Machine Learning Engineer II

Job Description:

Our Opportunity:

Chewy is seeking a Machine Learning Engineer II to join our Legal Department in one of our hubs (Plantation, Boston, or Seattle)! This role is focused on fundamentally improving how legal work gets done.

You will work 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, you will be responsible for identifying what is not working, prioritizing high-impact opportunities, and delivering solutions that drive measurable results.

From intake and triage to contract workflows and knowledge access, you will redesign how work flows through the Legal team. You will own 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 role 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.

What You’ll Do

Workflow Discovery & Prioritization

• 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

Solution Design & Build

• 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

AI & Automation

• 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

Adoption & Enablement

• 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)

Cross-Functional Partnership

• 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

What You’ll Need

• 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

Technical Skills

• 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)

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

Legal & Business Acumen

• 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

Ways of Working

• 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

• The specific salary offered to a candidate may be influenced by a variety of factors including but not limited to the candidate’s relevant experience, education, and work location. In addition, this position is eligible for 401k and a new hire and annual equity grant. C08+ positions may also be eligible for annual bonus.

We offer different types of insurance and benefits, such as medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident. We offer parental leave, family services benefits, backup dependent care, flexible spending accounts, telemedicine, pet adoption reimbursement, employee assistance program, and many discounts including 10% off pet insurance and 20% off at Chewy.com. 

Exempt salary team members have unlimited PTO, subject to manager approval. Team members will receive six paid holidays per year. Team members may be eligible for paid sick and family leave in compliance with applicable state and local regulations. 

Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact CAAR@chewy.com.

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