Staffing Companies


Work First is the only insurance company with an executive team that brings experience in running a staffing company.

Hi, I’m Bruce Winterrowd, Vice President of Underwriting. Since 2005, we have provided a stable market for workers’ compensation, offering two types of policies: Guaranteed Cost and Medium Deductible. We operate in all 50 states and the District of Columbia, which means we can cover your clients almost everywhere. All of our new policies are underwritten personally by me. If you have any questions, please contact me directly at (630) 416-7954 or email I’d love nothing more than to speak with you personally!

Click below for more information

We have written hundreds of Guaranteed Cost policies for staffing companies ranging from our minimum premium of $75,000 to over $6,000,000. Furthermore, we have been tremendously successful in assisting people just like you in lowering their experience modifiers and ultimately their cost of insurance.

Consider what a Guaranteed Cost policy from Work First can do for you:

  • Your premium won’t fluctuate regardless of loss experience, guaranteed
  • Enables accurate budgeting of insurance cost
  • Lowering your experience modifier will reduce your premium

You are free to cater a policy to match your needs by selecting among deductible amounts ranging from $5,000 to $75,000. The choice is yours – the higher the deductible, the more opportunity to save. Regardless of your deductible level, you will receive our world-class claims service and prompt underwriting attention.

Gain access to these features with a Medium Deductible program:

  • A Medium Deductible policy doesn’t cost nearly as much as a fully-insured policy
  • If you reduce your claims, you won’t pay as much for your workers’ compensation program
  • You are responsible for your claims only – your ‘risk’ is not pooled together with the risk of other companies (not a captive program)
  • Deductibles are billed monthly and you don’t need to post a loss fund

We would love to have you become one of our satisfied clients!  To be considered, we have some guidelines you should be aware of:

  • Minimum Premium $100,000 ($75,000 for clerical only risks)
  • Minimum of 3 years in business
  • No PEO, Leasing Exposures, USL&H Exposures, Construction, Recycling or Day Labor
  • Limited exposure in IL, NY, SC and LA – ideally incidental exposure in an otherwise conforming submission

Click below to find out more information