The Ultimate Cheat Sheet On Getting In The Door

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There is a subject, call it a pet peeve if you will that is near and dear to my heart.  As a CIO who has spent 30 years in IT (15 years in IT Sales and 15 years in Executive IT Management), I am somewhat of an aficionado when it comes to recognizing great IT sales talent.   Unfortunately, I see very little of it in the marketplace today.  Oh don’t get me wrong, there are some good sales people that are aggressive, high achievers, and always wanting to “understand my needs and objectives for the year”.

But there are very few that I really look forward to meeting with when I see a meeting notice on my calendar.  I’m talking about the type of person that brightens your day when you see their number come up on your phone.  The type of person that intrinsically knows me and my business “before” they walk in my door.  They bring real solutions to my problems (business and technical) as well as serving as a reality check on things me and my team are trying to accomplish.  The best of the best even admit when they don’t have a solution for me, but are still willing to help out any way they can.  This is a true partnership.

There is an old adage, “people buy from people they like”.  In IT Sales, this is the golden rule.  Your job as a sales executive for your company is to make me happy when you win and sad if you ever lose.  Believe it or not, most mature CIO’s I know really root for our favorite partners.  It may not help you during the procurement process but we really want you to do well.  When you do well, we generally win.  Best solutions, best pricing, best resources all go to clients that have a great relationship with their partners.

So I’ve been asked numerous times what advice would I give to sales execs trying to earn their way into my trusted inner circle.   Let’s start at the beginning.   Just as in any relationship, the first interaction is the key to a long, successful relationship.  Think back to the first interaction you had with your best friend, significant other or spouse.  You had to put some thought about what you were going to say “before” you approached them.   You didn’t run up to them and give them a 15 minute bulleted speech or PowerPoint about why you were the best person to be a life-long friend or partner.  You put your best foot forward and did everything you could to get a conversation started.  It’s the same way when your approaching a new client at a prospective new account.  You one chance to make a first impression.

I get on average 40 – 50 emails and phone calls every day from vendors wanting to “just get 15 minutes of my time” or “meet their Senior Executive who will be in town next Tuesday” or “solve all of my problems while saving me 30% on my XXX budget”.  You may find this shocking, but I don’t read past the first line and I don’t listen past the first sentence of these type of general sales voicemails.  So, how do you get to me?   Here is a list of the best ways to approach me and I have to assume most new client CIO’s:

  • Network – Find someone who knows me and get them to introduce you.  Not through LinkedIn, even though that’s better than nothing.  Make it a face to face introduction, either at a conference, or business lunch.  If you do this, be prepared with your elevator pitch.  Tell me something in less than 30 seconds that will make me want to meet with you a second time.  Your goal for that first meeting should be to get a second meeting.
  • Event – Do what you can to get me to attend an event where you can have the face to face introductory meeting.  Meetings where other CIO’s are going to be are a good start.  However, understand my main interest is meeting the other CIO’s, so don’t be too pushy.  Make the event relevant for my industry.  Bring in a respected industry spokesperson. Again, practice your elevator pitch and try to get the second meeting.
  • Email of Voicemail – Believe it or not this CAN work.  But you have to do your homework.  Remember, I get a ton of these and give them about 10 seconds each before deleting.  So you have to get my attention in those 10 seconds.  You do this by doing research on me and my company.  In the subject line, make it something like “I see your IT spend is 4% of your company revenue, did you know your competitor’s is 3.2%, I have ideas on solving that”.  Or “I saw your presentation on IT Security, on slide 3 you mention remote offices, I have a way you may could do that less costly”.  In other words, compel me to meet with you.  Tell me something about my company, my industry or even my own IT strategy that I didn’t know before.  I will be blown away and call you immediately.  Even if you’re wrong, it shows you have really put thought into the meeting.  This is so easy to accomplish.  All of the information is at your fingertips on the Internet.  Most annual reports are online, or even in the company’s website.  There is enough personal information through LinkedIn, Facebook, etc. to get an idea of what I like, areas of interest, etc.  Personalize your message.

Bottom line, if you start the relationship off right, it’s not a guarantee of a long successful relationship but it goes a long way toward achieving your goals and making us both successful.

Good Selling!

by Mr. ” Hard To Get CIO”
Mr. Hard To Get CIO is the Chief Information Officer of the largest not-for-profit home and community-based health care organization in the country, serving nearly 150,000 New Yorkers annually – the vast majority of whom are Medicare or Medicaid beneficiaries, including those dually-eligible under both programs. In his leadership capacity, Mr. Hard To Get CIO also oversees the technology infrastructure used by the companies managed long-term care providers for the organization’s safety-net health plan, which serves roughly 30,000 members through both Medicare Advantage and New York State Medicaid Managed Care products. With over 30 years of comprehensive information systems experience in all phases of managing and marketing healthcare information technology solutions, Mr. Hard To Get CIO prior work includes leadership roles with the IBM Corporation and the BlueCross BlueShield of Tennessee, including its subsidiary, Shared Health. It is in this latter capacity at Shared Health where Mr. Hard To Get CIO was at the helm of the efforts that led to the establishment of the state of Tennessee’s primary multi-payer health information exchange (HIE) initiative, which at the time, served over 1.8 million Medicaid enrollees and was the largest public/private HIE in the country.


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