I applied online because I was super impressed by Grammarly’s innovative approach to their job postings. Completely transparent and thoughtful, it truly set the tone for a high potential workplace. After applying, I was contacted by the Head of Recruiting for an initial screen. Seemed like a pretty standard call, cordial and informative. Once finished, I was asked to spend a few hours onsite. Onsite, I was THOROUGHLY impressed by the people I met. It was a variety of potential peers, a co-founder and the Head of Communications; all awesome conversations which turned out positive as I was asked to set up a VC to chat with the CEO a few days after. That's when things took a turn for the worst. When I started the call, I was under the assumption that there would be two people present on the call: the CEO and the CEO’s Advisor. On the video, it was just the CEO. Advisor was in the room, not on camera which created an awkward dynamic. The CEO wanted to dive right in and talk about the product. Although an avid user of the free version, he seemed displeased that I didn't download the premium version (I was previously given a free quarterly trial code a few days earlier, but decided not to continue as they asked me to put my cc in, to be charged after the trial was finished). His disappointment was so apparent and in my view, seemed to sour the entire time thereafter. He was not warm, asked me REALLY GRANULAR questions about how I felt at each previous company, asked about tenure and overlaps in my timeline - all questions one would expect from a hiring manager or a first-round conversation. For what it's worth, the Head of Recruiting did a very similar interview onsite, so the ”micro-interrogative nature of the call really seemed odd to me. This interview lasted almost an hour, to where I was only able to ask 1 question back, paired with a half-lacking response and an abrupt cutoff. From that moment, I knew I wouldn't have the opportunity to continue in the process, only to be confirmed the following week. I do appreciate the decision being given over the phone (from one recruiter to the next, it's the right thing to do). Reflecting on that last chat though, two things come to mind: trust and potential bias, which really compromised the entire experience; super positive up to that point. Trust, because this interview could have been best executed by another team member in an earlier recruiting round. As mentioned earlier, IT WAS! As a c-level chat nearing the end, what would have made it much more effective is for the CEO to get to know the person his team has put in front of him, and answer as many questions as possible. This micro-focus makes me think he doesn't trust his team. Potential bias, because being that potential blocker at the ”11th hour” of a recruiting process could give the impression that this CEO is looking for a particular skill, trait, tone, almost as if there's one monotoned expectation and that this one person makes that decision. If not satisfied by this one interviewer, they can make the overriding decision from the rest. I see this being a huge bottleneck for scaled growth and a challenge towards embracing diverse presence. I supposed having an Advisor in the room could have been another data point, but without seeing this individual, who knows the actual intent was. All things considered, I still believed that the potential team I could have work with, and for, was the highlight of my exploration with Grammarly. No matter the outcome, I appreciate the time they all took. p.s., This review was combed through using Grammarly for iOS :)