Usage of the gerund preceded by the possessive adjective/determiner?

I agree with J.M. and Jimi.

It's semantically acceptable to use a gerund following a possessive adjective/determiner, but, as with anything, it can be clearer in some sentences (e.g., "his new shoes really helped with his running...") than in others ("Company X experimented with its expanding into a new business area...").

Just my two cents!

Jane loses her parents -> Jane's losing her parents [transitive]

The company expands -> The company's expansion [intransitive]

I think that if it is an intransitive verb that can be formed, it's more common to use the nominalized form instead.