Head of AI-Driven Customer Care Engineering

Chewy, Inc.; Boston (MA); On-site; USD 180,000 - 240,000; Full time

Job summary

Chewy is seeking an Associate Director of Engineering for the Customer Care Product & Engineering Team in Boston. You will lead the Agent Assist, Workflow and Tooling groups, setting the technical vision and driving delivery of scalable, reliable systems powering customer support.

You will partner with Product, Data Science, UX, and Operations to deliver AI/ML‑driven automation and enhanced agent experiences, while mentoring managers and building high‑performing teams.

Qualifications

• 8+ years in software engineering, systems design, and platform development.
• 2+ years leading engineering teams or managers.
• Bachelor’s degree in CS or a related technical field.
• Experience designing distributed, cloud-native architectures.
• Hands-on delivery of AI/ML–based solutions in production.
• Experience with modern cloud platforms (AWS, GCP, Azure).
• Strong CI/CD, DevOps, and observability practices.
• Collaborates with Product, Data Science, and cross-functional partners.
• Excellent communication to influence technical and non-technical stakeholders.

Responsibilities

• Lead and develop the Agent Assist, Workflow and Tooling teams; set direction.
• Architect scalable, highly available omni-channel care systems.
• Drive AI/ML solutions including Agent Assist tools and Workspace.
• Establish engineering best practices across design, testing, DevOps, observability.
• Collaborate with Product and Data teams to translate requirements.
• Oversee platform modernization for performance, scale, security.
• Foster data-driven decisions and experimentation to improve experiences.
• Mentor engineering managers and senior engineers.
• Manage roadmaps, resources, and cross-functional delivery.
• Ensure security, privacy, and reliability standards.

Skills

Distributed systems

Cloud-native architectures

APIs & microservices

AI/ML in production

CI/CD & DevOps

Team leadership

Stakeholder collaboration

Software architecture

Security & reliability

Education

Bachelor’s degree in Computer Science or related field

Tools

AWS

GCP

Azure

Job description

Chewy is seeking an Associate Director of Engineering for the Customer Care Product & Engineering Team in Boston. You will lead the Agent Assist, Workflow and Tooling groups, setting the technical vision and driving delivery of scalable, reliable systems powering customer support.

You will partner with Product, Data Science, UX, and Operations to deliver AI/ML‑driven automation and enhanced agent experiences, while mentoring managers and building high‑performing teams.