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 Accountant
Remote
$45,000-$65,000 Annually
We are looking for an Associate Accountant to join a specialty insurance company built on experience. This position will be responsible for various tasks including accounts payable, accounts receivables, expense report processing, journal entries, reconciliation, research, and month-end close. While this position is remote, candidates located in the Dallas Fort-Worth area are strongly preferred. Upland Capital Group, Inc. is an AM Best rated “A-” VIII specialty property/casualty insurer headquartered in Dallas, Texas. Through its wholly owned insurance carrier, Upland Specialty Insurance Company, the company markets, underwrites and services specialty insurance products in select markets to include excess transportation, construction casualty, excess casualty, primary general liability, excess public entity, professional liability errors and omissions as well as excess cyber liability. We focus on “old school” underwriting as a craft, add “new school” analytics and technology, and encourage a gritty, growth mindset among people called “we entrepreneurs.”
Senior Accountant
Remote
$90,000-$110,000 Annually
Upland Capital Group, Inc. is an AM Best rated “A-” VIII specialty property/casualty insurer headquartered in Dallas, Texas. Through its wholly owned insurance carrier, Upland Specialty Insurance Company, the company markets, underwrites and services specialty insurance products in select markets to include excess transportation, construction casualty, excess casualty, primary general liability, excess public entity, professional liability errors and omissions as well as excess cyber liability. We focus on “old school” underwriting as a craft, add “new school” analytics and technology, and encourage a gritty, growth mindset among people called “we entrepreneurs.” As an Excess and Surplus (E&S) carrier, we face unique and interesting problems every day. We are seeking a Senior Accountant to join our Finance department. We are looking for a Senior Accountant to join a specialty insurance company built on experience. This position will be responsible for a variety of complex accounting practices to include reinsurance accounting, statutory and GAAP accounting, journal entries, reconciliations, research, special projects and month-end close. As a Senior Accountant, the expectation is that the job will be performed with a high level of independence regarding day-to-day activities. This position will also assist in the handling of multiple tasks simultaneously, adhering to timelines and communicating clearly and effectively both oral and written.
Actuarial Analyst
Remote
$75,000-$115,000 annually
Upland Capital Group, Inc. is an AM Best rated “A-” VIII specialty property/casualty insurer headquartered in Dallas, Texas. Through its wholly owned insurance carrier, Upland Specialty Insurance Company, the company markets, underwrites and services specialty insurance products in select markets to include excess transportation, construction casualty, excess casualty, primary general liability, excess public entity, professional liability errors and omissions as well as excess cyber liability. We focus on “old school” underwriting as a craft, add “new school” analytics and technology, and encourage a gritty, growth mindset among people called “we entrepreneurs.” At our Risk and Analytics (R&A) team, we focus on Actuarial, Data Science, Data and Model Engineering, and Enterprise Risk Management functions. Our Actuarial and Data Science model environment and architecture is containerized, and we are cloud based, running on Azure. Our vision is to build highly automated and efficient processes to deliver actuarial insights into underwriting and claims handling processes. We look to create value by problem solving and a close collaboration with stakeholders across the organization, not limited by a ‘one size fits all’ mindset. As an Excess and Surplus (E&S) carrier, we face unique and interesting problems every day. We are looking for an aspiring Actuarial Analyst to join our R&A team. This role will report to the Actuarial Manager and is fully remote.
Actuarial Internship Summer 2025
Remote
$25.00/hour
As a specialty insurance company that strives to be the employer of choice, we strongly support investing in early career professionals! Upland Capital Group offers competitive, compensated internships for college students interested in a career in specialty insurance through our internship program. This internship allows students to participate in a paid summer program with Upland and learn different aspects of both the insurance industry and the operational environment of today. Students will participate in an approximate 9-week program aimed at learning and training through hands-on experience, mentorship and the opportunity to network with company executives and leaders.
Manager, Technical Underwriting Operations
Remote
$95,000-$130,000 annually
Upland Capital Group, Inc. is an AM Best rated “A-” VIII specialty property/casualty insurer headquartered in Dallas, Texas. Through its wholly owned insurance carrier, Upland Specialty Insurance Company, the company markets, underwrites and services specialty insurance products in select markets to include excess transportation, construction casualty, excess casualty, primary general liability, excess public entity, professional liability errors and omissions as well as excess cyber liability. We focus on “old school” underwriting as a craft, add “new school” analytics and technology, and encourage a gritty, growth mindset among people called “we entrepreneurs.” As an Excess and Surplus (E&S) carrier, we face unique and interesting problems every day. We are seeking a Technical Underwriting Operations Manager to join our Underwriting Operations team. This is a remote opportunity with up to 10% travel annually. The Manager of Technical Underwriting Operations oversees the management of Insurance Processing Operations, including new business, renewals, vendor relationships with BPO(s) and internal staff. This role involves training BPO(s) and Technical UW Operations (TUOA) teams to ensure quality and accuracy of work, while auditing, maintaining and updating SOPs. In addition, this position will be responsible for evaluating processes and technology to enhance submissions and collaborates with senior business and technology leaders to develop, articulate, and assess the evolving needs of the department.