Chewy

Director, Software Engineering

Chewy$213K — $300K *
Enterprise Technology
11 - 15 years of experience
Job Overview by Ladders

Qualifications

  • 12+ years of experience in software engineering with significant leadership roles.
  • Proven experience in building and scaling B2B SaaS platforms, overseeing everything from architecture to rollout.
  • Expertise in multi-tenant systems and subscription models, including enterprise integrations.
  • Strong background in developing omnichannel environments integrating online and in-store systems.
  • Experience with AI/ML capabilities to enhance automation and customer value.
  • Track record of managing managers and leading through ambiguity.

Responsibilities

  • Own and execute a 3-5 year technical roadmap for the PIMS platform used in Vet clinics.
  • Lead and develop a high-performing team of approximately 40 professionals.
  • Drive a culture of innovation, sponsoring internal programs and events.
  • Translate ambitious product goals into executable project plans in collaboration with product and design teams.
  • Ensure operational excellence and clear communication of project status and risks to senior leadership.

Benefits

  • Medical/Rx, vision, dental, life, and disability insurance.
  • Unlimited PTO with manager approval, plus six paid holidays annually.
  • Pet adoption reimbursement and discounts on pet insurance and Chewy.com purchases.
  • Parental leave and backup dependent care assistance.
  • Employee assistance program and flexible spending accounts.
  • Telemedicine services and various family services benefits.
Full Job Description
Job Description:

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.

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 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.
  • Build and Develop High-Performing Teams: 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.
  • Drive a Culture of Innovation: 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.
  • Implement with Operational Excellence: 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.


What You'll Need

  • 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.


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 SaaS, 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.

About Chewy

At Chewy, we view pets (and pet parents) as family and are obsessed with meeting their needs and exceeding customer expectations through every interaction. Customers love shopping our wide selection of products including more than 65,000 items (including our Private brands and Healthcare products), which we offer at competitive prices and fast 1-2 day shipping. Chewy’s commitment to customer service is the core of our brand, and our customers love us for it. We “WOW” pet parents through 24/7 assistance, advice and encouragement every day of the year. We make pet parenting easy with our convenient Autoship subscription program—which allows our customers to schedule their orders, so they never run out of their pet food, supplies and medication they need. Chewy is an experience company built on the back of product and technology. Innovation drives our operations and our team is constantly striving to find new and better ways to improve. From an easy-to-navigate website and highly-rated mobile apps, to detailed order tracking and personalized “Pet Profile” features, we are transforming the way pet parents shop.

Chewy Careers

Join the vibrant team at Chewy, where we offer exceptional job opportunities to advance your career in the dynamic world of e-commerce. As a leading company in the pet industry, Chewy is dedicated to making pet care easier and more enjoyable for pet parents everywhere. Work You’ll Do At Chewy, we are constantly on the lookout for passionate, driven professionals to join our diverse team. Whether you're seeking a position in IT, customer service, marketing, or logistics, Chewy provides a platform for professional growth and innovation in every career path. Our commitment to leadership and diversity training ensures that every team member is equipped with the skills to lead and innovate. By joining Chewy, you will work alongside a team of dedicated professionals who are always pushing the boundaries of what's possible in e-commerce and customer service. Internship and Employment Opportunities Chewy offers a variety of internship and employment opportunities that cater to a wide range of skills and interests. Our internships provide invaluable hands-on experience, helping you to enhance your resume and prepare for a full-time position within our company. Chewy is not just about hiring employees; it's about nurturing future leaders. Benefits and Culture At Chewy, we believe that the well-being of our team is paramount. We offer a comprehensive benefits package that supports the health, financial security, and work-life balance of our employees. Our culture is centered on open communication, respect, and a shared passion for our mission. We celebrate diversity and are committed to creating an inclusive environment for all team members. Innovation and Growth Chewy is at the forefront of innovation in the pet industry. We are constantly exploring new technologies and strategies to enhance our services and expand our market reach. This focus on innovation drives our company's growth and offers our team members numerous opportunities to get involved in exciting projects and advance their careers. Networking and Professional Development We encourage our employees to engage in networking and professional development activities that can enhance their career prospects. Chewy supports various initiatives, including workshops, seminars, and training sessions, to help our team members grow their professional network and develop new skills. Join Our Team Explore the job opportunities at Chewy by searching open positions that match your skills and interests. We are looking for curious, creative, and solution-driven team players who are ready to take their career to the next level. Stay Connected Keep up to date with career tips, insider perspectives, and industry-leading insights you can put to use today—all from the people who work here at Chewy. Job Alert Emails Personalize your subscription to receive job alerts, latest news, and insider tips tailored to your preferences. Discover the exciting and rewarding career opportunities that await you at Chewy. Chewy is more than a company; it's a community where you can grow your career and make a difference. Join us in our mission to be the most trusted and convenient online destination for pet parents (and partners) everywhere.
Learn more about Chewy
Size
21,300 employees
Market Cap
$15.9 billion
Industry
Net Income
-$174.4 million
Founded
2011
5 Year Trend
+136.6%
Revenue
$6.4 billion
NASDAQ

Similar Jobs

More Jobs at Chewy

More Enterprise Technology Jobs

Find similar Director, Software Engineering jobs: