I applied for the product manager position in late May and was contacted by a recruiter in late July to schedule a screening call. The process progressed to a hiring manager round in early September, followed by a comprehensive onsite interview—including engineering, design, strategy & metrics, a final presentation, and discussions about aspirations and work style—in late September. Between each stage, there were extended periods without communication, which made the process feel uncertain. I went through a total of eight conversations with various stakeholders. During one of the technical interviews, I explained the Medallion Architecture used in the data pipeline at my previous company. After my detailed explanation, the interviewer said, 'Thank you for the background—so what's the system design architecture?' This left me a bit puzzled, as I believed I had already covered the system design aspects in my explanation. So I went ahead and shared the specific technologies we used for the data pipeline—like Spark, Airflow, and Python data transformation scripts—and the interviewer said that was fine and moved on to the next topic. Eventually, I was informed that although I performed well, the company needed to reconsider the headcount and job description for the role. This indicated some internal uncertainty about how the position fits within the organization. As a predominantly engineering-led company, the expectations for the role seemed to require someone who is exceptionally technical and has significant leadership experience to influence/convince the engineering team. However, the evaluations of these qualities felt somewhat subjective and not clearly defined. It appears to me that there might be ongoing discussions within Retool about the balance between engineering and product management in driving the product roadmap. I appreciate the opportunity to interview with Retool but believe that clearer communication about role expectations and a more streamlined hiring process would enhance the experience for future candidates.