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:
HR Generalist
Westwood, MA
$80,000 - $95,000
We are seeking an experienced HR Generalist to join our dynamic, remote first rapidly growing organization. Our workforce is distributed across multiple U.S. states, and we have a growing international footprint. The ideal candidate has strong generalist skills, is highly adaptable, and thrives in a virtual environment. This is a hybrid role, working three days onsite at our office in Westwood, two days remote.