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Stock-based Compensation
 12 Months Ended
Dec. 31, 2022
Share-Based Payment Arrangement [Abstract]  
Stock-based Compensation Stock-based Compensation
Share option plan

2020 Incentive Compensation Plan
On July 2, 2020, the Company’s board of directors adopted and the Company’s stockholders approved the 2020 Incentive Compensation Plan (the “2020 Plan”), which became effective immediately prior to the effectiveness of the registration statement for the Company’s IPO on July 2, 2020. The 2020 Plan provides for the issuance of incentive stock options, non-qualified stock options, stock awards, stock units, stock appreciation rights and other stock-based awards.

The number of shares initially reserved for issuance under the 2020 Plan is 5,503,678 shares, inclusive of available shares previously reserved for issuance under the 2015 Incentive Share Option Plan, as amended and restated on September 4, 2019 (the “2015 Plan”). In addition, the number of shares reserved for issuance under the 2020 Plan is subject to increase for awards previously issued under the 2015 Plan which are forfeited or lapse unexercised. Annually, on the first day of each calendar year beginning on January 1, 2021 and ending on and including January 1, 2030, the reserve will be increased by an amount equal to the lesser of (A) 5% of the shares outstanding (on an as-converted basis) on the last day of the immediately preceding fiscal year and (B) such smaller number of shares as determined by the Company’s board of directors, provided that no more than 3,650,000 shares may be issued upon the exercise of incentive stock options. As of December 31, 2022, there were 3,214,826 shares of common stock available for future grants.

2020 Employee Stock Purchase Plan

On July 2, 2020, the Company's board of directors adopted and the Company's stockholders approved the 2020 Employee Stock Purchase Plan (the "2020 ESPP"), which became effective immediately prior to the effectiveness of the registration statement for the Company's IPO on July 2, 2020. The total shares of common stock initially reserved for issuance under the 2020 ESPP is limited to 1,000,000 shares. In addition, the number of shares available for issuance under the 2020 ESPP will be annually increased on January 1 of each calendar year beginning in 2021 and ending in and including 2030, by an amount equal to the lesser of (A) 1,000,000 Shares, (B) 1% of the shares outstanding on the final day of the immediately preceding calendar year and (C) such smaller number of shares as is determined by the board of directors. The board of directors or a committee of the board of directors will administer and will have authority to interpret the terms of the 2020 ESPP and determine eligibility of participants. There were no shares issued under the 2020 ESPP as of December 31, 2022.

2015 Incentive Share Option Plan

In July 2015, the Company adopted the 2015 Incentive Share Option Plan (“2015 Plan”). The 2015 Plan has been amended and restated from time to time to increase the number of shares reserved for grant and to enable the grant of options to employees of the Company's subsidiaries. Under the 2015 Plan, options to purchase common stock of the Company may be granted to employees, officers, directors and consultants of the Company. Each option granted can be exercised for one share of common stock of the Company. Options granted to employees generally vest over a period of no more than four years. The options expire ten years from the date of grant.
Pursuant to the 2015 Plan, the Company had reserved 7,312,590 shares of common stock for issuance. Effective immediately upon the approval of the 2020 Plan, the remaining shares of common stock available for future grant under the 2015 Plan were transferred to the 2020 Plan. As of December 31, 2022, there were no shares of common stock available for future grant under the 2015 Plan. Subsequent to the approval of the 2020 Plan, no additional grants were made under the 2015 Plan and any outstanding awards under the 2015 Plan will continue with their original terms.
Assumed Share Option Plans
As part of the Metromile Acquisition, the Company assumed the Metromile 2011 Incentive Stock Plan (“2011 Plan”) and Metromile 2021 Incentive Stock Plan (“2021 Plan”) (collectively referred to as “Assumed Plans”).The equity awards assumed of 404,207 were granted from the respective Assumed Plans and will be settled in the Company’s common stock (see Note 5). The remaining unallocated shares reserved under both the 2011 and 2021 Plan were cancelled and no new awards will be granted under these Assumed Plans.

Options granted to employees and non-employees
The fair value of each option granted during the year ended December 31, 2022 and 2021 is estimated on the date of grant using the Black-Scholes model with the following assumptions:
December 31,
20222021
Weighted average expected term (years)6.106.13
Risk-free interest rate2.7%1.3%
Volatility47%48%
Expected dividend yield0%0%
Expected volatility is based on companies at a comparable stage, as well as companies in the same or a similar industry. The expected term of options granted is based on the simplified method, which uses the midpoint between the vesting date and the contractual term in accordance with ASC 718, "Compensation — Stock Compensation". The risk-free interest rate is based on observed interest rates appropriate for the term of the Company's stock options. The dividend yield assumption is based on the Company's historical and expected future dividend payouts and may be subject to substantial change in the future.
The following table summarizes activity ($ in millions, except for option and weighted-average amounts):
Stock options
Number of
Options		 Weighted-
Average
Exercise
Price		 Weighted-
Average
Remaining
Contractual
Term
(Years)		 Aggregate
Intrinsic
Value
Outstanding as of December 31, 20216,573,744 $46.03 8.29$85.86 
Granted (1)
4,351,371 27.47 
Exercised(448,368)7.97 
Canceled(716,090)50.11 
Outstanding as of December 31, 20229,760,657 $39.43 8.17$8.05 
Options exercisable as of December 31, 20223,420,165 $28.38 6.87$7.93 
Options unvested as of December 31, 20226,340,492 $45.37 8.89$0.11 
(1) includes assumed options of 72,410 from Metromile Acquisition (See Note 5)
On July 28, 2021, the Board of Directors of the Company approved the reduction in exercise price of certain options granted to employees in the beginning of 2021, with original exercise price ranging from $142.64 to $159.02 and were each repriced at an exercise price of $90.70 per share. Incremental compensation expense resulting from the repricing was $3.0 million, and compensation expense amounted to $0.7 million and $0.8 million for the years ended December 31, 2022 and 2021. There were no changes in the vesting schedule or maturity term of the options.
Restricted Stock Units
Number of sharesGrant Date Fair Value
Outstanding as of December 31, 2021335,814 $66.94 
Granted (1)
1,821,066 22.50 
Vested(263,732)37.26 
Canceled(241,905)27.42 
Outstanding as of December 31, 20221,651,243 27.92 
(1) includes assumed restricted stock units of 331,797 from the Metromile Acquisition (See Note 5)
Stock-based compensation expense
Stock-based compensation expense from stock options and RSUs granted included and classified in the consolidated statements of operations and comprehensive loss, including assumed awards from the Metromile Acquisition for the year ended December 31, 2022, as follows ($ in millions):
December 31,
202220212020
Loss and loss adjustment expense, net$2.7 $1.5 $0.4 
Other insurance expense1.6 1.0 0.7 
Sales and marketing6.6 5.1 2.7 
Technology development24.4 18.2 3.1 
General and administrative24.0 18.3 3.7 
Total stock-based compensation expense$59.3 $44.1 $10.6 
Stock-based compensation expense classified by award type as included in the consolidated statements of operations and comprehensive loss is as follows ($ in millions):

December 31,
202220212020
Stock options$47.8 $40.1 $10.6 
RSUs11.5 4.0 — 
Total stock-based compensation expense$59.3 $44.1 $10.6 

The total unrecognized expense granted to employees and non-employees outstanding as of December 31, 2022 was $95.7 million for stock options and $42.5 million for RSUs, with a remaining weighted average vesting period of 1.4 years for stock options and 1.6 years for RSUs.