resend_ctm_files.rb

require "ctm_cancellations"
require 'ctm_daily_sales'
require 'ftp_transport'

(Date.parse("2020-07-07")...Date.current).each do |date|
  puts "--------------------------------------------------------------------------------"
  puts "Starting date: #{date}"
 
  # Sales
  extract = CtmDailySales.new(date)
  puts "Exporting sales"
  extract.export
  puts "Transmitting sales"
  FtpTransport.new(extract.filename, 'ctm').transmit
 
  # Cancellations
  puts "Exporting cancellations"
  extract = CtmCancellations.new(Date.current)
  extract.export
  puts "Transmitting cancellations"
  FtpTransport.new(extract.filename, 'ctm').transmit
  
  puts "Done date: #{date}"
end

Looks good.