Director, Software Engineering

Chewy • Boston, MA

1d • $213,000 - $300,000

About The Position

Our Opportunity At Chewy, it is our mission to be the most trusted and convenient destination for pet parents and partners – vets and service providers – everywhere. Our success is measured by the happiness of the people and pets we serve, not simply by the amount of pet supplies we deliver. That’s why we continue to think of outside-the-Chewy-box ways to delight, surprise, and thank our loyal pet lovers! We are seeking a forward-thinking Director of Software Engineering to lead our B2B Vet Clinics organization, delivering scalable, secure, and intelligent SaaS solutions that power veterinary practices nationwide. This leader will shape the technology vision that enables clinics to operate more efficiently, deliver better patient outcomes, and grow their businesses through modern, AI-enabled software platforms. We are looking for a strategic leader to own complex technical domains, cultivate a world-class engineering culture, and build teams that are creating the future of veterinary practice management and services. This role is suited for a leader who thrives on impact, communicates effectively, and is dedicated to developing individuals while delivering enterprise-grade products.

Requirements

• Demonstrated experience leading engineering organizations that have built and scaled B2B SaaS platforms, including full lifecycle ownership from architecture to rollout and adoption.
• Proven experience building and successfully rolling out SaaS software, including multi-tenant systems, subscription models, enterprise integrations, and customer onboarding.
• Experience building software that supports omnichannel environments (online and brick-and-mortar retail), including integration across digital commerce, in-store systems, and operational workflows.
• AI-first mindset, with experience embedding AI/ML capabilities into products to drive automation, intelligence, and differentiated customer value.
• 12+ years of experience in software engineering, with a significant portion in a leadership capacity, including proven experience managing other managers.
• A track record of leading through ambiguity, creating clarity from complexity, and delivering measurable results on multi-faceted, strategic problems.
• Deep technical expertise with the ability to operate at depth, guide teams through complex architectural challenges, and maintain an exceptionally high bar for quality.
• Proven experience authoring strategic documents and technical proposals for executive-level consumption.
• Bachelor's degree in Computer Science, a related field, or equivalent experience.

Nice To Haves

• Experience building software for healthcare, veterinary, or regulated industries.
• Experience with AI-driven workflow automation or clinical decision support systems.
• Experience in high-growth B2B SaaS, platform-as-a-service, or omnichannel retail technology organizations.

Responsibilities

• Define and execute a 3–5 year technical roadmap for our PIMS platform used in Vet clinics.
• Architect scalable, secure, multi-tenant systems that support veterinary practices across digital and physical environments.
• Ensure seamless workflows across in-clinic experiences, e-commerce, and partner ecosystems.
• Champion AI-first solutions that enhance workflow automation, clinical insights, and operational efficiency.
• Lead an organization of approximately 40, including Associate Directors and senior ICs.
• Hire and retain top-tier talent with SaaS, platform, and omnichannel systems experience.
• Foster a culture of technical excellence, operational rigor, and customer obsession tailored to B2B software delivery.
• Empower your teams to experiment, learn, and deliver breakthrough solutions.
• Be a key sponsor and driver for internal innovation programs that fuel events like our company-wide Innovation Days.
• Partner closely with product, design, and business partners to translate ambitious goals into concrete, well-managed execution plans.
• Own key business objectives, proactively de-risk complex projects, and communicate progress, risks, and trade-offs with absolute clarity to senior leadership.

Benefits

• 401k
• new hire and annual equity grant
• 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 including 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)

What This Job Offers

• Job Type: Full-time
• Career Level: Director