Director, Software Engineering

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 workflow 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. 

 
Who You Are 

• You think strategically and act deliberately. Your planning horizon extends beyond quarterly roadmaps to the multi-year strategic vision. Predict challenges, align team goals with business vision, and demonstrate influence on long-term strategy. 
• You lead with pragmatic ownership. You take ultimate accountability for your domain, from strategic roadmap to operational health. You make tough, data-driven decisions, strategically manage trade-offs, and when things go wrong, you own the outcome and the findings without blame. 
• You are a talent multiplier. Your passion is growing engineers and leaders. Demonstrating a solid history of coaching, mentoring, and nurturing growth opportunities for your Team Members. You delegate for growth, not just to offload tasks, and you handle difficult performance conversations with empathy and directness. 
• You influence with data and trust. You build consensus and inspire change through well-reasoned arguments and a deep understanding of the data. You are adept at aligning on scope, managing partner expectations, and guiding collaborators toward more viable solutions to enable your team's success while upholding the integrity of your technical vision. 
• You communicate with exceptional clarity. You build shared purpose and inspire confidence through precise, structured communication. You distill highly complex technical and business problems into clear, actionable strategies that drive focus and execution across your organization. 

What You'll Do

• Own the Technical Vision & Strategy: Define and execute a multi-year technology roadmap for our PIMS platform, balancing near-term business priorities with long-term scalability. Architect secure, resilient, multi-tenant SaaS solutions that support veterinary practices across clinical workflows, e-commerce, and partner ecosystems.
• Champion Customer-Centric Innovation: Bring a relentless focus to improving the customer experience for veterinary professionals and pet parents. Leverage emerging technologies, including AI-first solutions, to simplify workflows, increase operational efficiency, and unlock new product capabilities that drive meaningful customer outcomes.  
• Build and Develop High-Performing Teams: Lead and grow an engineering organization of approximately 40 engineers and leaders, including Associate Directors and senior ICs. Foster a culture of ownership, technical excellence, continuous learning, and customer obsession while attracting and retaining top engineering talent.  
• Operate with a Builder’s Mindset: Thrive in a fast-paced, highly ambiguous environment by bringing a hands-on, scrappy approach to problem-solving. Empower teams to move quickly, experiment boldly, learn from failures, and transform ideas into scalable solutions that deliver business impact.  
• Navigate Complex Decisions and Trade-offs: Lead through influence, sound judgment, and strong business acumen. Facilitate healthy debate, challenge assumptions, and drive alignment across stakeholders while balancing competing priorities, technical constraints, customer needs, and business objectives. 
• Drive Operational Excellence and Results: Partner closely with Product, Design, Operations, and business leaders to translate ambitious goals into clear execution plans. Own delivery against key business objectives, proactively manage risks and dependencies, and communicate progress, trade-offs, and outcomes effectively to senior leadership. 

What You'll Need 

• Demonstrated experience leading engineering organizations that have built and scaled B2B 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. 

Bonus Points

• 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, platform-as-a-service, or omnichannel retail technology organizations.