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About Us

Careers

Professionalism
Customer Focus
Management Leadership Excellence
Human Resource Excellence
Process Excellence
Product and Service Excellence
Recognized as a Best Practices Agency by Reagan Consulting and the Independent Insurance Agents and Brokers of America.
Professional Affiliations: Massachusetts Association of Insurance Women
Independent Insurance Agents and Brokers of America
Institute of WorkComp Professionals
Massachusetts Association of Insurance Agents
Associated Risk Managers
Member Berkshire Chamber of Commerce
Member Lee Chamber of Commerce
Member Lenox Chamber of Commerce
Member Southern Berkshire Chamber Chamber of Commerce

Regional
Toole Insurance provides risk management services to thousands of commercial and individual clients throughout the Northeast from our offices in the Berkshires.
  • Commercial Account Managers
  • Personal Customer Service Agents
  • Outside Sales
  • Claims Technicians
  • Marketing
  • Business Development
  • Technology Management
  • Accounting Management
  • Bookkeeping
  • Administrative Support
  • Facilities Maintenance
  • Courier

Synergy
Stable, Respected Employer
Family business since 1939
Local offices (Lee, Lenox, Great Barrington)
Regional client base
Progressive growth strategy
Strong community involvement
Team atmosphere

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Appreciated Employees
Competitive salary
Wellness program
Employee training program
Employer paid licensing and continuing education
Group medical insurance
Optional dental, accident, and supplemental life
Disability and life insurance
Retirement plan
Paid vacation and sick days
Employee bonus program
Long term employment car allowance

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VALUES-DRIVEN RESULTS

Growth
Stability
Quality of life