Associate Director, Software Engineering

Job Description:

Our Opportunity

Chewy is seeking an Associate Director, Software Engineering to lead our Pharmacy & Diet Engineering team. This leader will own the strategy execution and operational direction of multiple engineering teams responsible for the customer, prescriber, and pharmacy platforms that power Chewy’s retail pharmacy, compounding pharmacy, and vet diet businesses.

This role sits at the intersection of technology, healthcare operations, and customer experience. The Associate Director will partner closely with Product, Operations, Compliance, and senior leadership to deliver resilient, scalable platforms that support regulated workflows while accelerating business growth. This is a high-impact leadership role with visibility across the Pet Health organization and accountability for both technical outcomes and organizational health.

What You’ll Do

• Own execution of the Pharmacy & Diet Engineering functional strategy, ensuring delivery aligns to business priorities and operational goals.
• Lead and develop 2–3 engineering teams through Software Development Managers (SDMs), driving predictable, high-quality delivery at scale.
• Translate ambiguous business requirements into clear technical direction and multi-quarter roadmaps.
• Influence cross-functional prioritization decisions across Product, Operations, Data Science, and Compliance partners.
• Establish and inspect mechanisms that drive engineering excellence, including reliability standards, quality metrics, SLA performance, and on-call rotations.
• Drive cost efficiency and fulfillment speed improvements through platform innovation and workflow optimization.
• Recruit, develop, and retain high-performing engineering talent; build succession plans and maintain consistent performance standards across teams.
• Partner with senior leadership to evaluate technical tradeoffs, resource allocation, and investment decisions that impact the broader pharmacy business.
• Champion scalable architecture, long-term platform health, and continuous improvement practices.

What You’ll Need

• 12–15+ years of software engineering experience, including 5+ years leading multiple engineering teams and managers.
• Demonstrated success owning execution of functional strategy and delivering measurable business outcomes.
• Experience leading through managers and developing leadership bench strength.
• Proven ability to operate in regulated or highly operational environments with high reliability expectations.
• Strong judgment in balancing speed, quality, and long-term platform sustainability.
• Experience influencing senior stakeholders and driving alignment across cross-functional organizations.
• Ability to structure and solve complex, ambiguous problems with data-driven rigor.
• Excellent written and verbal communication skills; comfortable engaging executive leadership.
• Track record of building resilient, scalable distributed systems.

The base salary range for this role is $186,500 - $297,500.

• 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].