
	Options Outstanding	Weighted Average Exercise Price per Share		Weighted Average Remaining Contractual Life (Years)	Aggregate Intrinsic Value
Balance at January 1, 2023	31,795	$	23.31	6.95	$	504,222
Granted	843	73.07
Exercised	(1,203)	14.12
Forfeited and cancelled	(731)	39.79
Expired	(10)	214.50
Balance at June 30, 2023	30,694	$	24.58	6.56	$	1,524,201

Exercisable at June 30, 2023	24,542	$	24.87	6.42	$	1,228,008
Vested and expected to vest at June 30, 2023	24,637	$	24.84	6.42	$	1,233,197

During the three and six months ended June 30, 2023, the Company granted stock options for the purchase of 71,991 and 842,617 shares of the Company’s Class A common stock with a weighted-average grant date fair value of $44.74 and $40.85 per share, respectively, to certain employees of the Company. The stock options vest over three years at a rate of 1/12 per quarter.

As of June 30, 2023, there was total unrecognized compensation cost of $104.8 million related to unvested stock options. These costs are expected to be recognized over a weighted-average period of approximately 2.4 years.

The assumptions used under the Black-Scholes-Merton Option-Pricing Model and the weighted average calculated value of the options granted to employees were as follows:


	Three Months Ended June 30,				Six Months Ended June 30,
	2023		2022		2023		2022
Dividend yield	0.0	%	0.0	%	0.0	%	0.0	%
Expected volatility	93.7	%	67.6	%	90.5	%	56.2	%
Expected term (in years)	5.8		5.8		5.8		5.8
Risk-free interest rate	3.4	%	3.1	%	3.9	%	1.9	%

As of June 30, 2023, there were 77,213 shares of Class A common stock subject to repurchase related to stock options exercised early and not yet vested, but that are expected to vest. As of June 30, 2023, the Company recorded a liability related to these shares subject to repurchase in the amount of $1.5 million, which is included within accrued expenses and other current liabilities on the accompanying condensed consolidated balance sheets.

During the three and six months ended June 30, 2023 and 2022, stock-based compensation expense of $1.0 million and $1.9 million, respectively, was recognized related to this award.

During the six months ended June 30, 2023, the Company granted 803,966 PRSUs to an executive officer. See President & Chief Operating Officer Performance Award below for additional details regarding the PRSUs granted.


	Number of Shares	Weighted-Average Grant Date Fair Value Per Share
Balance at January 1, 2023	5,329	$	127.85
Granted	9,986	57.09
Vested	(5,211)	70.99
Forfeited and cancelled	(1,150)	124.21
Balance at June 30, 2023	8,954	$	82.50

As of June 30, 2023, there was total unrecognized compensation cost of $656.4 million related to unvested RSUs and PRSUs. These costs are expected to be recognized over a weighted-average period of approximately 1.3 years.

On April 20, 2023, the Company’s Compensation Committee granted the President & Chief Operating Officer an award of PRSUs covering a target of 401,983 shares of the Company’s Class A common stock and up to a maximum of 803,966 shares of the Company’s Class A common stock (the “2023 COO Performance Award”).

Up to 40% of the 2023 COO Performance Award is subject to vesting based upon achievement of certain cumulative revenue and cumulative adjusted EBITDA target values which are separately evaluated for the period commencing January 1, 2023 and ending on December 31, 2025, subject to her continued employment until February 20, 2026. Up to 60% of the 2023 COO Performance Award is subject to vesting in increments based upon a relative shareholder return target value for the three annual periods between January 1, 2023 and December 31, 2025, and the three year period between January 1, 2023 and December 31, 2025, subject to her continued employment through the applicable year end dates.

The total grant date fair value of this award was $25.1 million. The Company determined the fair value of the portion of the award subject to a market condition using a Monte Carlo Simulation Model (a binomial lattice-based valuation model). The Monte Carlo Simulation Model uses multiple input variables to determine the probability of satisfying the market condition requirements. The fair value of the award is not subject to change based on future market conditions.

The Company uses the accelerated attribution method to recognize expense for each vesting tranche over the requisite service period for the 2023 COO Performance Award. For the portion of the award subject to a market condition, compensation expense is recognized over the requisite service period regardless of whether or not the market condition is ultimately satisfied, according to the market-based fair value measured on the grant date, subject to continued service over the period.

For the portion of the award subject to financial performance conditions, the Company evaluates the cumulative revenue and the cumulative adjusted EBITDA results at each reporting date to determine which performance condition and level of achievement becomes most probable of being achieved for the three-year assessment period. Compensation expense is recognized over the requisite service period based on the result that is probable of occurring at each reporting date until the final vesting date, subject to continued service over the period.

During the three and six months ended June 30, 2023, stock-based compensation expense of $2.8 million was recognized related to this award.

As part of the Company’s acquisitions, the Company has issued shares of restricted Class A common stock. Vesting of this restricted Class A common stock is dependent on a service-based vesting condition that is generally satisfied over three years. The Company has the right to repurchase shares at par value for which the vesting condition is not satisfied. Activity of restricted Class A common stock is as follows (in thousands, except per share data):


	Number of Shares	Weighted-Average Grant Date Fair Value Per Share
Balance at January 1, 2023	1,275	$	139.72
Granted	263	64.51
Vested	(851)	141.53
Forfeited and cancelled	(29)	171.85
Balance at June 30, 2023	658	$	105.78

As of June 30, 2023, there was total unrecognized compensation cost of $48.0 million related to unvested restricted Class A common stock. These costs are expected to be recognized over a weighted-average period of approximately 1.8 years.

The ESPP allows eligible employees the option to purchase shares of the Company's Class A common stock at a 15% discount, over a series of offering periods through accumulated payroll deductions over the period. The ESPP also includes a look-back provision for the purchase price if the stock price on the purchase date is lower than the stock price on the offering date. The Company recognizes stock-based compensation expenses related to purchase rights issued pursuant to its ESPP on a straight-line basis over the offering period, which is 24 months. The fair value of purchase rights under the ESPP are estimated on the date of grant using the Black-Scholes-Merton Option-Pricing Model.

The grant date of the initial offering period was May 3, 2021, and that offering period ended on April 30, 2023. Subsequent offering periods will commence in each May and November after the start of the initial offering period. As of June 30, 2023, the Company recorded a liability of $3.3 million related to the accumulated payroll deductions, which are refundable to employees who withdraw from the ESPP. This amount is included within accrued expenses and other current liabilities on the accompanying condensed consolidated balance sheets.

Stock-based compensation is included in the following components of expenses on the accompanying condensed consolidated statements of operations (in thousands):


	Three Months Ended June 30,				Six Months Ended June 30,
	2023		2022		2023		2022
Technology and development	$	123,469	$	261,232	$	246,165	$	517,756
Sales and marketing	14,930		19,396		29,139		34,352
General and administrative	61,373		110,868		123,328		191,529
Restructuring	—		—		84,042		—
Total	$	199,772	$	391,496	$	482,674	$	743,637

During the three and six months ended June 30, 2023, $14.9 million and $29.0 million of stock-based compensation expense was included in capitalized software, respectively. During the three and six months ended June 30, 2022, $70.1 million and $71.5 million of stock-based compensation expense was included in capitalized software, respectively.