I recently completed a 2.5-month interview process at Sentry Insurance for a Software Engineering Manager role. The process involved five rounds beyond the recruiter screen, including interviews with the CTO, AVP of Commercial IT, and multiple directors. I was also considered for multiple open roles throughout the process, which made it seem like a promising opportunity. During that time, I was asked to travel on-site three separate times, each requiring a four-hour round trip, which I committed to with genuine enthusiasm. The conversations were engaging, and I appreciated the transparency from individual interviewers. However, after each round, I found myself needing to follow up with the recruiter multiple times just to get updates on next steps. This lack of proactive communication contributed to the sense of being kept on the hook rather than moving efficiently through a structured process. The way the process ended was also surprising and disappointing. After months of engagement and multiple high-level discussions, I received an automated system email informing me that Sentry had chosen to pursue other candidates, with a note that I could call HR for feedback. For a process that involved senior leadership and multiple on-site visits, this felt impersonal and unprofessional. The feedback given was that some of my answers were “lengthy” and that interviewers didn’t get to ask all of their questions—a valid critique if it had been surfaced earlier, but at the end of five rounds, it felt more like an excuse. If this was genuinely a concern, it should have been addressed in early rounds, allowing me to adjust and improve. Instead, I left each stage believing I was on track. Moreover, several questions were repeated across rounds, even by the same interviewers on different panels. I answered consistently and referenced my previous responses, but it gave the impression that my presence was more for optics than genuine consideration. One interview was also reformatted last minute from two planned 1:1 sessions to a combined panel, reducing the time each interviewer had—yet this time constraint was later part of the feedback. Finally, the role was reposted just weeks after my rejection, which raises questions about whether my candidacy was ever genuinely considered or if I was kept in the loop to broaden the candidate pool. Pros: -Insightful conversations with leadership -Strong culture messaging and impressive facilities -Initial recruiter communication was clear Cons: -Lengthy 2.5-month process ended with only an automated rejection email -Multiple follow-ups required to get updates after each round -Feedback at the end felt misaligned with the stage of the process -Repetitive questions across interviewers, signaling a lack of coordination -No real-time feedback to help adjust or improve after early rounds -Role was reposted within weeks, suggesting earlier decisions were not definitive Advice to Management: If candidates are going through five rounds and on-site visits with senior leadership, there should be transparency and clarity in feedback much earlier. If interview performance is not meeting expectations, candidates deserve to know in the initial rounds, not after months of interviews. Additionally, if candidates are being considered just to widen the pool, it’s important to recognize that their time and investment matter too. More thoughtful screening at the beginning could have saved time for both sides. Lastly, relying on automated rejections after such an involved process reflects poorly on the candidate experience.