Lead AI Engineer for Legal Tech & Innovation

Bridge Legal; Chicago (IL); On-site; USD 140,000 - 230,000; Full time

Benefits offered by this job

Competitive compensation and benefits

Unlimited PTO

Bonus opportunities

Flexible work-life balance

On-site office in Chicago

Career growth and mentorship

Job summary

Bridge Legal, a Chicago-based AI-powered legal tech startup, seeks an experienced leader to own technology and AI for a prominent U.S. plaintiff law firm with environmental practice.

You will work from our Chicago office with product and engineering, driving the AI roadmap from discovery through deployment and adoption. You will build and improve systems, coordinate across departments, and translate complex operations into scalable AI-enabled solutions, while ensuring security, reliability, and

Qualifications

• Ability to understand complex business operations and turn ambiguous problems into useful technology solutions.
• Hands on experience building, deploying, and maintaining production software and AI enabled workflows.
• Practical familiarity with modern AI tools, LLMs, AI agents, and AI assisted development.
• Strong understanding of data, databases, APIs, integrations, and software architecture.
• Demonstrated ownership of projects from discovery through deployment and adoption.

Responsibilities

• Own and maintain the firm’s AI roadmap and coordinate AI initiatives across departments.
• Identify useful applications for AI in legal and business workflows; evaluate models, tools, vendors, and build vs buy decisions.
• Develop or coordinate AI assistants and automated workflows, with human review, access controls, accuracy checks, and cost monitoring.
• Train attorneys and staff, measure adoption and business impact, and report progress to firm leadership.
• Own a prioritized technology roadmap spanning applications, data, integrations, case management, reporting, infrastructure, security, and legacy modernization.

Skills

Business ops understanding

Production software expertise

AI/ML workflow development

Data architectures

Security/reliability judgment

Executive communication

Build vs buy judgment

Cross-functional collaboration

Tools

AI tools

LLMs

APIs

Job description

Bridge Legal, a Chicago-based AI-powered legal tech startup, seeks an experienced leader to own technology and AI for a prominent U.S. plaintiff law firm with environmental practice.

You will work from our Chicago office with product and engineering, driving the AI roadmap from discovery through deployment and adoption. You will build and improve systems, coordinate across departments, and translate complex operations into scalable AI-enabled solutions, while ensuring security, reliability, and