The Hartford

Director, Employee Benefits – Sales Quoting and Underwriting Software, AI Engineering Leader

The Hartford

full-time

Posted on:

Location Type: Hybrid

Location: Hartford • Connecticut, Illinois, North Carolina, Ohio • 🇺🇸 United States

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Salary

💰 $166,560 - $249,840 per year

Job Level

Senior

Tech Stack

AWSCloudGoogle Cloud PlatformKafkaMicroservicesSplunkTerraform

About the role

  • Execute Employee Benefits End-to-End Underwriting AI Transformation roadmap across all our market segments (~$12M annual budget in 2026)
  • Drive architecture strategy includes key legacy application modernization, application decommissioning and AI-enablement
  • Focus on installing deep software and cloud engineering skillsets to drive more effective planning and delivery including leveraging GenAI engineering uplifts across analysis, requirements, design, development and testing certifications
  • Run point for a critical vendor relationship for our up-market underwriting platform to ensure we have visibility and inputs to their product roadmap, drive workforce strategy, transparency into key metrics and continuous improvement to ensure we balance our total cost of ownership
  • Lead Agile delivery teams to deliver capabilities that translate business strategy into technology solutions, including strict adherence to key Agile metrics to drive effective delivery and continuous improvements
  • Champion cultural transformation, workforce strategies, and manage offshore partners
  • Provide human resource leadership, coaching, and mentoring to build the next generation of engineering and Agile leaders
  • Oversee financial management, understanding forecast to budget variances and proactive communication with Product Managers and Product Owners
  • Mature DevOps practices, improve automation for continuous delivery, observability for our non-production environments and test data management best practices
  • Collaborate with peers across Hartford’s technology organizations to proactively drive reuse of solutions to promote speed to market and optimize total cost of ownership.

Requirements

  • 7+ years of IT leadership experience executing large-scale programs and change management
  • Deep technical expertise in: Cloud platforms (AWS, GCP) and multi-cloud ecosystems; GenAI engineering, AI/Data Science, and advanced analytics; Agentic AI frameworks (e.g., LangChain, CrewAI, LangGraph)
  • Strong understanding of DevSecOps, CI/CD pipelines, reliability engineering and GenAI engineering automation
  • Experience managing complex vendor relationships and offshore delivery models
  • Excellent communication and executive engagement skills
  • Bachelor’s degree in Computer Science or related field; advanced degree preferred
  • Group Benefits or insurance industry experience preferred
  • Certifications: Google Professional Cloud Architect, AWS Solutions Architect – Professional, AI certifications
  • Hands-on experience with: Infrastructure-as-Code (Terraform, CloudFormation); Microservices, API management (Swagger, Apigee), and event-driven architecture (Kafka, Kinesis); Prompt engineering, vector databases, and hybrid memory systems
  • Familiarity with observability tools (Splunk, Dynatrace) and secure deployment practices
  • Expertise in GenAI-driven test automation and ethical AI governance.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
Cloud platformsGenAI engineeringAI/Data Scienceadvanced analyticsDevSecOpsCI/CD pipelinesreliability engineeringInfrastructure-as-CodeMicroservicesevent-driven architecture
Soft skills
communicationexecutive engagementleadershipcoachingmentoringchange managementcultural transformationvendor relationship managementteam collaborationcontinuous improvement
Certifications
Google Professional Cloud ArchitectAWS Solutions Architect – ProfessionalAI certifications