# Software Engineering Manager
**Role:** Software Engineering Manager · **Level:** VP
**Company:** [Chewy](https://scaleengineer.com/companies/chewy)
**Difficulty:** Very High
**Salary:** US$180000 - US$250000
**Experience:** 10 - 15
**Timeline:** ~30 days
Chewy is looking for a VP-level Software Engineering Manager to lead and mentor a team of talented engineers, drive technical strategy, and ensure the successful delivery of high-quality software solutions. This role requires a strong blend of technical expertise, leadership skills, and a deep understanding of the software development lifecycle.
Canonical: https://scaleengineer.com/interviews/chewy/vp-software-engineering-manager
---
## Overall evaluation

- Leadership and Technical Acumen
- People Management
- Technical Strategy and Execution
- Communication and Collaboration

## Questions asked

- Tell me about your experience leading large engineering teams and driving significant technical initiatives.
- Describe your philosophy on building and scaling high-performing engineering teams.
- How do you foster a culture of innovation and accountability within your engineering organization?
- Walk me through a time you had to make a critical technical decision that had a major impact on the business. What was your process, and what was the outcome?
- How do you balance the need for rapid feature delivery with maintaining code quality and managing technical debt?
- Describe your experience with strategic planning and roadmap development for engineering departments.
- How do you identify and develop future leaders within your teams?
- What are your strategies for managing cross-functional relationships with product management, design, and other business units?
- Tell me about a time you had to navigate significant organizational change. How did you lead your team through it?
- What are your thoughts on the current state of e-commerce technology and where do you see it heading?
- How do you ensure your teams are aligned with the company's overall business goals?
- Describe a situation where you had to deal with a major production incident. What was your role, and what did you learn?
- How do you approach performance management and address underperformance on your team?
- What are your key principles for effective communication as a leader?
- How do you stay current with new technologies and industry best practices?

## Preparation tips

### lists

- Deeply understand Chewy's mission, values, and business objectives.
- Review your past experiences and identify key accomplishments that demonstrate leadership, technical expertise, and people management skills.
- Prepare specific examples using the STAR method (Situation, Task, Action, Result) for behavioral questions.
- Familiarize yourself with common software engineering management challenges and best practices.
- Research current trends in e-commerce technology and software development.
- Understand Chewy's technology stack and engineering culture.
- Practice articulating your technical vision and leadership philosophy.
- Be ready to discuss your approach to hiring, mentoring, and retaining top engineering talent.
- Prepare thoughtful questions to ask the interviewers about the role, the team, and the company's future.

### studyPlan

- {"title":"Company & Self-Assessment","longDescription":"Weeks 1-2: Focus on understanding Chewy's business, culture, and technology. Review company reports, press releases, and the careers page. Identify key challenges and opportunities in the e-commerce space. Revisit your resume and identify core strengths and experiences relevant to a VP of Engineering role. Begin outlining key accomplishments using the STAR method.","shortDescription":"Weeks 1-2: Chewy Business & Culture, Resume Review, STAR Method Prep."}
- {"title":"Management Skills Deep Dive","longDescription":"Weeks 3-4: Deep dive into software engineering management best practices. Study topics such as agile methodologies, DevOps, team building, performance management, conflict resolution, and technical strategy. Read relevant books and articles on engineering leadership. Prepare examples for common management scenarios.","shortDescription":"Weeks 3-4: Management Best Practices, Agile, DevOps, Team Building, Conflict Resolution."}
- {"title":"Technical Leadership & Strategy","longDescription":"Weeks 5-6: Focus on technical leadership and strategic thinking. Review system design principles, scalability, cloud architecture, and emerging technologies. Prepare to discuss your approach to technical debt, innovation, and long-term technology roadmaps. Practice articulating your technical vision.","shortDescription":"Weeks 5-6: Technical Strategy, System Design, Scalability, Cloud, Innovation."}
- {"title":"Final Preparation & Mock Interviews","longDescription":"Week 7: Mock interviews and final preparation. Conduct mock interviews focusing on behavioral, technical, and leadership questions. Refine your answers and ensure they are concise and impactful. Prepare a list of insightful questions to ask the interviewers.","shortDescription":"Week 7: Mock Interviews, Behavioral Practice, Question Preparation."}

## Location differences

- {"location":"Any","differences":{"tips":["Research common business practices and industry trends in the specific region.","Be prepared to discuss your experience working with diverse teams and cultures.","Familiarize yourself with any local labor laws or employment regulations that might be relevant."],"interviewFocus":["Understanding of local market talent pool and compensation benchmarks.","Adaptability to regional work culture and communication styles.","Experience with specific regulatory or compliance requirements relevant to the location (if any)."],"commonQuestions":["How do you handle a situation where a key team member is underperforming?","Describe a time you had to make a difficult decision that impacted your team. What was the outcome?","How do you foster a culture of innovation and continuous improvement within your team?","What are your strategies for managing remote or distributed teams effectively?","How do you balance the need for speed with the importance of code quality and technical debt?"]}}

## Round 1: HR/Recruiter Phone Screen
**Type:** HR/Recruiter Screen · **Difficulty:** High · **Duration:** 60 min
Initial screening to assess cultural fit and basic qualifications.
This initial screening call with a recruiter or HR representative is designed to assess your overall fit for the role and Chewy's culture. They will review your resume, discuss your career aspirations, and provide an overview of the interview process. Be prepared to talk about your motivation for applying and your high-level experience.
**Interviewers look for:** Enthusiasm for Chewy and the role.; Clear and concise communication.; Professionalism and positive attitude.; Basic understanding of management principles.
**Evaluation criteria:** Alignment with Chewy's values and culture.; Initial assessment of leadership potential and communication style.; Understanding of the role and its responsibilities.
**Common rejection reasons:** Lack of strategic vision.; Inability to articulate a clear leadership philosophy.; Poor communication or interpersonal skills.; Failure to demonstrate experience in managing complex projects or teams.; Lack of understanding of business objectives.; Inability to provide concrete examples of past successes.
## Questions

- Tell me about yourself and your career background.
- Why are you interested in this Software Engineering Manager role at Chewy?
- What are your salary expectations?
- What do you know about Chewy?

## Preparation tips

- Research Chewy's mission, vision, and values.
- Prepare a concise summary of your career and why you're interested in this role.
- Be ready to discuss your salary expectations.
- Have questions prepared about the company and the role.

## Round 2: Technical Deep Dive & Architecture
**Type:** Technical Leadership & System Design · **Difficulty:** Very High · **Duration:** 60 min
Assesses technical vision, system design, and architectural decision-making.
This interview focuses on your technical leadership capabilities and strategic thinking. You will be asked to discuss your approach to building and scaling complex systems, managing technical debt, and driving innovation. Expect questions about system design, architecture, and your experience with various technologies relevant to Chewy's platform.
**Interviewers look for:** Deep technical knowledge and experience.; Ability to think critically and solve complex problems.; Strategic mindset and forward-thinking approach.; Clear communication of technical ideas.; Experience with cloud-native architectures and distributed systems.
**Evaluation criteria:** Technical leadership and strategic thinking.; System design and architectural decision-making.; Understanding of scalability, performance, and reliability.; Ability to manage technical debt and drive innovation.; Proficiency in modern software development practices.
**Common rejection reasons:** Lack of depth in technical leadership.; Inability to articulate a clear technical vision.; Poor understanding of system design and scalability principles.; Difficulty in explaining complex technical concepts.; Failure to demonstrate experience in managing technical debt.; Not aligning with Chewy's technical standards.
## Questions

- Design a scalable recommendation system for an e-commerce platform.
- How would you approach migrating a monolithic application to a microservices architecture?
- Describe your strategy for managing and reducing technical debt in a large codebase.
- How do you ensure the reliability and availability of critical services in a distributed system?
- What are your thoughts on serverless computing and its application in e-commerce?

## Preparation tips

- Review system design principles, scalability patterns, and distributed systems concepts.
- Be prepared to discuss your experience with cloud platforms (AWS, Azure, GCP).
- Think about how you would architect a large-scale e-commerce platform.
- Prepare examples of how you've managed technical debt and made architectural trade-offs.
- Understand Chewy's current technology stack and identify potential areas for improvement.

## Round 3: People Management Interview
**Type:** People Management & Leadership · **Difficulty:** Very High · **Duration:** 60 min
Evaluates your ability to manage, mentor, and develop engineering teams.
This interview focuses on your people management and leadership skills. You'll be asked to share examples of how you've built, managed, and developed engineering teams. Expect questions about hiring, performance reviews, career development, conflict resolution, and fostering a positive team environment. The interviewer will assess your ability to motivate, mentor, and lead engineers effectively.
**Interviewers look for:** Proven ability to lead and inspire teams.; Empathy and strong interpersonal skills.; Experience in developing individual contributors and managers.; Effective conflict resolution and feedback delivery.; Commitment to diversity and inclusion.
**Evaluation criteria:** People management and team leadership skills.; Experience in hiring, onboarding, and retaining talent.; Ability to mentor, coach, and develop engineers.; Conflict resolution and performance management.; Fostering a positive, inclusive, and productive team culture.
**Common rejection reasons:** Inability to demonstrate effective people management.; Lack of experience in hiring, mentoring, and performance management.; Poor conflict resolution skills.; Failure to foster a positive team culture.; Difficulty in motivating and developing engineers.; Not aligning with Chewy's people-centric approach.
## Questions

- Describe your approach to hiring and building a high-performing engineering team.
- How do you handle underperformance on your team?
- Tell me about a time you had to resolve a conflict between team members.
- How do you mentor and develop engineers to help them grow their careers?
- What steps do you take to foster a culture of psychological safety and inclusion on your team?

## Preparation tips

- Prepare specific examples using the STAR method for questions related to team building, conflict resolution, performance management, and mentorship.
- Think about your leadership philosophy and how you create a positive and productive work environment.
- Be ready to discuss your approach to hiring and retaining top talent.
- Consider how you foster diversity and inclusion within your teams.
- Reflect on challenging situations you've faced as a manager and how you handled them.

## Round 4: Business & Strategy Alignment
**Type:** Business Acumen & Strategy · **Difficulty:** Very High · **Duration:** 60 min
Evaluates strategic thinking, business alignment, and cross-functional collaboration.
This interview assesses your ability to think strategically and align engineering efforts with business objectives. You'll discuss how you collaborate with other departments, manage stakeholders, and make decisions that impact the business. Expect questions about product strategy, business priorities, and how you translate business needs into technical solutions.
**Interviewers look for:** Understanding of business drivers and how technology supports them.; Ability to influence and collaborate with peers and senior leadership.; Clear and concise communication of complex ideas.; Strategic vision that aligns with company goals.; Data-driven decision-making.
**Evaluation criteria:** Strategic thinking and business acumen.; Cross-functional collaboration and stakeholder management.; Communication skills, especially with non-technical audiences.; Ability to align engineering efforts with business objectives.; Problem-solving and decision-making in a business context.
**Common rejection reasons:** Lack of strategic alignment with business goals.; Poor cross-functional collaboration skills.; Inability to influence stakeholders.; Weak communication with non-technical audiences.; Not demonstrating a clear understanding of business impact.; Failure to articulate a compelling vision for the team's contribution to the business.
## Questions

- How do you ensure your engineering team's roadmap is aligned with the company's overall business strategy?
- Describe a time you had to influence stakeholders from other departments to adopt a particular technical approach.
- How do you measure the success of your engineering teams beyond just code delivery?
- What are the biggest technical challenges facing e-commerce companies today, and how would you address them?
- How do you prioritize competing demands from product, marketing, and operations?

## Preparation tips

- Understand Chewy's business model, key metrics, and strategic priorities.
- Think about how technology can drive business growth and customer satisfaction in e-commerce.
- Prepare examples of successful cross-functional collaborations.
- Practice explaining technical concepts and their business impact to a non-technical audience.
- Be ready to discuss your approach to prioritizing initiatives based on business value.

## Round 5: Executive Leadership Interview
**Type:** Executive / Final Interview · **Difficulty:** Very High · **Duration:** 60 min
Final discussion with senior leadership to assess vision and executive fit.
This final interview is with a senior executive, often the CTO or SVP of Engineering. It's a high-level discussion about your vision, leadership philosophy, and strategic thinking. They will assess your executive presence, your ability to lead at scale, and your overall fit with the company's senior leadership team and long-term direction. Be prepared to discuss your aspirations and how you see yourself contributing at the VP level.
**Interviewers look for:** Visionary thinking and long-term perspective.; Strong executive presence and confidence.; Ability to lead and inspire at scale.; Alignment with Chewy's core values and leadership principles.; Sound judgment and decision-making at the highest level.
**Evaluation criteria:** Executive presence and leadership potential.; Vision and strategic thinking at a VP level.; Cultural fit with senior leadership team.; Ability to inspire and influence at an organizational level.; Overall assessment of suitability for a VP role.
**Common rejection reasons:** Lack of executive presence.; Inability to articulate a compelling vision.; Poor alignment with the company's long-term goals.; Failure to demonstrate strong leadership potential at the VP level.; Not a good cultural fit with senior leadership.; Inability to answer high-level strategic questions.
## Questions

- What is your vision for the future of engineering at Chewy?
- How would you describe your leadership style at the executive level?
- What are the most critical factors for success in a VP of Engineering role at a company like Chewy?
- How do you foster a culture of continuous learning and adaptation within a large engineering organization?
- What are your long-term career aspirations, and how does this role fit into them?

## Preparation tips

- Reiterate your understanding of Chewy's strategic goals and challenges.
- Articulate your long-term vision for engineering at Chewy.
- Be prepared to discuss your leadership philosophy and how you inspire large organizations.
- Think about how you would contribute to the company's culture and success at the executive level.
- Have thoughtful, high-level questions ready for the executive.