Director, Software Engineering

Reposted 13 Days Ago
Boston, MA, USA
Hybrid
213K-300K Annually
Expert/Leader
eCommerce • Healthtech • Pet • Retail • Pharmaceutical
At Chewy, our mission is to be the most trusted and convenient destination for pet parents and partners, everywhere.
The Role
Lead the B2B Vet Clinics software engineering organization, defining the technical vision, building high-performing teams, and driving innovation within the SaaS space, particularly for veterinary practices.
Summary Generated by Built In
Job Description:
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.

The base salary range for this role is $213,000 - $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 [email protected].
To access Chewy's California CPRA Job Applicant Privacy Policy, please click here.

Skills Required

  • 12+ years of experience in software engineering
  • Demonstrated experience leading engineering organizations that have built and scaled B2B SaaS platforms
  • Proven experience building and rolling out SaaS software, including multi-tenant systems
  • Experience with AI/ML capabilities in products
  • Bachelor's degree in Computer Science or related field

What the Team is Saying

Amy
Olivia
Mark
Joyce
Michael
Sumit
Victoria Kenney
Crystal

Chewy Compensation & Benefits Highlights

How does Chewy ensure its pay and bonus plans are competitive?

Chewy approaches compensation through a total rewards strategy that combines salary, bonuses, equity opportunities, healthcare benefits, employee discounts, and career growth opportunities. The company emphasizes supporting employees across ecommerce, healthcare, pharmacy, customer service, technology, and fulfillment operations while competing for talent in both retail and tech markets.

Competitive compensation and bonus opportunities: Chewy offers market-based compensation packages that may include salary, performance bonuses, commissions, and equity depending on role and level. Built In also notes benefits such as relocation assistance, employee discounts, and bonus opportunities across multiple teams and functions. 

  • Healthcare and wellness support: Benefits include medical, dental, vision, prescription coverage, HSA/FSA options, life insurance, disability coverage, telemedicine, mental health resources, and wellbeing programs. Chewy also offers wellness-focused resources designed to support employees physically, mentally, and financially.
  • Retirement and financial wellbeing: Employees receive 401(k) plans with company matching along with financial wellness resources and broader support programs. Benefits are designed to support both short-term needs and long-term financial planning.
  • Pet-focused and family-oriented benefits: Chewy offers pet insurance discounts, employee discounts on Chewy products, parental leave, fertility support, family-focused benefits, and caregiving resources. The company’s benefits package is closely aligned with its pet-focused identity and customer mission.
  • Flexibility and workplace support: Corporate employees may have access to hybrid work arrangements, flexible scheduling, commuter benefits, PTO, paid holidays, and wellbeing initiatives. Employees also cite supportive managers and collaborative teams as important parts of the broader employee value proposition.
  • Long-term career investment: Compensation is reinforced through career growth opportunities, mentorship, leadership development, cross-functional learning, and exposure to large-scale ecommerce, automation, healthcare, and logistics initiatives. Employees often describe growth opportunities as an important part of the overall company experience.
  • External signals: Comparably reports that 70% of employee reviews are positive overall. Employees frequently highlight healthcare benefits, employee discounts, coworkers, and growth opportunities as strengths of the company experience. (Glassdoor; Comparably) 

 

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The Company
HQ: Boston, MA
17,800 Employees
Year Founded: 2011

What We Do

Who We Are Chewy is where pet parents find everything they need for life with pets, from food to fun to pharmacy. We make pet care easier, more informed, and more joyful through fast, reliable delivery and award-winning 24/7 Customer Care, including access to pet health support when it’s needed. Founded in 2011, Chewy combines the convenience of online shopping with a high-touch, personalized experience built around the real moments of pet parenthood. Our Mission Chewy’s mission is to be the most trusted and convenient destination for pet parents and partners, everywhere. What We Do We support pet parents through the highs, lows, and everyday moments of the pet parenting journey with: • Pet food, treats, and daily essentials • Supplies for dogs, cats, fish, birds, reptiles, equine, and small pets • Pharmacy and veterinary services, including prescriptions and medications • Pet wellness and health products • Autoship for convenient recurring deliveries • Chewy+, our premium membership offering exclusive savings, faster delivery, and personalized pet care benefits • 24/7/365 customer support from knowledgeable, pet-loving experts What Makes Chewy Different Chewy is known for industry-leading service, deep personalization, and our customer-obsessed culture. We combine trust, convenience, and care, and pet parents come to us for: • Exceptional customer care • Human- and pet-centered product and experience design • Fast, dependable fulfillment across a nationwide operations network • A mission-driven culture built on empathy, trust, and passion for pets Our Culture Chewy’s culture is built for people who thrive on ownership, innovation, and impact. We value curiosity, creativity, and continuous improvement across all our teams. We empower Team Members—our Chewtopians—to learn, grow, and unleash their full potential in a collaborative, supportive, mission-driven environment. How We Work Chewy’s Operating Principles guide how we think, innovate, collaborate, and execute. These principles shape our character, decision-making, and approach to delivering results while connecting our people and culture in support of our mission. Where We Work Chewy headquarters: Plantation, FL, and Boston, MA Additional hubs: Bellevue, WA, and Minneapolis, MN

Why Work With Us

Why You Should Work at Chewy Chewy is a unique, fast-growing e-commerce and tech leader where builders, creators, and problem-solvers shape the future of pet care. Our teams drive innovation in a mission-driven culture that creates real impact for pets and the people who love them.

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Chewy Teams

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About our Teams

Chewy Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

Typical time on-site: Not Specified
HQBoston, MA
HQPlantation, FL
Bellevue, WA
Dallas, TX
Minneapolis, MN
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