You may have heard that the future is the cloud. Actually, that’s no longer true. For the majority of businesses, the cloud is how they manage their present.
But if you’ve never taken that step and still wonder whether to move your business to the cloud, you might be asking the wrong question. Moving to the cloud is no longer a binary question (Should we or shouldn’t we?). Today, the questions are smaller and more concrete: What should we move first, and what should we move next?
If you get this right, your business gains flexibility, security, and cost control. If you get it wrong (or wait too long) you risk falling too far behind or getting caught off guard.
The good news is, you don’t need a huge overhaul to begin benefiting from cloud services. In fact, the smartest businesses take an incremental, strategic approach. Move what makes sense now. Make a plan for what comes later. And along the way, get advice from someone who’s done it hundreds of times before.
Let’s start with three things it makes sense to move now:
1. Cloud File Storage and Team Collaboration
For many small teams, file storage platforms like Google Drive or Microsoft OneDrive may be all you need. (And yes, those are “the cloud” – belonging to and operated by Google or Microsoft.) They’re good places for freelancers or very small businesses to start. But for larger teams or companies with circumstances like those below, slightly different approaches may work better.
Do any of these sound like your company?
(a) We have large volumes of files
(b) Our files containing sensitive data
(c) Our company or our customers would suffer if the information was lost
(d) We have hybrid or remote workers
(e) We operate multiple locations
Businesses with these traits benefit from independent cloud plans that not only store your data, but make it easy to organize, access, and update.
These plans can:
(a) Keep your files in perpetuity
(b) Keep all the past versions of the file, so nothing is ever lost or overwritten (an often underused but powerful feature)
(c) Restrict who has access to which files (so salespeople can’t access payroll, etc.)
(d) Centralize control of file permissions for easier administration
(e) Enable search functions to find files easily
(f) Make collaboration between team members much easier and more efficient
With the right cloud storage, your team can access, edit, and collaborate on files from anywhere, securely. No more emailing versions and renaming documents each time they’re revised. No more calling someone to ask if the file is open.
Why would you want a more advanced system like this? Because despite the widespread myth, Google and Microsoft do not save your files forever. And they don’t offer many of the other advantages of other reputable cloud file-storage and file-sharing systems.
Pro Tip: Whatever file storage system you use, you still need backups. One copy isn’t enough. We have clients who, unfortunately, have lived with the consequences of losing all their data because they put off the installation of backup systems for too long. That’s why we always recommend redundant backups. Even if all your work “lives in the cloud,” back it up to a second location.
2. Email and Productivity Tools
If you’re still running an on-site mail server, you’re spending money and time on something the cloud does better. Cloud email platforms like Microsoft 365 and Google Workspace are secure, cost-effective, and come with a full suite of productivity tools your team probably already knows how to use.
You also get frequent security updates without having to patch anything yourself, as well as a basic level of built-in spam filtering.
3. Customer Relationship Management (CRM) in the Cloud
Your customer data is the beating heart of your business. Cloud-based CRMs like Zoho CRM, Freshsales, or Keap allow you to centralize, protect, and gain insights from that data without managing it all on a local server. Plus, they integrate with your website, your sales pipeline, your marketing tools, and your support team.
You’ll not only serve customers better; you’ll understand them better. Our clients who move to cloud CRMs often tell us they gain not just better visibility into their customers, but better team alignment between sales, support, and marketing.
Now, here’s what may require more planning before you move it:
1. Legacy Software: Plan Cloud Migration in Stages
Your business might rely on industry-specific or older software that wasn’t built for the cloud. If that’s the case, don’t worry. You don’t have to throw it out the window. But it’s a good idea to make a plan.
Some legacy apps can be “lifted and shifted” to the cloud as-is using virtualization or hosting platforms. Others need to be modernized or replaced. Either way, the right IT partner can help you figure out a smart roadmap before those old systems leave you stranded.
Remember, you don’t have to make this decision alone, or all at once. Many of our clients keep their legacy systems for a while, then gradually transition as better options become available.
Bottom line: Whatever you do, don’t wait for your legacy tools to fail. Plan their next chapter now, before that choice gets made for you.
2. Sensitive Financial Data: Configure Successful Compliance in the Cloud
If you’re in a regulated business (or work with one), you’ll need to approach client data privacy and protection with a little more care. But being cautious doesn’t mean avoiding the cloud.
Approach A: Lightly Regulated Businesses
If your business is not heavily regulated, cloud migration is still a strong move. Just choose a provider that offers robust security, access controls, and encrypted backups. (Companies like ours help clients understand and assess this every day.)
Approach B: Standard Regulated Businesses
If you’re in finance, healthcare, law, or a similar field, you already know that regulatory compliance is non-negotiable. Cloud platforms can meet HIPAA, PCI DSS, SEC, and other regulatory standards – but technical configuration matters. You’ll want an IT pro who knows the security landscape and sets up your cloud to meet your industry’s expectations. (In the Greater Philadelphia Area, that’s us; in other parts of the country, it’s other CMIT offices.)
3. Servers and Static Workloads: Flowing with the Cloud Rather Than Against It
Let’s bust a myth: “If it’s working, leave it alone.” The truth? Your on-site server has a shelf life. When it hits the 5- to 7-year mark, replacement becomes an urgent — and expensive — decision.
Think of your on-site server like a car with 200,000 miles. It might be running now, but how much longer can you count on it?
However, if you’re thinking about moving forward with the strong current of technology instead of against it, cloud infrastructure is the smarter investment. It scales when your business grows (or slows), doesn’t require you to purchase new hardware, and often comes with built-in failover and redundancy. That means even if one part of the system crashes, another takes over automatically, so your business stays up and running.
Importantly, as technology continues to evolve, it will favor or default to cloud-based solutions, offering fewer and less affordable options to those who are married to static gear.
Even static workloads (like accounting or order processing) can benefit from cloud reliability. And from a recruiting and retention standpoint, modern systems are more appealing to today’s talent. If you’re still running legacy servers, you’re signaling “old school” to prospective hires.
Final Thoughts: The Cloud Isn’t a Trend. It’s the Trajectory.
Whether you’re moving fast or just beginning, the cloud isn’t necessarily an all-or-nothing decision. It can be a series of smart, strategic, orchestrated moves, each tailored to your business’s size, structure, and future goals.
And you don’t need to figure it all out alone. That means it’s not just you, wandering through a forest of “we offer cloud services” websites, most of them written in unintelligible jargon. Companies like ours can help, just as we’ve helped hundreds of other businesses map out their path to the cloud, one plain-spoken and successful step at a time. If you’re in or near Philadelphia, talk to us about doing the same for you – balancing cost, timing, and business fit so every move makes sense.
It’s always the right time to talk about where you are today and where you want to be tomorrow.
Pictured: Me with a handful of the nation’s best IT services colleagues from around the country — all pros at helping small businesses move to the cloud.
