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Multifamily Insurance Specialists

MiddleOak® is the trade name for Holyoke Mutual Insurance Company in Salem and Middlesex Mutual Assurance Company, specializing in multifamily insurance for apartments and community associations across the country.

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Making Insurance Right® reflects the sum of our promises to agents, policyholders and employees. It is how we bring our values to life. Discover what it feels like to be proud of your contribution at the end of each day. MiddleOak® offers a competitive salary, excellent benefit package, including 401(k) with company match, company-paid pension, LTD, life insurance, tuition reimbursement, and excellent working environments.

To apply for any of the positions listed below, please email your resume to HR@MiddleOak.com or fax to 978-740-2118

The following employment opportunities are available at the designated offices.



Middletown CT

º Underwriting Manager of Small-Market

Salem MA

No Positions Currently Available

Remote Positions

No Positions Currently Available

MiddleOak is an Equal Opportunity Employer.

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