How a Startup VP Closed the Largest Deal in Company History Against All Odds

Published Monday, August 18, 2025
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INTERVIEWER

Interviewer

So I'd really like to talk about a time, you know, when uh uh hopefully a high note where you considerably. I'm trouble with that word today, considerably exceeded expectations. Uh, let's just start with what was the situation and, and how did you overachieve?

CANDIDATE

Candidate

Yeah, so, um, That's a good question. Uh. I wanted to use the Singapore Airport example because that was one where I, I was really proud of, um, even though, uh, even though it's something that uh I've never done before. Um, so if you're OK, I'll, I'll use that example. OK, sure. OK. Uh, uh, the reason why I'm very proud of that is because I, I, I, I, I, I did not know that I, I had the ability to work very closely with the, with the client from the beginning to the end, uh, and, and also guide them through the entire, uh, sales process and actually close the single largest uh deal for the uh for the company. Um, we at, at the, at the initial stage didn't think, uh, Singapore Airport would even work with us because we are a small little startup, and they talked to us about working with Google as well as Microsoft, um, and we actually, um, Uh, continue to work closely with them and, and continue to follow up. And I think because they, they like the fact that we were really diligent in working with them, um, uh uh uh and I was able to bring in the correct ML resources throughout the entire sales cycle in educating them on what we are able to do. Um, that entire experience was, uh, very positive for us. Uh, the fact that we were able to close the single largest deal in the history of the company, uh, that got everyone, uh, very excited. So that exceeded my own personal, uh, expectation because I didn't think I was able to do this. I thought I needed to bring in the VP of sales to help me close this. But, um, but he gave me enough guidance and and and and and detail where I was able to take this from the beginning to the end. So that was, that was the single largest achievement uh that I had that I had in at Petrol that I'm very proud of.

INTERVIEWER

Interviewer

And so what uh what was the biggest challenge you had to overcome throughout that?

CANDIDATE

Candidate

Uh, the biggest challenge is really, um, uh, internal, um. So, uh, uh, uh, so. Our leadership teams are academia folks. They never done business uh in real world before. So, um, part of, part of the, part of the, uh, uh, internal challenge was, um, one of, one of the, one of the founders basically said, Uh, Singapore Airport is a. It is a company that is well known, they wouldn't screw us. We should just sign the contract that I sent over without, without batting an eye. So, um, that was probably my biggest challenge in terms of, um, telling negotiating with our internal team, saying that we do need a lawyer to go look at the contract to make sure that we don't get screwed. Um, so that was an internal discussion that took on. Yes. It it it's, so the, the leadership team was desperate to sign something, but I wasn't willing to just go ahead and sign something um for fear that, um. It would hurt the company, um. So, so, so it took a lot of negotiations and convincing, but I did convince the found the, the co-founders to hire an external lawyer to go and work with me on, on, on the contract. But there was a big, there was a big one where I got a lot of pushback, wanting to, they wanted to move fast, move faster and sign the contract. Um, without reviewing it. Um, and then the, the, but we went ahead and I, I pushed ahead anyway to get the contract reviewed and and modified. Um, at the very end of the signing, um, the good thing was Singapore Airport actually told us that if we hadn't negotiated a contract, they would not have worked with us because they, they, they see that as, um, as a, as a company that doesn't do diligence in, in, in, in, in doing proper work, and, and a company that doesn't negotiate a contract with Singapore Airport, they automatically dismiss as a As as a company that is not uh trustworthy. So I was, I was happy at the end that that feedback went back to the leadership team, but, um, yeah, there was, there was a big challenge. I, I had to, I had to fight internally.

INTERVIEWER

Interviewer

And so what was your Tool to overcome that challenge. How did you get there?

CANDIDATE

Candidate

Uh, it was a lot of discussions with the, with the, with the co-founders. Um, I, I, uh, I had to find a lot of, uh, examples. I, well, I gave a lot of examples on what happens when I was at VMware. Um, and, and at the same time, uh, I reached back into the staff bank team gently. um, so there was a guy called Tony Coffey, who is the operating partner. Uh, so I so solicited his help to help me. Um, to give me advice on how I would work with, uh, uh, the founders, the co-founders on how to convince them, and he, uh, also reached out gently on my behalf, um, to, to, to, to let them know that if they need help on this, uh, he's able to uh to to provide guidance. So I think, I, I think between that, um, as well as me having a regular conversation with the, with the co-founders that eventually Um, allowed me to get resources from an external legal team to look at a contract, but, uh, but that, that took about two weeks to, I mean back and forth, um, internally. Got it.

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