

| 1957 | The companies that would eventually become Symetra Financial begin as life insurance and investments subsidiaries of a Seattle-based Fortune 500 insurance company. |
| 1959 | Enters the group insurance business. |
| 1967 | Total amount of insurance in force passes the $1 billion mark. |
| 1976 | Pioneers Medical Stop Loss insurance. |
| 1982 | Begins offering universal life insurance. |
| 1983 | Expands its Medical Stop Loss business with the acquisition of third-party administrator Employee Benefit Consultants Inc. |
| 1984 | Tops $1 billion in assets. |
| 1986 | Reaches $2 billion in assets. |
| 1987 | Enters the New York market with the establishment of the company now known as First Symetra National Life Insurance Company of New York |
| 1989 | Leads the way in automatic income distribution options. |
| 1995 | Reaches $10 billion in assets. |
| 1997 | Grows its individual life and fixed deferred annuity business with the acquisition of American States Life and WM Life. |
| 1999 | Acquires $120 million of group Medical Stop Loss from ING. Three years later, it acquires another $225 million from Swiss Re. |
| 2004 | Becomes an independent company when it’s purchased by an investor group led by White Mountains Insurance Group, Ltd., and Berkshire Hathaway Inc. |
| 2007 | Further strengthens its Medical Stop Loss business with the acquisition of Medical Risk Managers Inc. Celebrates its 50th anniversary. |
| 2008 | Surpasses $2 billion in total sales. |
| 2010 | Symetra begins trading on the New York Stock Exchange. |
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