Small business technology roadmap. Why you need one and how to get started.

Without any sort of directions to guide you, it can be hard to reach a destination you’ve not traveled to before. At least not with any speed or efficiency. Plausible questions include, “How long is the journey; what will I need along the way? A bag of chips or a bag of groceries?”

The same applies to your small business technology roadmap and the tech stack needed to get you to your destination - a profitable and sustainable business.

While terms like ‘tech stack’ might not be part of your daily lingo (stack of pancakes, yes; stack of tech, not so much) that’s fine. Because unless you’re in the business of IT, why would it be?

Tech stack simply means the collection of IT tools and services you use now and might need to use later to power your business and keep things running smoothly. Tech stacks typically include those software as a service (Saas) offerings or apps that employees use to collaborate internally, manage customer relationships, chat with customers, measure and manage effectiveness of your social media and marketing campaigns, and manage projects and workflow.

Do you know the size of your tech stack? You may be surprised. According to a 2023 Saas index report, for software-only tech stacks (i.e., we’re not talking servers here), the average small business with 500 or fewer employees has 172 apps.

And we’ll add, quite possibly, nary an IT department or staff in sight.

So what about that roadmap? What is it and why do you need one?

A technology roadmap undergirds or sits alongside your business plan. It outlines where you are, where you are headed and how you are going to get there — with technology.

The benefits of creating one are numerous — the exercise alone helps prioritize and gut check your overall vision — and not least of all, it helps prevent panic and short-sighted purchases. Those one-off solutions that might solve the specific crisis du jour but don’t necessarily work well (or at all) with the systems you already have or might need to add later.

Along with taking integration into account, your technology roadmap should consider scalability. You’ll want to think strategically and long term, ensuring any IT purchases — whether that’s hardware (your Thinkpad, printer, etc.,) or software — can keep up with changing demands. As you experience growth, the last thing you want is to be hobbled by systems that aren’t robust enough.

Eight-point checklist for your small business technology roadmap

Here’s a quick checklist of 8 additional and important considerations to keep in mind as you create your technology roadmap:

  1. Business goals and strategy. Be sure any technology investments you make support your strategic goals. Ask, “Will this solution help me drive growth and efficiency?” If the answer is no and it’s just cool tech, push pause.
  2. Take inventory. Just like streaming services and magazines you may have forgotten about but still pay for, evaluate your existing technology. As you do, identify strengths, weaknesses, and gaps. This will help you understand and decide what needs to be upgraded, replaced or maintained.
  3. Budget. Can you afford it? Conversely, can your business afford not to have it? Prioritize spending on technologies that offer the best return on investment and align with your most critical business needs.
  4. Integration. We’re repeating ourselves here, but this is an important consideration. No doubt your social media feed is awash with solutions that promise to solve your exact and most pressing challenges. And they just might — but it’s worth the time it takes to confirm that any new solution or tool will integrate easily with what you already have. If not, you may be creating problems down the road, even risk losing important data.
  5. Learning curve. Plan for the human aspect of technology adoption, including complexity and staff training. You may not need much time at all — but best to determine up front if you will and if so, how long it will take to get everyone up to speed and how steep the learning curve might be. Which brings us to…
  6. Vendor support and reliability. This is a big one. You’ve done the research, tested the product and are about to hit ‘buy.’ Before you do, have a look at the vendor’s reputation and support services. When downtime is a luxury you can’t afford, you’ll want the peace of mind knowing that if you do need support, you’ll get it. According to a 2023 Software Advice survey, lackluster support was the number one reason small businesses regretted a technology investment.

What to actually include in your small business tech roadmap

Just as your business strategy is unique, so is your tech strategy and full-circle, your roadmap.

While there’s likely no one-size-fits-all formula or template, there are some baseline components any small business roadmap should include. Note, much like your business is a work in progress, so is the roadmap. This will be an iterative process and chances are, you’ll likely need some level of buy-in and adoption from others.

That said, what follows are the basic components to include in your tech roadmap..

  • Business goals and objectives. The roadmap should start by clearly defining your short- and long-term business objectives and goals. These could range from increasing efficiency and reducing costs to scaling operations or improving customer engagement.
  • Technology requirements. This section of your roadmap will detail the technology requirements that align with your business goals. When you inventoried the technologies, tools and systems you currently have in place, were there any gaps? This is where you include what you have and what you need.
  • Stakeholder engagement. You’ll want to engage relevant stakeholders (such as IT staff and key employees) throughout the roadmap development process. Doing so provides for end-to-end functionality across your entire organization. Collaborating with sales, marketing, and operations stakeholders will create a much higher adoption rate as you roll out new apps and tools, and use them moving forward
  • Priorities. As a small business likely with some budget constraints, it’s important to prioritize any new investments. This will involve deciding which technologies will have the greatest impact on achieving your business objectives.

Another way to approach this is by assigning dates to your objectives and goals. For example, your business sells customized care packages for kids attending summer camps. This season, along with your standard inventory, you have five new options you’d like to launch.

Back into that date: Do you have the back-end systems in place to accommodate the added inventory and fulfill orders within the desired timeframe? If not, it should become clear what solutions you’ll need to add. Give yourself ample time to explore options and set up demos with vendors.

  • Budget allocation. Outline the budget for each technology investment, considering both the initial setup costs and ongoing maintenance costs.
  • Implementation timeline. Did you make new tech investments? Create a step-by-step plan for their rollout. The plan should include milestones, deadlines and responsible parties for each stage of the process. Don’t forget to factor in time to become acclimated to and test any tools you’ve added.
  • Risk assessment and mitigation. It’s a smart move to be proactive and plan for hiccups. In this part of your roadmap, detail any potential risks associated with implementing new technology (for example, training challenges, possible integration issues) and develop strategies in advance to mitigate these risks.
  • Training and support. Set yourself and your team up for success come go time. Ensure staff can adopt and use the new technology by providing initial training and ongoing support.
  • Review process. Establish a process for regular review of your technology roadmap. While scalability should always be a consideration, things change. You may find you need to replace an investment or size up. The point is to give your business a tech check-and-balance to ensure your stack remains aligned with the business’s evolving needs and goals.
  • Appendix and supporting documentation. This should be a relatively straightforward step (yeah!) as it’s general housekeeping. This section should include any technical specifications, vendor information, and other supporting documents that supplement the roadmap.

This action doesn’t have a direct impact on your bottom line, but it’s one of those activities you’ll be grateful for accomplishing when you need to refer to the fine print regarding your tech investments.

Developing a technology roadmap might sound a bit daunting but it’s worth the effort. Following the above considerations can help your small business create a technology roadmap that not only aligns with and supports your strategic business objectives, but can also reveal opportunities to cut costs and increase efficiency. That’s welcome momentum.

We want to know!

Maybe you’ve already created a tech roadmap. If so, please share your thoughts and experience with the Pro Community. Have you found it beneficial? What would you do differently and have you updated it? 

If you’re interested in learning more about creating the tech stack that’s right for you and your small business, you can catch the replay of Tech Stack Fundamentals for Small Businesses Owners, an interactive session where Ashley Chatman, 2022 Evolve Small honoree and founder of FitBody by Ashley, discusses the tech stack fundamentals that can set any small business owner up for success.

Stephanie has worked in the B2B tech space for more than 20 years for brands such as IBM and Oracle, as well as on the agency side at Uncompany, The Favorite Co., Ogilvy and Mather, Leopard and other agencies. Stephanie believes in putting the reader first and won't rest until she's communicated a motivating, "Why should I care?" message. When she's not writing on behalf of her freelance clients, in her spare time, Stephanie's working on a novel and the occasional poem.

Find her on Linkedin.


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