From CIO to CEO: Yvonne Wassenaar discusses the future of technology

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To survive today, companies need tech-savvy leaders. The convergence of cloud, SaaS, mobile, big data and more is turning every company into a technology company. As a result, CIOs need to step up and partner closely with business leaders to drive strategic initiatives and growth opportunities. In some cases, CIOs are even stepping up into the CEO role itself.

I sat down with former-CIO Yvonne Wassenaar, who recently transitioned into her current role as the CEO of Airware, an enterprise drone analytics company based in San Francisco. Yvonne has spent over 25 years in the technology industry, formerly serving as CIO of New Relic, Office of the CXO at VMware and partner at Accenture. As CEO of Airware, Yvonne is translating her IT skills to help customers develop actionable insights from drone analytics in order to improve efficiency, productivity and safety.

As a CIO-turned-CEO, Yvonne has a unique perspective on the technology landscape. In this Q&A, Yvonne discusses her transition, the opportunity CIOs have to partner closer with business leaders in order to guide their organizations successfully through digital transformation, and how she’s thinking about digital ecosystems. Let’s dive in.

Q: What’s been the biggest difference as CEO? And why are CIOs becoming CEOs?

Yvonne Wassenaar: I’m sure most CIOs can relate to this, but as CIO I was always trying to convince people of certain strategies. As CEO, that all changes. What you say, who you say it to, how you say it—your words carry long and far. You are the vision, the biggest cheerleader, the one who’s going to stand strong through thick and thin. The responsibility is tremendously different, as you are no longer a contributing member of the team but the sole person ultimately responsible for ensuring the future success and growth of the company. It’s a big change.

I believe CIOs are increasingly becoming CEOs for a few reasons. One, technology is entering every aspect of our lives, so successful CEOs need to understand how to leverage technology. That wasn’t as important a decade or two ago. Additionally, provocative CIOs are starting to get a seat at the executive table versus being hidden in the data center or back room. They’re more visible and driving real business impact. It’s an exciting time to be in IT.

Q: How have your IT skills translated into the CEO role?

YW: Successful CIOs build a lot of strengths that make them perfect CEO candidates. First, it’s one of the few roles that require a breadth of understanding across the entire company. As CIO, you’re the technical partner for all business functions—finance, sales, marketing and more. It’s critically important to understand these intersection points, as it’s usually where challenges come from.

A second skill set that’s wildly transferrable is portfolio management and conflict resolution. CIOs typically don’t have enough budget while simultaneously dealing with increasing demands from the business on what needs to get done. They’re constantly sorting out how to not only run the business but innovate faster, and how to get the broader organization to function well together. And that’s really what the CEO does too; the CEO is just not constrained by technology spend. As CEO, you need to have the ability to think through how to invest for the future while delivering today, how to prioritize today and tomorrow, and how to get teams to work together. CIOs do this all the time because they’re usually not independently empowered. They rely on collaboration and getting others to work together. That’s not true of every function in a company, so it positions CIOs in a unique way.

Q: What advice would you give CIOs looking to work closer with their CEOs?

YW: Avoid ultimatums and be really thoughtful on how you’re positioning challenges and resolutions. A lot of things can bear down on CIOs, from security requirements to data privacy. Rather than painting yourself as a victim and making demands, instead present options and position yourself as a business partner to the CEO. For example, lead a meeting with the CEO by laying out the new regulations coming up, where the company needs to be relative to where it currently is, what a few options are to close gaps, along with the risks and costs associated with each. Approaching a meeting with this thoughtfulness demonstrates you’re thinking like a business leader, and the CEO will be more likely to call on you for help in the future.

Also, don’t assume you’ll get a seat at the executive table. Don’t assume you’re owed a seat. Take it upon yourself to earn that seat. The best way to accomplish this is by deeply understanding what initiatives and imperatives are important to the C-suite and board. Then in a helpful—not demanding—way, suggest ideas and partnerships that you can implement to help them be more successful. The strongest CIOs are ones that can empathize with different people in different situations and be a team player.

Q: How should CIOs measure IT’s impact?

YW: There’s no doubt that IT needs a well-functioning shop and to manage spend. However, I think part of what holds CIOs back is measuring IT’s impact by cost per head, network downtime, and other increasingly less relevant data points. What I focused on when I was CIO at New Relic was how to measure things that I couldn’t see today. For example, what are the daily active users of a certain application? How are we reducing cycle time to serve new customers? We focused on visibility into how customers were engaging with us as a company and leveraging our technology because these metrics help us understand if we’re actually growing revenue and increasing retention.

Q: What is the biggest thing IT leaders need to pay attention to this year?

YW: We live in a world where if a company is too risk-averse and never experiments or innovates, it will die. On the other hand, if the company experiments too much and fails, it will also die. What becomes important is building an enterprise that is composable—in other words, really thinking about how you can build an application network and create an architecture, an infrastructure and an overall ecosystem where you can easily plug different technologies in and out as they evolve or as you need them. Having options so you don’t have to bet the entire business on one thing is brilliant. It’s future-proofing your organization.

Q: How do you think about enabling ecosystems around the data you collect?

YW: Everyone I speak to is building a digital platform of some type. But these platforms are not the end-all, be-all for any company’s complete operations. Companies need to be thoughtful around how they plug into their customers’ broader networks and their partners’ networks, and ultimately how they integrate various types of data and tie everything together. Some of that will be done in each company’s world, while some of that will be done in yours. Be strategic in where you draw those boundaries—where the customer can do what they want where they want versus what’s always going to be done a certain way because that’s your special sauce.

At Airware, we focus on how we’re building out our data and visualizing it. We’re working closely with customers who want to import their data into our platform so we can drive advanced analytics, as well as those who want to integrate our platform into their systems. As a result, we’re doubling down on APIs and how we think about accessibility and extensibility into the broader world. Ecosystems, powered by APIs, are the foundation of the future. One size no longer fits all. Companies today have to think about what different roles they might have and how they can successfully scale those.

Q: What tech trends are you paying attention to?

YW: We’re in a fabulous time where it’s no longer any one technology that is the game changer. It’s the collection of technologies coming together that’s so powerful. At Airware, we’re integrating mobility solutions, drones, cloud-based processing and visualization/collaboration, and machine learning and artificial intelligence (AI) to bring our customers powerful business insights. Increasingly, we’re also starting to integrate other data streams from the internet of things (IoT) to further enrich the insights we deliver. As far as newer tech trends go, CIOs need to understand the distinction between what’s hype and what’s ready to write a check for. Timing is incredibly important, along with understanding the market maturity. Who is actually using the technology? What are they using it for? Is there a reliable way to integrate it into business processes without damaging the company? Make sure you’re asking the right questions before diving in.

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