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I can tell you from experience that larger contracts typically have more complexity and unique challenges not seen with smaller deals.
Sure, working smaller deals is great prep and gives a solid base to work from, but it does not inherently make one proficient enough to successfully navigate large contracts. I am betting that your friend didn't come across in the interview as capable of succeeding in the enterprise space, so they weren't given the chance to prove themselves.
Dealing with any further higher contract in value ,doesn't necessarily mean your friend wasn't more than capable, when you have marketers and sales representatives reaching for documentated proof of this or that achievement trying to see if this person is capable!they are decreasing their moment of truth .