Sidecar Health Interview Questions
& Process

The initial phone screen went well, followed by a typical first round of interviews. However, like others have noted, the company went silent and didn't respond to multiple attempts over a month to check on the application status. It's important for candidates to be informed if the company is no longer considering them, even a rejection email is better than silence. Candidate experience matters because applying and interviewing takes up valuable, non-refundable time. Management should improve candidate communication during the process. I was really looking forward to interviewing here, and it seems those hired are happy working here. Improving the candidate experience and communication is key.

First, I had a few chats with the hiring manager about potential role and team fit. When we officially started the interview process, it moved fast but was comprehensive. Since I had another offer, Sidecar Health scheduled all my interviews in just a week so I could decide. I talked to 6 people, with each interview focusing on a different skill or topic. As someone who's recruited before, I could tell they put real thought into the process and prepped each interviewer. The hiring manager called to offer me the job verbally, then emailed the written offer with details. They were even available over the weekend for any questions.

I applied online and heard back from a recruiter about scheduling interviews. The whole process took about 3 weeks, with 7 interviews total, one each day over those weeks. I had a 45-minute chat with the chief architect, a 1-hour architecture/design exercise, and then shorter 30-minute sessions with the QA architect, another architect, the VP of product, and the CTO. I felt it went pretty well, but I didn't get an offer. My guess is they were looking for someone more hands-on, and if that's the case, I'd suggest tailoring the interviews to let candidates show that kind of experience, instead of focusing only on architecture/design/process questions.

Everyone on the team seemed nice during the process, but the hiring manager and recruiter became increasingly unprofessional in the latter rounds. This culminated in them strangely extending a written offer and then rescinding it less than 24 hours later. A few examples of points of friction I encountered in the process: After the onsite interviews, I asked for an expedited decision because another company had extended me an offer. Both the hiring manager and recruiter ignored my emails, so I had to chase down the recruiter over text message. The hiring manager then sent me a case study prompt that focused on the same question I had answered during the onsite. Given the date listed on the prompt materials and the recruiter having never mentioned this was part of the process, I was left with the impression that this had been newly created as either busy work to stall me while they advanced other candidates or unpaid consulting work to extract my product knowledge on document AI. I completed the case study and received an offer. The comp came in below my other offer. I tried to negotiate, but the hiring manager refused to counter. I had some questions on valuing the equity package that he declined to answer, citing a lack of knowledge of the equity terms, which I found odd since he's a publicly named member of the leadership team. The recruiter scheduled time for us to chat. He called me from a busy coffee shop and proceeded to talk publicly about sensitive information about my offer and the company's financials. I raised that the bonus amount was lower than what he had mentioned at the start of the process. I also proposed other ways to think creatively about compensation and he mentioned he'd check with the team. I then received a written offer with no changes despite the fact that we clearly weren't in verbal agreement on the terms. I then asked via email for further clarity on the equity based on something the recruiter said that struck me as strange. The hiring manager quickly responded and agreed this was a good thing to talk to the CEO about but then followed up in the morning to rescind my offer, citing that my comp expectations were too high. Equity mysteries aside, this leaves me wondering whether the culture is so stringently tops-down that any attempt to negotiate with leadership is viewed as inappropriate. Overall, I feel like having to rescind the offer is an unforced error on the hiring team's part. I repeatedly made clear that I wasn't expecting them to match the other company's offer. I would have gladly taken them honoring what they had first proposed on the amount of the bonus. Sharing my experience here in the hopes that the team is able to learn from it for future candidates.