Principal Software Engineer

Chewy•Boston, MA

2d•Hybrid

About The Position

Chewy is seeking a Principal Software Engineer to provide technical leadership across its Customer Care Product & Engineering organization. This influential role will establish the long-term technology vision, drive architectural strategy, and lead the design of scalable, resilient, and AI-enabled platforms that support customer and Team Member experiences. Customer Care is modernizing legacy contact center platforms, building a Unified Agent Workspace, and expanding AI-powered customer engagement, agent assistance, and workflow automation. The Principal Software Engineer will shape the architecture connecting these capabilities and ensure solutions are reusable and extensible. The role spans multiple engineering teams and partners with Software Engineering, Data Science, Product, and business leaders to turn complex challenges into cohesive technical strategies. The successful candidate will bring clarity to ambiguous problems, set architectural direction, make critical technical decisions, and enable teams to execute effectively. This is a hands-on technical leadership role requiring deep architectural expertise, sound business judgment, influence without direct authority, and a record of leading complex cross-organizational initiatives from vision through execution.

Requirements

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.
Experience operating as a Principal Engineer, senior architect, or equivalent technical leader with influence spanning multiple engineering teams or business domains.
A 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 designing 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.
Ability to evaluate architectural alternatives, make pragmatic technical trade-offs, and drive decisions amid 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.
Ability to influence without direct authority, build consensus where appropriate, resolve technical disagreements, and drive decisions to closure.
Strong technical judgment and 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.

Nice To Haves

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.

Responsibilities

Set the technical vision and architectural strategy for Customer Care across customer-facing experiences, agent tools, AI capabilities, and shared platforms.
Lead complex, cross-organizational initiatives, including the Unified Agent Workspace, Customer Care platform modernization, and AI-powered customer and agent experiences.
Architect scalable, resilient, and extensible systems using cloud-native services, distributed architectures, APIs, event-driven integrations, and enterprise platforms.
Drive AI platform architecture and integration, establishing reusable patterns for AI orchestration, conversational AI, agent assistance, knowledge retrieval, and intelligent workflow automation.
Translate ambiguous problems into executable technical strategies; evaluate alternatives, explain trade-offs, and develop recommendations that align stakeholders and accelerate execution.
Ensure cross-platform architectural alignment while balancing delivery speed, scalability, security, reliability, and cost.
Modernize platforms by simplifying legacy architectures, reducing technical debt, improving service boundaries, and increasing maintainability and extensibility.
Establish and champion engineering standards for system design, software development, automated testing, observability, operational excellence, security, and reliability.
Mentor Staff and Senior Engineers, guide complex design decisions, and enable multiple teams to execute without unnecessary dependencies or bottlenecks.
Identify risks, resolve cross-team dependencies, and ensure architectural strategies produce measurable engineering outcomes.
Partner with senior engineering, product, and business leaders on technology investments, build-versus-buy decisions, and recommendations framed in terms of customer impact, business value, cost, and risk.
Identify and validate innovation opportunities in AI, automation, agent tooling, customer engagement, and engineering productivity; guide promising ideas from exploration and prototyping through production.

Benefits

Comprehensive medical, dental, and vision benefits.
Wellness programs and resources.
401(k).
New hire and annual equity grant.
Annual bonus eligibility may apply to C08+ positions.
Medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident insurance.
Parental leave and family services benefits.
Backup dependent care.
Flexible spending accounts.
Telemedicine.
Pet adoption reimbursement.
Employee assistance program.
Discounts, including 10% off pet insurance and 20% off at Chewy.com.
Unlimited PTO for exempt salary team members, subject to manager approval.
Six paid holidays per year.
Paid sick and family leave may be available in compliance with applicable state and local regulations.
Team Member Resource Groups and opportunities to celebrate inclusivity through company events, programs, and activities.
A culture that encourages employees to bring their perspectives, grow their careers, and work with managers who value their career journeys.