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The IT handbook to choosing the right SaaS app

Rose Layton

March 31, 2020

7 minute read

FeaturedImage Best in Breed


Whether you’re in a SaaS-powered workplace or just dipping your toes into cloud software as you shift to a remote workforce, one thing is immediately clear: There are so many options out there.

Sometimes, choosing a new SaaS tool means combing through lists of dozens (dozens!) of similar apps, and it can be hard to tell which is the right one for the job. Some tools are called “best in breed”—meaning that they are generally ranked at the top of their market segment. Some obvious examples of best-in-breed solutions are Slack for chat and Zoom for video conferencing. Tools like these offer a positive user experience, superior reliability, and a clear forward-thinking vision about how software can make our workplaces more seamless and productive.

As an IT admin, however, there’s a lot more to consider than just “Does this get the job done?” when evaluating a new or replacement SaaS tool.

Today’s IT organizations have to deal with an incredible number of applications to administer and secure, on top of our more traditional tasks like supporting users, managing networks, and keeping the business running. And yet, IT admins are still very much needed to help evaluate SaaS applications before purchase. So how do we do this? And more importantly, how do we make this a sustainable, scalable process?

Over the last year, I would estimate that I have formally and informally evaluated about 100 SaaS applications, including cloud phone systems, project management tools, antivirus tools, marketing platforms, content management systems, MDM, and SaaS management tools. Sometimes, I’ll evaluate more than 10 apps for a single category! And yet, this is only a small fraction of my overall duties, and definitely only a tiny portion of IT’s overall responsibilities. So let’s talk about how we manage it.

Stages of evaluation

Who’s out there?
(Googling it, 101)

When any employee or business unit identifies a need for new software (including IT), the first thing I do is get a look at the space. This means using good old-fashioned Google, with specific search terms related to the task that we are trying to accomplish.

Be sure to include things like “marketing” if you’re looking for a CMS geared toward marketing copy, for example. If you have the name of a potential tool already, use sites like G2 Crowd or TrustRadius to find alternatives—but make sure to look in more than one place! The products shown in Gartner’s Magic Quadrant may be completely different from the products shown on Product Hunt, for example.

Feel free to crowdsource this part! Some of my most interesting evaluations and eventual purchases came from my teammates, or from my professional network in online IT communities like BetterIT, tabGeeks, and MacAdmins.

Let’s have a look…
(Initial evaluation)

After you have some names, the first step is the initial lookover. This is where we’re trying to decide if the app is even in the right ballpark—if we should cross them off the list now or dive in more. The first step is looking at the website for information about the app, then looking at reviews to see what customers have liked and disliked about it. (This is also why I try to leave detailed reviews on these sites when I can!)

If you are a G Suite shop, and everything on the product website is about Office 365, then you might just want to cross it off your list before going further. Likewise, if your organization has very strong single-sign on (SSO) adoption, and you don’t see SSO listed in the features, that would be a red flag in the early stages.

That’s not to say that you can’t move forward with the evaluation, if you want to! But if you have to look at 12 SaaS products, you are likely to find a winner without having to waste time talking to salespeople and sitting through demos, only to find out that they don’t meet one of your core requirements.

Yes, you probably have to talk to that salesperson
(Demo and full evaluation)

Hopefully after the initial pass, you’ve been able to cross some apps off your list, and you have a few that look promising or that you’re excited to learn more about. (Am I the only person who gets excited about using new software? Yes?) This is where you take the next step—yes, you’re probably going to have to talk to a salesperson to request a demo.

All jokes aside, trying to talk to a salesperson about their product can be incredibly enlightening. In one instance, I was asked to “sign off” and purchase an application by a different business unit. A visit to the website looked good, but trying to request a live demo and quote revealed something unbelievable… the company didn’t yet sell any of the products that were described on the website! I’ve encountered other instances where salespeople didn’t actually know how the product worked, or would talk up features that didn’t actually exist yet—all of these issues are more easily caught by someone who is used to talking to software vendors. As I’ll discuss in the next phase of evaluation, I also love to see products that offer free trials or demos without talking to someone. These products are usually well designed, easy to use, and offer strong features that stand on their own (and don’t need someone to prop them up or demystify them). After all, that’s how SaaS became so popular!

Unlike in the initial evaluation, this is the stage where you’re going to need to understand your organization or stakeholder requirements.

What needs are the stakeholders trying to meet? What do you already have in your organization, and how well are they meeting those needs? What are your security policies? What’s your budget?

It’s impossible for me to tell you what these are for every evaluation and every organization, but here’s a little glimpse of some of my general “checkboxes”:


  • Is it easy to navigate? Are the parts of the software laid out in a way that makes sense, or is the navigation “circular”? (Can the same thing be accessed from multiple places, or do I frequently have to go back out of one thing and into another?)
  • How responsive is it? How does it look on different sized screens or mobile devices? Do the pages load quickly?
  • How long will it take to learn to use? If I’m going to be rolling an app out to my entire organization, will my end users pick it up quickly, or will I have to train them?
  • Does the application have self-service support? Do they have public support pages and documentation? Do they have a chat option within the app if someone wants immediate help?
  • Does using it remind me of Windows XP/2000? (No seriously, this is a real litmus test that otherwise modern applications sometimes fail.)


  • Is there transparent pricing listed on the website? How much does it cost relative to other SaaS tools we use?
  • Does it support SSO? Is it SAML or OAuth? Do I have to pay more to get SSO?
  • Is there an API? Does it integrate with other tools in our SaaS stack? On a related note, does it support SCIM provisioning? Do I have to manage access manually?
  • What kind of analytics does it offer? Are they exportable?
  • Does it offer multiple admin roles? Does it offer custom roles?
  • What is the support SLA? Is there an option to buy a premium support package, if we want it?
  • How easy is it to get data in (or out)? If we decide to switch products in the future, will we have to start from scratch?
  • How reliable is the application? If it’s hosted on AWS and some AWS AZs go down, do they have continuity built in?
  • Is it hybrid or cloud-native? This can be more difficult to assess, but the rise of SaaS has also given rise to hybrid applications—where the product is hosted and managed by the providers, but it’s still isolated to individual servers and can require regular maintenance outages.

Security & Privacy

  • Are there system and admin logs? Can they be exported, manually or automatically?
  • If they send email on your behalf, is the provider able to provide DKIM/DMARC keys?
  • Do they have available GDPR/CCPA/other privacy documentation? Do they meet the security requirements for our organization?
  • Do they have security certifications, such as SOC 2 or ISO 27001?
  • Do they have a policy about data retention/deletion? If so, what is it?

Let me touch it!

(Final evaluation)

As you can see, there’s a lot to consider here, and not all of these questions can be answered in a demo or on calls with a salesperson. If you make it out of the main evaluation process and still have a couple of solid products on your list, the best thing to do is to get into the actual product. By digging in and actually using the software, you get the best sense of how difficult it will be to use and administer. Most SaaS apps these days will start you off with a trial anyway, or allow you to use a live demo on your own. These trials are time intensive, though, so I try not to do more than two or three apps for a single evaluation.

By the way, not every evaluation has a clear “winner”—sometimes you’ll end up purchasing something that has a less-modern UI because it meets your feature requirements, security requirements, or budget. Very few of the items I listed above are considered “deal-breakers” in my current organization, and if I move to another organization in the future, I’m likely to encounter an entirely different set of “deal-breakers.”

One question you might be asking now is “How do I keep track of all this? Is there some kind of template?” There are some out there. Here’s a sample spreadsheet to show what a theoretical evaluation could look like when it involves multiple people providing input. But again, nothing is one-size-fits-all. Personally, I usually use a plain document, with notes for each app under their own heading. When you cross one off your list, just remember to make a note of why you did, so if you ever come back to it, you’ll be able to see why it didn’t make the cut.

With thousands of SaaS apps out there, selecting the right one for your organization can feel challenging. It’s important to remember: There’s a lot more to consider than just “Does this app get the job done?” By understanding stakeholder requirements, doing your research, asking the right questions, and digging deeper into the software, you’ll set your organization up for success in the long run.

I provide a deep dive on the topics outlined here in The IT Handbook to Choosing the Right SaaS App. Get the complete eBook here. If you have any questions or additional suggestions on evaluating SaaS apps, I’d love to keep the conversation going! You can reach me in the BetterIT Slack community as @rose.