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CONSOLIDATED STATEMENTS OF CASH FLOWS - USD ($)
$ in Thousands
 12 Months Ended
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Cash flows from operating activities:      
Net loss $ (98,849) $ (53,845) $ (55,545)
Adjustments to reconcile net loss to net cash provided by (used in) operating activities:      
Depreciation and amortization 22,631 16,528 11,097
Amortization of debt discount and issuance costs 17,518 10,513 3,831
Stock-based compensation expense 63,888 40,664 27,593
Provision for doubtful accounts 1,997 2,241 740
Deferred income taxes 737 (645) (69)
Foreign currency re-measurement loss 263 255 757
Other non-cash items 168 (1,889) (506)
Changes in assets and liabilities:      
Accounts receivable (24,380) (14,800) (1,685)
Deferred contract acquisition and fulfillment costs (13,379) (11,306) (12,790)
Prepaid expenses and other assets (8,956) (13,691) (287)
Accounts payable (2,394) 92 3,675
Accrued expenses 8,640 4,759 6,018
Deferred revenue 37,428 18,686 22,870
Other liabilities (425) 1,018 367
Net cash provided by (used in) operating activities 4,887 (1,420) 6,066
Cash flows from investing activities:      
Business acquisitions, net of cash acquired (125,826) (14,607) (14,460)
Purchases of property and equipment (13,802) (29,428) (12,813)
Capitalization of internal-use software (6,130) (6,087) (3,265)
Purchases of investments (177,053) (148,047) (233,421)
Sales and maturities of investments 166,524 214,980 70,226
Net cash (used in) provided by investing activities (156,287) 16,811 (193,733)
Cash flows from financing activities:      
Proceeds from issuance of convertible senior notes, net of issuance costs of $7,201 and $6,879 for the years ended December 31, 2020 and 2018, respectively 222,799 0 223,121
Purchase of capped calls related to convertible senior notes (27,255) 0 (26,910)
Proceeds from follow-on public offering, net of offering costs of $608 0 0 30,907
Deferred business acquisition payment (150) 0 0
Payment of debt issuance costs (440) 0 0
Taxes paid related to net share settlement of equity awards (8,921) (6,952) (2,197)
Proceeds from employee stock purchase plan 7,082 5,521 3,637
Proceeds from stock option exercises 7,810 10,219 7,606
Net cash provided by financing activities 200,925 8,788 236,164
Effect of exchange rate changes on cash and cash equivalents 679 (331) (694)
Net increase in cash and cash equivalents 50,204 23,848 47,803
Cash and cash equivalents, beginning of period 123,413 99,565 51,762
Cash and cash equivalents, end of period 173,617 123,413 99,565
Supplemental cash flow information:      
Cash paid for interest on convertible senior notes 5,463 2,779 0
Cash paid for income taxes, net of refunds 312 400 188
Non-cash investing activities:      
Leasehold improvements acquired through tenant improvement allowance $ 0 $ 14,016 $ 0