Some fifteen years ago, “the cloud” entered the popular computing lexicon to much fanfare and confusion. The term evokes images of disembodied bits and bytes floating in the ether like so much water vapor, ready to magically rain down into your computer at the click of a mouse. What “the cloud” actually describes is far more down-to-earth, yet it was (and remains) no less revolutionary to modern business infrastructure. Instead of storing all of your digital data—your website files, your ERP and CRM systems, all of your company files and documents, all of your cybersecurity infrastructure, your customer data—on expensive local servers, cloud computing keeps it in massive server farms off-site, where businesses can access it remotely, via the internet. It’s an innovation that saved time and money and gave many small businesses on tight budgets access to the kinds of software and ecommerce tools once reserved for larger firms.

How It Works

Chances are, much of your business software is already on the cloud, whether it’s Google Workspace, QuickBooks, or a CRM like HubSpot or Keap. In the past, if you wanted, say,  accounting software, you’d buy big boxes of disks and install it on the computer of every employee who needed to use it, and you’d have to buy a new set of disks every time the developer released an update. Cloud computing puts that data not on disks that are installed on your computer but on a server in a data center that you connect to via the internet. Rather than buying software on physical media, you buy licenses or seats for however many employees will be using the software.

Using cloud-based systems is often as easy as going to the website of the developer, creating an account, and paying a subscription fee. The software and data is stored on the developer’s servers, and you can access the program from any computer you log into.

Like anything else, cloud-based software has its advantages and disadvantages, but for most businesses, the advantages outweigh the disadvantages. On the one hand, cloud-based systems are affordable for businesses of every size, scaling with you while giving you only what you need for whatever stage of growth you’re currently in. Customer support and regular updates will be part of any subscription plan, ensuring that your software is up-to-date at all times.

On the other hand, your apps and data are on someone else’s computer. While any reputable cloud-based software company will have stringent cybersecurity measures in place, systems can get hacked and your data exposed, and users don’t always keep their devices and passwords secure. Security is the responsibility of both the provider and the user. The user has to follow guidelines on strong password selection and be wary of phishing attempts and other scams that could see sensitive information fall into the hands of malicious actors.

The Benefits of Cloud-Based Systems

The most important benefit for many businesses is the cost. Heavy, compute-intensive systems like ERP systems were once the purview of big businesses that could afford to develop bespoke systems, host them on-site, and hire the vast IT teams needed to maintain them. Once you’re locked into this kind of system, making changes is difficult. Choosing the wrong system could end up being a costly mistake.

It takes a lot of thought, preparation, and buy-in to implement any new system. There’s not a lot of business software that is exactly “easy” to use. That said, cloud-based software is much easier to install, run, and maintain. Rather than large up-front investments in both software and the hardware to run it on, you’ll pay a monthly or annual subscription fee for most cloud-based systems.

You’ll also get a degree of strategic flexibility from the cloud. An on-site ERP might work for where your business is today, but business is always changing. As technology advances, you might find yourself saddled with an outdated system that will require a massive investment to change. Swapping ERP systems is never a walk in the park, but a cloud-based system with solid vendor support will reduce the headache from a crippling one to one you can take some ibuprofen for, so to speak. If something in your business isn’t working and a shift in strategy is required, it’s much easier to find new cloud-based systems or simply change your current subscription plan than it is to purchase, install, and implement new on-site hardware and software.

The cloud also makes your team more flexible. A cloud-based CRM can be accessed from anywhere, so salespeople on the road or at a trade show can update customer accounts from their laptops in real time. Teams can work remotely without ever losing touch with each other.

For a small but growing business, cloud computing offers far greater scalability than managing on-site infrastructure. Most vendors offer subscription tiers catering to businesses of different sizes. Pricing is often based on number of seats, so you’ll only pay for what you use, and you can add seats as you grow.

The cloud also makes maintenance easier, especially for businesses that can’t afford their own IT department. Updates can be automatically scheduled and installed. If anything goes wrong, or you need help with installation, support teams are often provided by the vendor.

Cloud Computing Best Practices

The question today is less “is cloud computing right for me?” and more “which cloud services are right for me?” Here are some questions to consider before making a decision. 

• How crucial is it to your business that these systems are always on and always available? Since you are accessing these systems via the internet, common issues like slowdowns during peak times or ISP outages can affect performance. While these are rare occurrences, they are still possible. Software hosted on-site will always be fast and available to everyone in the building.
• Is your data so sensitive that it is best kept on internal servers not connected to the internet? The fact that employees can access these systems anywhere and anytime is convenient, but it also carries a security risk if they’re using personal devices with weak passwords or saving passwords in their browser. This is a risk that can be mitigated, however, with a little training.
• What kind of customer service does the software vendor offer? Will representatives be available 24/7 to troubleshoot and solve problems?
• Are you dealing directly with a vendor or are you buying through a Value Added Reseller (VAR)? A VAR will work with you to get the right services for your business at the right price and help you implement the software, train employees, and integrate it into your tech stack.

Helping You Choose the Right Cloud Services

A revolutionary idea fifteen, twenty years ago, cloud computing is now as common as WiFi. The question is no longer “should I use cloud-based services?” but “which cloud-based services should I use and how do I get the most out of them?” That’s exactly where our expertise lies. We’re a technology-agnostic agency that excels in matching your business with the technology that aligns with your growth strategy and will help you meet your goals.

We hoped things would return to normal, or at least stabilize around a “new normal,” after the pandemic. What we got is anything but. Continued supply chain disruptions, war, tariffs, inflation, disruptive new technologies, and an unstable global order have marked the post-pandemic era. Who could have predicted some of the events of the past few years? Unpredictable events aren’t all bad, but even “good” unpredictability can disrupt your business all the same if you’re not ready for it. For example, what if one of your products takes off unexpectedly, but you don’t have the capacity to meet the demand? You never know what’s just around the corner. If you can’t predict the future, then you should do the next best thing: build resilience into your business so you can adapt to any change, no matter how unexpected.

Strategic Foundation

The success of any business begins with strategy. Your strategy lays out who you are, what you do, and what makes you unique, and translates that unique selling point into a plan to reach a particular set of customers through actionable, measurable goals.

A strategy of resilience includes a growth mindset baked in at the level of strategy. People and organizations with a growth mindset understand that we can learn new things, master new concepts, and constantly grow and develop throughout our lives. Those with a fixed mindset, on the other hand, believe that they know what they know, they are who they are, and they can never change or grow. A growth mindset is adaptable, curious, and confident. A fixed mindset holds you back by telling you, “I can’t do that. That’s not me. That’s not how I work. I can’t learn something new. I have to stick to what I already know.” When a growth mindset is a part of your strategy, you will be ready to shift gears at a moment’s notice knowing you can learn and do whatever you have to in order to overcome any challenge.

Operational Resilience

Operations encompasses the production process, product development, process documentation, customer service, and everything that keeps your business running on a day-to-day basis, along with the technology your operations run on.

Successful operations departments are built on consistent and repeatable processes so that no matter who is completing the task, it can be done the same way, to the same standard. Process documentation is not something you can do once and forget about. The rapid changes in technology, the economy, and the workforce mean that processes must be continually improved. There should be a process in place for improving processes, as well, in which employees can suggest and test changes and then implement the most successful ones.

It’s hard to achieve operational excellence without the support of the right technology. But what do you do when that technology fails? This is where system redundancy and diversity have to be built into your operations. Do you have backups of your website? If your cloud storage service (Google Drive, Microsoft OneDrive, Dropbox) experiences an outage, how will you access your files? How will you process payments if PayPal goes down?

While these things don’t happen often, they do happen. In 2024, a bugged update to cybersecurity software CrowdStrike crashed over 8 million business and government computers running Windows, resulting in $10 billion in losses. 2025, meanwhile, saw web infrastructure provider Cloudflare suffer three major outages in a row in September, November, and December, outages that brought down services as diverse as LinkedIn, the graphic design platform Canva, and the multiplayer online video game Fortnite.

It's not just tech that needs redundancies. What will you do if a key piece of equipment breaks down or a key employee leaves? What if supply chain disruptions or changes to tariffs mean you no longer have access to a key supplier or manufacturer? Developing risk assessment and mitigation strategies lays the groundwork for a resilient business that is ready for these kinds of emergencies.

A growth mindset is key in operations. Sometimes, the only valid response to an unprecedented crisis is an unprecedented solution. A business built on a fixed mindset will say, “We can’t do that. It’s never been done before. I guess it’s over for us.” A business with a growth mindset will do what seems impossible while constantly monitoring and improving their processes as they sail uncharted waters.

Supportive Culture

Building a growth mindset into your strategy involves encouraging and providing opportunities for growth and learning in your employees. Just as you are constantly reviewing and improving your processes, your employees should be empowered to constantly improve their skills, becoming more knowledgeable, more confident, and more resilient along the way.

Culture goes beyond the office or shop floor. It encompasses all of your stakeholders and networks, from suppliers to customers. If you’ve built solid, mutually beneficial relationships with all of them, you’ll be able to help each other through times of stress and come out stronger on the other end.

Resilience is Foundational

In areas prone to earthquakes, old buildings have to undergo seismic retrofitting to make them more earthquake-resistant. One technique for making these buildings stronger is called “selective weakening,” a process that involves finding the most rigid parts of the building and making the building “weaker” by removing them. It seems counterintuitive, but when you’re facing something that can shake you to your foundations, rigidity and inflexibility is a weakness. To withstand earth-shaking economic and social changes, standing firm and fixed in place will only result in collapse. Being able to shift and wobble without toppling as the ground moves under you is how you not only survive but grow in an uncertain economy. 

Technology is always changing, and today it’s changing faster than ever. On top of the speed of change, it seems that new innovations are becoming more disruptive and more confusing than in the past. That speed can be anxiety-inducing, and with heightened anxiety comes decreased decision-making ability.

With all kinds of new software and tech products coming thick and fast, you need a framework for separating the ones that will work for you from the ones that don’t. A technology roadmap provides exactly that, giving you the bird’s eye view of your business that you need to take control and make sense of it all.

Planning Your Growth Road Trip

We’ve talked about the importance of the strategic roadmap before over on the StrategyWerx blog. You don’t want to take a road trip without first consulting a map. Maybe you’ve taken this trip before and you know the route by heart, but you still need to plan. You don’t know exactly how this trip is going to go. You don’t know how traffic patterns might have changed, if there is construction on the route, if a bridge or ferry is out of service, or if a new highway offering a quicker route has been built since you last made the trip.

A map also helps you consider the “best way” to get to your destination given the purpose of your trip. There is no “best way” in business strategy or in road trips, only the way that helps you achieve your goals. If it’s autumn and you want to see all of the pretty colors, then the best way is the most scenic route, even if it’s not the fastest. If you’re on a tight budget, the best way is the one that avoids the $15 turnpike and the $12 bridge toll. It’s all about knowing what you’re trying to achieve so you can make the decisions that are best for you, today and in the future.

Intentional Choices Informed by Strategy

A technology roadmap serves the same purpose. When you have a decision to make regarding the types of technology to integrate into your operations, it won’t help to simply seek out “the best,” because what’s best for a corporation with 20,000 employees and what’s best for a ten-person agency are two different things. Consider also your industry. What’s best for a city government, for instance, is not what’s best for a manufacturing enterprise, a lesson the city of Birmingham, UK, learned the hard way after a financially devastating failed ERP implementation, which we wrote about here. When you develop a technology roadmap, you’ll be able to put your business’s needs and goals first. You’ll better understand your business and your goals, and you’ll get a much clearer sense of the tech that will and won’t work for you.

Roadmaps aren’t just about where you are now, but where you want to be and how long you plan to take to get there. Your roadmap will also get you thinking about how a piece of technology will serve you in the future, whatever your growth goals. “The future” is a different thing for a company that plans to grow quickly and bring on dozens of new employees in the next year and for a company looking for slower, steadier organic growth.

For example, the spreadsheet you calculate budgets on might work for you today, but will it work for the accountant or CFO you eventually hire? You’ll need accounting software that can handle the intricacies of your business and can be easily shared among and edited by your team. And while you might be able to manually send out promotion emails to your mailing list today, is that method going to be scalable when you’re delivering personalized emails to segmented lists of thousands of customers? When you choose a new CRM to help automate those email tasks, how are you going to get employees to buy in and learn the software? How long will it take, and what resources can you devote to training?

A tech roadmap gives you clarity on these and other questions, giving you greater control over the technological aspects of your business’s growth. This is especially important in uncertain times. You’ll be better equipped to ask the right questions and choose technologies that can help you today, grow with you tomorrow, and keep you running smoothly over any potholes you might not have seen coming.

Find the Tech That’s Right for You

At ProsperWerx, we’re technology agnostic. That means we’re not here to get you to adopt a particular piece of software. We’re here to help you work through these strategic questions so you can see the big picture and help you find the technology that’s right for your business, both where you are now and where you want to be.

Recently, Forbes reported that hackers discovered an exploit in the code of Windows 10 and 11 as well as older versions of Windows Server that allows them to force a machine to open a URL with the less-secure Internet Explorer browser, which Microsoft has retired in favor of the safer Edge browser. The URL then gives the hackers control of the computer. As a result, the US government has warned Windows users to update their computers or stop using them. Vulnerabilities like this one are exposed and then patched by developers almost every day. Most users will remain safe if they update their software regularly.

If you’re using a legacy system, however, the developer may no longer be releasing updates, and your computers—and your business—will remain at risk. This kind of security exploit is just one of the many dangers of relying on legacy systems.

Sometimes, outdated software or hardware is so deeply entwined with your workflow that you can’t imagine working without it. Game of Thrones writer George R. R. Martin, for instance, still writes on WordStar, an MS-DOS word processing program first released in 1978. But when it comes to business applications, especially those that are cloud-based or connected to the internet, hanging onto a 40-year-old legacy system would do little more than keep an organization from reaching its potential. Stepping into the unknown comes with some risks, but with a clear strategy guiding the process, you can make your business more secure, efficient, and scalable.

What Is a Legacy System?

The term “legacy” denotes something with a long and storied history that has lost a bit of relevance. Legacy systems are those software applications or other technologies that have become obsolete, whether because the company has outgrown the tech’s usefulness or because newer tech can do what a legacy system does more efficiently. Legacy systems include outdated programs like Windows 7 or that Quickbooks program you’ve refused to update since 2014, the inventory management system you so proudly wrote in Filemaker Pro in 2011, websites still running on the long-since-abandoned Adobe Flash, and mainframe systems that nobody under the age of 73 knows how to support any longer.

The Dangers of Relying on Legacy Systems

Replacing legacy systems isn’t just about being on the cutting edge for the sake of it. Relying on outdated technology can pose a real threat to your business. First of all, old systems may no longer be supported by their developers, who prefer to put their resources into supporting their latest applications. If a piece of software is no longer supported, that means the developers are not releasing new updates to fix bugs or security workarounds known to hackers. This means that if you have a problem with the tech, you might not be able to get help for it. More importantly, company data and private customer information could be at risk.

Compatibility with newer technology is another issue you face with outdated programs. When you update to the newest version of your operating system, for example, you might find that the program designed for a twenty-year-old operating system no longer works correctly, if at all. If an unsupported program is the centerpiece of your tech stack, you might find that it does not support the ecommerce integrations or marketing automations so vital to the modern business.

Finally, old systems could simply be slowing you down. They might take forever to boot up, they might have unintuitive interfaces that take minutes rather than seconds to navigate, or they might be prone to crashing. All of these minor inconveniences add up over the course of months.

When Is It Time to Modernize?

If the above dangers seem all too familiar to you, it might be time to modernize your tech stack. It’s possible that you haven’t run into any issues relying on an ancient program, but with tech that is no longer supported, it’s less a question of “if” than “when” you will run into security or compliance issues.

An old system that you’ve been using for ages and know well is fine if you’re a one-person operation with just a handful of customers. But if you have any desire to grow, it’s better to start modernizing now. No matter the application, there is tech out there that can grow with you, especially today in this era of software as a service, where developers offer various tiers of service with features designed for businesses of different sizes.

Planning Your Modernization Strategy

Adopting a new technology is a major change for a business. Getting it right often requires working closely with vendors and experienced consultants who know what can go wrong and how to prevent it. Every company’s modernization strategy will look different, based as it is in each company’s industry, size, and growth goals, but there are a few broad steps most businesses will take when upgrading legacy systems.

If you want to know more about choosing the right technology solutions for your business, check out this article. 

Analyze Your Tech Stack

The first step is to evaluate your current systems according to the guidance above. Are you facing any of the dangers associated with legacy systems? If so, then it’s time to look for an upgrade.

When evaluating any new software, analyze it in terms of your current tech stack and your overall business strategy. You’ll want a system that can scale with you, that is affordable, and is within the capabilities of your staff. There are also regulatory and compliance issues to consider, depending on your industry. You can find a more in-depth guide to choosing the right technology here.

Evaluate Your Approach

You might find that you need to rebuild your tech stack from the ground up, or it may be the case that just a single part of it is outdated. However many systems need to be replaced, consider how the new tech will integrate with what you’ve decided to keep. If you are replacing several systems, there may be a single piece of software that can do what used to require multiple, separate applications.

Make an Implementation Plan

With your IT team, determine if it would be better to slowly phase out a legacy system piece by piece or all at once. Whether your plan is to modernize gradually or swiftly, you’ll need a data migration plan that will move your data securely and cleanly (that is, without errors) from the old system to the new one.

Provide Ongoing Training and Support

Your new system might not be running perfectly from day one. People need time to learn the software and acclimate to new workflows. Make this transitional period as smooth as possible by working with developers who provide all the documentation and support you’ll need.

Get the Right Help

Updating legacy systems is time-consuming but necessary for both keeping your systems secure and your business running efficiently. Avoid the common pitfalls and the often overwhelming decision-making process by working with people who have experience in implementation and expert knowledge in all manner of business software. ProsperWerx is here to help you get a handle on the tech that supports your business so you can get back to doing the work you love.