Deductible Recovery Administrator – P&C Insurance

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 Deductible Recovery Administrator to join our Underwriting Operations & Technology Team.

Primary Function:

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.

Duties and Responsibilities:

• Deductible Recovery Management
  • Manage the lifecycle of deductible recoveries for General & Excess Liability claims, from identification through resolution.
  • Initiate deductible billing activity promptly using provided claims and financial data.
  • Draft, refine, and issue formal recovery correspondence in accordance with company standards.
  • Manage and monitor automated email follow up sequences to drive timely communication and escalation.
  • Perform manual follow ups with Claims Representatives, Underwriters, and senior leadership when recovery efforts stall or require business decisions.
  • Maintain accurate documentation of all recovery activity, responses, and outcomes within designated tracking systems.
  • Coordinate escalation of non-responsive accounts in coordination with leadership and collections partners when applicable.
• Premium Audit Support
  • Provide operation support to the Premium Audit function based on workload.
  • Assist with intake coordination, audit follow-up and documentation tracking.
  • Update audit status, notes and corresponding within audit tracking system.
  • Cross-train to provide more technical audit support, including completing audits and performing peer reviews.

Experience, Education, Special Skills Required:

• 2-4 years of experience in the insurance industry, and/or relevant experience in billing, collections or accounts receivable.
• Strong written and verbal communication skills
• Excellent organizational skills with the ability to manage multiple deadlines and follow up chains independently.
• Detail‑oriented, self-directed, and comfortable working in a fast‑paced evolving environment.
• Ability to prioritize effectively and pivot between tasks as business needs change.
• Proficient with Microsoft Office or similar software, with the ability to learn new systems quickly.

Preferred Skills

• Associate’s degree or higher a plus.
• 1 year P&C insurance experience.
• Background in insurance collections, deductible recovery, or post-claims financial recovery.
• Familiarity with insurance terminology and processes.
• Experience using Monday.com or other project management or workflow tracking platform

Disclosures:

Pay Estimate: $50,000 - $65,000/year

Other compensation: annual incentive program

Benefits: health insurance including FSA and HSA options and free access to Teladoc, vision, dental, disability and life insurance, parental leave, responsible time off (unlimited vacation days without an accrual system), paid sick time as required by law, 401(k), tuition reimbursement and employee assistance program.