Pick a language like Perl, where some packages are written in C and some are written in pure Perl, and you’ll get to experience the same cryptic GCC errors, sometimes. There’s no secret to pip; many Python developers upload wheels with pre-compiled binaries, including Windows-compatible binaries, and so you don’t have to run GCC because they already did it for you.

CPython is still 3-4x slower than PyPy.

Similarly, I hope that your technical leaders know that ActiveState has a fork of CPython 2.7 which is still receiving security patches, and also that PyPy for Python 2.7 is actively maintained and can improve the diversity and performance of your backend.