HTML email signature not displaying correctly in Outlook Windows and images not showing MAC

Hi,

I'm using Outlook 2011 for Mac and I made an HTML email signature. When I put it in my Outlook it looks fine like this:

BUT when my boss copy + pastes it in his Outlook it looks like this:

There's an unwanted space between the logo and the text. I don't know what's wrong because it looks fine on my side.

Also, when I reply to an email the images in the signature are not showing? I can't find a tutorial for Mac on how to fix this... Please help and thank you in advance.