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Other Liabilities and Accrued Expenses - Summary (Details) - USD ($) $ in Millions | Sep. 30, 2023 | Dec. 31, 2022
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Other Liabilities Disclosure [Abstract] |  |
Lease liabilities | $ 29.7 | $ 35.2
Ceded commission payable | 12.6 | 0.0
Uncertain tax position | 11.2 | 8.1
Employee compensation | 6.9 | 12.8
Accrued professional fees | 5.6 | 5.5
Accrued advertising costs | 5.0 | 6.8
Advance premium | 4.3 | 2.1
Premium taxes payable | 4.0 | 6.2
Accrued hosting and software | 1.4 | 2.0
Income taxes payable | 0.9 | 0.6
Warrant liability | 0.0 | 0.3
Other payables | 11.5 | 4.9
Total | $ 93.1 | $ 84.5

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