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Business Combinations - Schedule of Business Acquisitions (Details) - USD ($)
$ in Thousands
3 Months Ended
Mar. 31, 2020
Mar. 31, 2019
Feb. 01, 2020
Jan. 01, 2020
Business Combination, Consideration Transferred [Abstract]        
Cash consideration paid $ 44,272      
Fair value of contingent earnout consideration 3,237 $ 0    
Fair value of noncontrolling interest 12,177 $ 1,000    
Total consideration 59,686      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Cash 4,967      
Premiums, commissions and fees receivable 9,790      
Property and equipment 294      
Other assets 197      
Goodwill 33,061      
Total assets acquired 70,712      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]        
Premiums and producer commissions payable (9,882)      
Accrued expenses and other current liabilities (1,144)      
Total liabilities acquired (11,026)      
Net assets acquired 59,686      
Maximum potential contingent earnout consideration 16,828      
Lanier        
Business Combination, Consideration Transferred [Abstract]        
Cash consideration paid 24,450      
Fair value of contingent earnout consideration 1,628      
Fair value of noncontrolling interest 6,119      
Total consideration 32,197      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Cash       $ 2,413
Premiums, commissions and fees receivable       2,494
Property and equipment       294
Other assets       168
Goodwill       23,739
Total assets acquired       35,416
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]        
Premiums and producer commissions payable       (2,954)
Accrued expenses and other current liabilities       (265)
Total liabilities acquired       (3,219)
Net assets acquired       32,197
Maximum potential contingent earnout consideration       11,000
Highland        
Business Combination, Consideration Transferred [Abstract]        
Cash consideration paid 6,603      
Fair value of contingent earnout consideration 788      
Fair value of noncontrolling interest 4,500      
Total consideration 11,891      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Cash       1,542
Premiums, commissions and fees receivable       5,977
Property and equipment       0
Other assets       13
Goodwill       4,228
Total assets acquired       19,133
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]        
Premiums and producer commissions payable       (6,374)
Accrued expenses and other current liabilities       (868)
Total liabilities acquired       (7,242)
Net assets acquired       11,891
Maximum potential contingent earnout consideration       2,450
AgencyRM        
Business Combination, Consideration Transferred [Abstract]        
Cash consideration paid 7,061      
Fair value of contingent earnout consideration 679      
Fair value of noncontrolling interest 1,558      
Total consideration 9,298      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Cash     $ 573  
Premiums, commissions and fees receivable     1,002  
Property and equipment     0  
Other assets     4  
Goodwill     3,369  
Total assets acquired     9,838  
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]        
Premiums and producer commissions payable     (540)  
Accrued expenses and other current liabilities     0  
Total liabilities acquired     (540)  
Net assets acquired     9,298  
Maximum potential contingent earnout consideration     3,000  
VibrantUSA        
Business Combination, Consideration Transferred [Abstract]        
Cash consideration paid 6,158      
Fair value of contingent earnout consideration 142      
Fair value of noncontrolling interest 0      
Total consideration 6,300      
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Cash     439  
Premiums, commissions and fees receivable     317  
Property and equipment     0  
Other assets     12  
Goodwill     1,725  
Total assets acquired     6,325  
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Liabilities [Abstract]        
Premiums and producer commissions payable     (14)  
Accrued expenses and other current liabilities     (11)  
Total liabilities acquired     (25)  
Net assets acquired     6,300  
Maximum potential contingent earnout consideration     378  
Purchased customer accounts        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets 6,308      
Purchased customer accounts | Lanier        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       6,308
Purchased customer accounts | Highland        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       0
Purchased customer accounts | AgencyRM        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     0  
Purchased customer accounts | VibrantUSA        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     0  
Distributor relationships        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets 14,600      
Distributor relationships | Lanier        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       0
Distributor relationships | Highland        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       6,500
Distributor relationships | AgencyRM        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     4,300  
Distributor relationships | VibrantUSA        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     3,800  
Carrier relationships        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets 659      
Carrier relationships | Lanier        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       0
Carrier relationships | Highland        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       659
Carrier relationships | AgencyRM        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     0  
Carrier relationships | VibrantUSA        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     0  
Software        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets 565      
Software | Lanier        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       0
Software | Highland        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       0
Software | AgencyRM        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     565  
Software | VibrantUSA        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     0  
Trade names        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets $ 271      
Trade names | Lanier        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       0
Trade names | Highland        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets       $ 214
Trade names | AgencyRM        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     25  
Trade names | VibrantUSA        
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Assets [Abstract]        
Intangible assets     $ 32