1. What is a Product Manager?

At Castlight, the role of a Product Manager is pivotal to our mission of helping people navigate the complex world of healthcare. You are not just building software; you are creating the bridge between confusing benefits systems and the employees who need to access them. This role sits at the intersection of user experience, data complexity, and healthcare strategy.

As a PM here, you will drive the roadmap for products that empower users to make better health, financial, and wellness decisions. You will work within a B2B2C model, meaning you must satisfy the strategic needs of large enterprise clients while delivering a seamless, consumer-grade experience for individual users. The work involves high-stakes problem solving, as your product decisions directly impact how users access care and manage their health costs.

Successful Product Managers at Castlight are comfortable navigating ambiguity and regulatory constraints. You will collaborate deeply with engineering, design, and clinical teams to translate intricate healthcare data into simple, actionable insights. If you are passionate about fixing a broken healthcare system through technology and engagement, this role offers a platform to make a tangible difference at scale.

2. Getting Ready for Your Interviews

Preparing for an interview at Castlight requires a shift in mindset. You need to demonstrate not only standard product management excellence but also an ability to handle the specific nuances of the health-tech space. Approach your preparation with a focus on structure and empathy.

Your interviewers will evaluate you against these core criteria:

• Product Sense & User Empathy – How well can you identify user pain points in a complex ecosystem? We look for candidates who can simplify the user journey without losing the necessary detail required in healthcare.
• Structured Problem Solving – You will face "consulting-style" cases. We evaluate your ability to break down vague problems into logical components, drive toward a solution using data, and defend your assumptions.
• Execution & Rigor – Can you get things done? We look for a history of shipping products. You must be able to discuss your past work in concrete detail, dating back to the earliest stages of your career.
• Communication & Presence – Whether presenting to a hiring manager or a panel, you must be able to articulate your ideas clearly. We value candidates who can handle probing questions with composure and clarity.

3. Interview Process Overview

The interview process at Castlight is thorough and designed to test both your functional skills and your cultural alignment. While the timeline can vary, you should expect a multi-stage process that increases in depth at every step. Generally, the process begins with a recruiter screen, followed by a conversation with the hiring manager, and culminates in a comprehensive onsite loop.

Expect the process to be rigorous. Past candidates have noted that the onsite stage can be lengthy, sometimes involving a full day of back-to-back sessions. The interviewing team often includes a mix of peers, cross-functional partners, and leadership (from Directors to VPs). The philosophy here is to assess how you think on your feet; you will likely encounter unstructured case questions and be asked to dive deep into your past experiences.

A distinct element of our process for Product Managers is the presentation round. You may be asked to prepare a project or case study presentation. This is your opportunity to showcase your strategic thinking and ability to handle ambiguity. Be prepared for a process that demands patience; timelines can sometimes extend up to several weeks depending on team availability.

This timeline illustrates the typical flow from application to offer. Note that the Project/Presentation stage is often the "make or break" moment. Use the time between the Hiring Manager screen and the Onsite to deeply research our product suite and the current healthcare landscape, as this context will be critical for your presentation.

4. Deep Dive into Evaluation Areas

To succeed, you must excel in specific evaluation areas that our interviewers prioritize. We use a combination of behavioral questions and case studies to build a holistic view of your capabilities.

Product Strategy & Design

This area tests your ability to build the "right" thing. In the healthcare space, this means balancing user desires with clinical accuracy and client requirements.

• Identifying User Needs: How do you discover what users actually need versus what they say they need?
• Prioritization: How do you decide what to build next when resources are limited?
• Healthcare Context: While deep domain expertise isn't always mandatory, showing an aptitude for understanding the healthcare ecosystem is critical.

Analytical & Case Problem Solving

Candidates frequently report facing consulting-style cases. These are unstructured problems designed to test your logic.

• Market Sizing/Estimation: Be ready to estimate market opportunities or usage metrics on the fly.
• Root Cause Analysis: If a metric drops, how do you investigate it?
• Framework Application: Do not just guess; use frameworks to structure your answers (e.g., Porter’s 5 Forces, CIRCLES method) but adapt them to the specific context.

The Presentation Round

If you reach the onsite, you will likely present a project. This prompt may be intentionally broad to test how you deal with ambiguity.

• Clarity of Thought: Can you take a vague prompt and turn it into a concrete proposal?
• Defense of Ideas: Expect probing questions. Interviewers will challenge your assumptions to see if you crumble or if you can defend your logic with data.
• Communication Style: Your ability to engage the room and manage time is just as important as the content of your slides.

The word cloud above highlights the most frequent themes in our interviews. Notice the emphasis on Metrics, Strategy, Prioritization, and Stakeholders. This indicates that while "building features" is important, understanding the business impact and managing relationships are equally weighted in our evaluation.

5. Key Responsibilities

As a Product Manager at Castlight, your day-to-day work is dynamic. You are the central hub for your product area, responsible for the entire lifecycle from ideation to launch and iteration.

You will spend a significant amount of time collaborating with engineering and design. You are expected to write clear, concise requirements and user stories, often translating complex benefits logic into engineering tasks. You will also work closely with the Customer Success and Sales teams to understand the needs of our large enterprise clients, ensuring that our roadmap aligns with market demands without becoming a "feature factory."

Data analysis is another daily responsibility. You will monitor product engagement metrics to understand how employees are using the platform. whether they are searching for a doctor or comparing procedure costs. You will use this data to drive continuous improvement, ensuring that we are actually driving down healthcare costs and improving outcomes for our users.

6. Role Requirements & Qualifications

We are looking for candidates who combine technical fluency with strong business acumen.

• Must-Have Skills:

  • Product Lifecycle Management: Proven experience (typically 3+ years) managing products from concept to launch.
  • Data Fluency: Comfort with analytics tools and the ability to make decisions based on quantitative data.
  • Stakeholder Management: Experience managing expectations across diverse groups (Engineering, Sales, Marketing).
  • Communication: Exceptional verbal and written skills; ability to explain complex technical or industry concepts simply.

• Nice-to-Have Skills:

  • Healthcare Experience: Background in health-tech, insurance, or benefits administration is a significant advantage.
  • B2B2C Experience: Experience building enterprise software that has a consumer-facing front end.
  • Technical Background: A degree in CS or engineering, or significant experience working with complex APIs and data integrations.

7. Common Interview Questions

The questions you will face are designed to reveal patterns in your thinking. While you cannot memorize answers, you can prepare for the types of questions we ask. We mix behavioral questions with hypothetical scenarios.

Behavioral & Experience

These questions dig into your past performance. Be prepared to provide concrete examples.

• "Tell me about a time you had to manage a difficult stakeholder. How did you handle the situation?"
• "Walk me through a product you launched from start to finish. What went wrong, and how did you fix it?"
• "Describe a time you used data to change a strategic decision."
• "How does your current work apply to the challenges we face at Castlight?"

Product Design & Strategy

These questions test your product sense.

• "How would you improve the experience of finding a doctor on our platform?"
• "Design a feature for a user who has just been diagnosed with a chronic condition."
• "How would you prioritize a roadmap if you had half the engineering resources you needed?"

Case & Analytical

Expect unstructured questions that require you to break down a problem.

• "Estimate the market size for a new telemedicine feature."
• "Engagement on our mobile app dropped 10% last week. How would you diagnose the cause?"
• "How would you monetize a new health tracking feature?"

These questions are based on real interview experiences from candidates who interviewed at this company. You can practice answering them interactively on Dataford to better prepare for your interview.

8. Frequently Asked Questions

Q: How long does the interview process take? The process can vary significantly. While some candidates move through in a few weeks, others have reported processes taking up to 8 weeks. We recommend maintaining proactive communication with your recruiter regarding timelines.

Q: Is the presentation prompt always the same? No. The prompt changes based on the specific team and the current challenges the business is facing. It is often intentionally open-ended to see how you define scope and success metrics.

Q: Do I need a healthcare background to apply? While a healthcare background is highly valued and helps shorten the learning curve, it is not strictly mandatory for all PM roles. If you do not have healthcare experience, you must demonstrate a strong ability to learn complex domains quickly.

Q: What is the culture like for the Product team? The culture is collaborative but intense. We are mission-driven, which means people care deeply about the work. Expect a fast-paced environment where you are empowered to make decisions, but also expected to back them up with logic and data.

9. Other General Tips

• Clarify Before You Solve: especially during the presentation or case study rounds. If a prompt feels vague, it is often a test. Ask clarifying questions to narrow the scope before you start building your solution.
• Know the Product: Download the app or research our demos extensively. Understanding the difference between our navigation, wellbeing, and care guidance products will set you apart from generalist candidates.
• Be Ready for "Probing": Our interviewers, particularly senior leaders, are known to ask follow-up questions that challenge your initial answer. Do not take this personally; it is a stress test for your conviction and logic. Remain calm and walk them through your thinking.
• Follow Up Proactively: Given that the process involves many stakeholders, there can sometimes be gaps in communication. A professional, polite follow-up email to your recruiter is encouraged if you haven't heard back in a week.

10. Summary & Next Steps

Becoming a Product Manager at Castlight is an opportunity to work on problems that matter. You will be challenged to think critically, act strategically, and execute relentlessly. The interview process is rigorous because the work is demanding, but for the right candidate, it is incredibly rewarding.

Use the salary data above to understand the compensation landscape for this role. Remember that total compensation often includes equity, which is a key part of our long-term value proposition.

To succeed, focus your preparation on structured thinking, healthcare empathy, and concrete storytelling. Review your past experiences and identify the specific moments where you drove impact. Walk into your interviews ready to engage in a two-way conversation about the future of healthcare. We look forward to seeing what you can bring to the team.