In February 2020, the Company issued and sold 170,000 shares of Series C preferred stock at a price of $75 per share for gross proceeds of $12,750. The Company incurred $261 of issuance costs in connection with the issuance of the Series C preferred stock

In May 2020, the Company issued and sold 1,342,750 shares of Series C preferred stock at a price of $100 per share for gross proceeds of $134,275. The Company incurred $750 of issuance costs in connection with the issuance of the Series C preferred stock.

In conjunction with the Company’s IPO in September 2020, all shares of convertible preferred stock then outstanding, totaling 15,525,685 shares (pre-split), were automatically converted into an equivalent number of shares of Class A common stock on an 8.8-to-1.0 basis pursuant to a stock split and their carrying value, totaling $801,813 was reclassified into stockholders’ equity on the consolidated balance sheet.

In connection with the IPO, the Company filed an Amended and Restated Certificate of Incorporation which authorizes the issuance of 100,000,000 shares of undesignated preferred stock, par value of $0.01 per share, with rights and preferences, including voting rights, designated from time to time by the board of directors.

In connection with our IPO in September 2020, we filed an Amended and Restated Certificate of Incorporation which authorizes the issuance of 100,000,000 shares of undesignated preferred stock, par value of $0.01 per share, with rights and preferences, including voting rights, designated from time to time by our board of directors. No shares of preferred stock were issued or outstanding as of December 31, 2022.

In September 2020, upon completion of the IPO, the Company sold 45,681,499 shares of Class A common stock at an offering price of $18.00 per share, including 4,459,277 shares of Class A common stock pursuant to the exercise in full of the underwriters' option to purchase additional shares. The Company received net proceeds of $767,568, after deducting underwriting discounts and commissions of $49,336 and offering costs of approximately $4,906. In September 2020, the Company sold 5,555,555 shares of Class C common stock in connection with the stock purchase agreement with Google, LLC for net proceeds of $99,100, after deducting offering costs of $900.

Concurrently with the IPO, the Company used $24,157 of the proceeds from the IPO to repurchase 1,340,354 shares of Class A and Class B common stock from certain executive officers and other employees, to permit such executive officers and other employees to pay taxes owed in connection with the vesting of equity awards, including the repayment of third party loans incurred to finance the payment of such taxes.

In connection with the IPO, the Company filed an Amended and Restated Certificate of Incorporation which authorizes capital stock of 1,000,000,000 shares of Class A common stock, par value $0.01 per share, 100,000,000 shares of Class B common stock, par value $0.01 per share, and 200,000,000 shares of Class C common stock, par value $0.01 per share.

Except for the rights noted below, each Class A, Class B and Class C common stock have the same rights, are equal in all respects and are treated by us as one class of shares. Each share of Class A and Class C common stock is entitled to one vote per share on all matters presented for a vote, except that Class C common stock does not have the right to vote for elections of directors. Subject to certain conditions, Class B common stock is collectively entitled to a number of votes equal to the product of (x) 1.0408163 and (y) the total number of votes that would be cast at such time by the holders of the Class A and Class C common stock and any other preferred stock entitled to vote under the certificate of incorporation at such time (resulting in the Class B common stock collectively holding 51% of the total outstanding voting power), and each share of Class B common stock will be entitled to a number of votes equal to the total number of votes held by all Class B common stock divided by the total number of then outstanding shares of Class B common stock. Shares of Class B and Class C common stock will be converted into shares of Class A common stock on a one-for-one basis upon the occurrence of certain events. Shares of Class B common stock will automatically convert on the first business day (i) after the date on which the outstanding shares of Class B common stock constitutes less than 5% of the aggregate number of shares of common stock then outstanding, (ii) after the date on which neither founder is serving as an executive officer or (iii) following seven years after the date the amended and restate certificate of incorporation becomes effective, provided that, such period may, to the extent permitted by law and applicable stock exchange rules, be extended for three years upon the affirmative vote of the holders of a majority of the voting power of the then-outstanding shares of Class A common stock entitled to vote thereon, voting separately as a class. Shares of Class C common stock will be convertible at the option of the holder upon determination that a Hart-Scott-Rodino Antitrust Improvements Act (“HSR”) filing is not necessary prior to the holder’s conversion of such shares or, if required, upon expiration or termination of the HSR waiting period.

Common stockholders are entitled to receive dividends, as may be declared by the board of directors, if any, subject to the preferential dividend right of the preferred stockholders. No dividends have been declared through December 31, 2022.

In August 2021, the Company issued 4.7 million and 8.1 million shares of Class A common stock at a fair value of $11.20 and $10.51 per share in connection with the acquisitions of Conversa and SilverCloud, respectively (see Note 8). In the year ended December 31, 2022 the Company issued 1.0 million and 5.0 million shares of Class A common stock at a fair value of $4.21 and $2.61 per share in connection with the settlement of the earnouts for Conversa and SilverCloud, respectively (see Note 6). In the year ended December 31, 2022 the Company also issued 0.6 million shares of Class A common stock in relation to the early settlement of the bonus escrow.

In the year ended December 31, 2022 no shares of Class B common stock were converted to Class A common stock. As of December 31, 2022 the par value of the Class A, Class B and Class C shares was $2,435, $275 and $56, respectively.


	Shares Authorized		Shares Issued		Shares Outstanding
Class A		1,000,000,000		244,193,727		244,193,727
Class B		100,000,000		27,390,397		27,390,397
Class C		200,000,000		5,555,555		5,555,555
		1,300,000,000		277,139,679		277,139,679

As of December 31, 2022 and 2021, the Company had reserved 68,617,245 and 61,989,749 shares of common stock for the exercise of outstanding stock options, the vesting of restricted stock units and the number of shares remaining available for future grant, respectively.

The Company maintains the 2006 Employee, Director and Consultant Stock Plan as amended and restated (the “2006 Plan”) and 2020 Equity Incentive Plan (the “2020 Plan” together, the “Plans”) under which it has granted incentive stock options, non-qualified stock options, and restricted stock units to employees, officers, and directors of the Company. In connection with the adoption of the 2020 Plan, the then-remaining shares of common stock reserved for grant or issuance under the 2006 Plan became available for issuance under the 2020 Plan, and no further grants will be made under the 2006 Plan. The 2020 Plan is administered by the board of directors with respect to awards to non-employee directors and by the compensation committee, with respect to other participants, are collectively, referred to as the plan administrator. The exercise prices, vesting and other restrictions are determined at the discretion of the plan administrator. Options issued under the Plans are exercisable for periods not to exceed ten years, and vest and contain such other terms and conditions as specified in the applicable award document. Options to buy common stock are issued under the Plans, with exercise prices equal to the closing price of shares of the Company’s common stock on the New York Stock Exchange on the date of award.

Stock options granted under the Plan typically vest over four years and expire ten years after the grant date. The Company had 8,156,870 shares available for grant as of December 31, 2022.

Activity under the Plans is as follows:


	Number of Shares			Weighted Average Exercise Price		Weighted Average Remaining Contractual Term (Years)		Aggregate Intrinsic Value
Outstanding as of January 1, 2022		15,893,755		$	4.81		5.9	$	23,876
Granted		—		$	—
Forfeited		(2,081,214	)	$	6.04
Expired		(82,542	)	$	5.58
Exercised		(2,690,448	)	$	2.11
Outstanding as of December 31, 2022		11,039,551		$	5.23		5.5	$	996
Vested and expected to vest as of December 31, 2022		10,951,967		$	5.02		5.5	$	996
Options exercisable as of December 31, 2022		10,417,259		$	4.97		5.4	$	996

The aggregate intrinsic value of stock options exercised during the years ended December 31, 2022, 2021 and 2020, was $5,167, $106,407 and $31,194, respectively. The aggregate intrinsic value of common stock options is calculated as the difference between the exercise price of the stock options and the fair value of the Company’s common stock for those stock options that had exercise prices lower than the fair value of the Company’s common stock.

The weighted-average grant date fair value of common stock options granted during the year ended December 31, 2020 was $4.17. There were no options granted during the years ended December 31, 2022 and 2021.

The Company received cash proceeds from the exercise of common stock options of $5,740, $20,806 and $5,932 during the years ended December 31, 2022, 2021 and 2020, respectively.

The weighted average of assumptions that the Company used to determine the fair value of the common stock options granted to employees and directors were as follows:


	Years Ended December 31,
	2022	2021	2020
Risk-free interest rate	N/A	N/A		1.09	%
Expected term (in years)	N/A	N/A		6.1
Expected volatility	N/A	N/A		52	%
Expected dividend yield	N/A	N/A		0	%

Each CEO has received restricted stock units, equaling up to 1.5% of the Company’s fully-diluted outstanding capital stock as a result of the IPO (“IPO RSUs”), 50% of the IPO RSUs (representing 0.75% of the Company’s fully diluted outstanding capital stock immediately prior to the IPO or 3,230,750 shares of Class A common stock) were granted on the closing date of the IPO based on the closing price per share on the IPO closing date, and 50% (representing up to 0.75% of the Company’s fully diluted outstanding capital stock immediately prior to the IPO or 3,230,750 shares of Class A common stock) was granted on the 180-day anniversary of the IPO, based on a specific range of the price per share of the Company’s publicly traded common stock prior March 16, 2021, and will vest over a three-year period, with one-third vesting on the first anniversary of the IPO’s closing date and the remaining vesting in equal quarterly installments thereafter. As the issuance of the second 50% tranche is based upon events that are probable the expense related to both tranches of the IPO RSUs was recognized in the three months ended September 30, 2020.

The grant-date fair value of each of the awards issued on the IPO closing date and to be issued on the 180-day anniversary of the IPO were estimated using a binomial lattice approach. The main inputs to valuing the IPO RSUs include the fair value of Class A common stock ($9.96 post-split), expected volatility (60%) and the expected date of the IPO (September 30, 2020). The Company recognized a total of $23,644 in stock-based compensation expense, which included

both tranches of the IPO RSUs for each CEO, on the date of the IPO as the requisite future service of the awards is not substantive for accounting purposes.

The following table summarizes the unvested restricted stock unit activity for the year ended December 31, 2022:


	Shares			Weighted Average Grant Date Fair Value
Unvested as of January 1, 2022		11,718,813		$	19.63
Granted		15,430,438			4.15
Vested		(5,372,060	)		12.09
Forfeited		(2,460,732	)		8.45
Unvested as of December 31, 2022		19,316,459		$	10.78

The total grant date fair value of RSU’s granted for the years ended December 31, 2022, 2021 and 2020 was $63,987, $152,550 and $195,655, respectively. The aggregate intrinsic value of restricted stock units vested for the years ended December 31, 2022, 2021 and 2020 was $22,218, $90,726 and $73,836, respectively.

In the year ended December 31, 2022 the Company granted performance-based market condition share awards to certain members of the Company’s management team, which entitle these employees with the right to receive shares of common stock, upon achievement of certain market capitalization milestones measured over a rolling thirty day trading-period, subject to the satisfaction of the applicable service vesting conditions. The performance-based market condition share awards for management (other than the co-CEOs) consist of six tranches with six separate specified award values that become payable upon the achievement of certain market capitalization milestones, which can result in a vesting range of up to 12,275,886 shares. Also in 2022 the Company granted performance-based market condition share awards to the co-CEOs, which entitle these employees with the right to receive shares of common stock, upon achievement of certain market capitalization milestones measured over a rolling thirty day trading-period, subject to the satisfaction of the applicable service vesting conditions. The performance-based market condition share awards for the co-CEOs consist of eight tranches with eight separate specified award values that become payable upon the achievement of certain market capitalization milestones (subject to specified vesting caps during each of the first two years of the performance period), which can result in a vesting range of up to 7,500,000 shares for each co-CEO. As of December 31, 2022, no portion of the performance- based market condition share awards have satisfied both the applicable market capitalization milestones and the service vesting conditions and, as such, no awards have vested. These performance-based market condition share awards have a performance period of three years.

The total grant-date fair value of performance-based market condition share awards granted during the year ended December 31, 2022 was $63,157 and no performance-based market condition share awards were granted during the year ended December 31, 2021 and 2020.


	Shares			Weighted Average Grant Date Fair Value
Unvested as of January 1, 2022		—		$	—
Granted		27,275,886			2.32
Vested		—			—
Cancelled/Forfeited		(1,673,481	)		2.62
Unvested as of December 31, 2022		25,602,405		$	2.30

The weighted average estimated fair value of the performance-based market condition share awards granted during the year ended December 31, 2022 was determined using a Monte-Carlo valuation simulation, with the following most significant weighted-average assumptions:


	Years Ended December 31,
	2022			2021	2020
Risk-free rate		2.34	%	N/A	N/A
Term to end of performance period (yrs)	3 years			N/A	N/A
Weighted average valuation date stock price	$	3.50		N/A	N/A
Expected volatility		75	%	N/A	N/A
Expected dividend yield		0	%	N/A	N/A

In July and August 2020, the Company’s board of directors adopted, and the Company’s stockholders approved, the 2020 Employee Stock Purchase Plan (“ESPP”). Rights granted under the ESPP will be issued only with respect to shares of Class A common stock. The purchase price of the shares will not be less than 85% of the fair market value of Class A common stock on the lower of the purchase date, which will be the final trading day of the purchase period, or the enrollment date, which will be the first trading day of the offering period.

During the years ended December 31, 2022, 2021 and 2020 the Company issued 703,148, 178,021, and no shares under the ESPP. As of December 31, 2022 4,501,960 shares remained available for issuance.

Stock-based compensation expense was classified in the consolidated statements of operations and comprehensive loss as follows:


	Years Ended December 31,
	2022		2021		2020
Cost of revenues	$	1,605	$	1,655	$	1,087
Research and development	$	10,236		7,613		4,793
Selling and marketing	$	7,182		7,666		4,147
General and administrative		50,121		26,875		108,331
Total	$	69,144	$	43,809	$	118,358

As of December 31, 2022, total unrecognized compensation cost related to the unvested common stock-based awards was $104,961, which is expected to be recognized over a weighted-average period of 2.6 years.