As a sales rep for a large computer conglomerate I find myself making calls on a daily basis to multi-million dollar companies trying to talk to individuals on the Executive level. There is one thing I can tell you on this level of sales those sneaky, underhanded tactics won't work and in fact you will never develop a relationship with the company you are pursuing. The best way past a gatekeeper is to call with a purpose. If you present the gatekeeper with a well constructed purpose then he/she is more likely to open the gate because he/she will feel like there is something important in your message. For Example, Check the company website for press releases or updates. Usually I use Google News with the Company name in quotations Here is a good one. A law firm just settled or opened a class action lawsuit and are looking for individuals to step forward. I would simply call and when the secretary answered I would state it like this. "Hello, This is David McAnulty (say it like they are supposed to know you) I understand that your law firm has just opened a class action law suit. Let me speak to Bob Major (lawyer) about this so that I can get some more information. When Bob gets on the phone I start (Hello Bob, This is David McAnulty with **** Computers I understand from your secretary that your company is in the early stages of a class action law suit. Great. The purpose of my call is to determine what that means for your company as it pertains to the current IT infrastructure and what challenges to you see as result of this new initiative? Its simple and works on a professional level without any unethical tricks. Recap: -Refer to the gatekeeper as if he/she thought it important enough to tranfer the call -State your purpose early -Ask open ended questions that will result in more than a 1 word answer -Build the conversation from there