Forward Deployed Engineer (AI & Tech)

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 is a hyper-growth tech startup that provides an AI-powered platform to help plaintiff law firms and litigation funders streamline mass tort and personal injury casework and unlock value from legal assets. Bridge Legal’s technology transforms fragmented legal workflows into structured, scalable systems—enabling clients to move faster, reduce risk, and achieve better outcomes for those who have been injured and harmed. Through our software, we empower our law firm clients to fight for the rights of the “little guy” with AI, automation, analytics and workflow.

We pride ourselves on being at the forefront of helping provide individuals access to the legal system and bridge the justice gap by enabling law firms to use technology and AI to serve more clients than ever before.

At Bridge Legal, we believe that teamwork and collaboration are the key drivers of success. Our team is made up of talented and passionate individuals who work together to achieve our goals and deliver exceptional results. We value open communication, mutual respect, and a willingness to go above and beyond for our customers and each other. If you're looking for a supportive and collaborative work environment where your ideas and contributions are valued, we invite you to join our team.

Mission:

We are looking for a business minded builder to lead technology and AI for a leading U.S. plaintiff law firm with a significant environmental litigation practice. You will work from our Chicago office alongside our product and engineering team, while dedicating your work to this law firm. You will have direct access to its leadership and the support of a broader technology organization.

You’ll gain a deep understanding of how the firm operates, own its technology and AI roadmap, and take ideas from discovery through implementation and adoption. Your delivery will be critical to both the firm’s operational success and our ability to deliver meaningful value as a technology partner. This role offers broad ownership for someone who can both build solutions and make sound decisions about what’s worth building.

Status: (In-Office or Remote)

Outcomes:

Lead AI initiatives

• 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 versus 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.

Understand the firm and set priorities

• Work closely with attorneys, paralegals, operations, accounting, and leadership to understand the underlying work before proposing changes.
• Own a prioritized technology roadmap spanning applications, data, integrations, case management, reporting, infrastructure, security, and legacy modernization.
• Translate ambiguous operational problems into scoped projects and clear decisions.

Build and improve systems

• Take ownership of critical internal applications, integrations, data pipelines, reporting, and automated workflows.
• Design and deliver practical solutions from discovery and prototype through production, training, and measurement.
• Improve data quality and architecture, including safe access to internal information for AI systems.
• Assess when existing systems should be maintained, modernized, integrated, replaced, consolidated, or retired.

Protect reliability and continuity

• Work with specialists to improve monitoring, access controls, security, backup and recovery, incident response, and documentation.
• Reduce reliance on knowledge held by any one person and maintain a clear inventory of important systems and data flows.
• Coordinate the right engineering, data, product, infrastructure, or security expertise when a project needs it.

Skill 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.
• Sound judgment about security, accuracy, reliability, and sensitive data.
• Clear communication with executives and nontechnical colleagues, and curiosity about how people actually work.
• Ability to decide when to build, buy, integrate, automate, or simplify a process.
• Willingness to work primarily from our Chicago office and travel periodically to the law firm.
• Experience in legal technology is welcome but not required. We value learning ability, business judgment, ownership, and technical range more than any particular technology stack.

What We Offer:

• Competitive compensation with optimized health benefits (medical, vision and dental), 401K and FSA/HSA benefits
• Unlimited PTO
• Bonus opportunities based on performance
• Flexibility for a great work life balance
• Work building located in the heart of the city with beautiful views
• Comprehensive training and mentorship on an ongoing basis with career growth opportunities
• A friendly and diverse work environment with supportive colleagues and leadership team
• Professional autonomy

Bridge Legal is an equal opportunity employer and prohibits discrimination and harassment of any kind. We are committed to providing employment opportunities to all qualified applicants and employees without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other legally protected status as defined by applicable law. We welcome and encourage candidates from diverse backgrounds and experiences to apply for open positions.