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Pilgrim Insurance employees enjoy a highly competitive and comprehensive range of benefits with no waiting period, including:

  • Several medical insurance plan options, including a High Deductible Healthcare Plan with Health Savings Account option
  • Dental and vision coverage
  • Life and disability coverage
  • 401(k) program with company-funded bonus contribution option*
  • Nine paid holidays annually
  • Twelve days of company-paid vacation annually
  • Generous paid leave program including short-term and long-term disability
  • Company-subsidized fitness club membership
  • Tuition reimbursement
  • Pre-tax flexible spending accounts for both medical and dependent care
  • Commuter benefit flexible spending accounts
  • Personal auto and home insurance (with discounts!) payable through payroll deduction
  • Work/Life Programs, including a number of Wellness events each year
  • MBTA pass program payable through payroll deduction
  • Employee discounts to movies, sporting events and much, much more

*The Company presently intends to pay annual bonus awards under the 401(k) Plan to its eligible employees for each year in which it earns a profit. The bonus award will be set annually by the Company as a percentage of salary in the year for which the bonus is being paid.

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  • (800) 721-8294


  • (617) 956-6000

Outsourcing Clients

  • (617) 956-6000