1. What is an Engineering Manager at Castlight?

At Castlight, the role of an Engineering Manager is pivotal to the company’s mission of simplifying the healthcare journey. You are not just managing code; you are managing the teams that build the navigation platform used by millions to find care, understand costs, and improve their health outcomes. This role sits at the intersection of complex data challenges and user-centric product development.

You will lead a team of talented engineers, guiding them through the technical complexities of the healthcare ecosystem. The work involves high-scale data ingestion, personalized recommendation engines, and secure, compliant infrastructure. As a manager, your impact is measured by the health of your team—their growth, retention, and velocity—and the reliability of the products they ship.

This position requires a leader who can translate high-level business goals into actionable technical roadmaps. You will champion engineering excellence while collaborating closely with Product and Design to deliver features that demystify healthcare for users. It is a role for those who care deeply about organizational health and are motivated by solving real-world problems in a fragmented industry.

2. Getting Ready for Your Interviews

Preparation for the Engineering Manager role requires a shift in mindset from "how do I solve this technical problem" to "how do I enable my team to solve this problem." You need to demonstrate that you can scale yourself through others.

Your evaluation will focus on these core criteria:

People Management & Leadership In the context of Castlight, this means more than just approving time off. Interviewers assess your ability to mentor engineers of varying seniority, handle performance management (both high and low performers), and foster an inclusive culture. You must show how you build psychological safety and keep teams motivated, even during periods of ambiguity.

Technical Stewardship While you may not be coding daily, you must possess the technical acumen to earn the respect of your team. You will be evaluated on your ability to facilitate technical discussions, arbitrate architectural decisions, and ensure the team balances feature delivery with technical debt reduction. Expect questions on system design and development best practices.

Delivery & Process Management Castlight values managers who can deliver predictably. You will be assessed on your experience with Agile methodologies, cross-functional collaboration, and project planning. You need to demonstrate how you unblock your team, manage stakeholder expectations, and keep projects on track without burning out your engineers.

Mission Alignment & Soft Skills Healthcare is a sensitive and complex domain. Interviewers look for empathy, patience, and a genuine interest in the company's mission. Cultural fit is heavily weighted; you need to show that you are collaborative, transparent, and capable of navigating a dynamic environment.

3. Interview Process Overview

The interview process for an Engineering Manager at Castlight generally follows a standard structure, though candidates should be prepared for a timeline that can vary significantly. The process typically begins with a recruiter screen to align on your background, interest in healthcare technology, and compensation expectations. This is followed by a screen with a Hiring Manager, which digs deeper into your management philosophy and technical background.

If you pass the initial screens, you will move to a "virtual onsite" loop. This stage involves multiple interviews with peer Engineering Managers, Product Managers, and senior engineering leadership. The focus here shifts to specific competencies: system design, situational leadership, and behavioral questions. Castlight interviewers are generally described as bright and engaged, but the coordination of the process can sometimes be lengthy.

Candidates should approach this process with patience. Historical data suggests that the time between rounds can sometimes extend longer than average. It is crucial to maintain professional follow-up and stay engaged with your recruiter throughout the process.

The visual timeline above illustrates the typical flow from the initial recruiter touchpoint to the final offer stage. Use this to plan your preparation; ensure your high-level stories are ready for the early screens, and reserve your deep-dive technical and behavioral prep for the onsite loop. Be aware that scheduling gaps may occur between stages.

4. Deep Dive into Evaluation Areas

To succeed, you must prepare detailed examples and strategies for the following key evaluation areas.

People Management & Team Building

This is the core of the interview. You must demonstrate that you can build and sustain high-performing teams. Be ready to go over:

• Conflict Resolution – How you handle disagreements between engineers or between engineering and product.
• Performance Management – Specific examples of how you have managed underperformers and how you have accelerated high achievers.
• Hiring & Retention – Your philosophy on recruiting and how you keep engineers engaged in a competitive market.

Example questions or scenarios:

• "Tell me about a time you had to manage a low-performing engineer. What was the outcome?"
• "How do you handle a situation where two senior engineers disagree on an architectural approach?"
• "Describe your approach to 1:1s and career development planning."

Project Management & Execution

Castlight needs managers who can ship software reliably. You will be tested on your ability to manage chaos and deliver value. Be ready to go over:

• Agile Methodologies – How you run sprints, handle retro items, and adapt processes to fit the team.
• Stakeholder Management – How you say "no" to feature creep and how you communicate delays to leadership.
• Prioritization – How you balance roadmap features against technical debt and maintenance work.

Example questions or scenarios:

• "Tell me about a project that was behind schedule. How did you handle it?"
• "How do you ensure your team maintains a healthy work-life balance while meeting tight deadlines?"
• "Describe a time you had to influence a product roadmap based on technical constraints."

Technical Judgment & System Design

Even as a manager, you are a technical leader. You need to show you can guide the "how" without dictating it. Be ready to go over:

• System Architecture – High-level design of scalable web applications and data pipelines.
• Technical Debt – Strategies for identifying, tracking, and paying down debt.
• Quality Assurance – Your approach to testing, CI/CD, and production monitoring.

Example questions or scenarios:

• "How would you design a system to handle secure health records at scale?"
• "How do you decide when to adopt a new technology versus using an established one?"
• "Walk me through a major technical failure your team experienced and how you handled the post-mortem."

5. Key Responsibilities

As an Engineering Manager at Castlight, your day-to-day work balances immediate tactical needs with long-term strategic planning. You are responsible for the delivery and quality of your team's software. This involves active participation in sprint planning, stand-ups, and retrospectives, ensuring that the team has clarity on what needs to be built and why.

Collaboration is a massive part of the role. You will work constantly with Product Managers to define requirements and with Designers to ensure technical feasibility. You act as a shield for your team, protecting their focus time from external distractions while ensuring that the business remains informed about progress and risks.

Beyond delivery, you are responsible for the "people" side of the equation. This includes conducting weekly 1:1s, writing performance reviews, and driving recruitment efforts to grow the team. You are also expected to foster a culture of engineering excellence, encouraging code reviews, documentation, and knowledge sharing across the broader engineering organization.

6. Role Requirements & Qualifications

Candidates for this role generally need a blend of hands-on technical roots and proven management experience.

• Must-have skills

  • Management Experience: Typically 2+ years of direct people management experience (hiring, firing, performance reviews).
  • Technical Background: A solid background in software engineering (Java, Python, Ruby, or modern frontend frameworks like React) is essential to understand the stack.
  • Agile Fluency: Deep understanding of Agile/Scrum development processes and tools (Jira, Confluence).
  • Communication: Exceptional verbal and written communication skills to bridge the gap between technical and non-technical stakeholders.

• Nice-to-have skills

  • Healthcare Domain: Experience working with HIPAA-compliant data or in the health-tech space is a strong differentiator.
  • Cloud Experience: Familiarity with AWS or other cloud infrastructure platforms.
  • Scale: Experience managing teams in a high-growth or enterprise SaaS environment.

7. Common Interview Questions

The following questions are representative of what you might face. They are not a script, but rather a guide to the types of conversations you will have. Castlight interviews tend to focus heavily on behavioral patterns and situational judgment.

Behavioral & Leadership

• "Why do you want to work at Castlight, and why specifically in the healthcare space?"
• "Tell me about a time you made a mistake as a manager. How did you fix it?"
• "How do you keep your team motivated during periods of high pressure or ambiguity?"
• "Describe a time you had to deliver bad news to your team."
• "What is your philosophy on remote work and team cohesion?"

Situational & Process

• "If a Product Manager pushes for a feature that will introduce significant technical debt, how do you handle it?"
• "Your team is missing a deadline next week. What do you do right now?"
• "How do you onboard a new engineer to ensure they are productive quickly?"
• "Describe how you would improve the deployment process for a legacy application."

Technical Context

• "How do you evaluate the technical trade-offs of a distributed system?"
• "What metrics do you use to measure the health of your engineering team?"
• "Explain a complex technical concept to me as if I were a non-technical stakeholder."

8. Frequently Asked Questions

Q: How difficult is the interview process? Most candidates describe the difficulty as "Easy" to "Medium." The challenge often lies less in complex coding algorithms and more in articulating your management style and cultural alignment clearly.

Q: How long does the process take? The timeline can vary. Some candidates report a streamlined process, while others have experienced delays of several weeks between steps. It is important to ask your recruiter for a clear timeline upfront.

Q: Is this a hands-on coding role? Generally, no. While you need to be technically literate to guide the team, the Engineering Manager role at Castlight focuses on people and project management. You are not typically expected to write production code.

Q: What is the work culture like? The culture is often described as collaborative and mission-driven, with "bright" colleagues. The environment values open communication, though candidates should be prepared for the fast pace and occasional ambiguity typical of the tech sector.

Q: Is the role remote? Castlight has embraced flexible work arrangements. Many engineering roles are remote-friendly, but this should be confirmed with the recruiter for your specific team.

9. Other General Tips

• Clarify Compensation Early: Ensure you and the recruiter are aligned on salary expectations early in the process. This prevents misalignment at the offer stage, which has historically been a pain point for some candidates.
• Be Proactive with Communication: If you haven't heard back after a round, follow up professionally. The recruiting process can sometimes be disjointed, and showing initiative demonstrates your interest and management capability.
• Focus on the "Why": Castlight is mission-driven. When answering questions, connect your technical or management decisions back to the ultimate goal: improving healthcare for users.
• Prepare Your "Manager README": Have a clear, concise explanation of your management style ready. Know your strengths, your weaknesses, and how you like to work. Authenticity here is key.
• Ask Insightful Questions: In your interviews, ask about the team's current challenges, the roadmap, and the engineering culture. This shows you are evaluating them as much as they are evaluating you.

10. Summary & Next Steps

Becoming an Engineering Manager at Castlight is an opportunity to lead in a sector that desperately needs innovation. You will be tasked with solving difficult problems that have a tangible impact on people's lives. The role demands a balance of technical competence, emotional intelligence, and operational rigor.

To succeed, focus your preparation on your leadership stories. Be ready to discuss how you build teams, how you deliver software, and how you navigate the complexities of an organization. While the interview process may test your patience, staying organized and proactive will set you apart from other candidates.

The compensation data above provides a baseline for the role. Use this to inform your negotiations, keeping in mind that total compensation often includes equity components which can be significant in a public company environment.

You have the experience and the skills to succeed in this process. approach the interviews with confidence, clarity, and a focus on the value you bring to the team. For more insights and community-driven data, continue exploring Dataford. Good luck!