After 12 years in technology sales as a hunter, I co-founded Jigsaw in 2004 and became the hunted. My business card was on the front page of the website as an product example to literally millions of prospecting salespeople, so take my word for it- I’ve seen every first contact tactic out there. For 7 years I tried to coach our Jigsaw reps with the lessons I learned, and then I used the process myself at OtherScreen, where I cold called TV execs (tough crowd!). Now I am back knocking on doors in the sales and marketing data world at CircleBack. While I’m no Inside sales scientist (check out and for stats and tools), I think have know a thing or two about how to make first contact with a prospect. Here is a condensed list of what I know:


How to Make First Contact with a Prospect

1: Be Persistent. Sounds simple, but you would not believe the number of sales people that have “pursued” me that have given up after a single attempt! Today’s decision makers are beyond busy, and are inundated with a staggering amount of communications. Steve Richard from has a great infographic on his blog with avg numbers of emails and calls required to set a meeting. He has even coined a new phrase- Respectful Pest. Don’t move a prospect to the “loss” column until they have confirmed that they are the decision maker- and they have told you some acceptable form of “NO.”

2: Be prepared. Ever wonder what a dog would do with a car if he actually could catch it? I had a Sales VP who used to always answer his phone with some variation of “You have 30 seconds to convince me not to hang up on you.” Now there is no question that he is a jerk, but most people are essentially thinking the same thing when they hear a voice they don’t recognize on the other end of the phone. With all the information available out there on the internet, you better be armed with something other than product specs when you finally make contact. You don’t need to have prepared a 5 page dossier on everyone you call, but you better have checked out the company website and glanced at the guy’s LinkedIn profile.

3: Listen. I am nice person and out of professional courtesy will allow you to pitch me, but I will shut you down if you talk over me or ignore what I tell you. Your goal is to get the prospect talking, not to deliver the maximum amount of information in a minute. However, you have to earn the right to ask those open-ended questions that you learned in sales training. Believe me, the prospect has better things to do than tell you what his critical success factors are.

4: Be confident. There are plenty of execs that think that sales people shouldn’t be allowed to breath the same are that they do. Those people are stupid. Sales makes the world go round. Your prospect needs to hear what you have to say. This company needs your product. You are the best person in the world to deliver the message and get the process moving. There are 50 other people that you can contact and make your number if this call doesn’t work out. If these things aren’t true, make them true.

5: Be yourself. People connect with other people. My first job out of school, where I was a history major, was calling on CIOs in Fortune 500 companies and telling them that they needed to dump the mainframe that they had been using for 20 years and build their critical business applications on UNIX. I was totally mismatched in experience, technical expertise, life knowledge, patience- you name it. But I was ultimately successful because I came to follow the above points and I never tried to be somebody that I wasn’t.

That’s what I got. Despite what a million sales enablement technology companies (including CircleBack) will tell you, there is no magic bullet for inside sales other than working a process and playing the numbers. But that’s why you make the big bucks, right?

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