Director, Software Engineering
@ Chewy

Boston, Massachusetts, United States
On Site
Posted 4 days ago

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XXXXXXXXX XXXXXXXXXXX XXXXXXXXXX****** @chewy.com
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Job Details

Our Opportunity

At Chewy, our mission is to be the most trusted and convenient destination for pet parents and partners. We measure success by the happiness of the people and pets we serve. We continue to think outside-the-box to delight and surprise our loyal pet lovers.

We are seeking a forward-thinking Director of Software Engineering to lead our B2C Pet Health organization's mission of delivering seamless healthcare experiences for millions of pet parents. This role is for a strategic leader who excels at owning complex technical domains, cultivating a world-class engineering culture, and building strong teams for the future of pet care.

Who You Are

You think strategically and act deliberately by planning beyond quarterly roadmaps. You lead with pragmatic ownership, taking accountability from strategic roadmaps to operational health, and make data-driven decisions. You are a talent multiplier who coaches and nurtures engineers and leaders, delegating for growth while handling tough conversations with clarity and empathy. Your communication is clear and precise, distilling complex technical and business challenges into actionable strategies.

What You'll Do

  • Own the Technical Vision & Strategy: Define, communicate, and implement a 3-5 year technical roadmap while championing innovative technologies like AI.
  • Build and Develop High-Performing Teams: Lead approximately 40 team members including Associate Directors and senior contributors, focusing on hiring and talent growth.
  • Drive a Culture of Innovation: Empower teams to experiment and deliver breakthrough solutions through internal innovation programs.
  • Implement with Operational Excellence: Collaborate with cross-functional partners to translate ambitious goals into executed plans and manage risks with clarity.

What You'll Need

  • 12+ years of software engineering experience with significant leadership roles.
  • Demonstrable history of shipping large-scale platforms in agile environments.
  • Deep technical expertise and ability to guide teams through complex challenges.
  • Experience in authoring strategic documents for executive-level consumption.
  • Bachelor's degree in Computer Science or equivalent experience.

Bonus Points

Experience with AI/ML applications, high-growth technology domains such as e-commerce, healthcare tech, or platform-as-a-service.

Equal Opportunity

Chewy is an equal opportunity employer. All qualified applicants will receive consideration without regard to any legally-protected characteristics. For accommodation during the application process, please contact CAAR@chewy.com.

Key skills/competency

  • Software Engineering
  • Leadership
  • Technical Strategy
  • Innovation
  • Operational Excellence
  • Team Development
  • Data-Driven Decisions
  • Coaching
  • AI/ML
  • Strategic Roadmap

How to Get Hired at Chewy

🎯 Tips for Getting Hired

  • Research Chewy's culture: Understand mission, values, and recent achievements.
  • Customize your resume: Highlight leadership and technical accomplishments.
  • Prepare strategic examples: Showcase long-term vision in past roles.
  • Practice clear communication: Refine answers with structured, concise examples.

📝 Interview Preparation Advice

Technical Preparation

Review system architecture fundamentals.
Practice scalable software design patterns.
Study advanced data-driven decision making.
Refresh AI/ML integration concepts.

Behavioral Questions

Illustrate a challenging leadership experience.
Describe handling ambiguous project situations.
Explain motivating diverse teams effectively.
Share examples of conflict resolution.

Frequently Asked Questions