Specialist - Software Engineering Jobs in Massachusetts

At Chewy, taking care of pets and the people who love them through the highs, the lows, and the everyday is what drives us. Grounded in that purpose and focused on our mission to be the most trusted and convenient destination for pet parents and partners everywhere, we work every day to help people feel more confident, supported, and capable in caring for the animals they love—showing up with the products, services, care, and guidance they need, whenever they need it.

Bringing that to life takes exceptional leaders.

Leadership at Chewy is guided by our Operating Principles, which define how we lead, make decisions, develop talent, serve our customers, and grow our business. We value leaders who think strategically, stay close to the customer, and aren't afraid to roll up their sleeves alongside their teams. They solve complex challenges, build high-performing organizations, and partner closely with senior leaders to shape the future of Chewy.

If you're energized by building, leading, and making a meaningful impact, this leadership opportunity may be the right fit for you.

Your Opportunity

Chewy is seeking a Principal Software Engineer to provide technical leadership across our Customer Care Product & Engineering organization. In this highly influential role, you will establish the long-term technology vision, drive architectural strategy, and lead the design of scalable, resilient, and AI-enabled platforms that power exceptional customer and Team Member experiences.

Customer Care is undergoing a significant technology transformation, modernizing legacy contact center platforms, building a Unified Agent Workspace, and expanding AI-powered customer engagement, agent assistance, and workflow automation. You will play a critical role in shaping the architecture that connects these capabilities, ensuring we build reusable, extensible solutions.

As the senior technical leader spanning multiple engineering teams, you will partner closely with Software Engineering, Data Science, Product, and business leaders to translate complex business challenges into cohesive technical strategies. You will bring clarity to ambiguous problems, establish architectural direction, drive critical technical decisions, and enable teams to execute with greater speed and confidence.

This role requires a hands-on technical leader who combines deep architectural expertise with strong business judgment, the ability to influence without direct authority, and a demonstrated track record of leading complex, cross-organizational initiatives from vision through execution.

What You'll Do:

• Set the technical vision and architectural strategy for Customer Care, establishing a cohesive technology direction across customer-facing experiences, agent tools, AI capabilities, and shared platforms.
• Lead complex, cross-organizational technical initiatives, including Unified Agent Workspace, Customer Care platform modernization, and AI-powered customer and agent experiences.
• Architect scalable, resilient, and extensible systems spanning cloud-native services, distributed architectures, APIs, event-driven integrations, and enterprise platforms.
• Drive AI platform architecture and integration, partnering with Data Science and Engineering to establish reusable patterns for AI orchestration, conversational AI, agent assistance, knowledge retrieval, and intelligent workflow automation.
• Translate ambiguity into executable technical strategies, identifying critical architectural decisions, evaluating alternatives, articulating trade-offs, and developing clear recommendations that align stakeholders and accelerate execution.
• Own cross-platform architectural alignment, ensuring technical decisions across engineering teams support a consistent long-term strategy while balancing delivery speed, scalability, security, reliability, and cost.
• Lead platform modernization, identifying opportunities to simplify legacy architectures, reduce technical debt, improve service boundaries, and increase the maintainability and extensibility of our technology ecosystem.
• Establish and champion engineering standards across system design, software development, automated testing, observability, operational excellence, security, and reliability.
• Serve as a technical force multiplier, mentoring Staff and Senior Engineers, guiding complex design decisions, and enabling multiple teams to execute effectively without creating unnecessary dependencies or bottlenecks.
• Drive technical decisions and execution, proactively identifying risks, resolving cross-team dependencies, and ensuring architectural strategies translate into measurable engineering outcomes.
• Partner with senior engineering, product, and business leadership to shape technology investments, evaluate build-versus-buy decisions, and communicate technical recommendations in terms of customer impact, business value, cost, and risk.
• Lead technology innovation across Customer Care Engineering, identifying and validating new opportunities in AI, automation, agent tooling, customer engagement, and engineering productivity. Guide promising ideas from exploration and prototyping through production, creating reusable capabilities that improve customer and Team Member experiences.

What You'll Need

• Bachelor's degree in Computer Science, Software Engineering, or a related technical discipline, or equivalent practical experience.
• 12+ years of software engineering experience, including significant experience designing and delivering large-scale distributed systems and enterprise platforms.
• Demonstrated experience operating as a Principal Engineer, senior architect, or equivalent technical leader with influence spanning multiple engineering teams or business domains.
• Proven track record of establishing technical vision and driving complex, ambiguous, cross-organizational initiatives from architecture through successful implementation.
• Deep expertise in distributed systems, cloud-native architectures, microservices, event-driven systems, APIs, and modern software design patterns.
• Strong experience with AWS or comparable cloud platforms, including the design of highly available, scalable, secure, and cost-efficient systems.
• Experience architecting or integrating AI/ML-enabled applications, including conversational AI, LLM-based solutions, AI orchestration, or intelligent automation.
• Strong understanding of modern software engineering practices, including CI/CD, automated testing, observability, DevOps, and production reliability.
• Demonstrated ability to evaluate architectural alternatives, make pragmatic technical trade-offs, and drive decisions in environments with significant ambiguity and competing priorities.
• Experience modernizing legacy platforms and defining migration strategies that balance near-term business needs with long-term architectural sustainability.
• Ability to communicate complex technical concepts clearly to engineering teams, senior leadership, and nontechnical stakeholders.
• Proven ability to influence without direct authority, build consensus where appropriate, resolve technical disagreements, and drive decisions to closure.
• Strong technical judgment with the ability to remain hands-on through architecture, design reviews, prototyping, and investigation of complex technical problems.
• Demonstrated success mentoring senior technical talent and raising engineering standards across an organization.

• 
  Bonus:
  • Experience in e-commerce or retail
  • Experience with contact center platforms and technologies, including Genesys, CRM systems, omnichannel customer engagement, and agent workflow applications.
  • Experience designing AI-powered customer service solutions, including virtual agents, agent assist, retrieval-augmented generation (RAG), and knowledge management platforms.
  • Experience with enterprise AI platforms, LLM orchestration, vector databases, and AI evaluation or observability frameworks.
  • Experience leading large-scale legacy platform replacement or enterprise modernization programs.
  • Experience designing high-volume customer-facing applications in e-commerce or other transaction-intensive environments.
  • Familiarity with security, compliance, privacy, and governance considerations for enterprise AI systems.

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 become your best. #LI-Hybrid
• Development of meaningful connections with a diverse group of Chewtopians through Team Member Resource Groups, with opportunities to celebrate inclusivity through company events, programs, and activities.
• Comprehensive medical, dental, and vision benefits, in addition to wellness programs and resources, enabling you to be your best self in and outside of work.

The base salary range for this role is $190,500 - $300,000.00.

• 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.