When selling into enterprise markets, everybody wants to get to the Chief Information Officer (CIO), the Chief Security Officer (CISO), or whatever C-level is at the top of your company's buying chain. But CIOs are very busy with their own work, plus they are inundated with sales offers at every turn. This makes it particularly hard to stand out from the crowd.
HOW TO TALK TO A CIO AND THEIR MID-LEVEL STAFF
Show Expertise. As much as possible approach as a peer, ie. demonstrate deep and genuine knowledge about the space and trends, and genuine curiosity to learn more.
Be Honest. Do your homework about their company and industry, challenge their point of view, but don't presume to know too much. At the end of the day you are an expert in your world, they are an expert in theirs, crossing that boundary too quickly is disingenuous.
Because the space is noisy, help them understand where to "place" you, what label or group of companies, what Gartner MQ, etc. and eventually, your differentiators. If you are too unique then you risk being noise so help connect the dots.
Every touch point offer some value, something to think about, a link to useful reference material, a heads up about an upcoming conference or industry trend. This only works if actually relevant, otherwise it will just be ANNOYING!
Be in it for the long term, it's not so much about the sale as establishing relationship where down the road we may help one another.
Be a human being. There is so much junk science out there for sales people about how to talk to prospects, and it all sounds smarmy and gross to me. Anything that you say or do in your work life, ask yourself: "Is this what a normal human being sounds like?" If not, knock it off and just be a regular person
IF YOU ARE IN SALES AND MARKETING: HOW TO GET IN FRONT OF A CIO
Talk to Mid-level Staff First
CIOs and other C-levels are bombarded with promotions. Most of the time, you want to talk to mid-level managers first and let them eventually tell their CIO about you. This may feel very indirect, but ultimately is better because:
C-level Roundtables and Other Intimate Settings
Because the market is so noisy and channels are saturated, the more intimate approach where you are actually meeting customers face-to-face and making a human connection can produce more real opportunities than blasting a message to thousands of prospects online. At a past company I worked for this is how we got the bulk of our enterprise opportunities. In the IT security space for example, check out CISO Executive Network as an example where each local chapter hosts 3 speakers and 20 CISOs a month. Go speak at this conference, be credible and memorable, and then network the room.
Referrals and Partner Marketing
CIOs and CISOs rely on trusted partners such as consultants, managed service providers (MSPs) and trusted vendors who are already established in their ecosystem. Getting a referral from one of these trusted sources can be more effective than trying to make a cold introduction.
Find the top 100 MSPs in your market and meet them directly. Sometimes even being friendly with potential competitors makes sense here, whoever can refer you to the CIO rather than you trying to make a cold introduction. Companies in the IT security market has got this dialed in: everyone is both a partner when it comes to finding referrals (a necessity in such a noisy industry) but also competitors on other deals. For busy CIOs, you are way more likely to take a meeting from a trusted referral than a cold intro.