Reconciliation of income (loss) from operations and operating margin:

Three Months Ended January 31,

Year Ended January 31,

(in thousands)

2020

2019

2020

2019

GAAP loss from operations

$

(42,353)

$

(62,628)

$

(193,509)

$

(426,323)

Add: Stock-based compensation

55,605

49,271

206,404

410,978

Add: Amortization of acquisition-related intangibles

4,259

5,012

17,717

13,102

Add: Employer payroll tax on employee stock transactions

3,257

15,657

16,720

15,657

Add: Acquisition-related expenses

—

—

—

1,768

Non-GAAP income from operations

$

20,768

$

7,312

$

47,332

$

15,182

GAAP operating margin

(15)

%

(31)

%

(20)

%

(61)

%

Non-GAAP adjustments

23

%

35

%

25

%

63

%

Non-GAAP operating margin

8

%

4

%

5

%

2

%

Reconciliation of net income (loss) and net income (loss) per share, basic and diluted:

Three Months Ended January 31,

Year Ended January 31,

(in thousands, except per share data)

2020

2019

2020

2019

GAAP net loss

$

(47,407)

$

(66,244)

$

(208,359)

$

(426,458)

Add: Stock-based compensation

55,605

49,271

206,404

410,978

Add: Amortization of acquisition-related intangibles

4,259

5,012

17,717

13,102

Add: Employer payroll tax on employee stock transactions

3,257

15,657

16,720

15,657

Add: Acquisition-related expenses

—

—

—

1,839

Add: Amortization of debt discount and issuance costs

6,742

6,360

26,389

9,507

Less: Tax effect of the SpringCM acquisition ⁽¹⁾

—

289

—

(7,080)

Non-GAAP net income

$

22,456

$

10,345

$

58,871

$

17,545

Numerator:

Non-GAAP net income

$

22,456

$

10,345

$

58,871

$

17,545

Less: Preferred stock accretion

—

—

—

(353)

Less: Net income allocated to participating securities

—

—

—

(2,636)

Non-GAAP net income attributable to common stockholders

$

22,456

$

10,345

$

58,871

$

14,556

Denominator:

Weighted-average common shares outstanding, basic

180,859

167,269

176,704

135,163

Effect of dilutive securities

12,869

20,390

14,094

23,513

Non-GAAP weighted-average common shares outstanding, diluted

193,728

187,659

190,798

158,676

GAAP net loss per share, basic and diluted

$

(0.26)

$

(0.40)

$

(1.18)

$

(3.16)

Non-GAAP net income per share, basic

0.12

0.06

0.33

0.11

Non-GAAP net income per share, diluted

0.12

0.06

0.31

0.09

Represents a tax benefit related to the release of a portion of our deferred tax asset valuation allowance resulting from the SpringCM acquisition.