Stock Based Compensation (Tables)

3 Months Ended

Mar. 31, 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	(25,381)
Available for issuance as of March 31, 2021	3,763,036

(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	25,381	5.03
Vested	(379,514)	6.32
Unvested units as of March 31, 2021	599,012	$	6.59

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

	Three Months Ended March 31,			Three Months Ended March 31,
Granted	2021	2020	Vested	2021	2020
Directors	25,381	9,232	Directors	25,381	9,232
Employees (1)	—	469,257	Employees	354,133	364,984
Total Granted	25,381	478,489	Total Vested	379,514	374,216
			Taxes	(34,828)	(51,507)
			Net Vested	344,686	322,709

(1)    Includes 256,619 shares that vest ratably over three years and 212,638 shares that cliff vest in February 2021 for the three months ended March 31, 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, March 31, 2021	1,715,619	$	6.49	$	2.29	—
Weighted average remaining contractual term at March 31, 2021 (in years)	6.9

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	1,079
Vested	(1,358)
Unvested balance as of March 31, 2021	$	4,026

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 for the following periods:

Valuation Input (1)	Three Months Ended March 31, 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 three months ended March 31, 2021 as there were no new grants during the period.

Schedule of Stock-based Compensation Expense and Related Income Tax Benefit

Stock Based Compensation Expense

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 March 31,
	2021		2020
Employee compensation and benefits	$	955	$	1,543
Director compensation	110		73
Income tax benefit	(224)		(349)
Net stock based compensation expense	$	841	$	1,267

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
	March 31, 2021
	Stock options		Restricted stock awards and RSUs
Unrecognized compensation cost related to non-vested awards	$	434	$	4,721
Weighted - average recognition period (in years)	2.07		1.73