I myself, at my company before this one, had the experience of speaking directly to the top twice or so.
Literal
I myself [also-も], this-company [target-に] enter-company before [genitive-の] company [at-では], 2 times about top [target-に] direct-speak experience [subject-が] exists [polite-ます].
Formal business reminiscence. 直言 ('direct speech, speaking frankly') is a formal compound referring to candid/bold speech to superiors. 自身 is an emphatic 'self' (私自身 = 'I myself'). ~た経験がある ('have the experience of X-ing') parallels ~たことがある but sounds more formal. ほど ('about, approximately') softens '2 times' to 'twice or so.'