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Stockholders’ Equity
 6 Months Ended
Jun. 30, 2024
Equity [Abstract]  
Stockholders’ Equity
13. Stockholders’ Equity
Common Stock
The Company’s common stock and warrants trade on the New York Stock Exchange (“NYSE”) under the ticker symbols “HIPO” and “HIPO.WS,” respectively. Pursuant to its Certificate of Incorporation, the Company is authorized to issue 80 million shares of common stock, with a par value of $0.0001 per share. Each share of common stock is entitled to one vote. The holders of the common stock are also entitled to receive dividends
whenever funds are legally available and when declared by the board of directors. No dividends have been declared or paid since inception.

Stock Options
The following table summarizes option activity under the plans:
Options OutstandingWeighted-Average RemainingAggregate Intrinsic Value
(In Millions)
Number of SharesWeighted Average Exercise PriceContract Term
(In Years)
Outstanding as of December 31, 2023
1,589,529$16.13 6.8$0.2 
Granted—— 
Exercised(100,502)13.27 
Cancelled/Expired(69,472)15.49 
Outstanding as of June 30, 20241,419,55516.37 6.4$2.4 
Vested and exercisable as of June 30, 20241,346,313$16.39 6.3$2.3 
The aggregate intrinsic value of options exercised during the six months ended June 30, 2024 and 2023 was $0.5 million and $0.5 million, respectively, and is calculated based on the difference between the exercise price and the fair value of the Company’s common stock as of the exercise date. There were no options granted during the six months ended June 30, 2024 and 2023.
Total unrecognized compensation cost of $1.6 million as of June 30, 2024 is expected to be recognized over a weighted-average period of 1.1 years.
Restricted Stock Units and Performance Restricted Stock Units
The Company grants service based RSUs and performance based RSUs (“PRSUs”) as part of the Company’s equity compensation plans. The Company measures RSU and PRSU expense for awards granted based on the estimated fair value of those awards at the grant date. To estimate the fair value of PRSUs containing a market condition, the Company used the Monte Carlo valuation model. The fair value of all other awards is based on the closing price of the Company’s common stock as reported on the NYSE on the date of grant. The RSUs generally vest over a period of two to four years. The PRSUs vest based on the level of achievement of the performance goals and continued employment with the Company over a one to four year performance period.
Stock-based compensation expense for RSUs is recognized based on the straight-line basis over the employee requisite service period. Stock-based compensation expense for PRSUs is recognized on a graded accelerated basis over the employee requisite service period. The Company accounts for forfeitures as they occur.
The following table summarizes the RSU and PRSU activity for the six months ended June 30, 2024:
Number of SharesWeighted Average Grant-Date Fair Value per Share
Unvested and outstanding as of December 31, 2023
2,534,683$28.28 
Granted1,263,14819.52 
Released(788,735)25.61 
Canceled and forfeited(296,673)28.09 
Unvested and outstanding as of June 30, 2024
2,712,423 $25.01 
Total unrecognized compensation cost related to unvested RSUs and PRSUs is $45.8 million as of June 30, 2024, and it is expected to be recognized over a weighted-average period of 1.5 years.
2021 Employee Stock Purchase Plan
The Company adopted the 2021 Employee Stock Purchase Plan (the “2021 ESPP”), which is designed to allow eligible employees of the Company to purchase shares of the Company’s common stock with their accumulated payroll deductions at a price equal to 85% of the lesser of the fair market value on the first business day of the offering period or on the designated purchase date of the offering period, up to a maximum purchase amount of $25,000 during the calendar year. The 2021 ESPP offers a six-month look-back feature as well as an automatic reset feature that provides for an offering period to be reset to a new lower-priced offering if the offering price of the new offering period is less than that of the current offering period. During the six months ended June 30, 2023, 80,990 shares have been issued under the 2021 ESPP for $1.0 million. During the six months ended June 30, 2024, 104,384 shares have been issued under the 2021 ESPP for $0.8 million. In addition, the number of shares available for issuance under the 2021 ESPP is increased annually on January 1 of each calendar year ending in 2031, by an amount equal to the lesser of (i) one percent of the shares outstanding (on a converted basis) on the last day of the immediately preceding fiscal year and (ii) such number of shares as may be determined by the board of directors.
Stock-Based Compensation
Total stock-based compensation expense, classified in the accompanying condensed consolidated statements of operations and comprehensive loss was as follows (in millions):
Three Months EndedSix Months Ended
June 30,June 30,
2024202320242023
Losses and loss adjustment expenses$0.3 $0.1 $0.5 $0.6 
Insurance related expenses1.6 1.4 2.0 2.6 
Technology and development1.9 3.9 3.6 7.3 
Sales and marketing2.7 3.6 4.6 7.9 
General and administrative5.4 7.7 9.6 14.4 
Total stock-based compensation expense$11.9 $16.7 $20.3 $32.8 

Stock Repurchases
In March 2023, the Board authorized the repurchase of up to $50.0 million of its common stock, with no expiration date. Repurchases under the program may be made in the open market, in privately negotiated transactions or otherwise, with the amount and timing of repurchases to be determined at the Company’s discretion depending on market conditions and corporate needs. Open market repurchases will be structured to occur in accordance with applicable federal securities laws, including within the pricing and volume requirements of Rule 10b-18 under the Securities Exchange Act of 1934, as amended. The Company may also, from time to time, enter into Rule 10b5-1 plans to facilitate repurchases of its common stock under this authorization. This program does not obligate the Company to acquire any particular amount of its common stock, and may be modified, suspended or terminated at any time at the Company’s discretion. No share repurchases were made under this program during the six months ended June 30, 2024. As of June 30, 2024, $48.2 million of common stock remains available for repurchase. Shares repurchased by the Company are accounted for when the transaction is settled. As of June 30, 2024, there were no unsettled share repurchases. Direct costs incurred to acquire the shares are included in the total cost of the shares.