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The Hartford · 4 weeks ago

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

Columbus, OH

Full-time

Hybrid

Mid, Senior Level

$167K/yr - $250K/yr

7+ years exp

The Hartford is an insurance company committed to making a difference and enabling opportunities for growth. They are seeking a Director of Software Engineering to lead the technology transformation for the Sales, Quoting, and Underwriting Value Stream, overseeing a significant budget and driving AI-enabled solutions.

Auto InsuranceCommercial InsuranceEmployee BenefitsFinanceFinancial ServicesInsuranceLife InsuranceProperty Insurance

No H1B

Responsibilities

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

Qualification

Cloud EngineeringAI/Data ScienceGenAI EngineeringDevSecOpsCI/CD PipelinesInfrastructure-as-CodeVendor ManagementAgile DeliveryInsurance Industry ExperienceEthical AI GovernanceCommunicationTeam Leadership

Required

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

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