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HF

Hartford Fire Ins. Co

via Workday

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

Anywhere
Full-time
Posted 12/11/2025
Verified Source
Key Skills:
Cloud Engineering
AI/Data Science
GenAI Engineering
Vendor Management
Agile Leadership

Compensation

Salary Range

$167K - 250K a year

Responsibilities

Lead technology transformation and AI initiatives for the insurance company's underwriting platform, managing large budgets, vendor relationships, and engineering teams.

Requirements

Extensive experience in IT leadership, cloud platforms, AI/Data Science, vendor management, and Agile methodologies, with relevant certifications and technical expertise.

Full Description

Director Software Engineering - IE06FE 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. Key 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. Required Qualifications 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. Compensation The listed annualized base pay range is primarily based on analysis of similar positions in the external market. Actual base pay could vary and may be above or below the listed range based on factors including but not limited to performance, proficiency and demonstration of competencies required for the role. The base pay is just one component of The Hartford’s total compensation package for employees. Other rewards may include short-term or annual bonuses, long-term incentives, and on-the-spot recognition. The annualized base pay range for this role is: $166,560 - $249,840 Equal Opportunity Employer/Sex/Race/Color/Veterans/Disability/Sexual Orientation/Gender Identity or Expression/Religion/Age About Us | Our Culture | What It’s Like to Work Here | Perks & Benefits Every day, a day to do right. Showing up for people isn’t just what we do. It’s who we are – and have been for more than 200 years. We’re devoted to finding innovative ways to serve our customers, communities and employees—continually asking ourselves what more we can do. Is our policy language as simple and inclusive as it can be? Can we better help businesses navigate our ever-changing world? What else can we do to destigmatize mental health in the workplace? Can we make our communities more equitable? That we can rise to the challenge of these questions is due in no small part to our company values that our employees have shaped and defined. And while how we contribute looks different for each of us, it’s these values that drive all of us to do more and to do better every day. About Us Our Culture What It’s Like to Work Here Perks & Benefits Legal Notice Accessibility Statement Producer Compensation EEO Privacy Policy California Privacy Policy Your California Privacy Choices International Privacy Policy Canadian Privacy Policy Unincorporated Areas of LA County, CA (Applicant Information) MA Applicant Notice Hartford India Prospective Personnel Privacy Notice

This job posting was last updated on 12/12/2025

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