Prior to the IPO we issued Series A, Series A-1, Series B, Series B-1, Series C, Series D, Series E, and Series F redeemable convertible preferred stock. Upon completion of the IPO, all 100.2 million shares of our convertible preferred stock automatically converted into an aggregate of 100.4 million shares of our common stock. Refer to Note 1 for further information.


	January 31,
(in thousands)	2020	2019
RSUs outstanding	14,246	17,558
Options issued and outstanding	6,882	13,648
Remaining shares available for future issuance under the Equity Incentive Plans	24,726	17,519
Remaining shares available for future issuance under the ESPP	4,985	3,800
Total shares of common stock reserved	50,839	52,525

We maintain three stock-based compensation plans: the 2018 Equity Incentive Plan (“2018 Plan”), the Amended and Restated 2011 Equity Incentive Plan (the “2011 Plan”) and the Amended and Restated 2003 Stock Plan (the “2003 Plan”).

Our board of directors adopted, and our stockholders approved, the 2018 Plan during the year ended January 31, 2019. The 2018 Plan went into effect in April 2018, upon the effectiveness of our IPO Registration Statement. The 2018 Plan serves as a successor to the 2011 Plan and 2003 Plan and provides for the grant of stock-based awards to our employees, directors and consultants. No additional awards under the 2011 Plan or 2003 Plan have been made since the effective date of the 2018 Plan. Outstanding awards under these two plans continue to be subject to the terms and conditions of the respective plans.

Shares available for grant under the 2011 Plan that were reserved but not issued as of the effective date of the 2018 Plan were added to the reserves of the 2018 Plan. Additionally, any shares subject to outstanding awards originally granted under the 2011 Plan that: (i) expire or terminate for any reason prior to exercise or settlement; (ii) are forfeited because of the failure to

meet a contingency or condition required to vest such shares or otherwise returned to DocuSign, Inc.; or (iii) are reacquired, withheld (or not issued) to satisfy a tax withholding obligation in connection with an award or to satisfy the purchase price or exercise price of a stock award are added to the reserves of the 2018 Plan.

The 2018 Plan permits the granting of incentive stock options, nonstatutory stock options, stock appreciation rights, restricted stock awards, restricted stock unit awards, performance stock awards, performance cash awards and other stock awards. RSUs granted under the 2018 Plan generally vest over a four-year period, either quarterly or with 25% vesting at the end of one year and the remainder quarterly thereafter. Additionally, the Company grants performance-based and market-based RSUs to its executives on an annual basis.


(in thousands)			Year Ended January 31, 2020
Available at beginning of fiscal year			17,519
Awards authorized			8,570
Options canceled/expired			29
RSUs granted			(6,507)
RSUs cancelled			2,336
Shares withheld			2,779
Available at end of fiscal year			24,726

The 2018 Plan provides that the number of shares reserved will automatically increase on the first day of each fiscal year, beginning on February 1, 2019, and ending on February 1, 2028, by (i) 5% of the total number of shares of our capital stock outstanding on the immediately preceding January 31st (or such lesser number of shares as our board of directors or a committee of our board of directors may approve). The most recent automatic increase of 9.1 million shares occurred on February 1, 2020.

There were no options granted during the years ended January 31, 2020 and 2019. For the options granted during the year ended January 31, 2018, we calculated the fair value of each option award on the date of grant using the Black-Scholes option pricing model. We used the risk-free interest rates between 1.86% and 2.17% based on the U.S. Treasury yield curve in effect at the time of grant for the expected life of the award. We computed the expected life based on safe harbor rules as prescribed by the “simplified” method for estimating expected term, which resulted in an expected term of 6.05. We have assumed a 0% dividend yield, as we did not declare or expect to declare dividends. The expected volatility ranged between 44.99% and 45.53% based on a calculation using the historical stock information of companies deemed comparable to us for the period matching the expected term of each option and with an end date matching each of the various measurement dates. Determination of these assumptions involves management’s best estimates at that time.

$7.41 per share. The decrease in the value was primarily driven by an increase in the time-to-liquidity estimate, changes in industry trends and prices at which our common stock was transacted between third parties, such as employees, existing and outside investors. All such options were granted with an exercise price equal to the estimated fair value of our common stock at the date of grant.


(in thousands, except per share data and years)	Number of Options	Weighted-Average Exercise Price Per Share		Weighted-Average Remaining Contractual Term (Years)	Aggregate Intrinsic Value
Outstanding at January 31, 2019	13,648	$	12.27	5.38	$	507,371
Exercised	(6,737)	10.09
Canceled/expired	(29)	17.67
Outstanding at January 31, 2020	6,882	$	14.39	5.38	$	441,247
Vested and expected to vest at January 31, 2020	6,836	$	14.37	5.37	$	438,502
Exercisable at January 31, 2020	6,099	$	13.98	5.17	$	393,603

As of January 31, 2020, our total unrecognized compensation cost related to stock option grants was $5.7 million. We expect to recognize this expense over the remaining weighted-average period of approximately 1 year. The aggregate intrinsic value of options exercised during the years ended January 31, 2020, 2019 and 2018 was $325.7 million, $171.6 million and $83.6 million. The total grant date fair value of options vested during the years ended January 31, 2020, 2019 and 2018 was $10.5 million, $25.8 million and $33.6 million.

Substantially all the RSUs that we have issued on or before January 31, 2018 vest upon the satisfaction of both service-based and performance-based vesting conditions. The service-based condition is typically satisfied over a four-year service period. The performance-based condition related to these awards was satisfied upon the effectiveness of our IPO Registration Statement on April 26, 2018. On that date we recorded a cumulative stock-based compensation expense of $262.8 million using the accelerated attribution method for all the RSUs whose service conditions were fully satisfied. The total grant date fair value of RSUs vested during the years ended January 31, 2020 and 2019 was $223.0 million and $260.8 million. No RSUs vested during the year ended January 31, 2018.

The majority of RSUs granted after January 31, 2018, vest upon the satisfaction of a service-based vesting condition. From time to time, we also grant RSUs that are subject to either a performance-based or market-based vesting condition. The performance-based conditions will be satisfied upon satisfaction of certain financial performance targets. The market-based conditions will be satisfied if certain milestones based on our common stock price or relative total shareholder return are met. The weighted-average grant date fair value for RSUs granted during the years ended January 31, 2020, 2019 and 2018 was $56.05, $53.77 and $17.04 per share.


(in thousands, except per share data)	Number of Units	Weighted-Average Grant Date Fair Value
Unvested at January 31, 2019	17,142	$	34.56
Granted	6,507	56.05
Vested	(7,454)	29.91
Canceled	(2,336)	39.72
Unvested at January 31, 2020	13,859	$	46.28

During the year ended January 31, 2019, our board of directors adopted, and our stockholders approved the ESPP. In April 2018, the ESPP went into effect upon the effectiveness of our IPO Registration Statement. The ESPP allows eligible employees to purchase shares of our common stock at a discounted price by accumulating funds, normally through payroll deductions, of up to 15% of their earnings. The purchase price for common stock under the ESPP is equal to 85% of the fair market value of our common stock on the first or last day of the offering period, whichever is lower. The ESPP provides for separate six-month offering periods that begin in the first and third quarter of each year.


	Year Ended January 31,
	2020		2019
Risk-free interest rate	1.92 - 2.52 %		2.33 %
Expected dividend yield	—	%	—	%
Expected life of purchase right (in years)	0.5		0.5
Expected volatility	39 - 52 %		40 %
Weighted-average grant date fair value per share	$ 14.88 - 18.56		$ 14.24

The expected term for the ESPP purchase rights is estimated using the offering period, which is typically six months. We estimate volatility for ESPP purchase rights based on the historical volatility of our common stock price. The interest rate is derived from government bonds with a similar term to the ESPP purchase right granted. We have not declared, nor do we expect to declare dividends. During the year ended January 31, 2020, 0.5 million shares of common stock were purchased under the ESPP. Compensation expense related to the ESPP was $8.9 million and $2.9 million for the years ended January 31, 2020 and 2019.

The number of shares reserved under the ESPP will automatically increase on the first day of each fiscal year, starting on February 1, 2019 and continuing through February 1, 2028, in an amount equal to the lesser of (i) 1% of the total number of shares of our common stock outstanding on January 31 of the preceding fiscal year, (ii) 3.8 million shares, or (iii) a lesser number of shares determined by our board of directors. As of January 31, 2020, 5.0 million shares of common stock were reserved for issuance under the ESPP.