Is it permissible to send work portfolios containing a personal photo of a veiled woman wearing makeup to recruitment managers?

You must advise your friend that it is obligatory for women not to display their adornment to non-mahram (definition) men. If he replaces the picture with one that only shows what is necessary to show, then there is no harm in helping. Otherwise, it is not permissible to help, as it constitutes cooperation in sin and aggression, while also noting the prohibition of looking at such a picture.