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Stock Based Compensation (Tables)
 6 Months Ended
Jun. 30, 2024
Share-Based Payment Arrangement [Abstract]  
Summary of changes to issuances under 2017 equity plan
The table below summarizes changes to the issuances under the Company’s 2017 Omnibus Incentive Equity Plan for the periods indicated, excluding awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock:
2017 Equity PlanNumber of shares
Available for issuance as of December 31, 2023
2,260,550 
RSU, stock and option awards granted(87,403)
Forfeited11,485 
PRSU awards granted(1,420,833)
Available for issuance as of June 30, 2024
763,799 
Summary of changes RSUs and option activity
The following table presents changes to the issuances of RSUs under the 2017 Omnibus Incentive Equity Plan for the periods indicated:
Number of shares issuableWeighted average grant date fair value
Unvested units as of December 31, 2023
253,231 $14.25 
Granted
87,403 16.45 
Vested(40,513)14.22 
Forfeited(11,485)10.54 
Unvested units as of June 30, 2024 (1)
288,636 $15.23 
(1) Includes 139,888, 71,818 and 76,930 shares that vest in 2025, 2026 and 2027, respectively.

The following tables present the detail of the granted and vested RSUs for the periods indicated:
Six Months Ended June 30, Six Months Ended June 30,
Granted20242023Vested20242023
Directors9,043 15,661 Directors9,043 15,661 
Employees
78,360 81,874 Employees31,470 329,650 
Total Granted87,403 97,535 Total Vested40,513 345,311 
Taxes(11,395)(43,322)
Net Vested29,118 301,989 
The following table presents the Company's stock option activity for the current period:
Options outstandingWeighted average exercise price (in dollars per stock option)Weighted average grant date value (in dollars per stock option)Options exercisable
Balance, December 31, 2023
1,583,873 $6.51 $2.25 1,225,083 
Balance, June 30, 2024
1,583,873 $6.51 $2.25 1,442,114 
Weighted average remaining contractual term at June 30, 2024 (in years)
3.8
Schedule of performance restricted stock units, share price target The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.44 as adjusted for cumulative dividends paid to date).
Original Tiptree Share Price TargetNumber of PRSUs that Vest
$20516,667
$30775,000
$451,033,333
$601,291,667
$70
1,420,833
Schedule of assumptions used to estimate the fair values of the PRSUs granted
The following table presents the assumptions used to measure the fair value of the PRSUs as of the respective grant date, or June 7, 2022, when the original tranches were converted to equity awards.

Valuation Input
June 2022
October 2022
January 2024
Historical volatility38.75%39.23%39.10%
Risk-free rate3.04%3.95%3.80%
Dividend yield1.45%1.44%1.05%
Cost of equity11.72%14.19%13.65%
Expected term (years)6.05.95.5
Summary of changes to issuances of subsidiary RSU's under subsidiary incentive plan
The following table presents changes to the issuances of subsidiary awards under the subsidiary incentive plans for the periods indicated:
Grant date fair value of equity shares issuable
Unvested balance as of December 31, 2023
$20,609 
Granted1,670 
Vested(2,475)
Performance assumption adjustment171 
Unvested balance as of June 30, 2024
$19,975 
Schedule of stock-based compensation expense and related income tax benefit
The following table presents total stock based compensation expense and the related income tax benefit recognized on the condensed consolidated statements of operations:
Three Months Ended
June 30, 		Six Months Ended June 30,
2024202320242023
Employee compensation and benefits$3,338 $1,880 $7,114 $4,094 
Director compensation69 103 138 209 
Income tax benefit(715)(416)(1,523)(903)
Net stock based compensation expense$2,692 $1,567 $5,729 $3,400 
Schedule of additional information on total non-vested stock-based compensation
Additional information on total non-vested stock based compensation is as follows:
As of June 30, 2024
Subsidiary Stock options
Restricted stock awards and RSUs
Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards (1)
$16,916 $2,453 $14,680 
Weighted - average recognition period (in years)2.00.81.5
(1)    Includes unrecognized compensation cost of $16,916 related to stock options, $1,327 related to RSUs, and $444 related to PRSUs at The Fortegra Group.