Updating your resume is a pain, but we all have to do it. If you've kept your LinkedIn profile up-to-date, Creddle.io can make a resume from your entries.
We've covered LinkedIn Lab's Resume Builder before; by comparison, Creddle gives you more resume formats to choose from.
It also lets you export your resume to a .docx format so you can edit it before sending. Creddle has a cover letter option too, but it's still in beta and wasn't working when I tested it.