Overall, the interview process at Thoughtful.ai was disappointing. It spanned about a month and involved five steps. Unfortunately, I was not selected to move forward after the fourth interview with the CXO. The first three interviews went really well. The process started with a 30-minute phone screen, followed by a coding interview, and then an interview with the Forward Deployment lead. I felt confident in all three and had great rapport with the interviewers. Going into the fourth interview, a brief 15-minute conversation with the CXO, I was hopeful. Especially since, prior to the meeting, they reached out to confirm my base salary—something that made me think this interview might just be a formality or introduction. Still, I didn’t want to assume anything. I thoroughly prepared by researching the company’s “warrior culture,” listening to podcasts and interviews with the CXO and CEO, and reviewing common questions asked at this stage. During the interview, the CXO asked only two or three basic questions before turning it over to me to ask mine. The 15 minutes flew by. At the end, he said, “We’ll reach out to you by the end of the week regarding next steps.” Four days later, I received a generic rejection email. The CXO interview wasn’t a home run, but I also don’t believe it went poorly. I had already passed three interviews, so I assumed that would count for something. If the CXO interview carries that much weight, I wish they would have given me more time to speak and showcase myself. I was truly disappointed by the rejection. After a month of investing my time and energy, I received only a vague response: “We’ve decided to move forward with other candidates.” I later saw that they were hiring multiple Forward Deployed Engineers and continued to post listings on LinkedIn. This rejection felt different. I have a background in healthcare AI development and direct customer-facing experience, so I believed I was a great fit. I wasn’t ready to take no for an answer. I reached out to both HR and the CXO on LinkedIn. I managed to secure a follow-up video meeting with HR to discuss my experience and shared a letter I’d written to express my thoughts. During that meeting, HR said the only reason I wasn’t selected was because I “lacked polish.” They also mentioned that the CXO interview has the highest drop-off rate. I read my letter during the meeting, and it seemed to resonate. HR said they would speak with the CXO and explore whether a second meeting or reconsideration was possible. It’s now been two weeks since that conversation, and I haven’t heard anything back. I’ve followed up with emails, but received no response—just silence. I still believe I have what it takes to succeed at Thoughtful.ai. Unfortunately, they didn’t see the same potential. If you’re preparing for their interview process, just know that it’s a lengthy journey. The interviews themselves aren’t overly difficult, and everyone I spoke with was genuinely kind. I hope your experience turns out better than mine. Good luck.