Senior AI/ML Engineer

JOB OVERVIEW

Plan A Technologies is looking for a Senior AI/ML Engineer to design and build AI-powered systems for complex contract analysis and intelligence.

This is a highly hands-on engineering role. We are looking for a strong Python engineer with deep practical experience in LLMs and agentic AI, capable of building and evaluating AI agents from the ground up. The engineer should understand the underlying architecture and implementation rather than relying primarily on AI-assisted development tools.

The role combines LLM/agent engineering, RAG, document intelligence, data engineering, and observability, with a strong focus on extracting reliable and measurable results from complex legal documents.

Please note: you must have at least 5+ years of hands-on experience building and deploying systems with Large Language Models (LLMs), agent architectures, and OCR / Document AI pipelines to be considered for this role.

JOB RESPONSIBILITY

• Design and build LLM-powered agents and agentic workflows for contract analysis and intelligence.

• Develop production-quality AI services and pipelines primarily in Python.

• Build RAG pipelines, including document ingestion, chunking, embeddings, retrieval, ranking, and context management.

• Work with OCR and document AI to process contracts and related legal documents.

• Design systems capable of understanding contracts, amendments, clause versions, conflicts, obligations, and key contractual terms.

• Build and maintain evaluation frameworks to measure accuracy, reliability, relevance, and overall agent performance.

• Implement observability and monitoring for AI agents and pipelines, including tracing, metrics, failures, latency, and output quality.

• Work with relational, document, and/or vector databases as required by the architecture.

• Analyze agent behavior and continuously improve prompts, retrieval strategies, workflows, and system architecture.

• Collaborate with domain experts, data analysts, and other engineers to translate business and legal requirements into scalable AI solutions.

EXPERIENCE

• 5+ years of software engineering experience, with strong production experience in Python.

• Hands-on experience building and deploying LLM applications and AI agents in production or near-production environments.

• Strong understanding of LLM architectures, agent patterns, tool calling, orchestration, and context management.

• Solid experience with RAG and retrieval systems.

• Strong knowledge of databases, including experience with vector databases and traditional relational/document databases.

• Experience with AI/LLM observability, monitoring, tracing, and evaluation.

• Experience building evaluation strategies and metrics for AI systems rather than relying solely on subjective testing.

• Experience with OCR, document processing, document intelligence, or unstructured data pipelines.

• Strong software engineering fundamentals: testing, debugging, APIs, architecture, scalability, and maintainability.

• Ability to develop solutions independently and understand the underlying implementation, without depending on AI coding assistants such as Cursor or Gemini.

• Strong analytical and problem-solving skills.

• Experience working with commercial contracts and legal documents is highly desirable. The ideal candidate understands concepts such as: Statements of Work (SOWs), Contract amendments and revisions, Clause versions and dependencies, Conflicting or overlapping contractual terms, Key contractual obligations and dates, Contract parties and relationships and Extraction and normalization of contractual terms.

• A legal, contract-management, or legal-tech background is a strong plus.

• Excellent verbal and written English communication skills.

• Initiative and drive to do great things.

ABOUT THE COMPANY/BENEFITS

Plan A Technologies is a global engineering firm created to solve the toughest tech challenges facing today’s businesses. Founded by software entrepreneurs Aron Ezra and Slav Kulik, Plan A helps organizations analyze their tech ecosystem to identify exactly what needs to be improved across their products and infrastructure—and then builds the solutions to fix it.

Rather than offering theoretical ideas or software that never launches, Plan A combines elite engineering talent with custom-built, proprietary AI agents to deliver fast, secure, production-ready solutions. Its capabilities span proprietary AI agent deployment, custom software development, application modernization, data platforms, cloud migrations, systems integration, and practical technical advice.

With more than 500 successful product deployments completed worldwide, Plan A helps organizations of every size—from ambitious startups to global enterprises—modernize their systems, automate complex operations, and stay ahead of the technology curve.

Read more about us here: www.PlanAtechnologies.com .

Location: Work From Home 100% of the time, or come in to one of our global offices. Up to you.

Great colleagues and an upbeat work environment: You'll join an excellent team of supportive engineers and project managers who work hard but don't ever compete with each other.

Benefits: Vacation, Brand New Laptop, and More: You’ll get a generous vacation schedule and other goodies.

If this sounds like you, we'd love to hear from you!