As a long-time Perl fan, I found Ruby to be an absolute delight. It's as expressive as Perl in some ways and more expressive in others.
I started my career as a Perl hacker, and then moved on to PHP (bleah), before making the transition to Ruby on Rails.
I got my first Ruby job without actually having any Ruby work on my resume. I had the general experience, the business experience, the right attitude, and a desire to learn.
I think most enlightened employers will be more interested in the right fit for the company (personality, general ability) than in finding someone with a precise set of skills on their resume.