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6 Tips on how to sell to a CEO, CFO, CTO

C-suite buyers are a busy bunch with a lot on their plate.

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C-suite buyers are a busy bunch with a lot on their plate.

They’re consumed with margins, revenue and strategic goals and they’ve heard every pitch in the playbook.

While selling to a CEO, CFO, CTO and other big fish is challenging, it could be your organization’s best shot at a rapid, post-COVID recovery. As mentioned in a recent report, SMBs may be unable to invest in new solutions for several months.

Sellers must prove they’re different from the “bad” reps that came before by gaining a deep understanding of the mindset and motivations driving the typical CXO.

With a bit of planning and a few strategic plays, selling to the C-suite doesn’t have to be that hard.

In these next few sections, I’ll go over some of the best ways to connect with top decision-makers and win those big-ticket deals.

1. Use intelligence to warm up first-time interactions

Enterprise sales have always been the moneymaker of the sales pipeline. Lockdown a few top firms and hitting revenue goals starts to look easy.

That said, for reps used to chasing small and mid-size companies, advancing to the C-suite requires a different approach.

Prospecting C-level executives is a research-intensive process, as traditional cold outreach strategies don’t typically work on CXOs.

While this group tends to prefer solutions recommended by a trusted source, gathering the right intelligence is key when it comes to providing relevant solutions to someone you’ve never met.

According to LinkedIn, 89% of buyers won’t speak with a salesperson if they don’t share relevant insights about their business, while nearly 60% of respondents automatically reject any attempt at cold outreach.

That same report also found that 92% of buyers say they’ll engage with a seller who is considered a thought leader in their industry.

To learn more about leveraging social selling in B2B sales, this post breaks down the best practices you should know.

2. Get friendly with the gatekeeper & other stakeholders

Getting the CEO on the line might be your intention, but chances are slim that they’re manning the telephones. Most C-level buyers have an assistant that answers the phone to prevent spammers from harassing top brass.

While getting past the gatekeeper is a strategy in its own right, your best bet is to approach them as a potential ally instead of an obstacle.

Be sure to treat the gatekeeper with respect and explain your reason for reaching out and why their boss should care. Here, you’re not trying to “sell” the gatekeeper you’re making a connection who may put in a good word.

You’ll also want to spend time getting to know the stakeholders involved in the buying process.

Managers, directors and customer-facing teams are more invested in specific features and benefits, as they’re the ones who will be using the solution each day. They’re the ones researching solutions and comparing their options.

Your goal is to help buyers make sense of the information they’ve gathered, understand evaluation criteria and build consensus around a solution by sharing helpful insights.

Check out Gartner’s buyer enablement graphic to get a sense of what information best supports buyers through the process.

3. Build a narrative around the C-suite perspective

Okay, you’ve done your research and identified potential allies on the inside.

But, before you make contact, you’ll need to get your story straight.

As GrowthX founder, Sean Sheppard points out in our post-COVID recovery report, sellers need to orient themselves around the individual buyer and gain a deep understanding of the problem from their perspective.

Your product, solution or service is probably of zero interest to a CXO, for instance, unless it hits all the right pain points.

Additionally, reps must contend with the fact that execs are constantly being pursued by other sales teams, most of which they find disruptive, irrelevant or not quite right.

The C-level exec might have the final say, they’ll likely never use the solution, and as such, you’ll want to focus on

4. Position yourself as a trusted resource

You might know your stuff inside and out–the problem is, your prospect isn’t so sure.

Executives have seen their share of inflated claims and clueless reps, put aside your ego and avoid the urge to prove that you know more about their business than they do.

The RAIN Group recommends building trust with skeptical execs by using data to demonstrate past successes, stick to your commitments and admit it when you don’t know something.

Ultimately, this process takes time but focusing on being reliable, helpful and empathetic will pay off in the long run. As mentioned above, building out your online reputation can help you avoid resistance in the future.

Additionally, executives are always looking for new ways to gain a competitive advantage. As you research your prospect’s industry, look for opportunities or gaps they might not know about.

In cases where there aren’t any glaring strategic issues, introducing an emerging threat can have a similar effect.

By unearthing blind spots in their strategy, you’re creating a sense of urgency to act now or risk losing ground to the competition. The Challenger methodology, which centers on original ideas and debate might work well with this group.

5. Stay in control, even if execs try to dominate

When selling to the C-suite, reps often find themselves on one side of the spectrum or another when it comes to controlling the conversation.

Some sellers over-prepare and attempt to tackle too much at once, which means they end up doing all of the talking.

Others go in the opposite direction with the intention of asking discovery questions and letting prospects guide the conversation. The problem with this approach is, discovery questions don’t work that well at the executive level.

In fact, one study found that the more questions you ask, the shorter prospect responses become.

Discovery questions benefit the seller, allowing them to create solutions based on prospect answers. For end-users, answering questions stands to benefit them later on.

C-level decision-makers want you to tell them

  • Where’s the final destination?
  • What stops will you hit along the way?
  • Are there key points you absolutely need to hit?
  • Which ones are optional?

Additionally, you may want to prepare for a few “choose your own adventure” scenarios.

That way, you’ll have a few different routes memorized and can get the conversation back on track, even if it’s not what you initially had in mind.

6. Call during off-peak hours

In another recent blog post on C-level sales, we mentioned the importance of diversifying communication channels to see what works best.

Well, same goes for timing your outreach efforts. Instead of dialing prospects at the same time each day and leaving a voicemail,

Sales consultant Mike Brooks recommends calling prospects 3-5 times (not on the same day), at different times and on different days before you ever leave a voicemail.

The key, as always, is to be persistent, not annoying.

Essentially, Brooks’ approach allows you to gather intel on the “best times” to call, thereby increasing the chances of making a good impression.

According to sales expert, Marc Wayshak, you might even try calling executive buyers outside of typical business hours.

While this may be harder to pull off, calling on nights and weekends may be the best way to break through.

Final Thoughts

When you’re selling to the C-suite, it’s all about the big-picture. Focus on providing out-of-the-box ideas and alerting prospects to opportunities and threats on the horizon.

A few more things to keep in mind:

  • Don’t waste their time. Again, executives are busy. Failing to do your research before reaching out or going off topic will give off the impression you don’t respect their time.
  • Use LinkedIn, but be smart about it. It’s a great research tool for helping sellers identify the best path toward chatting up a CXO. However, you’ll want to hold off on messaging prospects on the spot to prevent any inadvertent spamming.
  • Demonstrate competence by being helpful. While the whole “rep as trusted advisor” is on the brink of becoming a cliche, keeping that role in perspective can help you stay focused on the buyer’s best interests.

In the end, C-level sales isn’t really that different from selling to lower-level decision-makers or SMBs. While they may not share objectives or pain points, trust, value and a laser focus on solving problems win deals at all levels.

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B2B content writer & strategist

Grace is an experienced B2B content writer & strategist for SaaS, digital marketing, & tech brands from Los Angeles, California. With a knack for turning complex concepts into compelling narratives, she has assisted numerous brands in developing impactful content strategies that engage audiences and drive business growth. Her wealth of experience in the ever-evolving tech world has equipped her with a unique perspective on industry trends and dynamics, enabling her to deliver content that resonates with a tech-savvy audience.