CIO Strategy: Managing a Cloud-First Transformation

The growth of cloud computing has led large organizations to significant IT transformation, with the goal of reducing costs and improving agility. But how can companies adapt their processes to these new demands? In this episode, we speak with Stacy Carron, CIO of Stout, a boutique investment bank, about the firm's technology strategy.


Nov 03, 2022

The growth of cloud computing has led large organizations to significant IT transformation, with the goal of reducing costs and improving agility. But how can companies adapt their processes to these new demands? In this episode, we speak with Stacy Carron, CIO of Stout, a boutique investment bank, about the firm's technology strategy.

Stacy describes Stout's transformation to a cloud-first approach as critical to their IT strategy, which has brought both financial and operational benefits.

The conversation covers these topics:

Stacy Carron is Stout’s Chief Information Officer. With over 22 years of information systems and technology experience, Stacy serves as a principal in the development of technological solutions for the firm and its clients, leads technology diligence and integration projects related to acquisitions, and is a key contributor to the firm’s strategic planning and critical business projects.

Stacy led Stout's infrastructure migration to a cloud-first platform and continually implements security systems and platforms to combat and scale the firm and clients along the ever-changing security landscape. Her additional areas of expertise include optimization of internal technology systems, network administration, software development, collaborative technology implementation, custom development of internal systems, technology compliance, strategic planning, project management, communications planning, and firm facilities management, including numerous office-relocation projects.

In 2022, Stacy was nominated as a finalist for the Michigan CIO© ORBIE® Awards for demonstrating excellence in technology leadership.


Stacy Carron: It's about flexibility and risk. You can build environments in minutes, hours, so it's ultimately flexible.

You have to change your mindset. You have to understand that it's about finding what's best for the business first.

Tell us about Stout and the Chief Information Officer role?

Michael Krigsman: That's Stacy Carron, Chief Information Officer of Stout.

Stacy Carron: Stout does a variety of things, specializing in investment banking, valuations, dispute and compliance. We have a large range of very smart experts that deliver solutions in complex financial situations.

Michael Krigsman: Can you give us a sense of the size of the organization? Do you focus on any particular sets of industries?

Stacy Carron: We don't focus on one industry. We service a wide range of those. We have about 700 employees across 16+ offices, and we continue to grow every day it seems.

Michael Krigsman: As the chief information officer, what does your role encompass?

Stacy Carron: I joke that I'm responsible for everything that has an electrical current, but it's actually true. I get involved in things all the way from office moves to acquisition.

It extends into our client solutions where we help clients in the public sector, for example, that have really large data sets. We get involved to help them digest that data and really use it to solve business problems.

Michael Krigsman: You're involved both with internal infrastructure as well as working with data that comes from outside the company.

Stacy Carron: Yeah, and it even extends beyond just data with our external focus. We actually build solutions at times to solve a business need or a project need in very specific use cases.

Describe your cloud-first journey?

Michael Krigsman: Stacy, you have used the term "cloud-first." You've said you're on a cloud-first journey. What do you mean by that?

Stacy Carron: That you've changed your mindset about technology to really turn compute into a utility. I think of compute as the Internet or having the lights on, and it allows you to kind of shift your perspective on the fun stuff of configuration and building solutions.

The goal is always to have everything in the cloud. There's no need to have a physical infrastructure.

Michael Krigsman: When you're building new software, when you're buying hardware, when you're building technology of any type, you're thinking about it in the cloud first.

Stacy Carron: And only, I would say.

What are the advantages of cloud computing?

Michael Krigsman: This cloud-first approach, why did you decide to go this way?

Stacy Carron: It really started back in 2017. We were pushing a work anywhere initiative so we could grow better nationally, and we needed to get our files really centrally located in the cloud.

Obviously, we took a hard look at the cost, which really netted out to be about the same. But the additional benefits you get from being in the cloud (from security, scalability – the list will go on and on. I'll run out of time) is endless.

Michael Krigsman: You looked at the financial aspects, and then you looked at the operational aspects as well.

Stacy Carron: And the ability to grow, which has been on our radar and our plan. We wanted to be able to scale and scale quickly, and you can't do that with physical infrastructure, at least not very well.

Michael Krigsman: Why? What about the cloud supported this growth?

Stacy Carron: Well, if you think about where we are today, and we needed servers or additional infrastructure to add more colleagues, we would not have been able to do that if we weren't in the cloud.

It also supported when we went – you know everybody went – work from home. We were prepped and ready. The next day, everybody was working from home with no business interruption.

Michael Krigsman: You know it's interesting. As I've spoken with other CIOs, literally to a person, the ones who have said, "When the pandemic started, we were able to flip the switch." At the same time, they said to me, "This is because we invested in cloud infrastructure over the previous number of years."

Stacy Carron: Absolutely.

Michael Krigsman: How is this different from what you had before?

Stacy Carron: Well, I'm no longer worried about if a network card is going to fail or if a server room is going to overheat.

Where your worries land are very different, and it's a lot more fun to be thinking about building new solutions, implementing new technologies, automating.

All those things get kind of pushed to the side.

Are there risks associated with cloud migration?

Michael Krigsman: What were some of the concerns that you had as you were planning this cloud journey out?

Stacy Carron: Definitely concerns around costs. You have to be diligent and monitor those costs.

It's a different mindset. You're not planning for what do I need for the next three years. Basically, what do I need right now and maybe tomorrow? So, you can scale up and scale down. But you have to monitor it so you're not paying for unused compute.

Michael Krigsman: I should ask where are you in this cloud transition journey.

Stacy Carron: We're virtually done – no pun intended. But for our domain controllers that are in our local offices, we've moved everything to the cloud.

We'll have workloads as time goes on with acquisitions that are onsite, and we have plans in place to migrate those as they come up. Now it's about maintenance and focusing on other things. We have a model and a process that we bring workloads in and move them to the cloud as quickly as the business allows.

What are the benefits of cloud adoption?

Michael Krigsman: You've kind of touched on this, but what are the benefits to Stout? What have you actually seen and experienced?

Stacy Carron: We had a huge workload at one point that was really tied to a specific client. When that client went away, we were still stuck with all of that investment, and it took us years to kind of work through that.

In the cloud world today, when we spin up an environment dedicated for a client project, when that project is done, we just turn it off and we stop paying for it.

It has also allowed us to grow rapidly over the course of the last three to five years, adding additional employees, additional projects.

Michael Krigsman: Is this primarily about cost and hardware then?

Stacy Carron: No, it's not. The cost is net neutral every time we've looked at it.

But it's about flexibility and risk. We've gained so much flexibility and minimized so much risk by being in the cloud.

You can build environments in minutes, hours, so it's ultimately flexible. You have a lot of design options.

You're not constrained by the size of a server room or the size of disk space or anything along those lines. Really, you're constrained by your own imagination of how you might be able to configure something to deliver what is being asked.

Then on the risk side, I know that's an area that comes up a lot. People historically – maybe less so now – are always afraid of the cloud. I don't really see it that different than a physical environment.

You have to have an external partner that's verifying your security and that's verifying everything that's being configured so that you can have trust that what's done is done right and done securely.

Michael Krigsman: It enables you to focus less on buying SANs and servers.

Stacy Carron: Correct.

Michael Krigsman: And database administration and freeing those people up to do what?

Stacy Carron: Definitely the client work has become more and more. We have people that are dedicated to just really supporting those initiatives and literally building isolated environments in the cloud to support client projects.

It enables us, like I said, to grow. We're doing so many acquisitions, especially this year, that being able to take on additional workloads (essentially, over a weekend).

What are the challenges of cloud migration?

Michael Krigsman: Stacy what are some of the challenges that arise when an organization is making this kind of wholesale change?

Stacy Carron: It's important for people to have a partner to go through this journey that's done it before and especially one that is very collaborative that helps train the team that's on the journey. Then they can do it going forward from that point.

Really, you do have to pay a lot more attention to the details of the finance of the spend. You have to build a process to review that. That's the one area where it can run away from people if you don't set up a process to ensure that.

Michael Krigsman: Are there other challenges that an organization can anticipate when they're doing this kind of migration?

Stacy Carron: In the past, there certainly are software and configurations that didn't lend itself well to being in the cloud. One example I would have is performance for file servers.

That's something we dealt with where it's different if you were sitting in an office with a file server versus if it was a cloud-based one. But there is a solution at this point for almost all of these scenarios.

For us, we had to put in file optimization software. The reality is, we need to do that anyway so that we can allow people to work from wherever they need to work from.

How did Workday support your cloud strategy?

Michael Krigsman: Stacy, we're at Workday Rising, and I know you're working with Workday. I'm very grateful to Workday for making our conversation possible.

Can you tell us about what your relationship is with Workday and the kinds of things you're doing?

Stacy Carron: It's not like we're doing everything with Workday. We're a full platform, so we use it for our finance, HCM, projects, learning, performance. The list goes on.

We use Adaptive for our planning and our budget and forecasting, which is very near and dear to our organization, being financial experts themselves. Numbers matter.

Michael Krigsman: We touched on security and trust. It's such an important issue. Can you speak a little bit more about that? What made your organization comfortable with that shift?

Stacy Carron: Definitely talking to other people that had already made that shift, finding advisors that were experts, finding independent parties to validate and verify from a security standpoint.

Michael Krigsman: To what extent was Workday a partner or playing a role in this cloud transition?

Stacy Carron: Workday came in at the perfect time during this transition, so we had six various applications that we were in the process of virtualizing and moving to the cloud. We knew we needed one consolidated system, one source of truth for all of our data, and it allowed us to migrate off all those platforms, consolidate it into one cloud-based integrated platform, and do it in about six months.

Michael Krigsman: Pretty fast.

Stacy Carron: Very fast. Lots of fun.

What is the impact of a cloud-first strategy on the CIO and IT organization?

Michael Krigsman: Let's talk about the role of IT and how IT evolves when an organization shifts to the cloud. What's the impact on IT when you make this, shall we say, pretty dramatic shift?

Stacy Carron: It's a dramatic impact, for sure. Skills need to be trained and people grow a lot during that transition.

You can take anybody that has a technical basis and help them on that journey take it over to the cloud. The biggest change I've found is definitely on the networking side. That is a different concept of networking in the cloud versus physical networking. But it opens so many opportunities for them to take on new roles that never existed before and gets them out of the weeds of burning a weekend to do physical infrastructure upgrades.

Michael Krigsman: What is it about the cloud that helps folks in IT be more connected to the business result of what they're doing?

Stacy Carron: In the past, it would be a lot more people involved to kind of work through all the infrastructure required, all the security required. All those things are still important, but there's a foundation and a process that allows you to scale that more efficiently than having to go through every single step and acquire all the equipment needed in order to support an ask like that.

How does cloud computing change the CIO role?

Michael Krigsman: Have you seen your role change as a result?

Stacy Carron: Absolutely. Definitely more engaged in the business side of things, understanding the business needs because we can deliver solutions in that area much more quickly and effectively without having to worry about all of the underlying infrastructure.

Michael Krigsman: How does a CIO make this big change?

Stacy Carron: You have to change your mindset. You have to understand that it's about finding what's best for the business first and, hopefully, it's technically practical versus the other way.

You need to have relationships throughout the business so you know what's important to all the different stakeholders because they all need something different. A lot of times, IT is the one that has to deliver to all five of them (or whatever number it is).

Michael Krigsman: That's a very, very interesting point. You said that historically the focus was first on the technology. Now it's on the relationships and understanding the business issues.

Stacy Carron: Yeah, you used to build a solution with, "Will I have this available to me right now, and this much space or this technology?"

Now, it's about setting that aside and first understanding what's needed, and then trying to marry it with what's technically practical. Sometimes you have to find solutions that at first aren't technically practical.

What is the impact of cloud o[n CIO metrics and KPIs?

Michael Krigsman: What kind of metrics do you look at as CIO? And also, how have those metrics evolved over time?

Stacy Carron: Definitely look at the typical stuff. How many servers, workstations, tickets, and so on?

What's different about how I looked at it in the past is I'm no longer worried about the capacity aspect. I'm just forecasting the growth on it.

The metrics, though, I find most interesting are the variable ones, which is how much is our IT spend as a percent of revenue, and then how much is our IT spend per employee? We use Adaptive, which helps us kind of forecast as our headcount scale.

That historically was a problem to forecast because we never knew how many people we'd have. With Adaptive, we scale our forecast and our budget as we're adding people.

Michael Krigsman: Clearly, you're measuring the efficiency of IT. Is there a way to measure the outcomes, the business outcomes that IT is delivering as well?

Stacy Carron: The best way for us to do that is especially dealing with client projects where we're tracking our time, our spend, and then we see the revenue related to that project, and we have a very real part in that. Also, on the internal project side, we track that in Workday as well so that we know how much effort certain initiatives have taken throughout the course of a year.

What advice do you have for CIOs looking at public cloud services?

Michael Krigsman: Stacy, there are so many CIOs who are looking at cloud migration right now, you're on this cloud-first journey. What advice do you have for CIOs who are looking at this and they're ready to start but they're just a little hesitant? What advice do you have?

Stacy Carron: You need a partner to do it. You need to find somebody that you can trust that has done it before that you can collaborate with to help you and your team really make that journey and understand how to keep it going after the initial transition.

Michael Krigsman: That was very important for you, having the right partner.

Stacy Carron: Absolutely.

Michael Krigsman: What are the attributes of a great partner?

Stacy Carron: You really don't want any vendor that hoards knowledge. They should be all about teaching their customers how to use the tools in the way they do.

Michael Krigsman: What advice do you have for CIOs who want to make this transition from being a pure technologist to being that business partner with other folks, other business leaders in the organization?

Stacy Carron: Learn your business. Learn it well, and really partner with people throughout the organization (from the CFO, HR, into the individual business units) so that you can understand what they need and how you can help make their jobs even more efficient.

Michael Krigsman: Any final thoughts on this cloud-first journey?

Stacy Carron: Just do it. You won't regret it. It's going to happen eventually, I would imagine, for most all organizations. Just lighten the load on yourself and the team and make that move is my recommendation.

Michael Krigsman: It's a great way to end because it's going to happen for pretty much everybody. It's just a matter of time.

Stacy Carron: Yep.

Michael Krigsman: Stacy Carron, Chief Information Officer of Stout, thank you for taking time to talk with us.

Stacy Carron: Thanks for having me. [Laughter]

Published Date: Nov 03, 2022

Author: Michael Krigsman

Episode ID: 766