AWS Cloud Enterprise Strategy Blog

7 Best Practices for Your Enterprise’s Journey to the Cloud

“Life is a Journey. When we stop, things don’t go right.” -Pope Francis

Last December, I wrote about cloud becoming the new normal, and that the process of meaningfully adopting cloud into an established enterprise is a Journey. This Journey is an iterative process that will take time. In my post from December, I laid out several stages that are commonly observed in enterprises that travel the Journey. And the month before that, I wrote a post detailing 10 things successful cloud enterprises do.

Since then, I’ve traveled to several continents and met with many more companies who are using the cloud as a platform to meet their business objectives. While my previous posts are still relevant, some of my thoughts around the Journey have evolved.

This post serves as an introduction to my new thinking, and lays out seven best practices I’ve seen in enterprises that are delivering results on their Journey. Over the course of the next few months, I’ll dive deeper into each best practice and talk about some of the things I’ve seen work (and not work) for each. I’d love to get your feedback along the way, so please send me your experiences or thoughts as this series come together.

Before we get into these practices, it’s worth reiterating that the Journey is an iterative process that takes time. Because the cloud is disrupting the way IT is delivered and consumed, you have a tremendous opportunity to scrutinize and rethink the way IT operates in your organization. Put another way, the Journey is a change-management exercise. It will touch your technology, governance, job functions, org chart, and many other aspects of your company. The good news is that the Journey is being traveled by thousands of companies already, and we can all learn from each other.

Here are the seven practices that I’ve observed working together to create a flywheel of success for enterprises on their Journey:

1. Provide Executive Support
Top-down support is essential for creating meaningful change — whether that change be technical or cultural. The CIO/CTO role is always evolving, and today more than ever technology executives need to be the company’s Chief Change Management Officer (CCMO™). Doing this job includes getting the support of the executive team and giving support and air cover to your own team. It means providing clarity of purpose, aligning business and technical objectives on desired outcomes, and making (or breaking) new rules. I will talk about this in more detail in my next post(s), and am dedicating a few sessions to this at re:Invent. (Hope to see you there!)

2. Educate Staff
People tend to be afraid of what they don’t know. When they’re afraid, they’re more likely to cling to what they’re comfortable with. In some cases, this can create roadblocks in your Journey. Equipping your staff with new skills is a great way to mitigate their fears. Acquiring new talent with the appropriate skills is great, but this method is unlikely to scale on its own. Giving those with institutional knowledge an opportunity to learn and participate will accelerate your Journey.

3. Create a Culture of Experimentation
The cost of experimenting in the cloud pales in comparison to that of on-premises environments. There are little to no up-front costs in the cloud, and no commitments to weigh you down if something doesn’t work out. When you look at each project as an experiment you can learn from, you’re likely to create an educational flywheel that will help the organization improve over time. Some enterprises will start with a single project in a single part of IT; others will tackle many projects at once. Whatever strategy suits your organization, make sure to celebrate successes and institutionalize what you learn from failures. Coupled with the right executive support, you have an opportunity to create an ongoing culture of experimentation.

4. Engage Partners
Most enterprises engage with some number of partners to deliver IT. These partnerships come in many shapes and sizes: staff augmentation, solutions delivery, managed services, licensed software, SaaS solutions, and so on. Every major IT services provider has had to determine how the cloud fits into their business, and many are making themselves available through the AWS Partner Network. You can look to your existing partners to help you on your Journey, or turn to any number of the born-in-the-cloud companies who have grown respectable businesses over the past few years. AWS would be happy to help you determine which partner is right for your needs. On top of this, many partners are making their solutions available in the AWS Marketplace, where you can procure and deploy their services the same way you procure AWS, which can greatly reduce oftentimes bureaucratic procurement processes.

5. Create a Center of Excellence
Throughout my career, I’ve often observed tension between application delivery and infrastructure teams. This system of checks and balances can be healthy, but I’ve also seen it become toxic. With the cloud taking away much of the heavy lifting associated with traditional infrastructure, and being heavily driven by code and automation, the line between these teams becomes much more blurry. The Journey creates an opportunity for organizations to rethink these boundaries and the protocols between them. Most organizations that I’ve seen that move swiftly through their Journey have created a Cloud Center of Excellence to institutionalize best practices, governance, and automation throughout the organization. When I was the CIO at Dow Jones, for example, we implemented this through our DevOps team, with a focus on excellent customer service, a run-what-you-build mindset, and a solid knowledge of what to expect in the months after implementation.

6. Implement a Hybrid Architecture
Most, if not all, enterprises have existing IT investments that are still providing benefit to the organization. Every organization approaches how it manages its legacy and refresh cycles differently, but none will be able to make an overnight move. Setting up a hybrid architecture allows you to get the most out of the cloud while still being able to take advantage of your existing investments. No provider has more experience or breadth in their hybrid offering as AWS does. So long as you avoid the three myths of a hybrid architecture, your center of excellence can get you up and running with a hybrid architecture in no time. Once this is in place, it becomes much more straightforward to enhance and migrate legacy applications. Hybrid creates a great opportunity to start chipping away at monolithic applications and implement decoupled services, which is a common pattern I’ve seen for dealing with mainframes.

7. Implement a Cloud-First Policy
As you gain experience, your organization will hit a tipping point. With the previous six pistons spinning your flywheel, you’re likely to become more efficient at operating IT in the cloud than you are on-premises. At this point, I’ve seen companies declare a cloud-first strategy, where they reverse the burden of proof for the IT projects from “why cloud?” to “why not cloud?” This sends an important message to the organization, and sets the stage for you to maximize the benefits from the cloud and devote more of your resources to your core business.

I’d love to hear your thoughts as we dive into each of these practices in the coming months.

Keep building,

Stephen Orban

Stephen Orban

Stephen is the GM (General Manager) of a new AWS service under development, and author of the book “Ahead in the Cloud: Best Practices for Navigating the Future of Enterprise IT” Stephen spent his first three-and-a-half years with Amazon as the Global Head of Enterprise Strategy, where he oversaw AWS’s enterprise go-to-market strategy, invented and built AWS’s Migration Acceleration Program (MAP), and helped executives from hundreds of the world’s largest companies envision, develop, and mature their IT operating model using the cloud. Stephen authored Ahead in the Cloud so customers might benefit from many of the best practices Stephen observed working with customers in this role. Prior to joining AWS, Stephen was the CIO of Dow Jones, where he introduced modern software development methodologies and reduced costs while implementing a cloud-first strategy. These transformational changes accelerated product development cycles and increased productivity across all lines of business, including The Wall Street Journal,, Dow Jones Newswires, and Factiva. Stephen also spent 11 years at Bloomberg LP, holding a variety of leadership positions across their equity and messaging platforms, before founding Bloomberg Sports in 2008, where he served as CTO. Stephen earned his bachelor’s degree in computer science from State University of New York College at Fredonia.