Until Apple releases a version of Pages that allows multiple attachements you could use GoodReader application to get two documents onto one Mail document.
It is convoluted, but does work.
First, in Pages, SHARE>EMAIL each document to yourself (it will take two or more Mails) then (assuming you have GoodReader installed) open each email and press-and-hold on the attachement until you see the dialogue "Open In..." and then select "Open In... GoodReader"; do this for each attachment. Then in GoodReader, open MANAGE FILES and select all the attachments and hit E-Mail from GoodReader, it can send multiple attachments in MAIL.
Since you are sending a resume, I strongly recommend sending your self a trial run to ensure all the attached documents appear correctly before sending them to a prospective new employer. Sometimes things don't work as planned; better to catch them first.
I bought an iPad a year ago and find it useless for business, its more for Facebook, games etc... My daughter aged 4 use the educational apps i've downloaded for her. My wife and myself use it for Facebook, games, banking and to retrieve mail. The device is very restricted when it comes to documents and the sending of it. You can not attach multiple files to an email, and that is very frustrating. Apple's file system is very limited and crap! My next buy will defiantly be the samsung note that do not have these restrictions and that can use Microsoft products, i.e.. word and excel etc. I'm very disappointed in the iPad an should have rather done research before i bought it. I wanted to use it for business and to be mobile but the restrictions make it useless for my needs. If you want a toy buy it, if you want to use it for business, don't! .