Navigating the Software Selection Process

Digital transformation is the integration of digital technology to transform your small business, allowing it to leverage the automation, scalability, and resilience offered by software and technology tools. 

If you’re a landscaper, for instance, you could switch from pen-and-paper inspections, estimates, and invoicing to using a business management software platform designed for your industry. This software can manage the following for your small business: scheduling, maintenance of customer contact information, integration with third-party vendors for easier supply chain management, and much more.

The changes your business will encounter will mostly be operational and cultural, as digital transformation is most successful when partnered with your willingness to experiment and challenge the status quo on how you’re delivering value to your customers.

Knowing what problems or pain points you want to solve for your business is the first step in the software selection process. It’s usually the first thing a salesperson will ask you. Pain points that impact you as a small-business owner might look like the following:

• Financial: Challenges caused by a lack of funding.

• People: Issues related to company morale, turnover, staffing, etc.

• Process: Any time-consuming manual processes that would benefit from automation.

• Productivity: Any barriers that keep your team from working efficiently.

• Security: Anything that may pose a threat to your company or customer data.

Your software must have the functionality your staff needs while helping you expand and become more efficient. We recommend the following five best practices from our software selection guide to make the process easier.

1. Plan and budget for new software

The first thing you need to do before investing in software is plan and budget. Firstly, identify the problem you're trying to solve—e.g., managing data or simplifying tasks.

Next, look at your budget. If you spend $25,000 on new software, how much are you expecting in ROI? If you don’t achieve your expected ROI, will you reduce your staffing levels or upskill employees to perform higher-level work? By when do you expect to see improvements as a result of your software investment?

2. Research your software needs

This is the most labor-intensive part of the software buying process. You may want to involve leadership to help evaluate processes, challenges, or shortcomings the software can resolve. Try to be as specific as possible when identifying your needs; this will help you home in on your best-fitting software solution.

From there, create a list of requirements to narrow down your choices as you research. Consider software price, availability of features, and user reviews.

3. Request a demo

Once you've identified a serious candidate for purchase, you’ll need to determine if the software does what it promises. Request a demonstration from the vendor to view the software features and functionality in action. You’ll get to see how the tool can address your company's unique requirements.

4. Take a trial run

Your next step should be a trial to check how the software performs on your business systems. Many vendors offer free or discounted trials from two weeks to a month. A trial run also allows your IT staff to get under the hood of the software to see how it integrates with your existing hardware and software systems.

5. Implement, train, and maintain

Upon completing a successful trial run, it's time to make a decision. If you decide to purchase, the final step is implementing the software, ensuring team members are trained to use it, and maintaining it. This is where support from the software vendor is essential if there are any issues. Your IT team also needs to maintain the software as you expand usage across your business.

A tech stack, also called a software stack, consists of the software apps and tools your business uses every day to get work done. For instance, your marketing tech stack—i.e., the tools used by your marketing team—could include email management, social media management, customer relationship management (CRM), and survey solutions. Similarly, your HR, IT, and operations teams could be using different sets of software tools to automate and streamline their daily workflows.

Due to less complex workflows, small businesses, like yours, usually have a smaller technology stack than enterprises. The HR team of a small firm, for instance, can use a single integrated human capital management (HCM) solution to handle all employee management workflows. A large business, on the other hand, would have to use dedicated tools for performance management, attendance tracking, benefits administration, and other HR processes.

Investing in software alone isn’t enough to build an ideal tech stack. You have to organize the tools within the stack as well as understand how each one supports your workflows. Let’s look at some ways to do that.

1. Identify workflows that can be automated

Look for processes or workflows that software can help automate. For example, if you send promotional emails manually to customers, consider using an email marketing platform to automate the process and save time. List all such workflows that can be automated using software to improve efficiency.

2. List workflows that can be managed using the same software

Certain workflows are similar in nature and can be served by a common tech solution. For example, you can use the same chat tool for team communication as well as collaboration between different departments.

Identifying such similar business processes will not only lower your tech investment but also optimize the use of software tools across your organization.

3. Find the right software to automate your workflows

Shortlist software tools that offer the functionality you need within your budget. Use third-party platforms such as GetApp to check which solutions best fit your tech stack. On GetApp, you can read reviews from software users on product features, integration capabilities, scalability, cost, vendor support, etc.

4. Review the performance of your stack regularly

The technology landscape changes frequently, and new tools and features enter the market every few years. Therefore, monitor your tech stack regularly to track current usage rates, identify bottlenecks, measure the ROI, and foresee any tech gaps. Add new tools or features based on how well, or poorly, your stack is performing.

Software integrations, also known as application integrations, allow you to connect a group of related applications to fulfill critical business requirements.

Let's use project management tools as an example. These solutions allow you to plan project timelines, assign tasks to team members, and track their completion. However, to effectively manage projects, your teams will typically use a range of other solutions too, such as chat applications, file sharing tools, and email tools. 

Integrating your project management solution with these systems can help your employees work faster and more efficiently. For instance, integration with email software would allow employees to instantly turn emails into tasks, and integration with accounting software would let you generate invoices using the same tool. Think of integrations as killing (ideally more than) two birds with one stone.

Cloud computing is a style of computing in which scalable and elastic IT-enabled capabilities are delivered as a service using internet technologies. In other words, cloud computing is the delivery of computing resources—storage, backup, applications, and hosting—as a service over the internet. There are three different cloud computing models: SaaS, PaaS, and IaaS.

Software-as-a-Service, or SaaS, can be considered equivalent to renting a fully-furnished room where the maintenance, management, and decor of the room are done by the software provider. In the SaaS model, your business doesn’t have to invest in IT hardware resources or in developing and maintaining the software. Everything is taken care of by the SaaS provider; you just pay and use.

Platform-as-a-Service, or PaaS, is a cloud software delivery model where you pay the PaaS vendor for using their servers, virtual machines, and software development tools. If you’re a software developer, you can use PaaS to build applications. The vendor provides the development environment, while you only have to manage your data and the application you’re building.

Infrastructure-as-a-Service, or IaaS, is a cloud infrastructure delivery model where you pay the IaaS vendor for using their cloud data storage, virtualization, servers, and networks. In this model, you manage your applications, data, and middleware, while the vendor provides the infrastructure.

Knowing how to select business systems comes down to your needs, budget, and capacity to train staff on new technology, among other factors. Below, we’ll dive deeper into the most important software selection criteria from our software selection template so you know what should be top of mind as you start comparing options.

• Software features

Most tools that cater to a specific industry offer a common set of features. Check if the features you need are available in the tools you’ve shortlisted. Our template lets you list essential vs. nice-to-have features so it’s easier for you to decide. It also mentions whether there’s any extra cost for the features so you have complete visibility into what you’re paying for.

• Software training

User training requirements differ based on the complexity of each software. Check with the vendor about the training support options available—live or recorded online training sessions, self-help resources, in-person training, etc. Also, check if the training support is provided for free or whether you’ll need to pay for it.

• Customer support

Customer support options vary depending on the pricing plan users select, but they usually include email, phone (24/7 or 24/5), online ticketing, live chat, and a knowledge base. Ensure the software you’ve chosen offers ample support resources so you know who to contact in case you run into technical issues.

• Operating specifications

The software you select must be compatible with your existing technology infrastructure and applications. Choose a suitable deployment model (on-premise or web-based), and check which operating systems (OS) are supported: Windows, Mac, or Linux. Also, inquire if the vendor offers mobile applications for iOS, Android, and Windows devices. This information will help you pick a software platform whose specifications are compatible with your current technology.

• Integrations

Make sure the software you select integrates well with your existing systems or at least supports integration with any other tools you have in mind. Since integration will involve sharing of data between applications, check with the vendor if there are any data security risks involved. Also, ensure the software complies with all applicable data privacy regulations.

• Pricing

For each tool you’ve shortlisted, check price-related details, including the total cost of ownership, upfront costs (if any), price per user, billing frequency (monthly, annual, or one time), contract duration, any hidden or additional fees, free trial details, and any special rates, discounts, or promotions.

At GetApp, we have an easy-to-use comparison tool that lets you compare multiple software solutions side by side. Below is a brief overview of how the tool works.

1. Select a category of software

GetApp has over 800 software categories for you to choose from. You can either browse for a specific type of software or search according to your industry using the search bar.

2. Check the compare box under each product you want to compare

You can compare up to four different software products and view their features and functionality listed side by side. Start by clicking the orange box at the top of the screen, or check the box that says “compare” under each product you want to compare.

3. Click “see comparison” to view your results

This last step will take you to our compare page where your selected products will be listed side by side. You can now compare overviews, screenshots, pricing, reviews, features, and more.

Software demonstrations or demos are an opportunity for vendors to showcase their products. They get to highlight the product’s best features, show how the product works, give an overview of the look and feel, and present a few use cases. It’s also an opportunity for you, the buyer, to see the product in action and get a feel for the features it offers. 

Unfortunately, a cookie-cutter presentation won’t give you everything you need to make an informed decision. If you’re attending a software demo, treat it as an opportunity to ask questions and get clarity on challenges that occur with the tool. Our demonstration checklist, summarized below, explains how you should prepare for a software demo

1. Identify software needs

Know which features will be “must-haves” and “nice-to-haves” ahead of the demonstration. Also, prepare a list of processes or scenarios that you’re planning to use the tool for, such as taking orders or managing inventory. 

2. Know which features distinguish one from another

Product differentiators are features or functionalities of the tool that offer unique value and are not common with other tools on the market. However, it’s important that you first understand what the top tools on the market offer. For this, explore the top vendors via listings such as our Category Leaders (here’s the listing for CRM software Category Leaders, for instance).

3. Understand the total cost of ownership

Whether it’s cloud-based or on-premise deployment, the actual cost of using a tool can end up much higher than what its price tag says. Use software demos as an opportunity to ask about these costs: Inquire about the fees for adding more users, present hypothetical scenarios requiring software customization, or discuss implementation charges. Check the storage costs, infrastructure requirements, support, and any potential need for updates.

4. Ask about vendor support and training

Vendor support and training requirements often fall among the points of discussion that users typically forget. However, they are critical to the adoption and success of any software. 

There are several variations when it comes to support costs—some vendors charge extra for different levels of support (such as email only vs. phone call), some offer support only to paid users, and some offer fast-track tickets for special users. Also, check the kind of training the vendor offers for adopting the tool. Software tools that are not as technical tend to require less training than those that are technical.

5. Confirm data storage and security measures 

Businesses taking software demos tend to be so focused on features and cost that they sometimes overlook data storage and security measures. The lack of proper data security can cost your business heavily in leaked information and reparation fines. 

Every software has a protocol to store user data safely, so be sure to ask the vendor what theirs is. This becomes even more important if the tool is cloud-based since a large part of the security aspect will remain out of your control and in the vendor’s hands.

Software selection should be a cross-team effort. It’s a good idea to include associates with diverse business expertise so you receive input from different business units. Below, we’ll cover some specific roles to have in your software selection team.

• Project manager: It’s wise to assign a single project manager who’ll oversee the software selection process and coordinate with vendors to schedule demonstrations and trial runs.

• Users: Which employees are going to use the software you buy? Finding out their pain points and getting their input will help you narrow down your list to the most helpful software options.

• Stakeholders: Executives and shareholders who can provide a high-level view of your organization’s goals and budgetary concerns are important to include for any major investment.

• IT personnel: Someone will need to integrate, monitor, and maintain the software under consideration. This is especially important for on-premise or hybrid deployment.

Software contract negotiation is a team effort that requires tons of preparation and a solid strategy. Preparation begins way before you meet the vendor’s sales team. It’s a long process that requires weeks or, sometimes, even months of research, discussions, and amendments before a deal is finalized.

Below are five steps to pave the way to a successful software contract negotiation.

1. Set up a buying/negotiation team

We already covered who should be involved in your software selection process. When the time comes to negotiate a contract, you’ll want to loop in your finance team and a legal advisor to look over terms and conditions as well as draft and review your contract.

2. Conduct thorough research on the vendor

Learn as much as possible about the vendor you’re negotiating with, and maintain an inquisitive stance throughout discussions. A Gartner study [1] found that 45% of a B2B buying group’s time is spent on research (via online and offline means).

Thorough research will help you shortlist vendors based on their product offerings, price discounts, and many more criteria. It’ll help you gather market insights and analyze the software pricing models of multiple vendors. It’ll also help identify vendors’ strengths and weaknesses, marketing strategies, unique selling points, etc. Our customer reviews are a great place to start your research.

3. Have a flexible negotiation strategy

Most negotiations revolve around three factors: price, support, and terms and conditions (T&Cs).

• Price is often the driving factor for most software buyers. The price and discounts listed on vendor websites may seem attractive, but always look out for hidden charges, such as installation and maintenance costs, data transfer charges, and service fees. Negotiate with vendors to lock in a price for the entire or part of the contract term, and seek discounts as your user count increases. 

• Support services include the technical support vendors provide for implementing and maintaining software, such as installation assistance, data migration support, product updates, and remote troubleshooting. Negotiate with vendors to access these services at no or minimal costs. A mobile app, a dedicated customer service representative, training videos, and community resources are some other support options to explore.

• Terms and conditions (T&Cs) refer to the fine print in a software contract. Many businesses make SaaS software purchases online without reading the T&Cs. These buyers risk paying additional costs, losing data privacy, or facing other issues later on. Therefore, you must ensure full disclosure of all T&Cs during the software evaluation phase itself.

For a list of terms you might see in a T&C document, look here.

Data security, training, and impact on critical business functions are three other factors that determine the level of risk you assume with any software tool. To help you weigh risk vs. value, we have a free investment risk assessment tool for you to download. 

This tool uses a set of questions and predetermined responses to assess the risk related to a software investment you’re considering. To select a response that best aligns with your circumstances, click the arrow on each row of the tool to access the answer dropdown. Once you select your answers, the tool will automatically score your investment risk level.

The best way to assess whether your new software is meeting your expectations is to develop a software implementation plan. Below are three strategies to get you started.

1. Designate superusers

Remember the users we identified earlier for your software selection team? Designate a few of them as superusers—meaning users who will champion the new software and help others learn and adapt to new workflows. Ideally, these would include employees who lobbied for the new tool, since they’ll be more enthusiastic about its use.

Superusers should be selected based on their technical ability and rapport with the rest of the team. During implementation, they should be kept apprised of all updates, problems, or glitches and act as a liaison between management and end users. Post implementation, superusers can help bring new hires or users up to speed and act as an ongoing resource.

2. Formally track your software implementation plan

If your software implementation plan is relatively straightforward, tracking its progress might only require a free tool, such as Google Sheets. More complicated plans, however, can benefit from a comprehensive task management tool. Optionally, you can track tasks using a resource your employees are already familiar with.

3. Be upfront with your team

Communication is key to successful software implementation, and you need to clearly explain the reasons for the change. Maybe you’ve outgrown an existing solution and need to replace it with something more robust, or perhaps you need a new solution to problems that have been piling up.

Explain to employees how exactly they’ll benefit from the new software and the ways in which it’ll make their jobs easier. Customize messaging according to how the software will be used by each department of your business.

Explaining the reasons for change and defining the expected benefits will comfort skeptical employees and help win over those who didn’t think there was anything wrong with the old ways.

Some business leaders have regrets after their first foray into software purchase. But don't lose hope if a certain software product ends up being more expensive than originally planned, too difficult to implement, or too confusing for your team to adopt efficiently.

Even if the software you chose didn't end up being the perfect fit, chances are it does most of what you need it to do. And now you have a better idea of what you need.

Remember that you can always switch software providers at the end of your agreement, and you'll walk away with more experience. A stronger sense of your software needs and experience with the buying process will make it more likely you'll find a great option next time.