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Why Sales Reps Fail To Woo C-Level Buyers

Jun 26th, 2017


I’ll never forget that phone call. It came from a sales representative, sitting in the parking lot outside a North Carolina office building. He was about to conduct the biggest sales meeting of his career – with the CEO of a Fortune 500 food manufacturer. I could actually hear him quaking through the phone and was worried he might pass out. As a sales consultant, I ran through his presentation with him one more time – telling him he was ready to rock and to give me a call the moment he was done. We’d been preparing for nine months, and now, waiting by the phone, it was among the longest two hours of my life!

Working at a small firm that sold maintenance and reliability consulting services, the rep and his colleagues were accustomed to selling to people with hard hats and metal desks – not the one at the walnut desk. Venturing outside that comfort zone was, to say the least, scary.

The fears that gripped him aren’t unique. C-level meetings are hard – as they often require a different approach and mindset – but they’re critical to closing more and bigger deals. Unfortunately, though, many reps simply don’t go after the C-level sell – and when they do, they approach it wrong. Consider this:

  • Eight out of 10 executive buyers say the sales meetings they take are a waste of time, according to Forrester Research. And while reps claim their meeting preparedness merits a “B” grade on average, C-level buyers rate them an “F”!
  • It’s no wonder – reps don’t demonstrate knowledge of their buyer’s business (according to 75% of executives), nor do they present solutions that address specific issues buyers face (per 77% of executives), also according to Forrester.

Shame on those reps? Perhaps. But there’s also larger blame to be placed at the organization level, as sales leaders fail to adequately prepare their team to secure and capitalize on C-level opportunities. Reps, in turn (and quite naturally), often default to what’s comfortable.

Sloughing off the status quo

Overcoming inertia isn’t easy. We’re often talking about a nine-to-12-month change management process. Along the way, reps need to develop the confidence and competencies for having C-level conversations. Management – from front-line sales managers, to sales and organizational leaders – needs to be vocal about their buy-in.

Of course, not every sale merits this approach; it’s typically reserved for strategic accounts. In those cases, it’s important to pivot to speak the language of business – showing business value at the place where it’s bought. At the maintenance consulting company, we had to elevate a staid and arguably boring concept and elevator pitch – which did resonate on the operational floor – and make a compelling case to senior organizational leaders.

I recommend three key steps for reps to get there:

  • Research, research, research: When it comes to getting well-versed in a prospect’s business drivers, strategic objectives, key challenges and industry news, Internet research is a start. Reps should be expected to pore over not just their target company’s website, but also its 10-Ks, quarterly earnings reports, etc. They should then confirm and expand their insights by talking to people within the target company. The rep I’d mentioned earlier dug deep into that Fortune 500 food manufacturer and found it was looking to grow through acquisition.
  • Gain C-level access: It’s no secret: CEOs don’t, typically, want to meet with salespeople. The easiest way to get in the door is by being “sponsored” through current relationships. Sometimes reps are blocked, though – with a contact insisting that he/she makes those purchasing decisions. In those cases, it helps to do a risk-reward analysis of circumventing the gatekeeper. Then, if reps do forge ahead, they need to cut through the clutter. While scores of emails go unopened, snail mail – especially in a FedEx express envelope – generally won’t. The rep I mentioned kicked off his letter with a quote from the target company’s earnings report, demonstrating knowledge of the business and how he might help.
  • Refine the presentation: Traditional sales calls focus on discovery – with reps asking questions, then gaining an appreciation of the buyer’s needs. On the C-level side, it’s different; reps can’t engage until they’ve done their homework and earned the right. It’s a delicate balance, though – they can’t appear too cocky, and need to demonstrate and validate their knowledge with humble language. In the rep’s case: “I understand sales are lagging, and you’re looking to grow through acquisition; is that right? If you could release money from maintenance to free assets up for these activities, would you be interested in that?” From there, the meeting can transition into more of a two-way conversation.

Sure, reps are the ones selling – but they’re not the only ones who need to be deeply familiar with these skills. This approach is often something new for managers too, and they need to be adept at coaching reps to mastery. I liken this to asking someone who’s coached baseball all his life to now coach cricket.

Implementing the approach 

So at the maintenance and reliability consulting company, we put this approach into action – preparing managers at every step, so they could reinforce and drive desired behaviors with their reps.

We developed eLearning courses and content for reps, too, that detailed how to do their homework and thoroughly research an account, reach C-level executives, and customize and build presentations. The reps consumed the content when it best fit in their schedules – without losing time in the field – and returned to materials as needed, with managers able to track eLearning completion.

Then it was time to take these concepts out of the theoretical realm and into the practical one. I held a two-day workshop, and reps had to come in with an account they planned to implement this approach in. Reps got up and delivered their presentations – we videotaped each one, and subsequently reviewed it with the rep. Each rep went through the process three times, and by their last presentation, they were ready!

At that point, I acted as many of the reps’ in-field coach – putting them through a dry-run right before their actual meeting.

It all pays off

The new, multi-pronged approach – reinforced by training and video coaching – was extremely successful. After undergoing this sales transformation, the manufacturing consulting company grew its business by 40 percent year-over-year, and deal size doubled in the accounts where C-level conversations were had.

And that panic-stricken rep I’d mentioned earlier? He was well-prepared, swallowed his nerves and totally nailed it. After explaining how money “hidden in the couch” of the food manufacturer’s factory could help fund acquisitions, he hooked the CEO, who noted that he wished his own employees knew the business as well as that rep did. “We’re putting you on our preferred vendors list,” the CEO further remarked, “and want you to start right away.” The rep called me immediately to share his excitement – and the fact that he nearly did a dance in the parking lot! It made the nine months of hard work all worthwhile.

This article originally appeared on on June 8, 2017.