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 Application & Model Engineer - Remote
Remote
$85,000 ‒ $110,000
At our Risk, Analytics, and Data (RAD) team, we focus on Actuarial, Data Science, Model Engineering, and Enterprise Risk Management functions. The Application & Model Engineering team develops and maintains the full stack of internally built RAD products - APIs, wireframes, frontend apps, model integrations, and infrastructure - that power and support rating, underwriting, data science, and actuarial functions and production workflows. Our engineers own deployment pipelines, manage application security, and optimize distributed systems performance to deliver business-critical capabilities across multiple product lines. Our application and model environment and architecture is containerized, and we are cloud based, running on Azure. Our vision is to build highly automated and efficient processes that require creative problem solving and a close collaboration with stakeholders across the organization, not limited by a ‘one size fits all’ mindset.
Deductible Recovery Administrator – P&C Insurance - Remote
Remote
$50,000 - $65,000
The Deductibles Recovery Specialist will focus on the recovery of deductible amounts for our General & Excess Liability policies while providing support to our Premium Audit department. This role will ensure that funds owed to the company are pursued diligently through automated and manual workflows.
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.
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.