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Stock Based Compensation (Tables) | 9 Months Ended
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Sep. 30, 2022
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 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 Plan | Number of shares (1)
Available for issuance as of December 31, 2021 | 2,344,814 |
RSU, stock and option awards granted | (235,822) |
Forfeited | 528 |
Amendment to plan | 4,000,000 |
Available for issuance as of September 30, 2022 | 6,109,520 |
(1) Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock.
Summary of Changes RSUs and Option Activity | The following table presents changes to the issuances of RSUs and stock awards under the 2017 Equity Plan for the periods indicated:
| Number of shares issuable |  | Weighted average grant date fair value
Unvested units as of December 31, 2021 | 599,012 |  |  | $ | 6.59 |
Granted | 235,822 |  |  | 12.93 |
Vested | (328,551) |  |  | 7.00 |
Forfeited | (528) |  |  | 6.26 |
Unvested units as of September 30, 2022 | 505,755 |  |  | $ | 9.64 |
The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:
| For the |  |  |  |  | For the |  |
| Nine Months Ended September 30, |  |  | Nine Months Ended September 30,
Granted | 2022 |  | 2021 |  |  |  | Vested | 2022 |  | 2021 |  |
Directors | 28,246 |  |  | 50,251 |  |  |  |  | Directors | 28,246 |  |  | 50,251 |  |  |
Employees (1) | 207,576 |  |  | — |  |  |  |  | Employees | 300,305 |  |  | 354,133 |  |  |
Total Granted | 235,822 |  |  | 50,251 |  |  |  |  | Total Vested | 328,551 |  |  | 404,384 |  |  |
|  |  |  |  |  |  | Taxes | (47,274) |  |  | (34,828) |  |  |
|  |  |  |  |  |  | Net Vested | 281,277 |  |  | 369,556 |  |  |
(1) Includes 94,410 shares that vest ratably over three years and 113,166 shares that cliff vest in 2025 for the nine months ended September 30, 2022. The following table presents the Company's stock option activity for the current period:
| Options outstanding |  | Weighted average exercise price (in dollars per stock option) |  | Weighted average grant date value (in dollars per stock option) |  | Options exercisable
Balance, December 31, 2021 | 1,715,619 |  |  | $ | 6.49 |  |  | $ | 2.29 |  |  | 712,542 |
Balance, September 30, 2022 | 1,707,476 |  |  | $ | 6.49 |  |  | $ | 2.29 |  |  | 1,050,767 |
Weighted average remaining contractual term at September 30, 2022 (in years) | 5.4 |  |  |  |  |  |
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 $19.80 as adjusted for cumulative dividends paid to date).
Original Tiptree Share Price Target |  | Number of PRSUs that Vest
$20 |  | 466,667
$30 |  | 700,000
$45 |  | 933,333
$60 |  | 1,166,667
Schedule of Assumptions Used to Estimate the Fair Values of the PRSUs Granted | The following table presents the assumptions used to remeasure the fair value of the PRSUs issued in 2021 as of June 7, 2022, when they were converted to equity awards.
Valuation Input |  |  |  |  |  | As of June 7, 2022 |  |
|  |  |  |  |  |  |  |  |  | Assumption |  |  |  |  |  |
Historical volatility |  |  |  |  |  |  |  |  |  | 38.70% |  |  |  |  |  |
Risk-free rate |  |  |  |  |  |  |  |  |  | 2.95% |  |  |  |  |  |
Dividend yield |  |  |  |  |  |  |  |  |  | 1.45% |  |  |  |  |  |
Cost of equity |  |  |  |  |  |  |  |  |  | 11.47% |  |  |  |  |  |
Expected term (years) |  |  |  |  |  |  |  |  |  | 6 |  |  |  |  |  |
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, 2021 | $ | 2,234 |
Granted | 282 |
Vested | (935) |
Performance assumption adjustment | 80 |
Unvested balance as of September 30, 2022 | $ | 1,661 |
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 September 30, |  | Nine Months Ended September 30,
| 2022 |  | 2021 |  | 2022 |  | 2021 |  |
Employee compensation and benefits | $ | 1,573 |  |  | $ | 1,401 |  |  | $ | 7,559 |  |  | $ | 3,372 |  |  |
Director compensation | 122 |  |  | 103 |  |  | 350 |  |  | 345 |  |  |
Income tax benefit | (355) |  |  | (316) |  |  | (1,660) |  |  | (781) |  |  |
Net stock based compensation expense | $ | 1,340 |  |  | $ | 1,188 |  |  | $ | 6,249 |  |  | $ | 2,936 |  |  |
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 September 30, 2022
| Stock options |  | Restricted stock awards and RSUs |  | Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards (1) | $ | 146 |  |  | $ | 806 |  |  | $ | 8,386 |
Weighted - average recognition period (in years) | 1.38 |  | 0.87 |  | 1.03
(1) Includes $122 of unrecognized compensation cost related to stock options at The Fortegra Group that vest ratably over three years..

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