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The Five Biggest Goofs Sales Teams Make with CXOs

Sharon Gillenwater
by Sharon Gillenwater on Oct 18, 2016 7:48:37 PM

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Longing for the good old days? You know, the Mad Men school of closing sales over leisurely three martini lunches or a game of golf? Yeah, enterprise B2B selling is harder these days. There are so many more stakeholders who have a role in the buying decision—especially when it comes to major technology purchases. And, increasingly, it’s top-level management—those in the C-suite—who are making these critical decisions. It doesn’t help that global enterprise IT spending growth has been flat—at 1 percent in 2016—according to Gartner. And yet even that small percentage still lays a lot of budget on the table—around $2.7 trillion globally.

So the pressure is on for sales teams to focus their efforts on wooing CXO decision makers. And that’s hard—mostly because sales organizations have to change not just how they do things, but their very philosophy around sales. Deals can take months and months to close and need a level of nurturing that sales teams aren’t necessarily equipped to do. Often, mistakes are made, potentially alienating the very people you are trying to impress.

Do these goofs sound familiar?

Making it all about you

CXOs don’t want to hear about how cool your product and your company is. The CXO expects your sales people to have developed some understanding of their business—their markets, their pain points, new initiatives—and their industry—what their competition is up to, how they can get ahead. You should equip your sales team with customer insight and train them to connect the dots so that going into a meeting or conversation they have at least one compelling nugget of insight about the customer—or their customer’s industry—and can connect it back to your solutions, and how they can address one of the customer’s initiatives or challenges.

Being a know-it-all

A little knowledge can be dangerous if it is not used in the right way. Let’s say you’ve been able to provide your sales team with key insights into the CXO, the organization, and the industry. They’ve studied and are primed for the meeting. But what they end up doing is spouting their newly acquired knowledge off like a student to a teacher, almost trying to one up the customer instead of using these insights to ask more probing questions that engage the CXO, demonstrate a sincere interest in their business, and create a learning opportunity. That takes training. Is your company training its sales people to have productive business conversations?

Taking things too fast

Salespeople are always under pressure to make quota. But coming on too strong with a CXO could get you frozen out of the C-suite. Spend some time getting to know the company and its decision makers and prove yourself to be a worthy business partner by providing thoughtful, relevant thought leadership and solutions. This might require that your company retool its sales goals and approach to compensation. You have to create an environment in which the account strategy is about the long game.

Trying to go it alone

Given how critical technology has become to enterprises, sending sales in alone to talk high-level business strategy with a CXO is a missed opportunity. Even if they do everything right, support from your own leadership team—like a CIO or one of her direct reports—can go a long way to help you advance the relationship and the deal. As CEOs in particular are becoming more engaged in technology transformation, they want to talk to their peers.

Having a “won and done” mentality

That hard-won deal was made months ago and your team has moved on to the next customer. But relationship building doesn’t end with the P.O.; be careful not to drop the ball! Does your company have the infrastructure to support ongoing customer engagement? No one likes to feel ignored after the deal is done. Relevant thought leadership, personalized invitations to events, and check-in calls from CXO peers can go a long way in making the customer feel appreciated and valued. It is in your interest to stay connected and engaged because change is constant; there may be new RFPs or important events like mergers, strategy shifts or new initiatives that pose new business opportunities for your company. If your team is not in touch, you’re not in the know—an invitation for your competition to move in on your customer.

Training your sales team to be effective CXO sellers is a complex undertaking that requires buy in and ongoing support from your own corporate and sales leaders. But if you consider the long-term benefits of successfully transitioning from one of many vendors to a valued and strategic business partner, isn’t it worth the effort?

Sharon Gillenwater is the founder and editor-in-chief of Boardroom Insiders, which maintains an extensive database of the most in-depth executive profiles on the market, from Fortune 500 companies to independent non-profits, to help sales and marketing professionals build deeper relationships and close more deals with clients. Gillenwater is a long-time marketing consultant with expertise in marketing strategy, account-based marketing, and CXO engagement programs.

For help establishing relationships with your top CXO prospects, learn everything you can about them by downloading their executive profile from our database. Wonder what our profiles contain? Take a look at our free sample profiles and you'll see.

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Sharon Gillenwater
Written by Sharon Gillenwater
Sharon Gillenwater is the founder and editor-in-chief of Boardroom Insiders, which maintains an extensive database of the most in-depth executive profiles on the market, from Fortune 500 companies to independent non-profits, to help sales and marketing professionals build deeper relationships and close more deals with clients. Gillenwater is a long-time marketing consultant with expertise in marketing strategy, account-based marketing, and CXO engagement programs.
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