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Stockholders’ Equity - Share-based Compensation Expense (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2023	Sep. 30, 2022	Sep. 30, 2023	Sep. 30, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	$ 14.0	$ 17.0	$ 46.8	$ 46.3
Losses and loss adjustment expenses
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	0.4	0.7	1.0	1.9
Insurance related expenses
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	1.1	1.4	3.7	3.9
Technology and development
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	2.8	5.1	10.1	15.9
Sales and marketing
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	3.3	4.0	11.2	9.3
General and administrative
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	$ 6.4	$ 5.8	$ 20.8	$ 15.3

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- Definition

Amount of expense for award under share-based payment arrangement. Excludes amount capitalized.

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