Join Upland

At Upland Specialty Insurance, we take pride in building a dedicated team of “we entrepreneurs” where you can focus your experience, skills, and creativity to craft solutions for the long-term success of the company, and you as individual team member. 

Are you a “we entrepreneur”? Do you value the individual freedom to practice your craft while enjoying the benefits of working as a team? Do you like to have fun at work while being challenged? Upland may be the company for you.
Current Open Positions:
Associate Underwriter
Chicago, IL
$55,000 - $75,000
The role of an Associate Underwriter is to assist with day to day functions of the Underwriting operation. As the Associate Underwriter gains experience, they will become responsible for underwriting renewal and new policies in compliance with established underwriting guidelines and within designated authority levels.
Underwriter - P&C Insurance
Dallas, TX
$125,000 - $155,000
The role of an Underwriter is to evaluate and write new and renewal policies within a designated letter of authority. The individual will underwrite a broad range of industries within our Excess Casualty business segment. Industries include (but not limited to) construction, manufacturing, wholesale/distributors, retail, & real estate. In addition to developing broker relationships, this role also serves as a mentor to other underwriters and associate underwriters.
Regulatory Reporting Manager - P&C Insurance
Remote
$135,000 - $155,000
The Regulatory Reporting Manager will lead the preparation, review, and submission of all statutory financial statements and GAAP statements for the company’s Property & Casualty insurance operations. This role ensures full compliance with NAIC, state regulatory requirements, and GAAP reporting standards, while driving process improvements and supporting strategic financial initiatives. The ideal candidate has deep technical insurance accounting expertise, strong regulatory knowledge, and proven experience managing reporting cycles in a complex insurance environment.
Senior Product Analyst - Risk, Analytics, and Data
Remote
$100,000 ‒ $130,000
We are looking for a Senior Product Analyst to join our Risk, Analytics and Data (RAD) team to support data, analytics, and technology initiatives involving high levels of collaboration across the organization. This role will report to the Director, Analytics Product Management.