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Business Combinations - Acquisitions (Details) - USD ($)
$ in Thousands
 12 Months Ended
Mar. 17, 2023
Apr. 01, 2022
Oct. 27, 2021
Sep. 09, 2021
May 20, 2021
Apr. 05, 2021
Jan. 12, 2021
Dec. 31, 2022
Dec. 31, 2021
Dec. 31, 2023
Dec. 31, 2020
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Goodwill               $ 244,697 $ 225,654 $ 191,907 $ 28,289
Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)               8 years 9 years    
Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)               5 years 4 years    
Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)               9 years 12 years    
Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)               7 years 2 years    
Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)                 7 years    
Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)                 8 years    
RWS                      
Business Combination, Consideration Transferred [Abstract]                      
Cash $ 2,100 $ 25,600           $ 25,572      
Issuance of common stock   3,600           3,552      
Holdback liabilities and amounts in escrow               1,000      
Contingent consideration - liability-classified   8,700           8,700      
Total purchase consideration:   $ 38,800           38,824      
Assets:                      
Cash, cash equivalents and restricted cash               2,030      
Current assets $ 200             525      
Property and equipment               497      
Operating lease right-of-use assets               871      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)   7 years 8 months 12 days                  
Goodwill               27,366      
Total assets acquired               46,229      
Current liabilities               (6,869)      
Operating lease liabilities, non-current               (536)      
Net assets acquired               38,824      
RWS | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               13,860      
RWS | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               500      
RWS | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               400      
RWS | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               180      
Other                      
Business Combination, Consideration Transferred [Abstract]                      
Cash               13,763 $ 27,121    
Issuance of common stock               0 3,026    
Holdback liabilities and amounts in escrow               1,500 1,775    
Contingent consideration - equity-classified                 0    
Contingent consideration - liability-classified               0 327    
Total purchase consideration:               15,263 32,249    
Assets:                      
Cash, cash equivalents and restricted cash               256 1,473    
Current assets               7 1,795    
Property and equipment               0 80    
Operating lease right-of-use assets               0 445    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Goodwill               10,698 14,499    
Other non-current assets                 3    
Total assets acquired               15,411 35,410    
Current liabilities               (148) (2,485)    
Operating lease liabilities, non-current               0 (204)    
Long term liabilities                 (46)    
Deferred tax liabilities, net                 (426)    
Net assets acquired               15,263 32,249    
Other | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 4,750    
Other | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Other | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               2,750 10,320    
Other | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               1,480 1,340    
Other | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               200 650    
Other | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               20 55    
Other | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Other | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Total                      
Business Combination, Consideration Transferred [Abstract]                      
Cash               39,335 283,698    
Issuance of common stock               3,552 35,707    
Holdback liabilities and amounts in escrow               2,500 9,825    
Contingent consideration - equity-classified                 6,685    
Contingent consideration - liability-classified               8,700 10,369    
Total purchase consideration:               54,087 346,284    
Assets:                      
Cash, cash equivalents and restricted cash               2,286 27,268    
Current assets               532 251,777    
Property and equipment               497 2,129    
Operating lease right-of-use assets               871 4,889    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Goodwill               38,064 197,365    
Other non-current assets                 55,193    
Total assets acquired               61,640 664,725    
Current liabilities               (7,017) (295,834)    
Operating lease liabilities, non-current               (536) (3,262)    
Long term liabilities                 (9,585)    
Deferred tax liabilities, net                 (9,760)    
Net assets acquired               54,087 346,284    
Total | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 4,750    
Total | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 4,960    
Total | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               16,610 48,370    
Total | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               1,980 35,965    
Total | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               600 21,700    
Total | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:               $ 200 225    
Total | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 400    
Total | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 9,734    
V12 Data                      
Business Combination, Consideration Transferred [Abstract]                      
Cash                 20,196    
Issuance of common stock                 0    
Holdback liabilities and amounts in escrow                 150    
Contingent consideration - equity-classified                 0    
Contingent consideration - liability-classified             $ 1,400   1,410    
Total purchase consideration:                 21,756    
Assets:                      
Cash, cash equivalents and restricted cash                 1,035    
Current assets                 4,939    
Property and equipment                 996    
Operating lease right-of-use assets                 1,383    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)             7 years 7 months 6 days        
Goodwill                 16,708    
Other non-current assets                 0    
Total assets acquired                 31,501    
Current liabilities                 (6,871)    
Operating lease liabilities, non-current                 (848)    
Long term liabilities                 (2,026)    
Deferred tax liabilities, net                 0    
Net assets acquired             $ 21,800   21,756    
V12 Data | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
V12 Data | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
V12 Data | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 1,650    
V12 Data | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 3,525    
V12 Data | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 1,225    
V12 Data | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 40    
V12 Data | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
V12 Data | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
HOA                      
Business Combination, Consideration Transferred [Abstract]                      
Cash                 84,370    
Issuance of common stock           $ 22,800     22,773    
Holdback liabilities and amounts in escrow                 1,000    
Contingent consideration - equity-classified                 6,685    
Contingent consideration - liability-classified                 0    
Total purchase consideration:           $ 114,800     114,828    
Assets:                      
Cash, cash equivalents and restricted cash                 17,766    
Current assets                 235,669    
Property and equipment                 615    
Operating lease right-of-use assets                 1,258    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)           9 years 6 months          
Goodwill                 45,370    
Other non-current assets                 55,165    
Total assets acquired                 397,795    
Current liabilities                 (269,460)    
Operating lease liabilities, non-current                 (898)    
Long term liabilities                 (7,434)    
Deferred tax liabilities, net                 (5,175)    
Net assets acquired                 114,828    
HOA | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
HOA | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 4,960    
HOA | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 16,700    
HOA | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
HOA | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 12,200    
HOA | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
HOA | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 400    
HOA | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 7,692    
Rynoh                      
Business Combination, Consideration Transferred [Abstract]                      
Cash         $ 32,300       32,302    
Issuance of common stock                 0    
Holdback liabilities and amounts in escrow                 3,500    
Contingent consideration - equity-classified                 0    
Contingent consideration - liability-classified                 0    
Total purchase consideration:         $ 35,800       35,802    
Assets:                      
Cash, cash equivalents and restricted cash                 408    
Current assets                 932    
Property and equipment                 334    
Operating lease right-of-use assets                 159    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)         10 years            
Goodwill                 22,051    
Other non-current assets                 0    
Total assets acquired                 40,374    
Current liabilities                 (517)    
Operating lease liabilities, non-current                 (72)    
Long term liabilities                 0    
Deferred tax liabilities, net                 (3,983)    
Net assets acquired                 35,802    
Rynoh | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Rynoh | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Rynoh | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 12,700    
Rynoh | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 2,800    
Rynoh | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 900    
Rynoh | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 90    
Rynoh | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Rynoh | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP                      
Business Combination, Consideration Transferred [Abstract]                      
Cash       $ 43,800         43,750    
Issuance of common stock                 0    
Holdback liabilities and amounts in escrow                 2,500    
Contingent consideration - equity-classified                 0    
Contingent consideration - liability-classified                 0    
Total purchase consideration:       $ 46,300         46,250    
Assets:                      
Cash, cash equivalents and restricted cash                 5,078    
Current assets                 8,221    
Property and equipment                 17    
Operating lease right-of-use assets                 913    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)       7 years              
Goodwill                 45,681    
Other non-current assets                 25    
Total assets acquired                 62,677    
Current liabilities                 (15,487)    
Operating lease liabilities, non-current                 (685)    
Long term liabilities                 (79)    
Deferred tax liabilities, net                 (176)    
Net assets acquired                 46,250    
AHP | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:       $ 700         700    
AHP | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
AHP | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:       $ 2,042         2,042    
Floify                      
Business Combination, Consideration Transferred [Abstract]                      
Cash     $ 76,000           75,959    
Issuance of common stock     9,900           9,908    
Holdback liabilities and amounts in escrow                 900    
Contingent consideration - equity-classified                 0    
Contingent consideration - liability-classified                 8,632    
Total purchase consideration:     $ 95,400           95,399    
Assets:                      
Cash, cash equivalents and restricted cash                 1,508    
Current assets                 221    
Property and equipment                 87    
Operating lease right-of-use assets                 731    
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Weighted Average Useful Life (in years)     5 years 7 months 6 days                
Goodwill                 53,056    
Other non-current assets                 0    
Total assets acquired                 96,968    
Current liabilities                 (1,014)    
Operating lease liabilities, non-current                 (555)    
Long term liabilities                 0    
Deferred tax liabilities, net                 0    
Net assets acquired                 95,399    
Floify | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Floify | Insurance licenses                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Floify | Customer relationships                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:     $ 7,000           7,000    
Floify | Acquired technology                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:     28,300           28,300    
Floify | Trademarks and tradenames                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:     6,025           6,025    
Floify | Non-compete agreements                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:     $ 40           40    
Floify | Value of business acquired                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 0    
Floify | Renewal rights                      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Intangible Assets, Other than Goodwill [Abstract]                      
Intangible assets:                 $ 0