Key strategies for effective C-level appointment setting

To sell million-dollar deals, you must grind through long sales cycles, multiple decision committees, and lengthy nurturing periods. And then it all can fail in a millisecond. 

No hard feelings — it’s just that the decision-makers didn’t know the fantastic value behind your price and the offer forwarded by your champion landed 4th or 5th in the pile. 

Tough luck. No wonder seasoned sales pros prefer speaking directly to decision-makers in B2B sales. 

Yet setting an appointment with the C-suite is a challenge. They are elusive, always busy, and guarded by ruthlessly polite assistants. 

Luckily, we at Belkins know how to break through to the C-level. Stick with us for the walk-through below. 

Do you really need a C-level appointment?

Sales professionals have split opinions about the necessity of approaching the C-suite for each deal. Of course, you need the right person to champion your product within the company. But it’s not necessarily the highest-sitting executive.

There are 2 strategies for big-ticket sales in B2B: 

Top-to-bottom selling

In the top-to-bottom strategy, the sales process starts with high-level executives, like CEOs, especially in smaller companies where they’re key decision-makers. This method also works in large organizations, as a C-level endorsement will influence lower management. When a CEO points you to the right director, it helps you navigate the complex decision-making process and improves your chance of closing the deal.

Bottom-to-top selling

The bottom-to-top approach suits organizations and enterprises with decentralized decision-making. Here, multithreading outreach to lower-level stakeholders helps you understand what drives the interest in solutions to distinguish between must-haves and nice-to-haves. This method overcomes the challenge of cold-selling busy top executives by driving sales from the ground up.

How to set a C-level appointment

How to get appointments with decision-makers? Be ready to invest time and effort, especially if you don’t have a good network of contacts. 

If the timing is tight or you wear multiple hats already, outsourcing C-level appointment setting might be your solution. However, ensure that your outsourcing vendor is proficient in your industry. 

📚 Below, we focus on executive appointment setting. For C-level prospecting strategies, go here: How to effectively do sales prospecting in B2B.

Let’s address the common challenges and common mistakes to avoid when setting appointments with C-level executives, step-by-step.

Set the right target

In executive appointment setting, the first step is to target the right audience. 

CHALLENGE: You need to speak to executives who are interested in your offer and have the authority to approve your product or service within their organization.

You want to reach influential executives (champions) who can benefit from your solution. Research the company’s LinkedIn, website, and leadership structure to identify the decision-makers, possible influencers, and gatekeepers. 

Beware of the quasi-decision-makers. These might be mid-tier managers who eagerly communicate and confidently overpromise. To see if they are worth your time, ask: 

1. “How often do you have meetings with the decision-makers?”
2. “What recent products/services/initiatives have you brought into company processes?”

You want someone who is in touch with the C-suite multiple times a week and has influenced several purchases. 

Your next question is:

3. “Can you arrange a meeting with whoever needs to sign the deal?” 

If they will not or cannot give you access, be open with them. Say, “I do not doubt you can help get this done. My concern is I’ve been in situations where the boss comes in and says it’s not right. The last thing I want to do is take up a lot of your time if there is a chance that this doesn’t get through. Let’s make sure that the needs of all people involved are met before we get too far ahead. Does that sound fair?”

If it still doesn’t work, a deal is unlikely. Keep looking. 

Cut through the noise

The multi-touchpoint strategy with persistent, personalized messaging works best with executive-outreach methods. 

📚 Read more about multi-touchpoint sales here: How to set sales appointments.

Do the cold calling. Yes, 1 in 50 pick up the call, but sometimes you get lucky. Besides, the main reason for cold calls is voicemail.

Always leave a voicemail. 

How to leave voicemails for the C-level:

• Leave your name quickly and informatively.
• Lay out your proposal, emphasizing what’s in it for them. (Personalization is paramount in C-level outreach.) 
• Let them know you’ll follow up.
• Send a follow-up email with a subject that references the voicemail. 

This way they will know your name, and your email will stand out in their inbox. 

Try calling at different times. Avoid Monday mornings and Fridays, as C-level execs are likely busy planning or closing their week during these times. Midweek works best, especially after 4 p.m. when executives catch up on their emails.

MISTAKE: Your approach is too aggressive or persistent, causing executives to be put off. 

There is persistence, and then there’s annoyance. Your goal is to be pleasantly persistent. 

First of all, sales is about relationships. You may push your benefits all you want, but people only buy from people they like. 

The right path to closing is: 

1. Build rapport first.
2. Talk less, listen more.
3. Avoid cliches and canned answers.
4. Hear what people say and adjust your answers.
5. Seek constructive feedback when handling objections.
6. Aim to help, not sell.

CHALLENGE: There is a lack of brand recognition or trust in your company.

Get in front of them. Send your probable future champions content and goodies to get the company’s name in front of them. No strings attached, no “what is your business problem” at this stage. When the time is right and there is a deal to be worked on, they will come into the picture.

Invest time in connecting online. Use LinkedIn connections and shared groups to engage with decision-makers. Here’s how:

• Leave meaningful comments.
• Ask questions.
• Step in with relevant expertise.
• Share useful links.

When doing this, make sure your profile mentions your company and is visible when commenting.  

Do personalized multi-touch offline. A good practice is sending books and handwritten notes. 

Here is a solid strategy recommended by r/sales:

1. Send the CXO a coffee-table book about one of their hobbies or a book about your service subject matter, yet nothing too salesy. For example, you could send a book about the future of the Cloud if you do web hosting.  
2. A few days later, follow up with a helpful document describing your product (but not selling it). Write this guide specifically for this CXO. 
3. Follow up in a week with a handwritten note on nonbranded paper asking them a question, as they’re an expert in the industry. The last line should be “Hopefully, I can call you about this in a few days?” 
4. End the letter with your name, number, and email. Add “PS — Hope you liked the book!” (Now they will know who sent it.)
5. Send it as a certified letter, wait till it’s delivered, and then call. The chance that they’ll pick up will be much higher. 

CHALLENGE: If you have no one to refer you to the decision-maker, they may brush you off. 

Yes, if a friend of a friend can say a kind word about you, this will get you in the door much faster. So comb through your contacts. 

If you don’t have a good point of contact already, it can take time to establish one. 

Keep building your sales with smaller businesses and develop your connections. Be where the C-levels are, attend all live events, and network as much as possible. You’ll eventually get a referral, which is invaluable in the big leagues.

CHALLENGE: Your sales timing inconveniently coincides with busy periods or company crises.

Understand the company’s business cycle. Avoid periods like end-of-quarter or fiscal year-end, when executives are likely busiest. Check the company’s LinkedIn feed and press releases to stay informed about their calendar.

Consider the cultural specifics. No one works the first week or two in the U.S. in July because of the Fourth. In many Asian countries, like China and Vietnam, all businesses close for 2 weeks to celebrate Lunar New Year. 

So if you run into a timing issue, remember to identify a more convenient time — and follow up then.

CHALLENGE: There is a general misconception or misunderstanding about your product or service that’s leading to a lack of interest from the executives.

Have a solid personalized reason for your outreach. How does your specific product solve the prospect’s particular high-level problem? Reinforce your answer with successful case studies from similar companies in the industry. You could even attach a white paper or a link to an article that clears up the misconception.

Get past the gatekeeper

Gatekeepers have the power to block you off completely, or they can get you into the fast lane if you can make a compelling case and overcome their objections.

CHALLENGE: Gatekeepers, such as other managers or personal assistants, could effectively block access to the C-level executives.

C-levels may not always answer their phones, but their assistants do. They also screen their voicemails, monitor their inboxes, and manage their calendars. Sometimes they can set up a meeting for you without the executive knowing about it! 

If you first speak to the gatekeeper, treat them like you would treat the prospect. Convey a valid reason for wanting to speak with the decision-maker. Don’t make it about you or your solutions. Instead, focus on their pains and challenges. Show that you get their business and want to talk about their needs.

How to handle the gatekeeper:

• Treat them with respect and build rapport.
• Еxplain that your case is about them, not you.
• Mention that you’ve talked to the decision-maker via email. 
• Cc them in your emails to the decision-maker.
• Get their name and connect on LinkedIn. 
• If you land a meeting, send them a thank-you message.

Be ready to talk

When setting appointments with senior decision-makers, get on the same level, speak the same language, and maximize your time. 

That’s where good research pays off. Being prepared keeps you from wasting their time asking questions and allows you to get straight into business.

MISTAKE: Lack of experience or confidence is evident and reduces credibility in the eyes of the C-level executives.

Don’t worry. Remember: However high-tier this businessperson is, they’re a person, just like you.

Take a deep breath. Drop your script, or you’ll sound robotic. Be human and authentic. 

What you lack in experience, you can always make up for in knowledge. This will help you speak the same language and be able to help them:

• Prepare for all possible product questions beforehand.
• Research the specifics of your prospect’s organization and industry.
• Have all the relevant costs, rates of return, and case studies readily accessible.
• If you don’t know something, say you’ll find out and get back with them.

Proper preparation helps you lead a brief and organic exchange that explains specifically how you can help their business. 

MISTAKE: The prospect picked up the phone unexpectedly and caught you off guard. You panicked, stumbled through the pitch, and wasted an opportunity. 

This has happened to hundreds of SDRs. 

C-levels answer the phone about once for every 25–50 times you call them. No wonder it’s surprising when they do pick up. 

The lesson here? Avoid falling into “going through the motions” when calling the top dogs. These will help:

• Open each client’s profile as you are calling them. 
• Bring up the last personalized email you sent.
• Change the client status in the CRM to “active” (change it back if they don’t pick up).

Even if you dropped the ball, there is still a chance to get your foot in the door. 

Own it. Follow up by email saying, “Hi, Joe, I’m the sales rep who stumbled.” Then promise to be on top of your game next time.

It will present you as a confident salesperson who is not ashamed to be honest. 

CHALLENGE: The industry or sector you target is experiencing a downturn, making executives less open to new engagements.

Be ready for the objections C-levels will give you. Pick your battles; keep pursuing only if you are confident your solution will help.  

For example, with the current layoffs in tech, startups may not be very keen to purchase costly HR solutions. What can you do? 

• Acknowledge the situation.
• Lay out the potential benefits of your proposal in this market.
• Throw in some valuable services, like team onboarding or audit, for free.
• Lean into short-term ROI vs. delayed gratification.

If it still doesn’t work and the prospect’s reasoning is sound, all you can do is gracefully agree. Say it’s unfortunate, and promise to get back in 6 months. 

Being honest in this situation helps build a good relationship and monetize it later. 

CHALLENGE: C-level executives have existing commitments or partnerships that conflict with your offer.

Find out if they are happy with their current solution as well as what they love most and least about it. If there is something that you can do significantly better, don’t be shy to say it.

Ask about the conditions of their current commitment. You may discover ways to tweak your proposal or find bargain opportunities that would incentivize the client to break up with their current vendor.

CHALLENGE: The executive is already in talks with competitors, making them less receptive to additional offers.

If you know that competitors will undercut you, be open about it. Tell prospects what will happen — it builds credibility. Ask them what they would do in that situation.

If competitors drop their prices but your quality is better, don’t panic. Voice your value and emphasize your speed of delivery. 

Should the prospect still want to go with a competitor, advise them to ask for a 90-day return guarantee, just in case. After all, sometimes the best solution is to let them try out another vendor and call back in 6 months when it doesn’t work out. 

CHALLENGE: The current economic or political climate is making executives cautious about new investments and unwilling to onboard new vendors.

When the economy is down, businesses tighten their belts. There is no silver bullet here, but you can try these: 

• Restructure your pricing and billing to make the load lighter for buyers.
• Lean heavily into any partnerships you have and ask existing clients for referrals.
• Segment the market to focus on the audience that keeps buying.

Political turmoil causes one more challenge: controversy. Salespeople have to be very careful with what they say today. Your clients may have strong opinions on some issues. Tread carefully and stick to broader topics like sports and weather.    

Hone your pitch

Here are 5 steps to make a perfect pitch to sell to the C-level:

1. Start with an executive summary.
2. Identify the problem.
3. Quantify it with real dollar values.
4. Identify the opportunity they have to solve the problem successfully.
5. Paint a picture of what the future will look like with your solution in place.

Focus on the high-level goals and don’t get into technicalities unless asked about them.

CHALLENGE: C-level executives perceive your offer as irrelevant to their current business needs.

Find a 10-K of the company or direct C-suite quote online. Look at the strategic initiatives the company or executive has stated (for example, “investing in technology to drive customer acquisition”). Now create a message around how your product has facilitated those goals in other companies. 

Name-drop similar customers and how you’ve brought them value. Use metrics if you have them.

CHALLENGE: Executives might have had previous negative experiences with similar products, services, or salespeople, leading to general skepticism.

If you feel like they are dismissing you based on prejudice, voice it: “I feel you’re not very keen on HR automatization. Did you have a bad experience?” Then listen carefully and let them talk. 

Acknowledge their arguments and offer new food for thought: “I see, yes, the technicalities could be a pain for the HR staff. This killed many early products in the field, which is why we now provide full support from our engineers for the tech side at no cost.”

Be authentic, and avoid taking on any negativity. Convey the idea that you are different from their previous experience. You are a new proposition with lots of value.

MISTAKE: Your offer might lack a clear and compelling value proposition that resonates with C-level executives.

When you talk value to the C-suite, keep it high-level and focus on the results. The 4 aspects they care about are: 

• Revenue/cash
• Profit margins
• Return on assets
• Speed to value

Use wording that shows you know their company and industry well; mention strategic initiatives, current issues, industry norms, big projects, etc. 

Try to bring something new to the table.

Talking to C-personas: What is going through their minds?

MISTAKE: The sales pitch lacks data or case studies to convincingly demonstrate the value or ROI of the product or service.

A few relevant success stories of similar organizations are must-haves. These prove your product is not an experiment; it produces tangible results. 

People trust other people’s experiences, especially competitors’ experiences that give them an edge. So you want to do these things:

• Gather cases from your clients.
• Tell what results your organization has if it uses the product.
• Practice descriptive but concise storytelling.
• Be ready to provide references.

It would be even better if you could loop in your deep knowledge of the industry’s current issues or trend-setting projects at this stage.

MISTAKE: You are unprepared to pitch the product or service to this particular company or address their specific challenges. 

Do extra research on the company. Find their 10-K online and check their strategic goals and directions. Tie it to your pitch by connecting your solutions with the client’s goals. 

Find and learn the names of department heads. Look at their social media to see if they have any complaints. Incorporate them in your pitch: “I’m sure Linda would love a better resource management system for the delivery department.”

Know what you want

Remember the next step you’d like to secure as you talk to your prospect. Will it be a Zoom call or a lunch meeting? 15 minutes or 45? Does anyone else have to be there? 

When you feel your prospect is ready to set the appointment, give them 2–3 time slots to choose from. 

Avoid saying that any time works for you. The C-suite doesn’t make time for people who have all the time in the world. Even if your day is wide open, say, “I have tomorrow at 3 p.m. open for a 15-minute discovery call. Can you make that work? Any questions you have beforehand that I can be prepared to answer?”

MISTAKE: There is a lack of personalized follow-up, leading to lost interest or forgotten communications from the executives.

Ensure your follow-up email is a personalized extension of your chat. A canned message may get the job done but will certainly not help build rapport. 

Include everything that you mentioned in your talk. If you promised to give numbers on specific case studies, loop in certain tech specialists, or provide the contact info of the best groomer for the CEO’s favorite poodle, make sure to do it. 

MISTAKE: There are no proper reminders set up to ensure that the C-levels show up for the meeting. 

Send them a text reminder a day before the appointment and then an hour or two before the appointment to their mobile number. If they can’t make it, it’s easier to reschedule. 

Takeaway

People signing checks don’t need approvals; they know what they need and will talk with people who can solve their problems. 

When setting appointments with decision-makers, make sure your offer solves a high-level problem they care about. Ditch the pushy scripts, know what you’re talking about, and tell them what you can do for them. 

Be concise and direct and schedule the right time and place, and within several days, you’ll have them watching your product demo and talking about leveraging your product in all their branches. 

Now go get them!