I came across the interesting Skype4Com API that could aid users to dial several numbers using skype.
To install Skype4Com simply unzip the contents of the archive and execute the following command:

c:\> regsvr32 Skype4Com.dll

Upon executing this you can use the Skype4Com API using .Net (C#, VB Script) and even Python.
One can even generate DTMF tones to dial in to 1-800-numbers and automate the process so you can directly get through the initial wait times and directly speak to the customer representative.