How To Assess Business Software Without Committing to a Purchase

Looking for answers on how to effectively assess a billing platform before purchase?

You’re not alone.

Switching billing platforms should help you — not hinder you. But the wrong tool can impact productivity so much that you’ll spend more time dealing with the transition than you ever did with your old tool.

Still, most business owners don’t properly assess their options before making a purchase. Which means headaches aplenty down the road…

Table of Contents

  1. Why Businesses Keep Getting Software Purchases Wrong
  2. What Makes A Small Business Billing Tool Worth Trying?
  3. How To Effectively Run A Software Trial And Assessment
  4. How To Tell If A Billing Tool Fits — Assessment Checklist
  5. Wrap Up: Stop Guessing — Start Testing Software Trials
  6. Frequently Asked Questions About Software Trials And Assessments

Why Businesses Keep Getting Software Purchases Wrong

When asked how they chose their current billing platform, most owners would answer they just picked one and got started.

Think about how you pick your favorite restaurant…

You don’t sample five menus first. You find the first one that looks tasty and hope it lives up to the hype.

Except business software isn’t foie gras. A small business billing tool must work for how you do business. Invoicing schedule, payment reminders, reporting features, integrations — everything should support existing processes.

When new software fails on just one of those pillars, businesses feel it. Which is why using a free trial period to test Prime Software before buying can pay massive dividends.

Did you know that according to Capterra’s 2024 Tech Trends Report, 60% of software buyers regret a technology purchase made in the last 18 months? And 56% of those businesses say the financial impact was “significant” or “monumental” in terms of cost.

You don’t want to learn that lesson the hard way.

The good news? You don’t have to.

What Makes A Small Business Billing Tool Worth Trying?

FREE trials are great. But they don’t guarantee a great experience…

Software vendors know that if you try their product once, you’re likely to buy it. That’s why some of them will simply withhold key features during trial periods.

You know when you’re getting the real deal:

When full access is given. During the trial.

That means access to every bit of functionality. There are two reasons you need that:

  1. You need to test every aspect of the billing tool to know it works for your needs.
  2. If the vendor locks down features during the trial, how will they treat you once you’re a paying customer?

Here are the crucial features and functions to test when trialling a small business billing tool.

  • Invoicing. Can you create and send an invoice? Does it include everything you need? Can you record a payment against that invoice? Is the invoicing process smooth from start to finish?
  • Dashboard. If the dashboard isn’t intuitive out-of-the-box, it’s never going to get any easier. You should be able to log in and immediately know where to find key metrics.
  • Integrations. Most businesses use software to help run operations. Billing platforms should integrate with existing software, not replace them. Ensure any must-have apps integrate before you buy.
  • Reporting. Don’t settle for ugly spreadsheets. Modern accounting tools should include reporting features that do the legwork for you. Profit margins, cashflow, overdue invoices — these basics should be available at your fingertips.

Note: Don’t just “try it out.” Assess the platform as if you were using it for a full week at work. That’s the only way to truly test if it fits.

How To Effectively Run A Software Trial And Assessment

Are you still purchasing software the same way most people do?

Make a guess. Press “buy.”

If you want to guarantee yourself a costly headache, keep navigating that software store the way you are.

Here’s how to vet billing software so you can stop guessing and start knowing.

Step 1: Build Your Requirements List Before Testing Software

Take out a pen and paper.

No seriously. Write down what your business needs from a small business billing tool before you start trying any of them. Without a list, you’ll assess every option through a lens of guessing and assumption.

Your list should cover the basics.

  • Monthly invoicing volume
  • Multiple user logins
  • Recurring billing
  • Automated payment reminders
  • Financial reports needed (overdue accounts, net profit, cashflow, etc.)

You can use this list to grade every software option you trial. Making sure you pick the best one, not just the shiny one.

Step 2: Run A Real World Scenario During The Trial Period

You know how most people use spreadsheets?

Open one up, play with the buttons and say “Meh, looks fine.”

Software trials are no different. Just clicking around and testing buttons won’t highlight problems. Instead, run through a real-world process from start to finish.

Create a client account. Add any products or services that you sell. Send an invoice. Receive a payment. Generate a financial report.

If the billing tool hiccups at any point in that process, make a note. So you can avoid that headache post-purchase.

Step 3: Involve Others During The Trial

The owner is not always the end-user.

Many small businesses have accounting teams or admin staff that spend all day, every day, in their chosen billing tool. They’re the experts. And chances are, they’ll catch issues you didn’t think to look for.

Make sure they’re involved in the trial process. It’ll save you time in the long run.

Step 4: Test The Support Team Before You Need Them

There’s one step in the software assessment process that every small business skips.

Too often.

Customer support.

Don’t just trust that the support team will be there to help down the road. Contact them during the trial period with a question. Make note of how long it takes to get a response and if the answer was helpful.

Excellent software features are useless if you can’t easily get help when you need it.

How To Tell If A Billing Tool Fits: Assessment Checklist

  • Test every aspect of the platform. Ensure it can handle your business’ billing needs start-to-finish.
  • Involve your team. Get input from everyone that uses the billing software on a daily basis.
  • Request support. See if you can get a response from the support team while you’re still a trial customer.
  • Does the dashboard/software interface make sense to everyone who uses it?
  • Can it integrate with existing tools your business relies on?
  • Are the reporting features robust enough to generate the reports your business needs?
  • Was a real-world task tested from start to finish?
  • Is the cost up-front? Are there any hidden fees?

Know what you need before you buy. Test those features during the trial period. If everything checks off on that list, you can buy knowing your team will love the new platform.

No guesses.

Wrap Up: Stop Guessing — Start Testing Software Trials

Selecting a new billing tool shouldn’t be a shot in the dark.

Take the time to properly vet your options. And you’ll never have to say those dreaded words again:

“Why did we switch billing platforms?”

Frequently Asked Questions

Q: What is software assessment? A: Evaluating a tool before purchase. Including but not limited to testing core features, completing a real-world task from start to finish and checking software integrations.

Q: How long should a software trial last? A: Long enough to run real business tasks through it. Most free trials are one month. But you can get more value out of one week of serious use than 30 days of browsing around.

Q: Why do businesses regret software purchases so frequently? A: Cost. Features that were advertised didn’t actually exist. And poor customer support during onboarding. Properly assessing software before buying can alleviate these problems.