Senior Legal AI & Workflow Engineer (Contract/Flexible)

About Pacific Street Systems

Pacific Street Law is building the next generation of legal services, combining exceptional attorneys, cutting-edge technology, and a new approach to delivering sophisticated legal work faster, more efficiently, and at transparent, predictable prices.

At the center of this model is Pacific Street Systems, our legal technology company. We build proprietary AI-powered software that supports how our firm operates, from intake and knowledge management to legal research, analysis, drafting, and quality control.

Our technology is developed alongside the attorneys who use it, integrating AI into sophisticated legal work while amplifying expert judgment.

The Opportunity

We are seeking an exceptional legal AI and workflow engineer to help build and expand Pacific Street Systems.

This is a hands-on, part-time contract opportunity for someone with deep experience developing AI applications and a strong understanding of legal workflows. You'll work directly with our attorneys to understand how they practice, translate their expertise into reliable software, and train them to use and improve the tools we build.

You'll also have opportunities for additional contract engagements supporting Pacific Street clients with AI assessments, implementation, workflow redesign, and training.

This is an opportunity to help shape the technology powering a growing law firm, with the potential to expand your role as our platform and client work develop.

Who You Are

You're an accomplished AI builder with a track record of developing sophisticated applications that people actually use. Your expertise is demonstrated by what you've built, not your years of experience or job titles.

You understand how legal work gets done. You're familiar with legal research, document review, drafting, and other complex workflows. You can break down legal processes, identify where AI adds value, and design systems that preserve appropriate attorney oversight.

You have deep technical expertise in LLM applications, agentic workflows, retrieval systems, and model orchestration. You know how to build reliable tools for real-world use, not just impressive demonstrations.

You're also an effective collaborator and teacher who can translate attorney feedback into better technology and help lawyers integrate AI into their daily work.

Qualifications

• Demonstrated experience building and deploying sophisticated AI applications, with strong hands-on software engineering capabilities.
• Understanding of legal workflows and experience translating complex professional processes into reusable tools and software.
• Expertise with LLM APIs, agentic systems, retrieval-augmented generation, model orchestration, and document processing.
• Experience developing evaluations, testing AI outputs, and improving system accuracy and reliability.
• Strong communication, training, and user engagement skills.
• Sound judgment regarding data security, confidentiality, and quality control.
• Experience building legal technology or working directly with lawyers is strongly preferred. A law degree is not required.

What You'll Do

• Build Pacific Street Systems: Develop proprietary AI applications supporting legal work and firm operations.
• Translate legal expertise into software: Work with attorneys to map workflows, identify decision points, and develop reusable tools, playbooks, and automations.
• Engineer sophisticated AI capabilities: Build agentic workflows, document pipelines, retrieval systems, and integrations.
• Ensure quality and reliability: Develop evaluations, testing protocols, and safeguards appropriate for high-stakes legal work.
• Train and support attorneys: Help lawyers maximize the value of our tools and incorporate their feedback into ongoing development.
• Support client AI engagements: Assist with AI assessments, implementation, workflow redesign, and training for Pacific Street clients.
• Shape the platform: Help prioritize new capabilities and influence our technical architecture and roadmap.

Why Pacific Street Systems

• Help reinvent how legal services are delivered. Build the technology infrastructure of a law firm designed around AI from the ground up, rather than adapting legacy systems and workflows.
• Turn legal expertise into powerful software. Work directly with accomplished attorneys to transform sophisticated legal reasoning, judgment, and processes into scalable AI capabilities.
• Shape the architecture and direction of a growing platform. Have meaningful ownership over technical decisions, product development, and the systems that will define how our firm operates.
• Extend your impact beyond our firm. Help businesses rethink their own operations through client-facing AI assessments, implementation, and training.
• Grow with the business. Start with a flexible contract engagement, with opportunities for deeper involvement as Pacific Street Systems and its client work expand.

Engagement & Compensation

• Flexible, part-time contract engagement on a project-by-project or agreed-upon hours basis.
• Competitive compensation based on expertise and engagement structure.
• Remote work or in-person collaboration in Tribeca, New York City.
• Potential for increased hours and long-term collaboration.