6 Ways to Avoid Regretting Your SaaS Software Purchase

Marketing Technology


I recently purchased a new pair of ballerina flats from Margaux New York, as they are a staple in my ‘woman in tech’ business uniform. The company sells high-quality, ready-to-wear, and made-to-measure shoes. Before I made my purchase, I first ordered a fitting kit to help me choose the right size.

The instructions contained a delightful little expression: Measure twice, cut once.

This is an old adage in the fashion industry but also heard often in carpentry. Whether you’re sewing a dress or handcrafting a table, measuring your materials twice (or thrice!) before cutting helps ensure precision and prevent mistakes.

Okay…but what does this have to do with SaaS software? You just wanted an excuse to talk about shoes.

Valid point—but ‘measure twice, cut once’ is also a great expression for any process that requires strategy and careful planning.

I’ve written previous blogs on how people buy with emotion and back it up with logic. Consider this post the logical side of your decision, as there is definitely a proper process to consider when evaluating and buying software. Following the steps below will help everything go smoothly, meaning that you won’t have to go back and “re-measure”.

Read on for my personal observations and patterns in how companies run successful evaluations, as well as gaps in the process that end up wasting resources and resulting in the wrong decision (or no decision at all):

1. Conduct Product Demos Fairly Close to Your Decision

Avoid shopping just for shopping’s sake. There is a perfect sweet spot for evaluating your top vendors before you’re ready to make a decision. Generally speaking, this sweet spot is about eight weeks out from signing an agreement. Anything longer and you risk forgetting or conflating the feature sets of each product. With most SaaS platforms shipping new releases anywhere from weekly to quarterly, there’s also a strong chance that the product you evaluated in January will look very different in July.

If you’re switching off another product, do not begin your vetting process unless you’ve 100% decided that you’re switching. If you don’t have a clear and compelling pain, then the grass will not be greener on the other side.

2. Clearly Define Your Priorities

Once you are ready to evaluate, it is vital that you define your absolute must-haves and your deal-breakers. Which features will help drive your business forward and make you look like an absolute rockstar to your boss? Focus on those–and conversely, don’t get hung up on flashy features that aren’t direct revenue drivers for your business.

3. Vet Implementation as Thoroughly as the Tool Itself

Most SaaS solutions are ‘sticky’: they require resources to stand up and a full-fledged project plan should you need to migrate to another tool. This means that you should thoroughly vet your SaaS vendor’s level of experience with implementation. Your implementation team should have a lot of repetitions under their belt with companies similar to yours and your use cases. Bonus points if they’ve implemented the solution themselves as end users because they’ve been in your shoes and can show you a clear path to success.

4. Beware of Making a Choice Based on Price Alone

Good enough” can be a dangerous proposition. Unfortunately, I’ve heard this refrain countless times: “At the time it was good enough, cheap, and we didn’t know what we didn’t know, so we just went with it and now we regret it. I knew this day would come [where they’d have to rip-and-replace], I was just putting off the inevitable.”

In choosing a SaaS solution, play the long game. It is far better to pay a little more upfront for long-term benefits and ROI than it is to run a new evaluation every 12 months and face a rip-and-replace situation.

5. Be Clear on How You’ll Get the Project Done Internally

If you’re still ironing out who is involved in your evaluation, know that it will slow down your purchasing process. Do leverage your SaaS account team for best practices in navigating this process. They should have resources on their end to help you build a compelling business case and get it in front of the right people. If at all possible, try and avoid unnecessary frustration in the form of new people adding their voices/opinions at the very end of your evaluation. This has the potential to undo months of hard work and careful vetting.

A clear project plan also includes defining a budget and timeline. As outlined above, the most important part of your timeline is conducting demos later as opposed to sooner. I know this is counterintuitive, but it will keep feature sets sharp in your mind.

6. Focus Your Search

Too many products = paralysis by analysis. You know those restaurants that present you with an encyclopedia, masquerading as a menu? You open the menu to a random page, feverishly scan hundreds of options, and when the waiter gets to you, you panic and pick something random. This is really not that big of a deal for minor decisions like lunch but when you’re choosing software, it has the potential to spiral out of control very quickly. Instead, take 30 minutes to hunt on LinkedIn. Find a few businesses that look similar to yours and ask their team(s) what they use, what they like about it, and what they would improve upon.

Success leaves clues. Whether you’re evaluating software for the very first time or fondly remember implementing JD Edwards in the 80s, I hope that these tips and tricks help you and your business make a successful, pain-free evaluation.

If you’ve purchased software in the past or are currently in a cycle, I would love to hear about a time when you “measured twice and cut once”–or, if you have any battle stories in your arsenal. Leave a note in the comments below!

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