DOCUSIGN, INC.

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS

(Unaudited)

Three Months Ended January 31,

Year Ended January 31,

(in thousands)

2020

2019

2020

2019

Cash flows from operating activities:

Net loss

$

(47,407)

$

(66,244)

$

(208,359)

$

(426,458)

Adjustments to reconcile net loss to net cash used in operating activities

Depreciation and amortization

13,266

12,003

50,182

38,027

Amortization of deferred contract acquisition and fulfillment costs

20,387

12,223

69,747

42,112

Amortization of debt discount and transaction costs

6,742

6,360

26,389

9,507

Non-cash operating lease costs

5,592

—

19,435

—

Stock-based compensation expense

55,605

49,271

206,404

410,978

Deferred income taxes

1,245

2,346

1,287

(5,001)

Other

401

2,879

(1,741)

800

Changes in operating assets and liabilities

Accounts receivable

(78,377)

(43,937)

(63,293)

(42,571)

Contract assets

5,715

1,430

(1,508)

4,204

Prepaid expenses and other current assets

(1,106)

(900)

(3,142)

(3,283)

Deferred contract acquisition and fulfillment costs

(37,923)

(28,324)

(115,723)

(80,869)

Other assets

612

656

1,538

2,658

Accounts payable

1,543

(1,390)

3,849

(7,380)

Accrued expenses and other liabilities

4,662

(1,122)

9,353

6,449

Accrued compensation

12,329

23,868

5,636

26,039

Contract liabilities

85,957

65,018

130,266

100,874

Operating lease liabilities

(3,738)

—

(14,624)

—

Net cash provided by operating activities

45,505

34,137

115,696

76,086

Cash flows from investing activities:

Purchases of marketable securities

(107,318)

(415,132)

(861,252)

(415,132)

Maturities of marketable securities

166,599

—

627,309

—

Purchases of strategic investments

—

—

(15,500)

—

Cash paid for acquisition, net of acquired cash

—

—

—

(218,779)

Purchases of property and equipment

(29,975)

(11,317)

(72,046)

(30,413)

Net cash provided by (used in) investing activities

29,306

(426,449)

(321,489)

(664,324)

Cash flows from financing activities:

Proceeds from issuance of convertible senior notes, net of initial purchasers' discounts and transaction costs

—

—

—

560,756

Purchase of capped calls related to issuance of convertible senior notes

—

—

—

(67,563)

Proceeds from issuance of common stock in initial public offering, net of underwriting commissions

—

—

—

529,305

Payment of tax withholding obligation on RSU settlement

(41,216)

(215,332)

(166,504)

(215,332)

Proceeds from exercise of stock options

9,914

34,846

72,177

50,211

Proceeds from employee stock purchase plan

—

—

23,872

—

Payment of deferred offering costs

—

(319)

—

(4,011)

Other financing

—

(250)

—

(250)

Net cash provided by (used in) financing activities

(31,302)

(181,055)

(70,455)

853,116

Effect of foreign exchange on cash, cash equivalents and restricted cash

(137)

(2,955)

(447)

(4,136)

Net increase (decrease) in cash, cash equivalents and restricted cash

43,372

(576,322)

(276,695)

260,742

Cash, cash equivalents and restricted cash at beginning of period

198,111

1,094,500

518,178

257,436

Cash, cash equivalents and restricted cash at end of period

$

241,483

$

518,178

$

241,483

$

518,178