[Hiring] AI Development Lead @ZipStaff

Role Description

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.

• 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.

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

Company Description

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