if ( $text=~m/\b(director|resignation)\b/ )
# code that shows which word matched:
    {
        if( $1 eq 'director') {
            print "That's the director? Get rid of him!\n";
        }
        else {
            print "You can't resign, you're fired!\n";
        }
    }
[download]

Hello graff, I really like your print response hahaha :)

In 5.10+, see also named capture buffers:

>perl -wMstrict -le
"my $str = 'The CEO of WidgeCo resigned today.';
 ;;
 $str =~ m{ (?<BIGWIG> chairman | president | ceo ) }xmsi;
 ;;
 if (exists $+{BIGWIG}) {
   print qq{a $+{BIGWIG} was mentioned};
   }
"
a CEO was mentioned
[download]

Update: For the position in the string of the match(es), see @- and @+ in perlvar.

my %count;
while(/\b(director|resignation)\b/ig) {
    $count{$1}++;
}
my @found = sort keys %count;
print "Found the words: @found\n";
[download]

Then use logic to do more complicated AND's and OR's on the subset of the words that matched.

#!/usr/bin/perl -w
use strict;

my $text = "Mr. X is a bozo and was hired and then resigned.";

#build an "OR" regex from a list of search words
#add \b (boundary) in front and back, then | between

my @search_words = qw(bozo hired resigned);
@search_words = map{"\\b$_\\b";}@search_words; 
my $search_regex = join("|",@search_words);
#print "search_regex is: $search_regex\n"; #debug

my %matched = map{$_=>1}($text =~ m/$search_regex/gi); #match global

print "This bozo resigned - thank goodness!" 
       if ($matched{bozo} and $matched{resigned});

#prints: This bozo resigned - thank goodness!
[download]