Director of AI Operations and Insurance Domain Quality Job Listing at JDA TSG in Richmond, VA (Job ID 1374-Richmond, Virginia, US)

Description

Overview

At JDA TSG, we equip world-class enterprise brands with top-tier talent and operational leadership, because we know our people are our true differentiator. As Director of AI Operations & Insurance Domain Quality, you will stand up, scale, and lead a high-performing team of commercial insurance domain experts evaluating live AI outputs across active enterprise workflows. We believe AI operational success relies on deep domain authority and rigorous quality governance. By building our operational infrastructure from the ground up, establishing reviewer calibration standards, auditing complex policy edge-cases, and partnering directly with client product leadership, your work ensures flawless AI execution across commercial insurance workflows.  

Title: Director of AI Operations & Insurance Domain Quality 

Location: Remote, USA 

Salary: $135,000 to $145,000 USD 

Must Have: Active Property & Casualty (P&C) Producer / Agent License 

• Program Stand-Up & Scaling Leadership: You will design and execute the operational blueprint for our AI evaluation function, starting with an initial team of 10 domain evaluators and scaling the program as client demand grows. Success is measured by program launch velocity, queue capacity growth, and time to proficiency speed.  

• Quality Assurance Governance & Deep Domain Audit: You will establish productivity evaluation standards, build quality audit rubrics, and conduct secondary reviews and coaching. Success is measured by evaluation accuracy, and error rate reduction across active AI queues.  

• Operational Queue & SLA Management: You will build and manage daily workflow queues, monitor reviewer throughput, and optimize resource allocation to meet strict client turnaround SLAs. Success is measured by SLA compliance, reviewer productivity metrics, and queue bottleneck elimination.  

• Cross-Functional Engineering & Product Feedback Loops: You will synthesize team audit findings, identify systemic AI failure patterns, and lead recurring feedback sessions with product and machine learning engineering teams to refine prompt logic and model accuracy. Success is measured by the quality of defect reporting, model accuracy improvements, and reduction in repeat AI processing errors.  

• Team Enablement & Performance Calibration: You will hire, mentor, and evaluate junior and senior domain evaluators, partnering with learning to design continuous training programs on emerging insurance policy standards and AI audit tools. Success is measured by team retention, skill advancement, and calibration consistency across the evaluation team.  

To feel confident and equipped from day one, you need: 

• At least 8 to 10+ years of progressive leadership experience in commercial P&C insurance operations, underwriting quality control, brokerage management, or insurtech program operations.  

• Active Resident or Non-Resident Property & Casualty (P&C) Producer License (or relevant professional designations such as CPCU, CIC, or ARM) strongly preferred.  

• Demonstrated experience standing up new operational teams, designing workflow queues, and establishing quality assurance frameworks from scratch. 

• Deep technical expertise across commercial P&C lines (General Liability, Commercial Property, Workers' Compensation, Umbrella/Excess, Cyber) and mastery of standard forms (ACORD, ISO, manuscript endorsements).  

• Proven track record of managing team capacity, tracking operational SLAs, and scaling programs from small initial pods (10+ headcount) to larger enterprise operations. 

• Familiarity with AI/ML evaluation workflows, document extraction platforms (e.g., Applied Epic, Vertafore, Hyperscience, Glider), or RLHF (Reinforcement Learning from Human Feedback) methodologies.  

• Exceptional executive communication skills to interface directly with client product leads, machine learning engineers, and executive sponsors.  

• Healthcare - Comprehensive coverage for you and your family 

• Employee Assistance Program - Get support when you or your family need it with counseling and coaching 

• 401K with company match 

• Paid time off 

• Paid parental leave 

• Volunteer Day Off 

• Life insurance - Protect your loved ones and their future 

• Business travel accident insurance 

The specific pay rate offered for this role depends on candidate qualifications, relevant experience, technical expertise, and role requirements. Final individual offers are determined through candidate evaluations during the interview process 

We are an equal opportunity employer committed to building an inclusive workplace. To view our Equal Employment Opportunity (EEO) policy, please click here.

To feel confident and equipped from day one, you need: 

• At least 8 to 10+ years of progressive leadership experience in commercial P&C insurance operations, underwriting quality control, brokerage management, or insurtech program operations.  

• Active Resident or Non-Resident Property & Casualty (P&C) Producer License (or relevant professional designations such as CPCU, CIC, or ARM) strongly preferred.  

• Demonstrated experience standing up new operational teams, designing workflow queues, and establishing quality assurance frameworks from scratch. 

• Deep technical expertise across commercial P&C lines (General Liability, Commercial Property, Workers' Compensation, Umbrella/Excess, Cyber) and mastery of standard forms (ACORD, ISO, manuscript endorsements).  

• Proven track record of managing team capacity, tracking operational SLAs, and scaling programs from small initial pods (10+ headcount) to larger enterprise operations. 

• Familiarity with AI/ML evaluation workflows, document extraction platforms (e.g., Applied Epic, Vertafore, Hyperscience, Glider), or RLHF (Reinforcement Learning from Human Feedback) methodologies.  

• Exceptional executive communication skills to interface directly with client product leads, machine learning engineers, and executive sponsors.  

• Program Stand-Up & Scaling Leadership: You will design and execute the operational blueprint for our AI evaluation function, starting with an initial team of 10 domain evaluators and scaling the program as client demand grows. Success is measured by program launch velocity, queue capacity growth, and time to proficiency speed.  

• Quality Assurance Governance & Deep Domain Audit: You will establish productivity evaluation standards, build quality audit rubrics, and conduct secondary reviews and coaching. Success is measured by evaluation accuracy, and error rate reduction across active AI queues.  

• Operational Queue & SLA Management: You will build and manage daily workflow queues, monitor reviewer throughput, and optimize resource allocation to meet strict client turnaround SLAs. Success is measured by SLA compliance, reviewer productivity metrics, and queue bottleneck elimination.  

• Cross-Functional Engineering & Product Feedback Loops: You will synthesize team audit findings, identify systemic AI failure patterns, and lead recurring feedback sessions with product and machine learning engineering teams to refine prompt logic and model accuracy. Success is measured by the quality of defect reporting, model accuracy improvements, and reduction in repeat AI processing errors.  

• Team Enablement & Performance Calibration: You will hire, mentor, and evaluate junior and senior domain evaluators, partnering with learning to design continuous training programs on emerging insurance policy standards and AI audit tools. Success is measured by team retention, skill advancement, and calibration consistency across the evaluation team.