Being a force for change in a growing organization is difficult, especially when it comes to overhauling attitudes and infrastructure the company may have built a foundation on. One of the most formidable challenges an organization will face is the shift to cloud technology. We should know – we went through it ourselves. But building consensus among leadership, partnering with key stakeholders, and framing the conversation correctly will set you up for success.

All growth leads to cloud

Today’s commercial landscape dictates that companies are growing in complexity, and regardless of industry are looking to new software and technology to provide long-term solutions. In turn, businesses are competing harder for growth and increasing their spend on research and development. And whether you’re working in finance, technology, pharmaceuticals, or transportation, this commitment to IT means changing priorities for teams across the board, and the need to evolve old processes and standards.

When you’re trying to bring change to your organization, it’s important to identify the factors that are most important not just to your team, but to the business as a whole. Leaders and decision-makers, no longer responsible for a single line of business, must consider how their department contributes to the overall success of the company. In fact, today’s CIOs and CTOs have a new shared responsibility: growth.

When tackling the challenge of growth, there are three considerations that business leaders need to balance in order to stay competitive.

  1. With disruptors lurking around every corner, they need to be vigilant to future-proof their organizations and to compete long-term.
  2. Every CIO/CTO/CXO is being asked to do more with less, to innovate faster with higher product quality. As these businesses grow, being able to deliver effectively is becoming even harder.
  3. And ultimately, growth is built on the backs of customer loyalty. So how do businesses navigate a hyper-competitive market to fight for the hearts and minds of customers, long-term?

An organizational shift to cloud technologies can help tackle each of these areas, but it’s often more obvious to the team working directly with the product than it may be to your business leaders and budget owners.

So, for those who want to implement a digital transformation within your organization, we’ve put together some best practices to help communicate to leadership and build your case – here’s how to become a cloud change agent.

Framing the conversation

Getting serious about cloud migration

When leading change and building consensus to move to cloud within an organization, it’s important to understand two things: IT leaders are being tasked with solving new macro challenges they’re likely unfamiliar with, and they’re looking for experts to provide solutions to ensure the long-term health (and growth) of the business.

The key strategies you want to emphasize when you broach the cloud-migration subject conversation are: 

  • Review the competitive landscape. Identify changes that have already been made in your industry and how competitors are winning your business. Build consensus around the challenge you’re trying to solve.
  • Compare multiple outcomes. Give insight into what will happen if changes aren’t made, and coordinate shared goals based on ideal outcome – not just risk avoidance. Convey a sense of urgency around time to market, and emphasize the importance of shipping high-quality products that satisfy and delight customers.
  • Convey the business value of migrating. Look for an edge to differentiate your organization in a crowded market. Compare aspects like total cost of ownership, five-year horizons, and opportunity cost.

Remember, this is a conversation starter, not an implementation plan. The goal of these early talks with your team is to get alignment and to socialize the idea of moving to the cloud before you do the due diligence of planning a migration.

Review the competitive landscape

According to Forrester, three-quarters of enterprises are shifting their infrastructure resources to the cloud, despite the known expense and effort to migrate.  More than 57 percent already have some services in the cloud.

Many smaller companies started with their operations in the cloud, and never had to migrate. These companies hold distinct advantages over larger companies that continue to manage their own services in that they don’t have the big cash expenditures for hardware and labor, meaning they’re more agile, fast-moving, and often quicker to market. Cloud frees up people and resources so IT admins can focus on supporting the business.


It’s possible your org is already adopting cloud tools, just on a team-by-team basis and without the oversight of your central IT org. In a recent survey, CIOs estimated on average that they had 51 cloud services running in their organization, while the actual average was 730. Learn more about the rise of shadow IT and how to leverage this information to bring consistency and transparency to your organization.

Compare multiple outcomes

It’s much easier to run a department or strategy based on what you don’t want to happen. You don’t want server downtime – so you don’t upgrade versions. You don’t want to lose control – so you don’t adopt new databases. The problem with this mentality is it’s not sufficient in a high-growth market. You didn’t upgrade server versions? Now you’re susceptible to the latest security breach. You didn’t upgrade your database? Now you’re more likely to suffer data loss during an outage.

How entrepreneurship, trust, and a whole lot of failure helped shape our platform

These are just examples, but it’s often easier to make a decision based on what you don’t want to happen – and all leaders want to avoid a bad or unpredictable outcome. It’s easier to decide on a new path, or less predictable change if you’ve seen successful examples of those in similar situations.

It so happens that our own Head of Cloud Platform, Mike Tria, wasn’t immediately sold on cloud. In a previous job many years ago, he found he needed to hire two engineers a quarter just to do the tasks of maintaining hardware, like swapping out hard disks for RAID failures. 

“What changed things for me was scale,” Tria says. Throwing people at problems was no longer tenable. “Oh, you’re dealing with RAID failures? Look at you, Mr. Yesterday,” he jokes. “No one was dealing with those problems anymore because they’d moved over to the cloud.”

Now compare that potential scenario to what happened at Redfin when Evan Lerer, Director of Engineering, joined the company. “We were managing too much of our own infrastructure. I would much rather be building new things that help us improve, rather than maintaining old things,” Evan says. “If I’m spending one-eighth or one-half of an engineer managing our infrastructure, that’s a very high number compared to a year’s worth of licensing.” After Redfin migrated to cloud, they recognized more than $60,000 in savings, and lowered total cost of ownership even further when accounting for labor savings.

Convey the business value of migrating

Your executive team will want to see how moving to cloud will impact the company’s bottom line. Do some research to build the case for your particular business. Figure out how much time and budget your team spends maintaining systems, managing security policies, and updating software and servers. In most cases, at least one FTE can be attributed to server maintenance – time and resources that are likely better served towards your customers.

Framing the conversation to focus on total cost of ownership (TCO) instead of budget line items and license costs can help you present the hard costs and time spent on your self-managed systems. See below:

comparing total cost of ownership for self-managed vs cloud delpoyment

Here’s an example: After one particularly painful – and expensive – outage, Jimmy Seddon of Igloo Software realized that maintaining a self-managed server for Jira, Bitbucket, and Bamboo was going to put this growing company at risk. After calculating the cost of that four-hour downtime that impacted 80 percent of employees across the company, he figured out that moving to a cloud service, while a big-budget line item, would be far less expensive than another outage.

Bringing meaningful change to your organization can be extremely rewarding, though often difficult. Leaders and teams must align on problem, goals, and solutions when adopting a new technology. Providing examples of similar organizations’ success, highlighting potential business and budget impacts if you don’t make the change, and framing trade-offs in a tangible way to stakeholders can help make sure you’re successful in your digital transformation.

Remember, starting the conversation is only the beginning – good intentions and a common goal will only get you so far. But fostering a spirit of change and a common perspective of the future with the leadership of your organization will serve as the foundation of an actionable cloud migration strategy, setting you up for success as you grow.

Framing an organizational shift to cloud