Agent Assistant Jobs in Boston, MA (NOW HIRING)

Associate Director of Engineering – Customer Care Product & Engineering

At Chewy, we believe great work starts with great people!

Here, you’ll be part of a team that values who you are, what you bring, and where you want to grow. We offer meaningful work, competitive compensation, and opportunities to develop your career in an environment built on trust and collaboration.

Your Opportunity

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.

What You'll Do

• 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.

What You'll Need

• 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.

Bonus

• 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.

What You'll Get

• A place where you can be your authentic self and grow your career. Our pet parents and partners are from everywhere—different places and different walks of life. It is what makes them unique. Likewise, Chewtopians are encouraged to bring their perspectives to deliver on our mission!
• Work in a culture that cares, with managers who value you and your career journey. Be empowered to think big, thrive on delivering results, and to become your best.
• Development of meaningful connections with a diverse group of Chewtopians through Team Member Resource Groups and celebrate inclusivity with various company events, programs, and activities.
• Comprehensive medical, dental, vision benefits, in addition to wellness programs and resources, enabling you to be your best self in and outside of work.

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• 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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