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Stockholders’ Equity - Share-based Compensation Expense (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	$ 57.5	$ 61.9
Losses and loss adjustment expenses
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	1.2	2.6
Insurance related expenses
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	4.9	5.4
Technology and development
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	12.5	19.2
Sales and marketing
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	13.1	13.7
General and administrative
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense	$ 25.8	$ 21.0

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- Definition

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

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