Machine Learning Engineer II

Chewy • Boston, MA

1d • Onsite

About The Position

Chewy is seeking a Machine Learning Engineer II to join their Legal Department in one of their hubs (Plantation, Boston, or Seattle). This role focuses on fundamentally improving how legal work gets done by working directly with stakeholders across the Legal team to understand day-to-day workflows, identify inefficiencies, and build practical solutions using AI, automation, and modern tools. Operating at the intersection of legal, engineering, and AI, the engineer will be responsible for identifying what is not working, prioritizing high-impact opportunities, and delivering solutions that drive measurable results. This includes redesigning how work flows through the Legal team, from intake and triage to contract workflows and knowledge access. The role involves owning initiatives end-to-end, from concept through implementation, and will be responsible for driving adoption, training team members, and ensuring solutions deliver sustained impact. This position is best suited for someone who has experience identifying real problems, building solutions, and deploying them in a way that drives meaningful day-to-day use.

Requirements

• Bachelor’s degree in Computer Science, Engineering, or related field, or equivalent practical experience
• 3+ years building and deploying solutions in software, automation, or data/AI environments
• Proven ability to build practical tools using modern technologies (e.g., Python, APIs, LLMs, low-code platforms)
• Experience working with business teams and translating real-world problems into technical solutions
• Experience working in environments where behavior change is required for success
• Strong programming fundamentals (Python or similar) and experience integrating systems via APIs
• Experience designing and implementing LLM-powered applications, including RAG-based systems
• Familiarity with document ingestion pipelines, including parsing, transformation, and semantic chunking strategies
• Understanding of embeddings, vector storage, and retrieval techniques
• Experience with system integrations, including authentication methods such as OAuth
• Familiarity with automation tools (for example, Retool, Zapier, UiPath)
• Interest in legal workflows, legal technology, or operational process improvement
• Ability to quickly understand ambiguous processes and identify opportunities to simplify and scale
• Awareness of legal risk considerations and the importance of accuracy, auditability, and defensibility in legal outputs
• Strong ownership mindset with the ability to operate independently
• Ability to prioritize and focus on high-impact work
• Clear communicator who can work effectively with non-technical stakeholders
• Ability to train others and drive adoption of new tools and processes

Nice To Haves

• Exposure to cloud and data platforms (for example, AWS, Snowflake)

Responsibilities

• Partner with Legal team members to understand workflows, pain points, and inefficiencies
• Identify opportunities to simplify, automate, and scale processes
• Develop and maintain a prioritized roadmap of high-impact initiatives
• Design and build solutions using AI, automation, and modern tools to improve legal workflows
• Automate repetitive work (e.g., intake, triage, contract support, reporting, knowledge access)
• Prototype quickly, iterate based on feedback, and scale what works
• Integrate solutions with existing systems (e.g., M365, intake tools, document repositories), including system-to-system integrations via APIs and authentication frameworks
• Apply AI and generative AI to improve core legal workflows, with a focus on document-centric use cases
• Design and implement retrieval-augmented generation (RAG) architectures, including document ingestion, parsing, semantic chunking, embedding strategies, and retrieval patterns
• Evaluate new tools and recommend practical, production-ready use cases
• Ensure all solutions align with Chewy’s AI governance framework, including required review, approval, and partnership with AI, IT, Security, and Compliance stakeholders
• Design solutions that incorporate appropriate human review and align with legal and risk tolerance requirements
• Train team members and drive adoption of new tools and workflows
• Develop clear documentation and playbooks
• Partner with Legal leadership to evolve how work is delivered
• Define and track success metrics (usage, time saved, error reduction)
• Partner with Legal Ops, IT, Security, and Data teams to deliver scalable, secure solutions
• Translate legal needs into technical requirements and communicate solutions clearly
• Collaborate with Compliance and Security teams to ensure solutions meet data privacy and regulatory standards

Benefits

• 401k
• New hire and annual equity grant
• Medical/Rx insurance
• Vision insurance
• Dental insurance
• Life insurance
• Disability insurance
• Hospital indemnity
• Critical illness
• Accident insurance
• Parental leave
• Family services benefits
• Backup dependent care
• Flexible spending accounts
• Telemedicine
• Pet adoption reimbursement
• Employee assistance program
• Discounts including 10% off pet insurance
• 20% off at Chewy.com
• Unlimited PTO (for exempt salary team members, subject to manager approval)
• Six paid holidays per year
• Paid sick and family leave (may be eligible in compliance with applicable state and local regulations)

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 5,001-10,000 employees