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Goodwill and Intangible Assets - Schedule of Definite and Indefinite Life Intangible Assets (Details) - USD ($) $ in Millions | Dec. 31, 2021 | Dec. 31, 2020
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Finite-Lived Intangible Assets [Line Items] |  |
Finite-Lived Intangible Assets, Gross | $ 706.4 | $ 607.5
Indefinite-lived Intangible Assets (Excluding Goodwill) | 50.3 | 47.8
Intangible Assets, Gross (Excluding Goodwill), Total | 756.7 | 655.3
Finite-Lived Intangible Assets, Accumulated Amortization | 413.5 | 335.2
Finite-Lived Intangible Assets, Net | 292.9 | 272.3
Intangible Assets, Net (Including Goodwill) | 343.2 | 320.1
Trade Names |  |
Finite-Lived Intangible Assets [Line Items] |  |
Indefinite-lived Intangible Assets (Excluding Goodwill) | 5.2 | 5.2
Insurance Licenses |  |
Finite-Lived Intangible Assets [Line Items] |  |
Indefinite-lived Intangible Assets (Excluding Goodwill) | 45.1 | 42.6
Value of Business Acquired |  |
Finite-Lived Intangible Assets [Line Items] |  |
Finite-Lived Intangible Assets, Gross | 237.5 | 194.5
Finite-Lived Intangible Assets, Accumulated Amortization | 218.5 | 174.2
Finite-Lived Intangible Assets, Net | 19.0 | 20.3
Customer Relationships |  |
Finite-Lived Intangible Assets [Line Items] |  |
Finite-Lived Intangible Assets, Gross | 43.8 | 39.0
Finite-Lived Intangible Assets, Accumulated Amortization | 38.1 | 35.6
Finite-Lived Intangible Assets, Net | 5.7 | 3.4
Agent Relationships |  |
Finite-Lived Intangible Assets [Line Items] |  |
Finite-Lived Intangible Assets, Gross | 81.6 | 74.4
Finite-Lived Intangible Assets, Accumulated Amortization | 23.6 | 16.8
Finite-Lived Intangible Assets, Net | 58.0 | 57.6
Trade Names |  |
Finite-Lived Intangible Assets [Line Items] |  |
Finite-Lived Intangible Assets, Gross | 1.8 |
Finite-Lived Intangible Assets, Accumulated Amortization | 0.9 |
Finite-Lived Intangible Assets, Net | 0.9 |
Internal Use Software |  |
Finite-Lived Intangible Assets [Line Items] |  |
Finite-Lived Intangible Assets, Gross | 341.7 | 299.6
Finite-Lived Intangible Assets, Accumulated Amortization | 132.4 | 108.6
Finite-Lived Intangible Assets, Net | $ 209.3 | $ 191.0

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