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Income Taxes (Tables)

12 Months Ended

Jan. 31, 2021

Income Tax Disclosure [Abstract]

Components of Pre-Tax Loss

The domestic and foreign components of pre-tax loss were as follows:

			Year Ended January 31,
(in thousands)			2021						2020						2019
U.S.			$	(240,175)					$	(228,476)					$	(460,627)
International			10,683						24,920						32,419
Loss before income taxes			$	(229,492)					$	(203,556)					$	(428,208)

Income Tax Provision

The components of our income tax provision (benefit) were as follows:

			Year Ended January 31,
(in thousands)			2021						2020						2019
Current
Federal			$	(35)					$	—					$	—
State			269						239						413
Foreign			15,951						3,277						2,838
Total current			16,185						3,516						3,251
Deferred
Federal			(243)						—						(7,083)
State			5						(43)						(2)
Foreign			(2,172)						1,330						2,084
Total deferred			(2,410)						1,287						(5,001)
Provision for (benefit from) income taxes			$	13,775					$	4,803					$	(1,750)

Reconciliation Federal Statutory Rate

The reconciliation of the statutory federal income tax rate to our effective tax rate was as follows:

			Year Ended January 31,
(in percentage)			2021						2020						2019
U.S statutory rate			21.0		%				21.0		%				21.0		%
State taxes			2.7						3.5						3.1
Foreign tax rate differential			0.1						0.5						0.3
Increase (decrease) unrecognized tax benefit			(5.6)						—						—
Stock-based compensation			87.1						47.2						17.5
Change in valuation allowance			(118.4)						(80.3)						(43.6)
Research and development credits			9.1						8.2						4.0
Other deferred adjustment			(1.1)						—						—
Other			(0.9)						(2.4)						(1.9)
Effective tax rate			(6.0)		%				(2.3)		%				0.4		%

Components of Net Deferred Tax Balances

The significant components of net deferred tax balances were as follows:

			January 31,
(in thousands)			2021						2020
Deferred tax assets
Net operating loss carryforwards			$	682,872					$	423,379
Accruals and reserves			14,744						5,668
Stock-based compensation			30,377						33,405
Operating lease liability			36,148						40,495
Research and development credits			60,386						39,480
Other			14,398						7,536
Total deferred tax assets			838,925						549,963
Less: Valuation allowance			(723,767)						(445,746)
Deferred tax assets, net of valuation allowance			115,158						104,217
Deferred tax liabilities
Operating lease right-of-use asset			(27,654)						(32,736)
Deferred contract acquisition costs			(61,432)						(36,567)
Convertible debt			(18,854)						(24,737)
Acquired intangibles			(11,939)						(13,493)
Other			(893)						(1,457)
Total deferred tax liabilities			(120,772)						(108,990)
Net deferred tax liabilities			$	(5,614)					$	(4,773)

Total Unrecognized Tax Benefits

A reconciliation of the beginning and ending balance of total unrecognized tax benefits was as follows:

			January 31,
(in thousands)			2021						2020
Unrecognized tax benefits balance at February 1			$	12,885					$	9,733
Gross increase for tax positions of prior years			2,012						90
Gross decrease for tax positions of prior years			—						(94)
Gross increase for tax positions of current year			18,882						3,156
Unrecognized tax benefits balance at January 31			$	33,779					$	12,885

Summary of Valuation Allowance

The following table represents the rollforward of our valuation allowance:

			Year Ended January 31,
(in thousands)			2021						2020						2019
Beginning balance			$	445,746					$	282,141					$	119,153
Valuation allowance charged to income tax provision			269,135						163,605						201,646
Valuation allowance from acquisitions			9,354						—						—
Convertible senior notes settled			14,985						—						—
Convertible senior notes issued			(15,453)						—						(31,594)
Acquisition of SpringCM			—						—						(7,064)
Ending balance			$	723,767					$	445,746					$	282,141

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Tabular disclosure of the reconciliation using percentage or dollar amounts of the reported amount of income tax expense attributable to continuing operations for the year to the amount of income tax expense that would result from applying domestic federal statutory tax rates to pretax income from continuing operations.

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