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

The Hartford•Hartford, CT

7d•Hybrid

About The Position

We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future. The Hartford’s Employee Benefits organization is seeking a Director of Software Engineering to lead technology transformation for the Sales, Quoting, and Underwriting Value Stream. This IT leadership role will manage a $12M annual investment budget, drive architecture cohesiveness, and ensure Agile productivity effectiveness while expanding engineering capabilities across the enterprise. A critical focus will be leading Underwriting End-to-End Underwriting AI transformation, including establishing our Agentic AI framework to enable next-generation intelligent automation. This role requires a strong technical foundation in Cloud Engineering, Software Engineering, GenAI Engineering toolsets, and AI/Data Science, combined with proven experience managing external vendor relationships. This role will have a Hybrid work schedule, with the expectation of working in an office (Columbus, OH, Chicago, IL, Hartford, CT or Charlotte, NC) 3 days a week (Tuesday through Thursday). Candidate must be authorized to work in the US without company sponsorship. The company will not support the STEM OPT I-983 Training Plan endorsement for this position.

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.
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.

Nice To Haves

Group Benefits or insurance industry experience preferred.
Certifications: Google Professional Cloud Architect, AWS Solutions Architect – Professional, AI certifications.

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.