Revenue - Disaggregation of Revenue By Distribution Channel Offering and Geographical Area (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	$ 384,527	$ 323,255
Earned premium recognized under ASC 944	403,061	295,824
Total revenue	787,588	619,079
U.S.
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	355,732	298,080
Canada
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	23,250	19,617
Europe
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	5,545	5,558
Agent
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	166,483	144,862
Direct
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	218,044	178,393
Commission and fee revenue
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	307,238	271,571
Commission and fee revenue
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	247,448	214,236
Commission and fee revenue | U.S.
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	224,255	193,520
Commission and fee revenue | Canada
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	19,142	16,782
Commission and fee revenue | Europe
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	4,051	3,934
Commission and fee revenue | Agent
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	133,584	115,310
Commission and fee revenue | Direct
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	113,864	98,926
Contingent commission
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	59,790	57,335
Contingent commission | U.S.
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	59,664	57,424
Contingent commission | Canada
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	0	(383)
Contingent commission | Europe
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	126	294
Contingent commission | Agent
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	32,899	29,552
Contingent commission | Direct
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	26,891	27,783
Membership, marketplace and other revenue
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	77,289	51,684
Membership revenue
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	45,234	40,605
Membership revenue | U.S.
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	41,893	37,688
Membership revenue | Canada
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	3,341	2,917
Membership revenue | Europe
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	0	0
Membership revenue | Agent
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	0	0
Membership revenue | Direct
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	45,234	40,605
Marketplace and other revenue
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	32,055	11,079
Marketplace and other revenue | U.S.
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	29,920	9,448
Marketplace and other revenue | Canada
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	767	301
Marketplace and other revenue | Europe
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	1,368	1,330
Marketplace and other revenue | Agent
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	0	0
Marketplace and other revenue | Direct
Disaggregation of Revenue [Line Items]
Total revenue from customer contracts	$ 32,055	$ 11,079