Cold Calling the CEO – 7 Tips to Get Your Foot in the Founder’s Door

Cold calling the CEO is the scariest, most intimidating part of sales. In fact, research shows that most sales reps simply shy away from phone calls and prefer to email, because it’s more convenient. Most first contacts happen via email, and most commonly, sales reps will just send one single email before giving up on their targets.

However, cold calling still works, if you do it right. This is what we established after an analysis of 1 million cold calls that showed 6.3% of these calls will lead to a meaningful conversation with a prospect.

But what does it mean, to get cold calling right?

We asked sales professionals of all industries to tell us how they get their C-level prospects to respond, and got a few tips. Certainly, there’s not one answer or a silver bullet, but most sales professionals seem to include the cold call into a broader sequence of sales activities.

Cold calling is no longer about just picking up the phone and calling.

It might include sending an email before your call, doing some research to personalize your message, attending an event your target attended, or sending them a small gift.

Persistence is Key

The stat that shows us most sales reps use a sales cadence of one single email is concerning. When it comes to C-levels, persistence is key for establishing contact, and the best sales reps know this well. This is because they are simply harder to reach and have more to do in a day.

“The number one thing you need for cold calling CEO’s is persistence. C-levels are very busy. One cold call is seldom enough to get in touch with them. I once had to work through a sales cadence for four weeks, with 2-3 touches per week before I got through to someone. This included both calls, emails, social touches. Once we did connect we had a good conversation, but imagine if I had given up after one call. It’s just not enough,” said Braden Latham, account executive for XANT.

Content is King

Content is king, and I’m not saying this just because I’m a marketer. Bill Gates said it first. You can reach C-levels easier if you can offer them 100% personalized content to their needs and issues. So when cold calling, make sure you provide something specifically tailored to their company, said Mike Schultz, president of RAIN Group.

“Our research found that the No. 1 content type that influences buyers to accept a meeting or otherwise connect was ‘primary research data relevant to our business.’ Use this to your advantage and educate buyers with new research data that could impact their business. Share insight into new and emerging business issues or market trends,” said Mike Schultz, president of RAIN Group.

Don’t Stick to One Communication Channel

Email might be the preferred communication method for sales reps today, but that doesn’t mean it’s the most effective. The truth is, we can no longer discuss cold calling in a vacuum. CEO’s and founders need persistence and they need to be reached through a variety of communication channels.

“The first step you should take is to send them an email so that you have something to reference when calling them. We send a custom-made video or website audit to prospective clients before cold calling which we’ll usually include in the email. This shows that we have invested time into research and planning. We are not just using the spray and pray approach,” said Derek Cosgrove, senior account manager at seoplus+.

Using Video in Sales Is A Great Way to Personalize

Using video is becoming more popular among sales reps when trying to get in touch with high-level prospects. This allows them to get more personable in their approach and show their human side.

“What we found works well is using interactive video emails and posting these videos to the CEO’s LinkedIn chat as personal messages. What increased conversions for us was screen recording their LinkedIn profile, with a personal message about how we can help them. We send the interactive video both as a LinkedIn chat message and a personalized email message.”

“Because the videos are interactive, the CEO can contact us while engaged watching the full screen video. The CEO can email or call us directly back right from the video. No web page is required. While standard cold emails have a 1 to 4% conversion rate, this method has a 23-37% conversion rate,” said V. Michael Santoro, co-founder of Vaetas, LLC.

However, Michael warns that at this time, video cannot be embedded directly and play in an email message. “Do not send the video as an attachment. The file size may be to big to deliver and it can trigger the spam filters. Instead embed either a static image or animated GIF of the video; that links to the video. Prospects can then click on the graphic and automatically be sent to the video for viewing,” added Michael.

direct mail in sales research

Direct Mail Works Better Than Email

Direct mail is a forgotten art that’s making a comeback today, simply because all of our inboxes have been flooded with irrelevant emails. We still take the time to read what’s in the mailbox. In an XANT study, 65.6% of leaders said they were likely to respond to direct mailers.

The best gifts are useful and creative, while the gifts which are perceived the worst are cheap gifts, according to our study.

“Ten days before making the call, you can send a creative gift to the CEO. For example, it can be a gift for the office like a pen that digitizes what you write, or even a small toy for the office. The objective is to transform a cold call into a hot call. This way, when you call the CEO he/she will know exactly who is calling and will listen to what you have to share. Thanks to this simple, but powerful strategy we were able to increase our cold calling effectiveness by 37.1%,” said Cristian Rennella, CEO and co-founder of

Do Your Research

It’s true pre-call research is a tedious task, one that often takes too much of a sales rep’s time, but with decision-makers, it’s not a good idea to skip it. When cold calling the CEO, make sure you know who you’re talking to, what are their problems and how your solution solves them. This allows you to give a short sales pitch and not waste their time.

Be prepared for your call. Explain your value proposition in a clear and concise manner and have deliverables ready that they can digest on their own time. But also be ready to close on the spot (have Docu-Sign ready, etc.) – you’re dealing with the ultimate decision maker. If they want to sign on the line, make sure you’re ready for it. Finally, do your research – understand the target company’s business model so you can speak to how your product or service will benefit the organization,” said Jeffrey Bumbales, marketing director at Credibly.

Don’t Burn Bridges

The funny thing about CEOs is, they tend to hang around other CEOs, told us Nick Bequette, executive sales manager at Abstrakt Marketing. This is why you need to be very careful with your reputation and professional demeanor.

“When you get a little overzealous in one of your conversations, you run the risk of hurting your reputation with multiple other potential partners. Be confident in your message and confident in the value you bring, but also respectful of their timelines and their priorities,” said Nick.

Here’s hoping you get in touch with the best prospects using these cold calling tips. Let us know in the comments if you’ve found some other strategies that work to get in touch with founders and CEO’s.

For more cold-calling strategies, watch the webinar with MarketSource and XANT.

cold calling is not dead - three cold calling techniques guaranteed to help you win

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