When a salesperson sends a message to a lower-level prospect, they can afford to try a stronger ask at first and then tweak it or scale back as necessary. But when you’re pitching to a CEO, you really only have one shot to engage them. Bungle the ask and you might miss the runway entirely.
With this in mind, salespeople must be deliberate and thoughtful in how they approach CEOs if they hope to receive any kind of response. Here are nine tips for how to contact executives. They'll ensure your pitch lands smoothly and maximize your chances of getting a reply.
How to Get a CEO's Attention
1. Use a gentle ask
CEOs are extremely busy, so in my outreach, I’m not going request a meeting or a conference call. Deploying an overly strong ask in the initial email or call will pretty much guarantee never getting a call back. And at this stage, a response is all I’m after -- not a signed contract.
CEOs aren’t usually willing or able to give of their limited time. So instead of trying to think of the magical sentence or statistic that will prompt the executive to drop everything and meet with you, I encourage salespeople to consider what CEOs are willing and able to give.
In general, CEOs are friendly and outgoing since they’re constantly representing their companies to a variety of audiences. They’re extremely savvy when it comes to social dynamics and credibility.
Take this information and play in their wheelhouse. Rather than a meeting or call request, soften and socialize your close by asking the CEO for a referral or a connection to more information. Not only do these asks require significantly less time and attention, CEOs actually like giving references and information.
For example, an email using this approach might read something like this: “I want to make sure I don’t sound foolish when I call your organization about X issue. Where/from whom can I get the best information on this topic?”
Instead of coming to the CEO as a credible sales rep, you’re now approaching them as a curious student, and you’ll likely find that they’re much more willing to engage on this level. And once they start to engage, you can ramp up the relationship bit by bit.
Another benefit of making it ridiculously easy for the CEO to respond to your message: Getting any sort of response automatically boosts your credibility with others in the organization.
Maybe you're trying to book a meeting with the VP of HR. You think it's more likely they'll agree to your call when you say "Well, I got in touch with your CEO last week, and she said X ... "? Instant credibility earned.
2. Write emails on your phone
CEOs are constantly on the go, which means nine times out of 10, they’re reading email on a tablet or smartphone. If an email from an unknown recipient requires them to scroll, it’s not getting read.
Bearing this in mind, write any email intended for a CEO on a smartphone. That way, you see exactly how it will appear to them when they read it. Salespeople often make emails to C-level buyers overly long and complex, because they think they need to sound smart and impressive. But when it comes to getting a response, short and simple is always better.
Don’t sit in front of your desktop computer and fill up the screen with a novel. Get out your phone, type out a few brief sentences, and send.
3. Don’t dismiss the EA
The common perception among salespeople about executive assistants is that they handle C-level professionals’ calendars and block others’ access to them. End of job description.
Maybe that was the case 20 or 30 years ago. But in 2016, executive assistants are extraordinarily competent in a plethora of areas, and their duties extend far beyond administrative tasks. Beyond keeping their boss’ calendars, EAs also represent their managers at internal and external meetings and sometimes even make decisions on their behalf.
Because of this, I think of the executive assistant as the CEO by proxy. Instead of trying to bypass the EA, work with them to get the information you need and indirectly engage the CEO. Sometimes interacting with and posing your ask to the EA is more beneficial then accessing the CEO.
For example, if I was building an ROI calculator to strengthen a presentation and needed data from the CEO to complete it, getting it from the EA is just as good -- and much faster. When it comes to any other ask besides signing the contract, I don’t distinguish between the CEO and their EA due to how closely they work together.
It's also a good idea to call the EA and pick their brain before you reach out to the CEO -- after all, they know more than anyone else what works with their boss and what doesn't. However, EAs are busy people too, and they won't just give you the information you want simply because you asked for it.
Keeping in mind that EAs get countless calls from salespeople pitching "value and benefits" for the CEO, differentiate yourself from other reps by showing your vulnerability. For example, here's how you might kick off your call with the EA:
"Hi, Mike. I'm going to be reaching out to Wendy soon, and I don't want to look stupid ... what's the one thing I definitely shouldn't say?"
Ah -- now you've got their attention. The EA can be critical in your campaign to reach the CEO, so don’t shoot yourself in the foot by dismissing them.
4. Draw on the college connection.
Salespeople often try to find common contacts, interests, or employers when reaching out to prospects. This is a smart technique, but it can be tailored even further with CEOs.
The most powerful connection you can use with the chief executive isn’t their current company, their former company, or any of their colleagues past or present. It’s their college. In general, CEOs are extremely involved with their alma maters, and if you went to their school or know someone who did, use that as an in. Reminiscing about college days can quickly become talking about current business.
5. Call late
Common sales wisdom holds that salespeople should call executives early in the day, before they get too busy. But in my experience, connect rate (which I define as a phone call over 60 seconds long) is notoriously low in the morning hours. Why?
When a CEO gets to their office, they might not have gotten in the swing of things quite yet, but they're distracted -- thinking about all the tasks they have to get done that day. Not the ideal time to hear from a salesperson.
The end of the day tends to be a better time to call the C-suite -- think 5 to 8 p.m. local time. Later in the day, you'll find that the person on the other end of the line is less distracted, a little tired, and in an overall better mood.
You might be concerned that a late call will be a bother to an executive. But to me, this is a non-issue. If your call comes at a bad time, they simply won't pick up. Not to mention that what a CEO finds "bothersome" has little to do with your timing and everything to do with your message. If you have a good message, they'll be interested in what you have to say -- even if it's a bit late.
6. Use a 45-day cadence
Industry standard is five touches in 30 days. For CEOS, I advise five touches in 45 days.
CEOs' schedules rarely exist on a monthly cadence. They think about quaters, not months. Most prospects are available sometime within a month. No matter when I reach you, there will be sliver of time in four weeks that you're available -- even if for two of those weeks you're on vacation, sick, off-site, working on a major proect, and so on.
But many CEOs will disappear for an entire three weeks at a time, depending on what they're doing.
A CEO can’t stay away from her company for an entire 45 days, which is why I recommend an extended calling schedule.
7. Ask for a sneak peek of an upcoming presentation
Your typical CEO is a thought leader who’s actively engaged with their industry. Look for events where the CEO is speaking. These might include an event their company is sponsoring, a board event, a trade show, or an industry conference. Reach out a few weeks prior to the occasion and tell them you find the title of their speech interesting. Explain that you can’t attend the event but would love a sneak peek of their remarks.
Even a CEO who delegates most of their work is still preparing their own presentations -- and would welcome feedback. By asking them for a rundown on their remarks before the event, you get ahead of the many people who will follow up with questions and pitches after the fact.
If you’re reaching out this way, remember the presentation title should infer a connection to what you’re offering. If you’re selling billing software in the mid-market medical space, look at the speaking roster or recent blog publications from CEOs at hospitals or medical businesses.
Choose a topic about being more efficient or effective in a post-sale world and -- once you’ve heard their remarks and provided valuable feedback -- tie it back to what you sell.
In general, you won’t pitch to the CEO. But having this interaction gives you leverage when you speak to the lower-level decision maker. By saying, “I just had a conversation with your CEO about medical sales efficiency and how it ties into our offering …” you’ve created a climate of urgency with your buyer.
8. Take advantage of the economy
Unemployment is currently low and revenue is high which means the ability to meet employee growth targets is more difficult. The result can be bottlenecked company growth.
If you position your product or service as easing that issue, you might find a new audience. Is your technology an attractive tool for engineers? Position it as such for companies that currently have several engineering requisitions out.
Selling marketing software? Reach out to CEOs and explain you have a product that can speed up collaboration for marketers around the world. And if you offer sales training, reach out to CEOs at companies planning to poach sales talent.
Explain they’ll never be able to attract or retain that talent if they don’t have a strong training program -- and conveniently position your company as the solution.
By taking advantage of the economy and speaking to the bigger picture benefits that resonate with many CEOs, you’ll likely spark enough attention to get a meeting with the decision maker.
9. Ask for their data
This is a bold strategy, but one that works well if you’re already engaged with a decision maker not at the CEO level. This strategy allows you to engage with and understand how their company develops RFPs and ROIs giving you an advantage when creating a pitch down the road.
Reach out to the CEO’s office and explain, “I’m currently working with [insert team] on [insert solution].” I’d like to provide you with an accurate ROI calculation based on your data, not ours. What’s the best way to get real financial data with which to create this forecast?”
Now, let’s be honest. You’re not making this phone call to the CEO. You’re aim should be to disrupt and gain the attention of their executive assistant. You need two elements to build a fire: energy and oxygen.
Salespeople are great at adding wood to the fire but many of us forget to add oxygen. Reaching out to a CEO or, in this case, an executive assistant provides the oxygen you need to grow your deal.
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Originally published Aug 15, 2018 7:20:00 PM, updated August 23 2018