Title: AI Development Lead

Location: Chapel Hill, NC (Remote)

Type: Contract, 5 months

Overview:

ZipStaff is hiring an AI Development Lead for our client, a large national commercial insurance company. This 5-month contract is a 100% remote role for a hands-on technical lead who will triage unfamiliar enterprise applications, build reusable AI skills and agents, and guide development pods through safe technology and security upgrades while preserving application architecture and behavior.

Responsibilities:

Lead AI-assisted reverse engineering of legacy and current applications to discover architecture, dependencies, integrations, database touchpoints, security flows, and runtime and deployment characteristics, then turn findings into spec-driven plans for delivery pods.
Design, refine, and govern reusable AI skills and agents for reverse engineering, dependency analysis, forward engineering, code changes, migration, remediation, and verification, capturing patterns, failure modes, prompts, and verification steps.
Drive Java and .NET modernization (runtime, framework, dependencies, application server, and infrastructure) while preserving architecture and running safely on the target infrastructure rather than re-platforming.
Lead security modernization from LDAP/legacy authorization to token-based identity (Okta, OAuth/OIDC/JWT), and assess blast radius across databases, interfaces, shared libraries, batch jobs, connected systems, and pipelines before changes.
Break work into pod-ready increments, assign and review work, stay hands-on for high-risk work, mentor developers in agentic and spec-driven development, and partner with AI Test Leads, architects, security, and infrastructure on quality gates, production readiness, and incident/P1 root-cause analysis.

Required Qualifications:

7-10 years of IT experience as a Software Engineer, including production incident experience.
1-2 years of experience with agentic engineering and AI projects.
Hands-on technical lead experience guiding development pods through technology-stack and security upgrades while preserving application architecture and behavior.

Benefits:

Health Insurance
Dental Insurance
Vision Insurance
401(k) + matching
Paid time off
Referral Program

About ZipStaff:

ZipStaff connects skilled technology professionals with leading organizations across the United States, matching top talent with impactful contract and full-time opportunities.

To apply, submit your resume through this posting. Qualified candidates will be contacted by a ZipStaff recruiter.

ZipStaff Inc.

AI Development Lead

About the Job