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Revenue - Disaggregation of Revenue By Distribution Channel Offering and Geographical Area (Details) - USD ($)
$ in Thousands
 3 Months Ended 9 Months Ended
Sep. 30, 2024
Sep. 30, 2023
Sep. 30, 2024
Sep. 30, 2023
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts $ 157,688 $ 135,789 $ 433,390 $ 370,672
Earned premium 165,686 139,785 474,917 384,498
Total revenue 323,374 275,574 908,307 755,170
U.S.        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 146,305 125,972 402,351 343,920
Canada        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 8,112 7,544 22,900 20,783
Europe        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 3,271 2,273 8,139 5,969
Agent        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 63,854 56,212 182,606 156,552
Direct        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 93,834 79,577 250,784 214,120
Commission and fee revenue        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 116,161 103,173 333,817 287,972
Commission and fee revenue        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 105,463 81,775 301,334 227,275
Commission and fee revenue | U.S.        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 96,688 73,891 277,613 206,099
Commission and fee revenue | Canada        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 6,952 6,422 18,878 17,379
Commission and fee revenue | Europe        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 1,823 1,462 4,843 3,797
Commission and fee revenue | Agent        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 57,857 44,387 164,737 123,046
Commission and fee revenue | Direct        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 47,606 37,388 136,597 104,229
Contingent commission revenue        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 10,698 21,398 32,483 60,697
Contingent commission revenue | U.S.        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 10,544 21,360 32,235 60,590
Contingent commission revenue | Canada        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 0 0 0 0
Contingent commission revenue | Europe        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 154 38 248 107
Contingent commission revenue | Agent        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 5,997 11,825 17,869 33,506
Contingent commission revenue | Direct        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 4,701 9,573 14,614 27,191
Membership, marketplace and other revenue        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 41,527 32,616 99,573 82,700
Membership revenue        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 14,800 13,835 42,385 39,528
Membership revenue | U.S.        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 13,844 12,942 39,592 36,865
Membership revenue | Canada        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 955 893 2,792 2,663
Membership revenue | Europe        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 1 0 1 0
Membership revenue | Agent        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 0 0 0 0
Membership revenue | Direct        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 14,800 13,835 42,385 39,528
Marketplace and other revenue        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 26,727 18,781 57,188 43,172
Marketplace and other revenue | U.S.        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 25,229 17,779 52,911 40,366
Marketplace and other revenue | Canada        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 205 229 1,230 741
Marketplace and other revenue | Europe        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 1,293 773 3,047 2,065
Marketplace and other revenue | Agent        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts 0 0 0 0
Marketplace and other revenue | Direct        
Disaggregation of Revenue [Line Items]        
Total revenue from customer contracts $ 26,727 $ 18,781 $ 57,188 $ 43,172