.8
Stock-based compensation expense 257.4 175.5
Deferred income taxes 47.9 16.5
Restructuring and other exit costs, net 0.5 34.5
Other operating activities 10.8 14.8
Changes in operating assets and liabilities    
Accounts receivable (47.2) 129.4
Prepaid expenses and other current assets 37.6 8.3
Accounts payable and accrued liabilities (94.2) (181.0)
Deferred revenue 328.8 (73.8)
Accrued income taxes (3.8) 17.1
Net cash provided by operating activities 716.9 65.6
Investing activities:    
Purchases of marketable securities (19.9) (135.3)
Sales of marketable securities 22.4 61.3
Maturities of marketable securities 5.0 194.9
Capital expenditures (39.2) (49.4)
Acquisitions, net of cash acquired 0.0 (34.1)
Other investing activities (11.0) 2.3
Net cash (used in) provided by investing activities (42.7) 39.7
Financing activities:    
Proceeds from issuance of common stock, net of issuance costs 91.8 90.1
Taxes paid related to net share settlement of equity awards (79.9) (120.7)
Repurchases of common stock (261.9) (261.3)
Repayment of debt (350.0) 0.0
Net cash used in financing activities (600.0) (291.9)
Effect of exchange rate changes on cash and cash equivalents (4.0) (15.7)
Net increase (decrease) in cash and cash equivalents 70.2 (202.3)
Cash and cash equivalents at beginning of period 886.0 1,078.0
Cash and cash equivalents at end of period 956.2 875.7
Non-cash investing activities:    
Fair value of common stock issued as consideration for business combination $ 0.0 $ 44.8