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Selling to the CIO: Practical Tips from Insight Partners’ CIO-in-Residence Daniele Tonella

October 13, 2022| 1 min. read

Getting into the mind of your buyer is critical in today’s technology sales world. For many of Insight Partners’ portfolio companies, that buyer is the CIO.  

Unfortunately, when selling to the CIO, many companies fail at the first hurdle: understanding all sides of the problems they are solving and the challenges CIOs face.  

After all, the pressure on the CIO has never been higher. They are now not only responsible for IT delivery but are being measured on the overall company performance, and in some cases, the protection of the core business.

Every day, new startup and ScaleUp technology companies claim to solve some of these problems and vie for the ear of any CIO who will listen. As a sales executive, you must stand out and ensure your message gets through.  

Here are the top priorities of Insight Partners’ most recent CIO-in-Residence, Daniele Tonella, as well as some of his insider dos and don’ts for selling to the CIO.  

Understanding the CIO’s hierarchy of priorities 

It was once enough to keep the computers on and servers humming. However, today’s CIOs must juggle a complex set of priorities to drive the business forward, complete ambitious digital transformations, and inspire a vast team of experts and talents.  

To develop credibility as a CIO and leader, Daniele views his priorities in layers.  

First, the table stakes are that technology works, is stable and secure, and delivers against the ever-increasing demands of the end customer.  

Next comes the sustainability of IT, which includes taking care of the organization's technical debt, managing and maintaining the architecture, and ensuring that inherited projects, initiatives, and innovation don’t trip over each other.  

Third, and crucial to delivering the first two, is leading the organization that CIOs sit atop. This is where Daniele spends most of his time, inspiring and developing his entire team and embedding the frameworks to grow and retain the rest of the organization.  

It is only after having built this solid base that the CIO earns the right for new technology solutions to sit at the table and actively contribute to the overall business strategy. This could be as part of an overall digitalization of the customer experience, or a tech-enabled shift in the underlying business model.  

The key takeaway for ScaleUps selling to the CIO is to understand where in this hierarchy of priorities your solution fits. By understanding this, you can show that you recognize the challenges a CIO faces in achieving that specific priority and speak the same language from the first conversation. 

Helping CIOs manage complexity 

According to Daniele, complexity is the biggest enemy of any CIO delivering on these priorities and ambitions. Complexity is inherent in the size of their organizations (a team of 10,000+ individuals is typical in Fortune 500 companies), with the number of projects (often in the thousands) they deliver annually.  

There is also the historical layering of systems, applications, tools, and processes developed under preceding IT leaders. These give rise to a complex “zoo” that must be controlled.  

Finally, the stakeholder map in the wider organization, from IT out into the business lines or division, to the consulting partners for transformation, to cloud providers and even up to the board all add complex networks of influence that can frustrate rapid decision-making.  

Understanding this should lead a ScaleUp to consider two things when selling to the CIO:

  1. How can I demonstrate that my solution will not add to the “complexity zoo”? (Hint: Think sound governance, proper integrations, significant adoption, true decommissioning, etc.)  
  2. Can I show how I will help the CIO to get on top of this complexity?  

Ultimately, complexity gives CIOs difficulty demonstrating success, so if you manage or reduce complexity, you will stand out from the crowd.  

Dos and don’ts: Selling to the CIO 

When you have an opportunity to engage with the top IT executive at a target enterprise you and your team have been chasing, consider the following insider tips:  

Do: Personalize your message 

When speaking with C-suite executives with limited time, it is more important than ever to have targeted, personalized messaging. Personalize your message based on the business area you want to work with and the type of CIO you target. Stakeholders will all have very different priorities depending on their area of responsibility. For example: 

  • Business-minded CIOs will focus on speed, features, and business value.  
  • Operational risk/cyber-focused CIOs will usually be interested in aspects like the net complexity impact (increase or decrease), ease to integrate, your support structures, and sustainability patterns.  
  • Procurement-conscious CIOs and CPOs will look at formal credentials, footprint, reference customers, and revenue models.  

Do: Put yourself in the mind of your customer 

Your technology might be the most innovative and forward-thinking, but if you switch your perspective to that of your customer (i.e., the ones that will have to use, maintain, defend, and operate your tech), what are they getting, and what complexity are you adding? It is critical to highlight how any emerging issues your product will inevitably add to their landscape are still less important than the emerging value.  

Do: Articulate how you reduce complexity 

Technology organizations are permanently under pressure from the business to deliver faster and better solutions, and existing complexity is a paralyzing factor. So many controls and processes have been built to keep complexity at bay. The dichotomy in the mind of the CIO will always be, “Should I move fast and fix later?” or “Go slow and think?” How can you help technology teams fulfill business expectations without sacrificing long-term sustainability in the process? 

Do: Show the credibility of your business 

Exciting technology – especially for core components – is not enough to sell it. If a CIO adopts your product for productive loads or using sensitive data, you will have to credibly explain that you have enough top-quality engineers ready to deploy very quickly if anything happens. CIOs must balance the risk and opportunity of any new technology, but can you help them get comfortable with any operative or reputational risk introduced by your product? 

Don't: Forget the real competition

For many ScaleUps, the competition in a large organization isn’t the other similar solutions on the market. Rather it is the various home-built solutions or processes that currently address, possibly in a suboptimal fashion, the challenges you solve. The institutional viscosity that comes with very large organizational systems can resist the adoption of a new tool, too, particularly where it might add to the complexity. Consider asking how an organization is managing a particular problem today and build the picture of what needs to change (or disappear) for your solution to be net value positive.  

Don’t: Cut IT out of the picture 

If you try to sell software directly to a business, chances are you will reach some level of prototype and then you will have to link with IT for a scale deployment. The technology team may at best ignore your prototype, but in some cases could actively prevent product acquisition. This is not a matter of politics or personal sensitivities. Software is like an iceberg; businesses only see some part emerging from the water, but technology will have to take care of the submerged mass.  

You can seize the opportunity to be an internal “connecter” and ask the business to bring the technology team to your engagement earlier in the pursuit to keep everyone aligned and avoid unpleasant surprises. 

Don’t: Name drop 

Be careful with statements that suggest everybody is already using your platform, e.g.: “75% of Bank X’s revenue goes through our system,” or sharing a page filled with renowned logos. If some of your flagship customers have deployed your solution on only a fraction of their eligible scope, technically you have their logo, but in practical terms, their reference is not relevant.  

The real proof here is in pertinence and adoption. Share two or three robust case studies (even anonymized) that demonstrate the breadth of use and tangible results. 

The CIO-in-Residence program is an initiative of Insight IGNITE, the Technology Intelligence Ecosystem trusted by executives from the world’s most established businesses to connect, learn and drive decision-making and business excellence.   


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