Selling to the C-Suite: Five Keys to Success

Selling to the C-Suite: Five Keys to Success

The boss, truly, is in charge.

If selling during the pandemic has taught sales leaders anything, it’s that many of our buyers’ CEOs are taking a renewed interest in the procurement side of their business. After all, if the buck stops, truly, with them, it’s little surprise that in a time when budgets are strained and every dollar scrutinized, that CEOs are taking a more active role.

In fact, according to recent data from technology company, C-suite participation on the buying side is up an average of 80 percent. Both CEOs and CFOs are popping up more regularly on sales calls – in fact, they’ve replaced technical and tactical leaders on sales calls about 71 percent of the time.

The good news is that, with the company’s top-most decisionmaker along for the ride, deal throughput is increasing. Win rates, according to, improve by 38 percent when the C-suite is involved in the buying process.

So, what do your sales professionals need to do to ensure success with this much broader audience?

Be more insightful:

Given that sales pros have a direct audience with C-suite stakeholders, it’s critical that they bring their A-game. Look beyond the rote sales pitch and ask questions that get to the heart of their objectives and strategies and reveal their levers.

In a recent conversation with Sharon Gillenwater, Co-Founder and CEO at executive intelligence firm Boardroom Insiders, we discussed something called the “uncertainty gap” – a way to characterize this lingering uncertainty in the sales landscape where the only constant, truly, is change.

So, the goal of your conversation should be to help your buyer understand how your offering can offer a sense of stability, whether it be in the form of lower costs, lower maintenance expenses, higher profitability – in short, a counterpoint to the chaos.

Think like a startup:

According to a recent Deloitte article, the current environment has created both the need and opportunity for leaders to rethink their business models. As C-suite individuals work to understand what the next normal looks like, they are having to throw out the traditional playbook and consider how to retool their product lines or services to really fit the market right away.

In this sense, it is important that your sales team positions its offering to demonstrate how to really drive your buyers’ spirit of innovation.

Go beyond:

In lockstep with the previous point, be mindful of the fact that your buyer is not considering small changes – and, consequently, they won’t be swayed by diminutive solutions. Offering a better discount, or better payment terms, is less impactful than answering the big-picture question of how your offering can improve the process – for example, how it can help them operate more efficiently, or automate a portion of their existing process, or offering an online transaction portal that allows customers a greater degree of self-service.

Balancing defense against offense:

In the early days of the pandemic, CEOs had the weight of the world, quite literally, on their shoulders. They were dealing with furloughs, profitability, and how to keep the doors open. Now, with sufficient time to consider opportunities for progress in the next normal, they have shifted to an offensive posture – looking for ways to innovate, digitize, communicate – in short, not just survive, but truly thrive in the new world.

Your sales professionals’ ability to communicate how your offering can be a part of this offensive assault on the marketplace, through conversations that are largely strategic, is the key to earning a spot in the lineup.

Bring your arsenal:

Don’t be afraid to invite your key leaders into the conversation as well. It’s just a fact – C-suite executives like to talk to like-minded leaders. Bring your top executive and arm them with enough background details (gleaned from annual reports, blogs, investor conferences, etc.) to be an active participant in a strategic, problem-solving conversation.


Michelle Richardson

Michelle Richardson is the Vice President of Sales Performance Research. In her role, she is responsible for spearheading industry research initiatives, overseeing consulting and diagnostic services, and facilitating ROI measurement processes with partnering organizations. Michelle brings over 25 years of experience in sales and sales effectiveness functions through previously held roles in curriculum design, training implementation, and product development to the Sales Performance Research Center.

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