Associate Director, Software Engineering

Chewy•Boston, MA

About The Position

As the Associate Director of Engineering for the Customer Care Product & Engineering Team, you will lead the Agent Assist, Workflow and Tooling organization. You will drive the technical vision, architecture, and execution of scalable, resilient, and intelligent systems that power world-class customer support experiences. You will shape and deliver AI/ML-driven solutions that enhance automation, personalization, and operational efficiency across customer care channels. You will partner closely with Product, Data Science, UX, and Operations to build innovative platforms and experiences that empower Customer Care teams and delight pet parents. You will guide engineering strategy, foster technical excellence, and build high-performing teams capable of delivering secure, reliable, and forward-thinking solutions in a fast-paced environment.

Requirements

8+ years of experience in software engineering, system architecture, and platform development.
2+ years of experience leading engineering teams or managing managers.
Bachelor’s degree in Computer Science or a similar technical discipline.
Strong technical expertise in distributed systems, cloud-native architectures, APIs, and microservices.
Hands-on experience designing and building AI/ML-based solutions in production environments.
Experience working with modern cloud platforms (e.g., AWS, GCP, Azure).
Demonstrated experience delivering scalable, resilient systems supporting high-volume customer-facing applications.
Strong understanding of CI/CD, DevOps practices, and engineering operational excellence.
Experience collaborating closely with Product, Data Science, and cross-functional stakeholders.
Strong communication skills with the ability to influence technical and non-technical partners.

Nice To Haves

Master’s degree in Computer Science, Engineering, or related field.
Experience building conversational AI, LLM-based solutions, or intelligent automation platforms.
Experience in customer care or contact center technologies (e.g., CRM, CCaaS platforms).
Experience implementing observability and reliability engineering best practices.
Familiarity with data engineering pipelines and MLOps frameworks.
Experience leading platform transformation or modernization initiatives.

Responsibilities

Lead and develop the Agent Assist, Workflow and Tooling teams, setting technical direction and ensuring strong execution.
Architect and deliver scalable, highly available systems supporting omni-channel customer care (chat, voice, messaging, automation platforms).
Drive the design and implementation of AI/ML-based solutions, including AI based Agent assist tools, Unified Agent Workspace, RRC, CCRB and more.
Establish engineering best practices in system design, software development, testing, DevOps, and observability.
Partner with Product and Data teams to translate business requirements into robust technical solutions.
Oversee platform modernization efforts, ensuring performance, scalability, and security.
Champion data-driven decision-making and experimentation to continuously improve customer and agent experiences.
Build and mentor engineering managers and senior engineers, fostering a culture of accountability, innovation, and continuous improvement.
Manage roadmap planning, resource allocation, and cross-functional delivery alignment.
Ensure compliance with security, privacy, and reliability standards across all systems.

Benefits

Comprehensive medical, dental, vision benefits
wellness programs and resources
401k
new hire and annual equity grant
annual bonus (for C08+ positions)
medical/Rx insurance
vision insurance
dental insurance
life insurance
disability insurance
hospital indemnity insurance
critical illness insurance
accident insurance
parental leave
family services benefits
backup dependent care
flexible spending accounts
telemedicine
pet adoption reimbursement
employee assistance program
discounts (10% off pet insurance and 20% off at Chewy.com)
unlimited PTO (subject to manager approval)
six paid holidays per year
paid sick and family leave (in compliance with applicable state and local regulations)