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Stock Based Compensation (Tables)

9 Months Ended

Sep. 30, 2021

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, 2020			3,788,417
RSU, stock and option awards granted			(50,251)
Exchanged for vested subsidiary awards			(1,158,009)
Available for issuance as of September 30, 2021			2,580,157

(1)    Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock.

Summary of Changes to Issuances of RSUs under the 2017 Equity Plan

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, 2020			953,145						$	6.52
Granted			50,251						7.21
Vested			(404,384)						6.51
Unvested units as of September 30, 2021			599,012						$	6.59

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

			Nine Months Ended September 30,															Nine Months Ended September 30,
Granted			2021						2020												Vested			2021						2020
Directors			50,251						56,485												Directors			50,251						56,485
Employees (1)			—						469,257												Employees			354,133						474,721
Total Granted			50,251						525,742												Total Vested			404,384						531,206
																					Taxes			(34,828)						(53,438)
																					Net Vested			369,556						477,768

(1)    Includes 256,619 shares that vest ratably over three years and 212,638 shares that cliff vest in February 2023 for the nine months ended September 30, 2020.

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, 2020			1,715,619						$	6.49					$	2.29					—
Balance, September 30, 2021			1,715,619						$	6.49					$	2.29					712,542
Weighted average remaining contractual term at September 30, 2021 (in years)			6.4

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 as of September 30, 2021, which were granted in 2021 and classified as liability awards.

Valuation Input																		Nine Months Ended September 30, 2021
																														Assumption						Average
Historical volatility																														34.29%						34.43%
Risk-free rate																														1.55%						1.38%
Dividend yield																														1.59%						1.40%
Cost of Equity																														9.84%						9.88%
Expected term (years)																														10						10

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, 2020			$	4,305
Granted			1,278
Vested			(3,466)
Unvested balance as of September 30, 2021			$	2,117

Schedule of Assumptions Used to Estimate the Fair Values of the Stock Options Granted

The following table presents the assumptions used to estimate the fair values of the stock options granted in 2020.

Valuation Input (1)

Nine Months Ended September 30, 2020

Assumption

Average

Historical volatility

27.60%

N/A

Risk-free rate

1.51%

N/A

Dividend yield

2.20%

N/A

Expected term (years)

7.0

(1) Not applicable for the nine months ended September 30, 2021 as there were no new grants during the period.

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,
			2021						2020						2021						2020
Employee compensation and benefits (1)			$	1,401					$	2,287					$	3,372					$	5,750
Director compensation			103						202						345						408
Income tax benefit			(316)						(538)						(781)						(1,330)
Net stock based compensation expense			$	1,188					$	1,951					$	2,936					$	4,828

(1) Includes $350 related to liability awards recorded in other liabilities as of September 30, 2021.

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, 2021
			Stock options						Restricted stock awards and RSUs						Performance Restricted Stock Units
Unrecognized compensation cost related to non-vested awards			$	297					$	2,988					$	10,191
Weighted - average recognition period (in years)			1.02						0.68						3.23

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