use File::Slurp;

my $file = read_file( "file.rtf" );
$match = "Date of Last Update: ";

if ($file =~ /$match/){
						
open my $file, "<", "file.rtf";

my $startpos = "@-"+2;    #if date is 8 chars then change to "@-"+1 
seek $file, $startpos, 0;
read $file, my $calender_date, 31;    #if date is 8 chars change to 30

print $calender_date;

}

##</code><code>##

use File::Slurp;

my $file = read_file( "1.rtf" );

$match0 = "Date of Last Update: ";
$match1 = "Sign-Off Approvals";
$match2 = "Jane Doe, CEO";

if ($file =~ /$match0/){
						
open my $file, "<", "1.rtf";

my $startpos0 = "@-";    
seek $file, $startpos0 +2, 0;
read $file, my $calender_date, 29;    

if ($calender_date =~ /\\/){
seek $file, $startpos0 +2, 0;
read $file, my $calender_date, 31;
print "\n";
print "$calender_date\n\n";
	} 
	else {

print "\n";
print "$calender_date\n\n";

}
}
if ($file =~ /$match1/){
						
open my $file, "<", "1.rtf";

my $startpos1 = "@+";

seek $file, $startpos1 +42, 0;
read $file, my $first_sig, 66;

print "$first_sig\n";
print "Jane Doe\n\n";

}
if ($file =~ /$match2/){
						
open my $file, "<", "1.rtf";

my $startpos2 = "@+";

seek $file, $startpos2 +82, 0;
read $file, my $second_sig, 67;

print "$second_sig\n";
print "John Doe\n\n";

}



prints:
C:\Users\guy\Desktop\tests>test.pl

Date of Last Update: 10/15/2013

______________________________________________________/_____/_____
Jane Doe


______________________________________________________/_____/_____
John Doe

##</code><code>##

if (first_sig = "______________________________________________________/_____/_____"){
print "There is no first signature";
}
else{
print "Document has a first signature";
}

if (second_sig = "______________________________________________________/_____/_____"){
print "There is no second signature\n";
}
else{
print "Document has a second signature\n";
}