Headway (NY) Interview Questions
& Process

The interview process was super organized and the recruiter was highly communicative and polite. It felt like a minor tech company trying to act like Big Tech. It was a very drawn-out process, super intense and impersonal. There were 6+ interview rounds conducted in a very robotic way by people who used to work at Big Tech companies. It will require rounds of presentations and a lot of prep. A lot of the questions were repeated. The questions were more in line with a senior role, not mid-level management. It was hard to get a feel for the role and work environment because of all the questions and required presentations. The interviewers mentioned an intense work environment with high expectations and a CEO who lacks real-world experience. The compensation package was not great, with no bonus or 401K match. They offer equity, but it's not a public company. Overall, it didn't inspire trust or strong interest in the company, and I wouldn't recommend it.

This is my second time applying for the PGA role, and I'm really disappointed. After multiple interview rounds and explaining my skills, I wasn't considered because I lack healthcare experience. It's confusing why I was even considered if that was the main issue from the start. It was also weird having three recruiters for one role, making it unclear who to contact. The interview process itself is fast, with responses usually within 24-48 hours. There are 4 rounds: a phone screen, a mock sales call, a behavioral interview, and a leadership interview. The whole thing should take about two weeks. They're apparently hiring a lot of PGAS in 2026, so it's good if you have healthcare experience. Honestly, it was a disappointing experience since I'm qualified. Save yourself the trouble if you don't have healthcare experience; they don't make that clear upfront, making you think they're open to it, but they're not. Very disappointing.

This was the most organized interview process I've been through. Each stage had clear expectations, and they sent materials ahead for the later stages to help with preparation. Feedback was always super fast. My specific process for a staff level role included: A recruiter screen, then a hiring manager screen. After that was a panel interview split into two parts: the first half focused on behavioral questions and a collaborative session where we worked on improving a draft PRD they sent beforehand (I'd recommend marking it up before, but you could also just talk through it live). The second half of the panel was technical, and I had to present on my previous work. After that, they were really trying to sell me on the company, which was a refreshing change from other places where it felt like I was still being evaluated in the final conversations. I got to meet two people in person because I was in NYC, but there was no pressure to do so.

The interview process was well-thought-out and organized. It started with a recruiter call about my background and why I was interested. Then there were several conversations that mixed clinical and product topics. After that, I had a take-home case study that was interesting and made me think about patient safety, product design, and scaling operations. The panel discussion afterwards felt collaborative and people were curious about how I thought. Later, I spoke with senior clinical and product leaders, including the CMO and VP of Strategy & Operations. All these talks were fast and made me think, and were connected to the company's mission to improve mental healthcare access and quality. They were clear about what they expected, careful about role fit, and really wanted people who shared their values. The whole thing took about 4-5 weeks from the first contact to the offer.