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I don't know, but Russel O'Connor got his PhD in 2008, the same year that type classes were introduced in Coq.

There has been a lot of development on the Coq proof assistant since then. I don't imagine that working with Coq in 2008 was particularly pleasant. :)

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I don't think working with Coq has ever or will ever be particularly pleasant :-)

O'Connor gave a nice talk at TPHol's which I attended: https://arxiv.org/abs/cs/0505034

Keeping up with Coq shouldn't have been too difficult for him.

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