How to Assess the Right Software for SMEs and SMBs: A Comprehensive Guide

In today’s competitive world of business, having the right software can make all the difference. For Small and Medium-sized Enterprises (SMEs) and Small and Medium-sized Businesses (SMBs), choosing the ideal software solution is even more critical. The right tools can streamline operations, improve efficiency, and give you an edge over your competitors. This comprehensive guide will walk you through the steps to assess and select the right software for your business, and this is typically how we at Sentry Strategy also think about considering different software solutions for our customers.

Understand Your Needs

Before diving into the myriad of software options, it’s crucial to understand your specific business needs.

Key Areas to Consider
  • Operational bottlenecks: are there certain manual operational steps that are painful to you and your team members? These are often fantastic starting points. If you are saying to yourself “surely, there’s gotta be a better way”, then most likely there is a better way.
  • Data management needs: consider what are some insights that you would love to understand about your business but have not been able to pull the right information together. These insights will help you make an informed decision about your business and the next phase of growth.
  • Customer engagement: consider what are some areas where technology will greatly improve your customer experience, this will accelerate your growth and significantly raise your brand. Simply, it will set your business apart if you are able to deliver exceptional customer experience. 
Budget Constraints

Financial considerations are often at the forefront when selecting software for SMEs and SMBs.

Factors Influencing Budget
  • Initial setup costs: is there an initial set-up fee? Oftentimes, for enterprise solutions, you will often have to pay for an initial set-up fee. 
  • Subscription vs one-time payment: will this be a subscription or a one-time payment? And will the subscription increase based on your usage, or is it a fixed cost every month indefinitely?
  • ROI calculations: what are some initial short-term, medium-term, and long-term investments that you will get on this software? How many hours/days/months will this save your team members? It will be pretty clear that if the solution works, you won’t ever have to touch it again and this will free you up for other important tasks. 
Research and Shortlist Options

Once you have a clear understanding of your needs and budget, begin your research to shortlist potential software solutions.

Research Methods
  • Online reviews: online forums and Google reviews are often helpful to understand whether the solutions have solved similar problems for others. This might help you make decisions faster. 
  • Peer recommendations: if you know others in the same industry as you, it’s a great idea to see how they are leveraging technology to streamline their businesses. 
  • Free trials and demos: more often than not, software solutions will provide free trials or demos, and you should be able to see whether it is the right fit for you by signing up for a free trial or just seeing the demo. 
Evaluate Features

Not all features will be relevant to your business. Focus on those that meet your specific requirements, so typically, there are three (3) things that we recommend our clients to look for when considering different options that might meet their requirements. 

Must-Have Features
  • Usability: is the software intuitive? How big is the learning-curve for you or your team member when you use the software? If the learning curve is too high and the features are confusing, then the software is not user-friendly. 
  • Scalability: when it comes to the topic of scalability for SMEs and SMBs, cost is often involved. It’s good to understand whether cost will get higher if there are more transactions, activities, or activities in the software. As different softwares may have different pricing structures. 
  • Security: this is often also a concern for many business owners. It is completely okay to ask the software providers about security measures that they have in place in order to protect customer’s data. We often share with our customers how we treat their information and data. 
Vendor Credibility

Assessing the credibility of the software vendor can save you from potential headaches down the line.

Checking Vendor Credibility
  • Customer testimonials: this is often shared on the vendor’s websites or you can also ask their sales representative during the demo call to understand some typical use cases of existing clients they may have. By asking this, you will get an understanding of whether the solution might be a good fit for your particular needs. 
  • Years in business: understanding how long the solution has been in business helps you mitigate the risk whether they might exist in a year or not. If you want to go with a brand new solution on the market that is willing to work with you specifically for your business and build customized solutions for you, that specific solution might not exist if the company cannot scale. 
  • Certifications: typically, long-term software solutions will showcase relevant certifications that are appropriate for their customer, and you will be able to find these on their websites. If not, asking about them is also completely appropriate as well. 
Implementation and Training

Consider how easily the software can be implemented into your current operations and what training is required.

Implementation Strategies
  • Phased roll-out: depending on the scope of the software, you might want to consider phase roll-out of the software. Start with a business area where there might be low-risk and low-activities first, and then incrementally expand to other functions and departments of your businesses. This approach will help you mitigate any potential risk of the solution not working, and impact your operations. 
  • Parallel run: the parallel-run approach is also a fantastic way to ensure that the software is working properly. We’ve seen some of our customers utilized this approach until they are completely confident about the new process, and they simply sunset the old process and perform a mass communication to their team. 
  • Big bang: for some customers, the scope and solution might be extremely simple in that they want to completely remove the old process and implement the solution.
Training Requirements
  • On-site training: in the world we live in today, this might not be too relevant. But for some industries, this is still an effective way to ensure a smooth transition and deployment of the software. If this is the case for your business, ensure that your vendor can send out a representative for you and your team members to provide on-site training. 
  • Webinars: vendors will typically have various webinars to help their customers understand their softwares better, different use cases as well as connecting different businesses with each other. This is a fantastic way to stay in touch with the software provider and understand the various solutions that they might offer. 
  • Documentation: if this is not readily available, you should ask for relevant documentation so that you can share it around with your team members. This will help ensure that there is a guide to operate and use the software that is specifically implemented for your business. This will ensure continuity in your business if there are new team members that might be responsible for the specific function.
Test and Evaluate

Before finalizing your decision, test the software to ensure it meets all your requirements.

Evaluation Metrics
  • Performance: once you are at this step and before making a purchasing decision, make sure that it is performing in ways that you expected it to, and that the software is solving your biggest pain points. 
  • User-friendliness: consider how intuitive the user experience is when you first used the software, and how easy it will be for your team members in the future. This might be a helpful consideration when selecting the vendor as the learning curve for new software solutions might differ for team members. 
  • Customer support: throughout the process of trying out the software, it is important that you have a customer support representative that could answer your questions and have your interest in mind. If not, will there be customer specialist support that can be readily available for when you have questions? These are important considerations for you and your business as well, depending on your specific needs.


Choosing the right software for your business is a critical decision that can significantly impact your business operations and growth. By understanding your needs, considering budget constraints, thoroughly researching options, and evaluating features and vendor credibility, you can make an informed decision that will benefit your business in the long run. At Sentry Strategy, we are a firm believer of ensuring that you are always comfortable and reassured with your decisions. That is why for whatever solutions that you recommend, we do not charge our clients until our client is completely satisfied, and that we can all agree the solution is working.