When we hosted a recent MeetUp event, “Overcoming Roadblocks When Selling Enterprise IT,” we expected to hear about how to find and engage decision makers.

What we didn’t expect were all the passionate comments about how NOT to sell to CIOs!

Our audience, which consisted of both executive IT buyers and sales professionals, had a lot to say to each other. Here are our take-aways from this insightful exchange about selling to executive leadership.

First, a quick note: Our particular Meet-Up panel was comprised of CIOs specifically, but all of these tips could just as easily apply to CMOs and sales leaders. Our recent Purchasing Power Index revealed that the Sales department influences the purchase of most of a company’s technology (21% of the entire Sales budget); however, Operations and Marketing are close behind.

So what did our CIO panel have to say to the sales team? 

1. Don’t make a discovery sales call to the CIO.

The VERY WORST approach to use when selling to CIOs, we learned, is leading with: “Tell me a little bit about the technology that you are currently using, projects that you are working on, issues that you might be having.”

Every single CIO on our panel wants you to know about them and their company before they even pick up the phone. Read up on the company profile, and understand the organization’s business and technology landscape as well as organizational structure and budgets – before you make the call.

Only after you understand your prospect’s situation and the challenges of their IT environment, you can pick up the phone and talk about a solution.

And if you have access to more robust data on buyer intent and opportunity, look for leadership moves, acquisitions, vendor changes, and other initiative which signal buying events.

Check out our Pitch Perfect series and perfect your pitch: Selling to the CMO, Selling to HR, and selling to Legal Operations.

2. Do know the industry of your target CIO.

You should be able to speak to the specific needs of the CIO and his company – as well as those of the industry as a whole. Being well-versed in industry trends, terminology, and current issues shows your prospect that she can trust you to understand her priorities and environment.

Earn credibility with an understanding of current trends and pointing to movers and shakers, and industry reports and analysis.

3. Don’t try to sell everything to everyone.

CIOs have busy schedules and a demanding workload, so your approach should be tailored to their specific circumstances or you’re just wasting time.

Two of our CIO panelists mentioned the importance of having a very focused, personalized sales pitch.

One had an experience in which she had asked a vendor to speak to very specific topics and solutions, but he ended up giving a very generic pitch during the presentation. Another CIO had the opposite experience, in which he was dealing with a vendor that had a large portfolio of products, but knew that the CIO was only interested in two of their solutions. The vendor only presented the two solutions discussed and nothing else.

Who do you think made the sale?

Concentrating on the CIO’s specific needs or pain points – not all of the others that you can solve – shows respect and builds trust. Make today’s sale today, and let it pave the path for tomorrow’s.

Read the study: 8 Major Differences in Selling to Men and Women

4. Do know your prospect’s org chart and the CIO’s “lieutenants.”

8 key differences in selling to women and men email


Each of the CIOs on our panel have people on their team who vet new and existing technologies. One of the CIOs referred to them as his “lieutenants.” This role functions as the second-in-command, and the first to shoot down solutions that won’t work, alert the CIO to potential obstacles – and the very person you want championing your solution.

CIOs lean on these individuals to identify needs and evaluate solutions for specific business challenges. These direct reports have the ears of the CIO and a strong influence – and often buying authority – over the selection process.

DiscoverOrg users love our org charts, which map out entire departments and identify the Lieutenants at your target accounts.

5. Do use the second in command as an advocate.

These direct reports hold a lot of weight in the selection process, often pitching the product to the CIO themselves.

One CIO stated that he spends 10% of his time talking to personnel to learn about technologies. Convince these Lieutenants of the value of your product, and you’ll gain insider help with selling your solution to the CIO. Knowing that time is always of the essence when it comes to selling to a CIO, arm your advocate with succinct information necessary to effectively present your product in a short window of time.

Help make your case by crafting a few concise talking points that speak directly to issues you’ve identified.

6. Do ask for referrals – and use them.

Selling to CXO - job title prospect insight report As the old adage suggests, “It’s not what you know, but who you know.” Nothing is more valuable than a referral from one CIO to another. CIOs really trust their network. When you close a deal, ask the CIO of the company to refer you to other CIOs. It’s an opportunity for you to sell your solution, as well as an opportunity for your happy client to network and establish themselves as a thought leader.


These referrals will get you in the door. After that, it’s up to you to make the most of your next steps when selling to the CIO. In fact, it’s considered bad form not to at least follow-up with a referral, if you know who it is – so if you ask for referrals, be prepared to follow through after the fact.

7. Don’t be afraid to miss a sales meeting.

No, don’t mean blow off the sales meeting all together. But know when to just send your engineering staff.

The CIOs on our panel described some of their best sales meetings as being very technically focused and involving only engineers. If you do attend, don’t let your engineer do all of the talking. Always provide value and show respect for the CIO’s time.

8. Don’t send generic emails in an account-based approach.

Imagine your inbox on an average Monday morning. Now quintuple it.

Yeah, CIOs get a lot of email. One CIO said that over 50% of his inbox was communication from vendors! How can a great solution stand out when the inbox is standing-room only? Like this:

  • Provide value.
  • Make your messages short.
  • Be specific.
  • Refer to recognizable customers.
  • Communicate your value proposition succinctly.
  • Personalize a highly relevant subject line.

If you’re executing account-based sales development (ABSD) or your marketing team is doing account-based marketing (ABM), this is especially bad form. ABSD and ABM rely on segmentation and personalization, so all communication with the CIO and others on the team should speak specifically to that person.

Get our free Sales Effectiveness Toolkit.

9. Do send mobile-optimized emails early in the morning.

By the time a CIO gets to the office, they doesn’t have much time (if any) to read email. Catch the CIO before she starts her day – on her morning commute or before she leaves the house – by sending emails before 8:00 AM.

Also make sure that your emails are text-based and mobile-optimized as they are probably being read on a smart phone. For a better mobile experience, keep sentences short and skip the graphics.

10. Do align with marketing.

Check with your marketing team before prospecting to make sure your website and marketing materials are updated with current product features.It undermines your solution – and your reputation – to have crossed-out phone numbers, old logos, or verbal or handwritten product updates that aren’t included on your website or sales materials.

When your prospect looks at your company and your offering, they should have a consistent experience every time they interact with your company.

Here is the bottom line: CIOs are busy people. Their time is valuable. You need to be prepared, show respect for their time and provide value. DiscoverOrg’s database can help you not only identify the key decision makers, but also give you access to their “Lieutenants” and sales intelligence, providing multiple points of entry, insight on the current IT landscape and shortening your sales cycle.

Contact our sales team to see how deep, accurate data can improve every step of the way.


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Henry Schuck
About the author

Henry Schuck

Henry Schuck is the CEO of DiscoverOrg, an 8-time Fortune 5000 company, which he co-founded at the age of 23. He has extensive experience managing the sales and marketing activities of fast-growing information technology data companies.