About Us


Work for a Market Leader!

Are you looking to join an inclusive team focused on growth and client service? Do you want to thrive in an environment that values and leverages the diverse talents, perspectives and ideas of all employees so that everyone can reach their fullest potential?

If so, meet Roosevelt Road Specialty.

As a leading provider of specialized insurance products, Roosevelt Road Specialty is looking for strong underwriting, risk management, accounting, compliance and other candidates who can help our clients navigate the risks and complexities of today’s insurance market.

If you’re interested in learning more about joining our team, contact Paige Wilson, Finance/HR Liaison at pwilson@tradesmanprogram.com.

Careers at Roosevelt Road

We are committed to attracting and retaining best-in-class talent and encourage you to join our team!

Roosevelt Road Specialty (RRS) and its affiliates do not accept unsolicited resumes or candidate profiles submitted by any staffing agency, placement service, or professional recruiter (“Agencies”), including any submissions made through our website or to email accounts of RRS employees. Agencies must obtain advance written approval from RRS’ HR department to submit resumes and candidate profiles, and then only in conjunction with a valid, fully executed contract for service and in response to the specific search for which RRS has engaged such Agency. Agency fee agreements will only be valid in writing and signed by a member of RRS’ HR team. No other RRS employee is authorized to bind RRS to any agreement regarding placement of candidates by any Agency. Any unsolicited resume or candidate profile received from an Agency without prior approval from RRS’ HR department and in compliance with RRS’ candidate submission process shall be considered unsolicited, gratuitous and property of RRS for recruiting purposes and, as such, is not subject to payment of any Agency fees.

Current Job Openings