What is a UX/UI Designer at Castlight?

As a UX/UI Designer at Castlight, you are at the forefront of transforming how people navigate their healthcare and wellbeing. Healthcare is notoriously complex, fragmented, and frustrating for the average consumer. Your primary mission is to distill this complexity into intuitive, accessible, and engaging digital experiences that empower users to make informed decisions about their care and benefits.

The impact of this position is profound. You are not just designing interfaces; you are shaping journeys that directly affect users' health outcomes and financial wellbeing. You will collaborate closely with product managers, engineers, and clinical experts to build features that span care routing, cost transparency, and personalized health recommendations. The scale of Castlight means your designs will touch millions of lives, requiring a delicate balance of empathy, accessibility, and high-performance product design.

This role is critical because the success of the Castlight platform relies heavily on user trust and adoption. You can expect to tackle highly ambiguous problem spaces where data privacy, regulatory constraints, and user anxiety intersect. A successful UX/UI Designer here is a strategic thinker who thrives in a fast-paced environment and possesses the resilience to advocate for the user across a diverse, cross-functional organization.

Common Interview Questions

The questions you face during your Castlight interviews will test your ability to think on your feet, reflect on your past experiences, and articulate your design philosophy. While you should not memorize answers, reviewing these patterns will help you structure your thoughts effectively.

Portfolio and Past Work

This category tests your ability to concisely present your previous projects and explain the rationale behind your design decisions.

• Walk me through a project in your portfolio that you are most proud of.
• What was your specific role and contribution to this project?
• Can you show me an example of a project that failed or didn't go as planned, and explain what you learned?
• How did you arrive at this specific visual design direction?
• Explain how you handed this project off to engineering.

Product Thinking and Process

These questions evaluate how you approach problem-solving, user research, and complex workflows.

• How do you balance user needs with business goals when they conflict?
• Describe your process for simplifying a highly complex workflow.
• How do you incorporate quantitative data and qualitative research into your design process?
• If you were asked to design a new feature for finding a primary care physician, where would you start?
• How do you know when a design is "done" and ready to ship?

Behavioral and Team Dynamics

This category assesses your cultural fit, adaptability, and how you collaborate with cross-functional partners.

• Tell me about a time you had to influence a stakeholder who was resistant to your design ideas.
• Describe a situation where you had to work with an ambiguous or poorly defined product requirement.
• How do you handle receiving critical feedback on a design you feel strongly about?
• Tell me about a time you had to step up and lead a project outside of your normal responsibilities.
• How do you ensure alignment when working with team members who have different priorities?

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Getting Ready for Your Interviews

Preparing for a design interview at Castlight requires a strategic approach to how you communicate your value. The team evaluates candidates across a few core dimensions, and understanding these will help you tailor your portfolio and responses.

Design Craft and Execution – This evaluates your hard skills in interaction design, visual design, and prototyping. Interviewers want to see that you can deliver polished, high-fidelity interfaces while understanding the underlying systemic patterns required for a cohesive platform. You can demonstrate this by showcasing end-to-end case studies that highlight your final deliverables alongside your iterative process.

Product Thinking and Problem Solving – This assesses how you approach complex, ambiguous challenges. At Castlight, you must understand the business goals and user needs before pushing pixels. You can show strength here by explaining the "why" behind your design decisions, discussing how you measure success, and detailing how you pivot when faced with technical or business constraints.

Communication and Stakeholder Management – This measures your ability to articulate design rationale and collaborate across disciplines. Because team structures can be fluid and highly cross-functional, you need to prove you can align diverse stakeholders. Demonstrate this by sharing stories of how you handled conflicting feedback, advocated for the user, and partnered effectively with engineering and product management.

Interview Process Overview

The interview process for a UX/UI Designer at Castlight is unique and requires specific preparation to navigate successfully. The timeline can sometimes be uneven; you may experience a waiting period after your initial application, but once the recruiting team engages, the process moves incredibly fast. After an initial recruiter phone screen, the team typically schedules the main interview loop within a week.

What makes this process distinctive is the structure of the final loop. Rather than a few long, deep-dive sessions, you will likely face a rapid-fire series of up to six 30-minute interviews. This high-density format means the pace is brisk, and you will meet with a variety of cross-functional partners, including other designers, product managers, and engineers. Because the sessions are short, you must be highly concise. You will likely find yourself repeating your core introduction to different interviewers, so having a tight, compelling elevator pitch is essential.

Furthermore, the fast pace means you will have to actively manage your time in each 30-minute slot. You must balance showcasing your portfolio and answering behavioral questions with leaving enough time to ask your own questions about the company and team structure.

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This visual timeline breaks down the typical progression from the initial recruiter screen through the rapid-fire onsite loop. Use this to anticipate the pacing of your interviews and prepare your energy for a day of quick, back-to-back conversations. Understanding this flow ensures you can tailor your portfolio presentations to fit strictly within the shorter time constraints of each round.

Deep Dive into Evaluation Areas

To succeed in the Castlight interview loop, you need to understand exactly what each rapid-fire session is designed to uncover. Below are the primary evaluation areas you will encounter.

Portfolio Presentation and Storytelling

Because your interview slots are only 30 minutes long, your portfolio presentation must be incredibly focused. Interviewers are looking for your ability to tell a compelling story about your work without getting bogged down in unnecessary details. They want to see your end-to-end process, but they prioritize the impact and the rationale behind your decisions.

Be ready to go over:

• Problem Definition – Clearly articulating the user and business problem you were solving.
• Iterative Process – Showing how you moved from low-fidelity concepts to high-fidelity execution, including how you incorporated feedback.
• Impact and Metrics – Discussing how you measured the success of your design and what you learned post-launch.
• Advanced concepts (less common) – Navigating strict regulatory constraints (like HIPAA) during the design process, or building and scaling a design system from scratch.

Example questions or scenarios:

• "Walk me through a project where you had to balance a complex user need with a strict technical constraint."
• "How did you measure the success of this specific feature after it launched?"
• "If you had more time on this project, what would you have done differently?"

Product Thinking and User Centricity

Castlight operates in the complex healthcare space, so interviewers need to know you can untangle convoluted workflows. This area evaluates your ability to think beyond the interface and understand the broader ecosystem. Strong performance here means demonstrating empathy for users who might be stressed, confused, or navigating sensitive health issues.

Be ready to go over:

• User Empathy – How you advocate for the user in a data-heavy, complex domain.
• Information Architecture – Your approach to organizing dense information so it is easily digestible.
• Trade-offs – How you prioritize features when resources are limited.

Example questions or scenarios:

• "How would you design a feature that helps a user understand a surprise medical bill?"
• "Tell me about a time you had to push back on a product requirement because it compromised the user experience."
• "How do you validate your design assumptions before moving into high-fidelity prototyping?"

Cross-Functional Collaboration and Adaptability

The organizational structure at Castlight can be highly collaborative and sometimes decentralized. Interviewers will probe how you handle ambiguity, differing opinions, and shifting team dynamics. They want to ensure you can drive design initiatives forward even if reporting lines or decision-making frameworks are complex.

Be ready to go over:

• Stakeholder Alignment – Techniques you use to get buy-in from product and engineering.
• Handling Ambiguity – How you operate when the product vision or team structure is not perfectly defined.
• Feedback Loop – How you give, receive, and implement constructive critique.

Example questions or scenarios:

• "Describe a time when you and a product manager strongly disagreed on a design direction. How did you resolve it?"
• "How do you ensure your designs are implemented accurately by the engineering team?"
• "Tell me about a time you had to take ownership of a project with very little initial guidance."

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Key Responsibilities

As a UX/UI Designer at Castlight, your day-to-day work will revolve around translating complex healthcare data into seamless digital experiences. You will be responsible for leading the design lifecycle for specific product features, starting from initial discovery and wireframing all the way through to high-fidelity prototyping and engineering handoff. You will frequently use tools like Figma to create responsive designs that work flawlessly across both mobile and web platforms.

Collaboration is a massive part of your daily routine. You will partner closely with product managers to define requirements and with engineers to ensure technical feasibility. Because healthcare is a nuanced domain, you will also interact with subject matter experts to ensure your designs are clinically accurate and compliant with industry regulations.

Beyond individual contributor work, you will play a role in maintaining and evolving the Castlight design system. You will participate in regular design critiques, providing feedback to peers and defending your own design choices. Your overarching responsibility is to be the relentless advocate for the user, ensuring that every interface simplifies the healthcare journey rather than adding to its complexity.

Role Requirements & Qualifications

To be a competitive candidate for the UX/UI Designer role at Castlight, you must demonstrate a blend of strong technical craft and exceptional soft skills. The team looks for designers who are self-starters and can navigate the intricacies of a complex product ecosystem.

• Must-have skills – A strong portfolio demonstrating end-to-end product design, high proficiency in modern design tools (Figma), deep understanding of user-centered design principles, and experience designing for both mobile and web platforms.
• Must-have experience – Typically 3+ years of experience in UX/UI or product design, with a proven track record of shipping digital products in an agile environment.
• Soft skills – Exceptional communication skills, the ability to articulate design rationale clearly, strong stakeholder management, and a high tolerance for ambiguity.
• Nice-to-have skills – Prior experience in healthcare, healthtech, or other highly regulated industries (like fintech). Experience contributing to or managing a centralized design system.

Frequently Asked Questions

Q: How long does the interview process typically take? The timeline can vary. You might experience a quiet period of a few weeks after applying, but once the initial phone screen happens, Castlight tends to move very quickly. The onsite loop is often scheduled within a week of the screen.

Q: How should I handle the 30-minute interview format? Be incredibly concise. With only 30 minutes, you do not have time for long, winding stories. Prepare a sharp 2-minute introduction and use the STAR method (Situation, Task, Action, Result) to keep your behavioral answers tight and impactful.

Q: Will I meet with a UX Director or central design leader? Team structures at Castlight can be fluid, and you may be interviewed by a mix of peers, product managers, and cross-functional leads rather than a single UX Director. Treat every interviewer as a key decision-maker and tailor your conversation to their specific role.

Q: What is the most common reason candidates fail the onsite loop? Candidates often struggle with time management during the short sessions, failing to get through their portfolio presentations. Others struggle to clearly articulate why they made certain design decisions, focusing too much on the final visuals rather than the strategic process.

Q: Do I need healthcare experience to get hired? While prior experience in healthtech or a similarly complex, regulated industry is a strong nice-to-have, it is not strictly required. Demonstrating that you can simplify complex data and workflows in any domain will make you a strong candidate.

Other General Tips

• Master the 2-Minute Pitch: Because you will face multiple short interviews, you will likely be asked "Tell me about yourself" several times. Craft a compelling, 2-minute pitch that highlights your experience, your design philosophy, and why you want to work at Castlight.
• Clarify Roles Early: If an interviewer's title or role seems unclear, politely ask them to clarify how they interact with the design team early in the session. This helps you tailor your answers to their perspective (e.g., focusing on implementation for an engineer, or business metrics for a PM).

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• Focus on the "Why": Whenever you present a design, proactively explain the constraints you faced and why you chose your specific solution over alternatives. Castlight values designers who are intentional and strategic.
• Drive the Conversation: In a 30-minute window, passive candidates get left behind. Confidently guide the interviewer through your portfolio, keeping an eye on the clock, and pause frequently to ensure they are following your narrative.

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• Follow Up Proactively: Communication can sometimes lag after the final loop. Send concise thank-you notes to your interviewers, but also maintain proactive communication with your recruiter to check on next steps and timelines.

Summary & Next Steps

Securing a UX/UI Designer role at Castlight is a unique opportunity to tackle meaningful, complex problems that directly impact people's health and financial wellbeing. The role demands a designer who is not only highly skilled in their craft but also resilient, communicative, and capable of navigating a fast-paced, cross-functional environment.

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This compensation data provides a baseline for what you can expect in this role. Use these insights to understand the market rate and structure your expectations, keeping in mind that total compensation often includes equity and benefits alongside the base salary.

To succeed in this interview process, your preparation must focus on clarity and brevity. The rapid-fire nature of the 30-minute interview loop means you must know your portfolio inside and out, ready to deliver high-impact stories at a moment's notice. Focus on demonstrating your ability to simplify complexity, collaborate effectively with diverse stakeholders, and advocate fiercely for the user.

You have the skills and the experience to excel in this process. By anticipating the structure, refining your narratives, and approaching each conversation with confidence, you can prove that you are the right designer to help shape the future of healthcare navigation. For further insights and community-driven preparation tools, continue exploring resources on Dataford. Good luck—you are ready for this!