# Software Engineering Manager
**Role:** Software Engineering Manager · **Level:** Associate Director
**Company:** [Chewy](https://scaleengineer.com/companies/chewy)
**Difficulty:** High
**Salary:** US$180000 - US$250000
**Experience:** 8 - 15
**Timeline:** ~21 days
Chewy is looking for an Associate Director of Software Engineering 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 blend of strong technical expertise, exceptional leadership skills, and a proven track record in managing complex projects.
Canonical: https://scaleengineer.com/interviews/chewy/associate-director-software-engineering-manager
---
## Overall evaluation

- Leadership and Technical Excellence
- Problem Solving and Cultural Fit

## Questions asked

- Describe your experience building and leading high-performing engineering teams.
- How do you approach setting technical direction and strategy for a team?
- Tell me about a time you had to make a difficult decision that impacted your team. What was the outcome?
- How do you balance the need for innovation with the need for stability and reliability?
- What are your key metrics for measuring team success and productivity?
- Describe your process for hiring and onboarding new engineers.
- How do you handle underperformance within your team?
- What is your experience with Agile methodologies and how do you ensure effective implementation?
- How do you foster a culture of continuous learning and improvement within your team?
- Tell me about a time you had to manage a significant technical challenge or project failure. What did you learn?
- How do you collaborate with product management and other cross-functional teams?
- What are your thoughts on technical debt and how do you manage it?
- How do you stay current with emerging technologies and trends?
- Describe a situation where you had to influence stakeholders to adopt a new technology or approach.
- What are your strengths and weaknesses as a leader?

## Preparation tips

### lists

- Review Chewy's mission, values, and recent news.
- Understand the challenges and opportunities in the e-commerce and pet care industries.
- Prepare specific examples using the STAR method (Situation, Task, Action, Result) for behavioral questions.
- Familiarize yourself with common software engineering management frameworks and methodologies (Agile, Scrum, Kanban).
- Think about your leadership philosophy and how you foster a positive and productive team environment.
- Be ready to discuss your experience with scaling teams and systems.
- Prepare thoughtful questions to ask the interviewers about the role, team, and company.

### studyPlan

- {"title":"Company and Industry Immersion","longDescription":"Weeks 1-2: Deep dive into Chewy's business, products, and technology stack. Understand the competitive landscape and industry trends. Review your own career accomplishments and identify key examples for behavioral questions. Focus on leadership principles and people management strategies.","shortDescription":"Weeks 1-2: Chewy business, industry trends, career examples, leadership principles."}
- {"title":"Technical Foundations","longDescription":"Weeks 3-4: Prepare for technical discussions. Review system design principles, architectural patterns, and common challenges in building scalable and reliable software. Refresh your knowledge of software development lifecycle, CI/CD, and DevOps practices. Practice articulating technical concepts clearly.","shortDescription":"Weeks 3-4: System design, architecture, SDLC, CI/CD, DevOps."}
- {"title":"Leadership and Behavioral Skills","longDescription":"Weeks 5-6: Focus on behavioral and situational questions. Practice answering questions related to team management, conflict resolution, performance management, strategic planning, and stakeholder management. Prepare specific examples using the STAR method. Refine your leadership narrative and vision.","shortDescription":"Weeks 5-6: Behavioral questions (STAR method), team management, conflict resolution, strategy."}

## Location differences

- {"location":"Any","differences":{"tips":["Research common business practices and cultural nuances in the specific region.","Be prepared to discuss your experience working with distributed or remote teams if the role involves it.","Highlight any experience with local talent acquisition strategies."],"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 applicable)."],"commonQuestions":["How do you handle a situation where a key team member is underperforming?","Describe a time you had to manage conflicting priorities between different projects. How did you resolve it?","What are your strategies for fostering innovation within your team?","How do you ensure your team stays up-to-date with the latest technologies and best practices?","Tell me about a challenging cross-functional collaboration you led. What were the outcomes?"]}}

## Round 1: HR Screening Call
**Type:** HR Screening · **Difficulty:** High · **Duration:** 45 min
Initial screening to assess basic qualifications and cultural fit.
This initial screening call with a recruiter or HR representative is designed to assess your overall fit for the role and Chewy. They will review your resume, discuss your career aspirations, and provide an overview of the interview process. Be prepared to talk about your experience in leadership and your motivations for applying.
**Interviewers look for:** Enthusiasm for the role and Chewy.; Clear communication style.; Basic understanding of leadership responsibilities.
**Evaluation criteria:** Leadership potential; Communication skills; Understanding of engineering management principles
**Common rejection reasons:** Lack of clear leadership vision.; Inability to articulate technical strategy.; Poor examples of people management.; Difficulty handling ambiguity or making decisions.; Lack of alignment with Chewy's culture and values.
## Questions

- Tell me about your background and experience in software engineering management.
- Why are you interested in this Associate Director role at Chewy?
- What are your salary expectations?
- What are your strengths and weaknesses as a manager?

## Preparation tips

- Research Chewy's mission and values.
- Be ready to provide a concise overview of your career.
- Articulate why you are interested in this specific role and company.
- Prepare questions about the role and the interview process.

## Round 2: Hiring Manager Interview
**Type:** Hiring Manager Interview · **Difficulty:** High · **Duration:** 60 min
Assesses leadership, strategic thinking, and people management skills.
This interview focuses on your leadership capabilities, strategic thinking, and experience in managing engineering teams. The hiring manager will delve into your past experiences, asking behavioral and situational questions to understand how you lead, motivate, and develop talent, as well as how you set technical direction and manage projects.
**Interviewers look for:** Demonstrated ability to lead and mentor engineers.; Clear vision for technical strategy.; Experience in managing projects and delivering results.; Ability to handle complex situations and make sound decisions.
**Evaluation criteria:** Leadership and people management skills; Strategic thinking and technical vision; Problem-solving abilities; Communication and interpersonal skills
**Common rejection reasons:** Lack of strategic thinking.; Inability to articulate technical vision.; Poor examples of team leadership.; Difficulty managing conflict or underperformance.; Weak problem-solving skills.
## Questions

- Describe your approach to building and scaling engineering teams.
- How do you set technical direction and ensure alignment with business goals?
- Tell me about a time you had to manage a difficult team member. How did you handle it?
- How do you prioritize work and manage competing demands within your team?
- What are your strategies for fostering innovation and continuous improvement?

## Preparation tips

- Prepare specific examples using the STAR method for leadership, team management, and project delivery.
- Think about your leadership philosophy and how you foster a positive team environment.
- Be ready to discuss your approach to strategic planning and technical decision-making.
- Practice articulating your vision for an engineering team.

## Round 3: System Design and Technical Deep Dive
**Type:** Technical Interview · **Difficulty:** High · **Duration:** 60 min
Evaluates system design, technical problem-solving, and architectural skills.
This round focuses on your technical expertise, particularly in system design and architecture. You will be asked to discuss how you would design a complex system, solve technical challenges, and make architectural decisions. The interviewer will assess your ability to guide technical direction and mentor your team on technical matters.
**Interviewers look for:** Strong understanding of software architecture and design patterns.; Ability to think critically and solve complex technical problems.; Experience in designing scalable, reliable, and maintainable systems.; Capacity to mentor engineers on technical best practices.
**Evaluation criteria:** System design and architectural skills; Problem-solving and analytical abilities; Technical depth and breadth; Ability to guide technical decisions
**Common rejection reasons:** Lack of deep technical understanding.; Inability to design scalable systems.; Poor problem-solving approach.; Difficulty collaborating on technical solutions.; Weak understanding of architectural trade-offs.
## Questions

- Design a system for [e.g., a ride-sharing service, a social media feed, an e-commerce recommendation engine]. Discuss scalability, reliability, and trade-offs.
- How would you approach optimizing the performance of a slow-performing application?
- Describe your experience with cloud platforms (AWS, Azure, GCP) and their services.
- How do you ensure code quality and maintainability within your team?
- Discuss your experience with microservices architecture and its challenges.

## Preparation tips

- Review common system design patterns and architectural principles.
- Practice designing scalable systems for various use cases.
- Be prepared to discuss trade-offs in design decisions.
- Refresh your knowledge of data structures, algorithms, and distributed systems.
- Think about how you would guide your team through technical challenges.

## Round 4: Senior Leadership Interview
**Type:** Leadership Interview · **Difficulty:** High · **Duration:** 60 min
Assesses strategic thinking, business acumen, and organizational leadership.
This interview with a senior leader (Director or VP) assesses your strategic thinking, business acumen, and ability to influence at a higher level. You'll discuss your vision for the engineering organization, how you align technology with business goals, and your experience driving significant initiatives. This is an opportunity to demonstrate your potential impact on the broader organization.
**Interviewers look for:** Vision for the engineering organization.; Ability to influence and align stakeholders.; Understanding of business objectives and how technology supports them.; Experience in driving large-scale initiatives.
**Evaluation criteria:** Strategic thinking and business acumen; Leadership presence and influence; Cross-functional collaboration skills; Ability to drive organizational change
**Common rejection reasons:** Lack of alignment with senior leadership.; Inability to influence or drive change at a higher level.; Poor strategic vision for the organization.; Difficulty collaborating with peers and senior stakeholders.; Lack of understanding of business impact.
## Questions

- What is your vision for an engineering organization at Chewy's scale?
- How do you ensure alignment between engineering and other departments (e.g., Product, Marketing, Operations)?
- Describe a time you had to drive significant change within an organization. What was your approach?
- How do you measure the success of your engineering organization?
- What are the biggest challenges facing engineering leaders in the e-commerce industry today?

## Preparation tips

- Understand Chewy's overall business strategy and goals.
- Think about how technology can drive business outcomes.
- Prepare examples of strategic initiatives you have led.
- Be ready to discuss your leadership philosophy at an organizational level.
- Formulate your vision for the engineering function at Chewy.

## Round 5: Team Fit and Collaboration Interview
**Type:** Team/Peer Interview · **Difficulty:** Medium · **Duration:** 30 min
Assesses cultural fit and collaboration style with potential team members.
This round often involves meeting with potential peers or team members. The focus is on assessing your cultural fit, collaboration style, and how you would integrate into the existing team dynamics. This is also an opportunity for you to ask questions about the day-to-day work, team culture, and challenges from their perspective.
**Interviewers look for:** Alignment with Chewy's core values.; Positive attitude and enthusiasm.; Ability to work collaboratively.; Genuine interest in the role and company.
**Evaluation criteria:** Cultural alignment; Motivation and enthusiasm; Teamwork and collaboration style; Overall fit with the team and company
**Common rejection reasons:** Poor cultural fit.; Lack of enthusiasm or engagement.; Inability to articulate personal values.; Mismatch in expectations regarding work-life balance or team dynamics.; Failure to ask thoughtful questions.
## Questions

- How do you approach collaboration within a team?
- What are your expectations from your team members?
- Describe a challenging situation you faced with a colleague and how you resolved it.
- What do you enjoy most about working in software engineering?

## Preparation tips

- Reflect on Chewy's values and how they align with your own.
- Prepare to discuss your preferred working style and how you contribute to a team.
- Think about what you look for in a team and colleagues.
- Prepare questions that will help you understand the team's dynamics and culture.