What is a Project Manager?

At Castlight, the Project Manager role is pivotal to the company’s mission of helping individuals navigate the complex healthcare system. You act as the strategic engine that drives client implementations, internal initiatives, and product rollouts. This position is not merely about tracking dates; it is about orchestrating cross-functional teams—including Engineering, Customer Success, and Product—to deliver seamless experiences for enterprise clients and their employees.

You will be responsible for managing the full lifecycle of projects, often focusing on the critical phase of onboarding new clients or integrating complex health benefits data. The impact of your work is direct and tangible: successful project management ensures that users gain access to their health benefits without friction. You will navigate the intricacies of healthcare data, manage stakeholder expectations, and translate high-level business goals into actionable execution plans.

This role requires a blend of rigor and adaptability. Castlight operates in a dynamic environment where regulatory requirements and client needs evolve. As a Project Manager, you are expected to bring order to ambiguity, ensuring that despite shifting priorities, the team remains focused on delivering value. It is a role for those who enjoy high-visibility work and thrive on solving logistical and interpersonal puzzles.

Getting Ready for Your Interviews

Preparation for the Castlight Project Manager interview requires a shift in mindset from general project management to specific, client-facing execution. You must demonstrate not just that you can manage a schedule, but that you can lead a team through the hurdles of a complex implementation.

Implementation Strategy – You must demonstrate the ability to take a high-level client request and break it down into a granular, executable timeline. Interviewers will look for your ability to identify critical path items, dependencies, and potential bottlenecks before they occur.

Stakeholder Communication – This is critical at Castlight. You will be evaluated on how you translate technical constraints to non-technical clients and business requirements to engineering teams. Clarity, conciseness, and the ability to manage expectations are paramount.

Presentation Skills – Expect to present your work. You will likely face a specific challenge where you must organize your thoughts into a slide deck. Interviewers assess your ability to synthesize information into a narrative that drives decision-making.

Adaptability and Resilience – The healthcare tech space moves fast, and priorities shift. You need to show that you can pivot quickly without losing momentum. Interviewers will look for evidence of how you handle scope creep, resource constraints, or sudden changes in project direction.

Interview Process Overview

The interview process for a Project Manager at Castlight is structured to test both your organizational competence and your ability to perform under pressure. Historically, the process can move quickly—sometimes concluding in under two weeks—though this depends heavily on team availability and the specific hiring cycle. You should expect a rigorous sequence that moves from behavioral screening to practical application.

After an initial recruiter screen to check your background and interest, you will typically proceed to a phone interview with a hiring manager or team lead. If you pass this stage, you will move to the "onsite" phase (which may be virtual). This final stage is intensive, often involving a panel of 3–4 interviewers, each spending roughly 45 minutes with you. The cornerstone of this stage is a presentation round, where you will be asked to prepare a case study—often a timeline for a new client implementation—and present it to the panel.

This timeline illustrates the progression from initial contact to the final decision. Note the heavy emphasis on the Onsite / Presentation phase. This is the most weight-bearing part of the process. You should use the time between the phone screen and the onsite to meticulously prepare your presentation materials, as this is often where the final hiring decision is made.

Deep Dive into Evaluation Areas

Your interviews will focus on specific competencies that define success at Castlight. Based on candidate experiences, the evaluation is heavily weighted toward practical execution and communication.

Implementation & Timeline Management

This is the core technical skill for the role. You are not just tracking tasks; you are designing the roadmap for success. Interviewers want to see that you understand the mechanics of a project launch from Day 1 to Go-Live.

Be ready to go over:

• Critical Path Analysis – How you identify tasks that directly impact the launch date.
• Dependency Management – How you handle technical dependencies (e.g., data feed integrations) that are outside your direct control.
• Status Reporting – Your specific method for keeping leadership and clients informed (e.g., RAG status reporting).

Example questions or scenarios:

• "Walk us through a timeline you developed for a complex client implementation."
• "How do you handle a situation where an engineering delay threatens the client's go-live date?"
• "Draft a high-level status slide for an executive update on a stalled project."

Client-Facing Communication

Castlight Project Managers often interface directly with external clients. You will be evaluated on your "executive presence" and your ability to deliver bad news constructively.

Be ready to go over:

• expectation Setting – How you prevent scope creep while maintaining a good client relationship.
• Crisis Communication – How you communicate errors or delays to unhappy stakeholders.
• Presentation Structure – The logic and flow of your slide decks.

Example questions or scenarios:

• "A client requests a feature that is not in the scope of the current implementation. How do you handle it?"
• "Present this project plan as if we are the client stakeholders."

Problem Solving in Ambiguity

Candidates have reported that interview questions can sometimes feel open-ended or "confusing." This is often intentional (or a reflection of the environment) to test your ability to drive clarity. You are expected to ask clarifying questions and structure the chaos.

Be ready to go over:

• Requirement Gathering – How you extract clear requirements from vague requests.
• Risk Mitigation – Proactively identifying what could go wrong.

Example questions or scenarios:

• "You are assigned a project with a fixed deadline but undefined scope. What are your first three steps?"
• "Tell me about a time you had to move forward with a project despite missing key information."

The word cloud above emphasizes terms like Timeline, Presentation, Client, and Implementation. This confirms that your preparation should be heavily focused on the practical aspects of rolling out a service to a client. Theoretical project management knowledge (like memorizing PMBOK definitions) is less valuable here than demonstrating you can build a realistic schedule and present it convincingly.

Key Responsibilities

As a Project Manager at Castlight, your day-to-day work revolves around structure and delivery. You will be the primary owner of project plans, responsible for creating detailed timelines that account for data ingestion, software configuration, and user acceptance testing. You will frequently utilize tools like Jira, Smartsheet, or Microsoft Project to maintain a "single source of truth" for project status.

Collaboration is constant. You will work closely with the Engineering team to understand technical blockers and with the Customer Success team to ensure the client’s voice is heard. A significant portion of your week will be spent in status meetings—both internal and external—where you will present progress, flag risks, and drive decisions. You are also responsible for the "unsexy" work of documentation, ensuring that meeting minutes, decision logs, and project artifacts are meticulously maintained.

Role Requirements & Qualifications

To be competitive for this role, you need a mix of hard project management skills and soft skills tailored to enterprise software.

• Must-have skills:

  • Experience with Client Implementations: Proven track record of launching software or services for external clients.
  • Presentation Proficiency: High comfort level creating decks (PowerPoint/Keynote) and presenting to groups.
  • Tool Mastery: Proficiency in project tracking software (Jira, Confluence, Smartsheet, or Asana).
  • Timeline Management: Ability to build Gantt charts and manage complex dependencies.

• Nice-to-have skills:

  • Healthcare Domain Knowledge: Familiarity with claims data, eligibility files, or benefits administration.
  • PMP or Agile Certification: While not always mandatory, these demonstrate a commitment to the profession.
  • Technical Fluency: Enough technical understanding to speak intelligently with engineers about API integrations or data feeds.

Common Interview Questions

The following questions reflect the patterns observed in Castlight interviews. They are not a script, but they represent the themes you must master.

Operational & Case Study

These questions test your ability to do the actual work.

• "Create a high-level timeline for the implementation of a new client, assuming a 3-month window."
• "What key milestones would you include in a status report for a project that is currently 'Yellow'?"
• "How do you estimate time for tasks when the team is unsure of the technical complexity?"

Behavioral & Leadership

These focus on how you work with others.

• "Tell me about a time you had to deliver bad news to a stakeholder. How did you approach it?"
• "Describe a situation where you had to influence a team member over whom you had no direct authority."
• "How do you handle a team member who consistently misses deadlines?"

Process & Methodology

• "How do you determine which project management methodology (Agile vs. Waterfall) to apply to a specific project?"
• "Walk me through your process for kick-starting a new project with a client."

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.

Frequently Asked Questions

Q: How difficult is the interview process? Most candidates rate the difficulty as Hard. The rigor comes primarily from the onsite presentation, which requires significant preparation time and the ability to think on your feet during the Q&A session.

Q: Is the presentation round always required? Yes, for Project Manager roles at Castlight, the presentation is a standard component. It is usually a take-home assignment where you are given a prompt (e.g., "Develop a timeline for a new client") and asked to present it during the onsite.

Q: What is the typical timeline from application to offer? The process can be quite fast, sometimes concluding in less than two weeks. However, be aware that there have been instances of delays or roles being put on hold. It is best to ask the recruiter for a timeline estimate upfront.

Q: Is this role remote or onsite? Castlight has a history of offering remote flexibility for this role, though some positions may be hub-based (e.g., San Francisco). Be sure to clarify the current policy for the specific team you are interviewing with.

Other General Tips

Clarify the Prompt Some candidates have reported that interview instructions can be vague. If you receive a presentation prompt that feels ambiguous, do not guess. Reach out to your recruiter for clarification or state your assumptions clearly at the beginning of your presentation. This demonstrates your proactive communication style.

Focus on the "Status Slide" When preparing your presentation, do not just build a Gantt chart. Include a "Status Summary" slide that an executive could read in 30 seconds. This shows you understand how to communicate upward, a key skill at Castlight.

Prepare for "Ghosting" Resilience While many candidates have a smooth process, some have reported gaps in communication. If you don't hear back within the expected window, send a professional, polite follow-up. Show that you are interested but continue your search elsewhere to manage your own anxiety.

Demonstrate Healthcare Empathy Even if you don't have a healthcare background, show that you understand the stakes. You are dealing with people's health benefits. Expressing empathy for the end-user in your answers can set you apart from candidates who treat it as "just another software project."

Summary & Next Steps

The Project Manager role at Castlight is an opportunity to work at the intersection of complex technology and human health. It is a demanding position that requires you to be a master of timelines, a skilled communicator, and a steady hand during chaotic implementations. The interview process is designed to verify these traits through a rigorous presentation round and behavioral panels.

To succeed, focus your preparation on practical application. Do not just talk about project management theory; show them how you build timelines, how you manage risks, and how you communicate status. Treat the presentation as your first deliverable for the company—make it polished, professional, and clear.

Review the compensation data to understand the market rate for this level of responsibility. With the right preparation and a focus on execution, you can demonstrate that you are the leader they need to drive their client success. Good luck.