Today’s CIO Needs To Be Able To ‘Dream Big’

Ben Askin, CIO of Vertex
It’s hardly the model most think of when they consider IT leaders, but curiosity, an adventurous spirit and creativity are critical, says Ben Askin, CIO of Vertex.

What does a modern CIO look like? Your idea might be out of date.

Ben Askin, CIO of Vertex, a tax compliance software and services company based in King of Prussia, Pennsylvania, tells StrategicCIO360 the most important quality of a top information chief is the ability to dream. He shares why it’s critical to be able to think big and how he coaches future IT leaders.

What’s the most important quality a CIO should have?

In my view, the most important quality the modern CIO should have is the ability to dream. To dream the dreams of a company’s biggest aspirations and realize those dreams into highly effective and measurable business enablement solutions. 

Today’s CIO must be a multifaceted leader that inspires teams to drive digital business innovation in every corner of the enterprise. The CIO must also provide a grand vision with respect to the overall business solution architecture that will propel the organization forward in terms of growth with cost effective operations. 

Today’s CIO must have an extremely strong understanding of what the company does and how the company runs both operationally and financially. This is extremely important when CIOs and their teams determine the best enabling technologies to use within the organization to optimize both work efficiency and decision-making, informed by high quality, well-organized data.  

This level of strong business acumen cannot be understated in today’s fast-paced business environment. Including deep understanding of the differences between leveraging SaaS based platforms to drive cost effective business growth versus traditional on-premise technology.

I cannot stress enough the need to understand the economics, payoffs and pitfalls of the new modern SaaS world that we are in.  SaaS-based everything is game changing but if you don’t understand the intricacies, you’ll find yourself and your company upside down very quickly. 

Finally, today’s CIOs need to be highly curious and adventurous with ways that machine learning and artificial intelligence can be used to drive new levels of business, employee and customer performance. Moore’s law of computing power as the driving force behind technology advancement has now been obliterated with the rise of generative AI. How to effectively harness the power of this amazing technology while protecting the company and customers is simply going to change everything, like the personal computer and the internet. It is going to be a big shift.  

CIOs and technology leaders have the unique opportunity and an ethical responsibility to help businesses, customers and humans leap forward for unimaginable gains in performance and productivity.  

How can a CIO stand out in today’s business climate?

For the modern CIO, especially those that work in high-growth companies, the business and technology landscape is changing quickly. Stand out by ensuring you have the right technology foundations and capabilities in place to support the most important business drivers at your company. For Vertex, it is all about time to market and product growth, all supported by highly optimized and cost-effective operational business processes.  

Our customers, partners and the global tax regulations are moving so fast that we need to adapt to changes within weeks, not months—and certainly not years. Our entire IT business architecture is completely SaaS componentized and business solution product centric. Meaning, we run IT like a commercial SaaS software company. This enables us to go fast, and we can change out underperforming processes and technology enablers in days, keeping our business teams focused on doing the work of Vertex. 

Historically, IT departments have operated as cost centers, but that isn’t the case anymore. Today CIOs are business innovation leaders enabling everyone in the company to operate at their highest level of performance. Differentiating CIOs work to drive the company forward, with a focus on innovation that helps business teams evolve, scale and grow globally across a variety of customer ecosystems and a diverse set of solution offers.

Gone are the days of making sure everybody has a laptop, an email account and a finance system. It is also important to understand that your business data is the new gold of your enterprise. At Vertex, we exhaustively work with modern cloud data technologies that ensure our employees, customers and partners have highly reliable data at their fingertips, so they can make rapid and reliable decisions.

With that, great data ensures artificial intelligence and machine learning can drive performance through incredible decision support for our employees and leaders. The architecture and interplay of robust business platforms, standard business process and data technology enable us to go faster, and allow us to make great decisions and run highly cost-effective business operations. 

I like to boil it all down this way. The company’s leadership team will make multi-million-dollar decisions each week regarding the direction of the company. As CIO, it is your job to ensure there is world-class decision support ensuring leaders and teams have what they need to make the best decisions as possible in a timely manner. This means all the process, data and technology components that make up your operational enterprise have to be perfectly architected and operationally mastered by your IT team.   

How do you describe the growth process of successful IT leaders?

Here is what I look for in aspiring IT leaders. First, you must be coachable. Do you have that willingness to hear what you need to hear versus what you want to hear and then immediately act on that coaching? Do you have the courage to dream big and go for it? It’s a risk-reward situation. You must play to win. I look for that courage in somebody who has confidence in themselves that they can move something forward, while inspiring their team to drive the challenging work ahead of them.

Secondly, emerging IT leaders need to be super curious people that will engross themselves in all of the technological elements across data, processes and user experience. Technology is evolving all the time, so you must stay on top of it to be agile and responsive. 

Finally, you need to really understand your customer. At Vertex, we work with a diverse range of customers from Fortune 500 companies, large marketplaces to mid-market growing companies. Each customer ecosystem will have totally different business models and particular needs that our employees are trying to service.

As an aspiring IT leader, you need to be astute and quick to understand these needs and be thoughtful and expeditious in deploying technology processes needed to support them. Make it a great experience for your customers and a great experience for your employees. As an emerging IT leader, be an obsessive student in understanding the business aspects of your organization, which I would say is about 60 percent of my role as a CIO.

How do you coach future IT leaders?

As a CIO, my job is to put future IT leaders into positions to lead, grow and learn without over-managing them. I provide structured coaching, including direct communication along the way. Emerging IT leaders must learn to take calculated risks in order to move the organization forward. Therefore, it is natural to fail and make mistakes, but the way you respond is what makes you a leader.

Strong leaders use failure to grow and they understand the bounce-back moment and how it defines their leadership development needs. This pragmatic and realistic approach will ensure a successful growth trajectory for the emerging IT leader. 

IT leaders are like aspiring athletes. They dream big, work hard and understand that they always have a lot to learn and can always do better. It’s up to the CIO to coach them on how to improve, how to learn and how not to be afraid of failure. To continue pushing the limits of what is possible, which will result in driving the organization and their career forward.

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