Justin Skelton is SVP and CIO of Dine Brands, a leading chain restaurant company based in Glendale, Calif., with 345 franchisees operating more than 3,400 restaurants for its two flagship brands, Applebee\u2019s and IHOP.\n\nAs CIO, Skelton is a member of the Executive Team at Dine Brands Global. His responsibilities extend from digital and business intelligence platforms and product and project management to restaurant and corporate technologies and infrastructure and operations.\n\nCIO.com\u2019s Derek Hulitsky caught up with Skelton at the recent Future of Cloud Summit to discuss leadership strategies necessary to get technology buy-in from key stakeholders from individual franchisees all the way to the Board of Directors. What follows are edited excerpts of that conversation. For more insights, watch the full video below.\n\nOn working with the Board:\n\nAll Boards of Directors have decisions to make around capital allocation. They have to decide \u2026 Are we going to invest in technology? Are we going to do share buybacks? Are we going to pay dividends? So, it\u2019s important for us, at Dine Brands, to make sure we have articulated a clear vision and a strategy for how IT can, in fact, improve company results.\n\nWe meet with the Board of Directors probably on a quarterly basis, in various forms, various committees. We talk about the strategy. We talk about our vision for technology. In many ways we educate them around some of the technologies that are out in the rest of the world and how those technologies are applicable to [our business] and how they would add that [business] value.\n\nThe other thing that Boards want to know, they want to know how you are improving. How you are performing? What\u2019s the return on investment? So, it\u2019s extremely important that you are able to articulate [your] performance.\n\nOn Dine\u2019s cloud strategy:\n\nOur journey started back in 2019, when we endeavored upon getting all of our workloads\u2014all of our data center workloads, as well as workloads we had in our regional support centers\u2014migrated [to the cloud]. We set up a very aggressive target. We said 100% of everything needs to be moved to the cloud. And while we knew that it would not be possible to get 100%\u2014there would have to be some components left behind\u2014that was our target.\n\nWe do a lot more buy than we do build these days, and so we are leveraging the marketplace to go off and use some of the technologies that are already cloud-enabled.\n\nWhen we thought about [replacing] our point-of-sale system, part of that configuration is having tablet capabilities as well. And everything needing to be based into the cloud, right? So, part of that frictionless environment with the tablets is being able to swipe your card right on the tablet. All of the data, all of the information is actually transmitted to the cloud.\n\nSo that relieves the operational management support of the back-of-house server, but it also [creates a] frictionless environment for the guest, because we are extending those capabilities with the tablets to our customers.\n\nOn IT talent management:\n\nWithin IT, it is a challenge already, right? Because we compete for talent across industries.\n\n[One] thing I think is extremely important is that we are doubling our portfolio size between this year and next year, in terms of our capital investments in IT. And in my experience, a lot of technologists want to know they are working on really interesting technologies. And, tied to that, of course, is the opportunity for development, learning new tools, learning new skills.\n\nAnd then, with IT people, it is important to connect the dots between the work that they do and how that work contributes to the success of the organization. When we are able to connect those dots, people feel a sense of value and worth [tied] into the company\u2019s results.\n\nOn being an effective technology leader today:\n\nYou have to be able to actively listen. You have got to listen to your stakeholders, listen to your business partners, listen to your staff. And what it means is asking questions for clarification. In my business, in the field we are in, where we have franchisees as stakeholders, we have the different owners as stakeholders, we have a Board of Directors as a stakeholder, and your leaders\u2014your teams\u2014being able to understand what their needs are [is critical].\n\nWhen you actively listen, it gives you the opportunity to build a strategy where there is alignment.