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Condensed Consolidated Statements of Cash Flows (unaudited) - USD ($)
$ in Thousands
6 Months Ended 12 Months Ended
Jun. 30, 2020
Jun. 30, 2019
Dec. 31, 2019
Cash flows from operating activities:      
Net loss $ (44,605) $ (26,197)  
Adjustments to reconcile net loss to net cash used in operating activities:      
Depreciation and amortization 13,976 7,700  
Amortization of deferred costs 5,735 3,607  
Deferred income taxes (3,014) 83  
Accretion of interest on convertible senior notes 10,949 2,424  
Provision for credit losses and sales reserve 1,387 389  
Stock-based compensation 21,588 15,793  
Other non-cash adjustments   (245)  
Changes in operating assets and liabilities:      
Accounts receivable 3,341 (1,387)  
Prepaid expenses (3,265) (3,461)  
Deferred costs (6,943) (4,398)  
Other assets (3,429) 83  
Accounts payable 2,164 3,669  
Accrued payroll and employee related liabilities (334) (2,864)  
Accrued expenses (593) (719)  
Deferred revenue (2,722) 1,523  
Other liabilities 2,696 511  
Net cash used in operating activities (3,069) (3,489)  
Cash flows from investing activities:      
Capital expenditures (1,175) (3,875)  
Proceeds from landlord reimbursement   1,143  
Payments for acquisition of business, net of acquired cash (44,265) (6,764)  
Additions to capitalized software development costs (4,673) (3,949)  
Purchase of short-term investments   (1,975)  
Maturities of short-term investments   44,265  
Net cash provided by (used in) investing activities (50,113) 28,845  
Cash flows from financing activities:      
Proceeds from public offering, net of costs   139,110  
Restricted stock units withheld to settle employee tax withholding liability (927) (449)  
Proceeds from employee stock purchase plan 1,710 1,283  
Proceeds from stock option exercises 4,585 13,487  
Other (131) (548)  
Net cash provided by financing activities 5,237 152,883  
Effect of exchange rates on cash, cash equivalents and restricted cash (419) (52)  
Net increase (decrease) in cash, cash equivalents and restricted cash (48,364) 178,187  
Cash, cash equivalents and restricted cash—beginning of period 539,662 60,068 $ 60,068
Cash, cash equivalents and restricted cash—end of period 491,298 238,255 $ 539,662
Supplemental disclosures of cash flow information:      
Interest 974 863  
Taxes, net of refunds received 476    
Supplemental disclosure of non-cash activities:      
Capitalized assets included in accounts payable and accrued expenses 373 217  
Capitalized development costs included in accounts payable and accrued expenses 3 14  
Common stock issued in connection with acquisitions 35,508    
Acquisition-related deferred common stock consideration 895    
Contingent consideration in connection with acquisitions 4,220    
Purchase accounting payable, net 619    
Stock-based compensation capitalized for software development $ 152 $ 338