Be ready to go over:

• Technical Decision Making – Explaining the "why" behind your choice of tools, data models, or analytical methodologies in past roles.
• Handling Stakeholder Pushback – Demonstrating how you navigate disagreements with product managers or operations leads regarding data interpretations.
• Translating Tech to Business – Showing your ability to simplify highly technical concepts for non-technical audiences.

Example scenarios:

• "Walk me through a complex analysis you delivered. Why did you choose that specific methodology, and what would you do differently today?"
• "Describe a time when a product manager wanted to launch a feature but your data suggested it wasn't ready. How did you handle the conversation?"

As a Data Analyst at Headway, your day-to-day work will be highly dynamic and deeply integrated with the broader business operations. You will not operate in an analytical silo; instead, you will act as a strategic partner to product managers, engineers, and operations leads.

Your primary responsibility will be to own the data lifecycle for your assigned domain. This includes writing dbt models to clean and structure raw data, building intuitive Looker dashboards to democratize data access, and conducting deep-dive analyses to uncover growth opportunities. You will help the team understand marketplace liquidity, patient acquisition costs, and insurance claim success rates.

Additionally, you will play a key role in product experimentation. You will collaborate with product managers to design A/B tests, define success metrics, and analyze results to determine whether new features should be shipped, iterated on, or scrapped. Your insights will directly influence the product roadmap and help ensure that Headway scales its infrastructure efficiently.

To be competitive for the Data Analyst position at Headway, you must possess a strong foundation in data analytics, combined with excellent communication skills and a passion for solving complex, unstructured problems.

• Must-have technical skills – Advanced SQL proficiency (CTEs, window functions, query optimization), experience with modern business intelligence tools (such as Looker or Tableau), and familiarity with data warehousing concepts (such as Snowflake or Redshift).
• Must-have soft skills – Exceptional structured communication, the ability to collaborate with cross-functional stakeholders, and a resilient attitude when receiving technical feedback.
• Nice-to-have skills – Experience using dbt (data build tool) for data modeling, basic proficiency in Python or R for advanced statistical analysis, and prior experience working in a double-sided marketplace or within the healthcare/health-tech sector.
• Experience level – Typically, candidates should have at least 2 to 5 years of experience in a dedicated data analytics or product analytics role.

Q: How technical is the SQL assessment? A: The SQL assessment is highly practical and focuses on your ability to solve real-world analytical problems under time constraints. You do not need to memorize obscure syntax, but you must be incredibly comfortable with window functions, complex joins, and aggregations.

Q: What is the company culture like for the data team? A: The data team at Headway is highly collaborative, supportive, and mission-driven. They place a strong emphasis on transparency and continuous learning, though they also maintain high standards for technical execution and logical rigor.

Q: How long does the entire interview process take? A: The process typically takes between three to five weeks from the initial recruiter screen to the final decision. Headway is generally responsive and moves candidates through the stages quickly if they meet the evaluation benchmarks.

Q: Are the interviews conducted remotely? A: Yes, the entire interview process is conducted virtually. You will need a reliable internet connection, a quiet environment, and a working webcam for all video interviews.

• Understand the business model: Before your interviews, make sure you thoroughly understand how Headway operates as a double-sided marketplace that integrates with insurance providers. Be ready to discuss how this unique model impacts data tracking and analysis.
• Be structured in your case study: When walking through the case study, explicitly state your assumptions, outline your framework before diving into details, and tie your analytical recommendations back to Headway's core business objectives.
• Prepare your references early: Headway utilizes an exceptionally detailed and unique reference check stage later in the process. Keep your references informed and ready to provide deep insights into your working style and past performance.

• Practice active listening: In the cross-functional and behavioral interviews, listen carefully to the interviewer's questions and follow-up prompts. Do not get defensive if they critique your past projects; instead, treat it as a collaborative brainstorming session.

The Data Analyst role at Headway offers an incredible opportunity to leverage your analytical skills to solve meaningful, real-world challenges in the mental healthcare sector. By combining technical excellence in SQL with structured business intuition and a collaborative mindset, you can make a significant impact on how patients access affordable care.

As you prepare for your interviews, focus on mastering your technical fundamentals, refining your behavioral stories, and practicing structured problem-solving frameworks for the case study. Remember that the hiring team values clear communication and logical thinking just as much as clean code.

The salary insights above represent the competitive compensation packages offered by Headway for this role. Use this data to align your expectations and prepare for compensation discussions during the offer stage, keeping in mind that total compensation may also include equity and comprehensive benefits designed to support your overall well-being. For more detailed interview experiences and prep tools, explore the additional resources available on Dataford. Good luck with your preparation!