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How to Buy Software

Updated: Nov 17, 2023



We know you have a business to run. And we know you already have a lot on your to-do list. Figuring out software doesn’t need to be added - we’re here to help. Here are our 15 tips and lessons learned from years of experience in this space!


Think about what you need! Odds are that there’s already a solution out there that will help. Make a list of what you’d like. And then ask around internally to make sure you don’t already have something that can do that!

Figure out your key stakeholders well before you start looking for a software provider. Let those people know what you’re thinking about. They may be able to offer recommendations on tools, or on who to talk to. Mostly, though, you’ll get a sense of what they might need or want from a product - which lets you fill out your list of what you want and helps avoid that awkward “Oh, I thought it would do this…” conversation after you’ve bought a product.

Once you have a list of things you’d like technology to solve for your business, schedule some time with your team. Outline what functionality you need and would like ahead of time. If possible, prioritize it into three lists: must-haves, would like to have, and nice to have but not important. Most software companies will show up with a list of hundreds of things that their toolsets can do. Make sure it does what you need first - and can do it well!

Time to do your research! Conferences, networking groups, or searches here on Linkedin can be a great way to get a sense of what software solutions are out there. Ask your peers what tools they’re using to automate their business processes too. Most of us are happy to share information when you reach out. Talk to people - and don’t be afraid to ask pointed questions about what works and what doesn’t!

Now that you have a list of prospective providers, reach out to those providers with a list of questions. Listen carefully to the answers! Does the software currently offer the functionality you need? Will it help you streamline your current processes? If the answer is no, it’s not the solution for you. If the answer is yes, how easy is it to access that functionality? Are your requirements features of the software, or just tricky workarounds? Make sure to confirm that the software’s current version offers the automation and processes you need as part of its current iteration, and make sure it’s designed to do what you need it to do!

Don’t settle for the phrase “it’s on our roadmap” - or similar phrases like “we’re building it now and would love to get your feedback.” That’s an easy way for a salesperson to say that they might at some point have the feature or toolset you want - but don’t have right now. Even if they show you your roadmap, remember that roadmaps change. Priorities shift. Their vision for the software may change before they get to that item, or a bigger client may request something else entirely and push your request to the bottom of the list. You want software designed to do what you need it to do today. Think of a riding lawnmower. It can get you from one place to another… but it doesn’t replace a car. Don’t settle for a lawnmower.

Separate the salesperson from the software. This is hard to do, especially after you’ve developed a good relationship. Unfortunately, salespeople are busy, and while you may talk to them frequently leading up to the sale, you may not hear from them again until it’s time to renew. Find out who will be your day-to-day contact and understand who (if anyone) you’ll be able to reach out to with questions after the deal closes. What experience will your day-to-day contact have with your business and your industry? Do they know what keeps you up at night?

Know what you’re buying. There are different types of software packaging. The apps you buy for your smartphone, for example, or software you purchase once a year to do your taxes, is subscription-based software. You pay a subscription fee, and you get a specific, unchangeable product. Software as a service (or SAAS) is not the same thing. SAAS products typically include full and responsive support, an onboarding process, and ongoing interactions with the team that built the software – all for one annual or monthly fee. You want a SAAS toolset with all of the support it provides.

Along with the category of software you’re buying (SAAS vs subscription), you’ll want to understand how easy it is to get started with the software. After you purchase it, will you need to find a team of developers to help you install it? Or pay for a series of “integrations” that someone will need to build to connect your existing tools to the software? Will you have to pay for training on how to use it? Always confirm the steps (and additional costs, if any) to begin using the software before you buy.

Make sure the company you’re planning on buying software from knows how to make software! Functionality and user experience are critical. If your vendor is focused mainly on hardware, take a close look at how well their software offerings work. One great way to understand this: ask how well the software works with hardware products that aren’t their own. Unfortunately, especially now that supply chain issues have impacted supply, hardware companies are pushing software to have something to sell. If it’s not their main product, move cautiously.


Find out who supports the software, and how. Does the company you’re buying from have developers on staff? Are they writing their own software, or outsourcing it to another firm while they focus on building hardware? If they do have developers on their team, do those developers understand how you work, and what your workflow will be on a daily basis, and how your business operates? Have those developers ever worked directly inside a firm like yours?

Compare prices. Ask what the pricing model is, and don’t be afraid to ask about the cost. Once you have that, understand how it fits into your budget. For carriers, the revenue-generating unit is usually the subscriber per month. If an average subscriber pays $50 a month, and the software costs $5 per month - can you really afford to spend 10% of your revenue on it? Make sure you understand the value that you’ll be getting for that cost.

Ask about price increases. When was the last time they did one? How much was it? How often do they raise prices? Feel comfortable asking for the names of a few customers to validate this. And take a look at market pressures too. If you’re buying from a hardware company that sells software too, but can’t sell any hardware because of the supply chain - what’s the likelihood that they’ll raise the price of the software to make up for the hardware shortages?


Get references. While it doesn’t hurt to ask your salesperson for references, remember that those people will be listed because they’ve agreed to give a positive review. Ask around for other sources. Asking your peers what they think - at conferences, via LinkedIn, through industry networking groups, etc can lead to more reliable information. Be sure your questions are designed to get the answers you need. Even if people haven’t used the software directly, they may have insight into the company’s reputation.

You’ve made it to the contract stage! Read the contract terms carefully, and understand what you’re giving up in exchange for any discount. One shortcut some software companies will take is to ask you to sign multi-year agreements, in exchange for a discounted or locked-in price. The downside? If the software isn’t right for your team, or if those promised “on our roadmap” features never materialize, you’re stuck paying for years of software you’ll never use.


Buying software requires a lot of knowledge - technical, financial, and legal. We’re always here to help you every step of the way! You can see our complete top 15 software buying tips on the blog here. Or, send us a note - we’re always happy to talk through them with you!

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