Always Be Selling: How CIOs Can Improve Their Sales Skills

Success as a technology leader requires much more than just the effective technical implementation of a new system. In fact, that’s often the least challenging aspect of achieving anticipated technology-driven business outcomes, whether that’s increased revenue, decreased cost, or reduced risk.

The biggest success factor for most CIOs is how effectively they can drive change. Getting others in the organization — from users and technology team members to the board of directors and the C-suite — to think and behave differently is an essential capability.

In short, CIOs need to be able to sell the changes they seek. But it’s a role that may not come naturally for many IT executives.

Why Selling Matters for CIOs 

Sales tends gets a bad rap — not least among tech leaders. But the art and science of selling has emerged as a critical skill for the modern CIO.

For many IT leaders, particularly those who rose through the tech ranks, early successes hinged on how well they performed a specific task or solved a particular problem. As they rise through the ranks, however, their roles involve less doing and more directing or influencing.

Many IT leaders may not even realize how often their salesmanship (or lack thereof) played a role in their careers. As CIOs, we continuously influence our board and executive team. We are painting a picture of how, using digital levers, we can improve business outcomes, remove friction and cost, or even transform the organization and its products or services. Once we’ve got top leaders on board, we must sell the change internally — both to our own technology teams and the broader organizations — in order to make the vision a reality and reap the business benefits for the organization. In many cases, we also must sell our customers on a new technology, process, or approach.

A CIO needs to be more than just technically proficient. Without the ability to sell business leadership, stakeholders, customers, and our own technology teams on the value of any new initiative, we’re bound to fail.

Advanced Sales for CIOs: Know Your Audience

How do you sell change? In short, it depends.

When it comes to technology-driven change, there are three main audiences to consider: employees of the organization (including — and sometimes, especially, those in the IT function), the executive team and board of directors, and end customers. Winning over each of these groups requires an understanding of their needs and motivations. Let’s look at each audience and how IT leaders can best influence them:

1. Employees (Including the IT Function): What’s In It For Me?

It’s essential for CIOs to sell their vision to their own technology staff and the rest of the organization. After all, if our colleagues do not understand where our organization is trying to go, how can they help us get there?

IT leaders see increased engagement when they are able to connect the dots between a proposed technology change and the organization's mission and values. However, full buy-in is critical to getting the broader workforce driving toward the same goals to achieve the intended outcomes of technology-driven change. That requires greater specificity.

What employees and your IT team members want to know is what’s in it for them. A helpful approach is mapping out how implementing the strategy or initiative will benefit various groups. Everyone tends to be more dedicated to change if they understand how it helps them personally. If a CIO can’t sell the broader enterprise on that, their programs are likely to flounder and fail to deliver expected (and available) value. For example, implementing a new online reservations system for a restaurant chain will fail if the individual restaurant managers refuse to open their schedules. They need to know how the new system and processes will make their lives easier in order to buy into change so that expected benefits can be captured. 

2. Executive Leadership and the Board: A Strategy-First Approach

The primary audience for selling a technology change is an organization’s C-suite and board of directors. A CIO’s executive peers, CEO, and the board are critical partners in establishing digital strategy. Not only does this group decide on prioritization and funding, their ongoing buy-in and support is essential to moving digital initiatives through delivery and beyond.

Selling top leaders on technology investments hinges on business alignment. The pitch should be centered on business benefits and how the change will further the organization’s strategic goals. However, the persuasion should begin before the official board presentation or IT steering committee meeting. Smart CIOs work to win C-suite and board members over through informal discussions and one-on-one meetings to explain their ideas, their business benefits, and the financials involved. This creates buy-in to your vision.

Most importantly, effective CIOs never lead with the technology itself; they sell the leadership on the ways their digital proposals can facilitate and accelerate business outcomes. In a previous role, I led a discussion with senior leaders about how we could collect more customer payments before we provided service, thereby reducing our risks and collection costs. Based on the time I’d spent with customers (in this case, medical practices), I understood the root causes and painted a picture of how a digital solution would enable customers to schedule, check-in, and pay their bills via self-service, thereby accelerating receivables. The executive team recognized the business value and gave us the green light to implement the pre-service digital capabilities and drive adoption.

An alternate approach is to enlist a peer or business unit leader and together do your bidding to the executive team or board. Partnering with a COO, CFO, or CMO who shares your vision can make the sales pitch can be even more powerful than going it alone. 

3. End Customers: Building Trust and Relationships

The ultimate buy-in for many external-facing technology changes or digital products will come from the end customer. If the customer is willing to use your new product or — even better — pay for it, you have truly created measurable value. IT leaders who invest time in understanding their customers are best positioned to sell the value of the products or new customer-facing changes they develop. The way to do this is to go find out what customers do, and how they use your products.

Most successful sales professionals know that listening to a customer is more important than making a pitch to them. Learning from customers and getting buy-in from them is about more than direct sales of a specific product or new way of interacting. CIOs earn the trust and respect of end customers by spending time with them to understand what their frustrations are, what excites them, or what their goals are.

One interesting way for IT leaders to do this it to join the business development team for larger deals. A CIO on the team can bring an understanding of the technology value embedded in a product or service. Even more importantly from a CIO-as-salesperson perspective, working in business development gives the IT leader more facetime with the end customer and greater understanding of what products, services or features would create the most value for them. Spending time with sales teams is another way to get closer to end customers. 

When I worked in pharmaceutical services, I was involved in business development and led discussions with our customers about how digital would enhance our services and create more value for them. Talking customers through this in a workshop setting enabled them to visualize the uniqueness of our offer and the potential benefits for their organizations. This differentiated our sales pitch from our competitors and helped us win deals. I also found that customers appreciated a member of a vendor’s executive team spending time with them. Learning what makes end customers tick and how your company’s products and services meet their customer needs (and how they don’t) not only earns you social capital but provides insight for selling digital change to your board, executives, and other potential customers.

The Importance of Selling Digital

Ultimately, the difference between success and failure for sales professionals boils down to how well they understand their target audience’s needs and motivations and the extent to which they can offer them something that helps customers achieve their own goals. The same is true for CIOs. The ability to sell technology-powered change — to our teams, our executive peers and board members, and our customers — is vital to being not only a successful technology leader, but a full business leader managing the digital portfolio. And, as technology becomes even more intrinsic to business performance and growth, that’s the role every CIO must play.