Questions to Ask When Evaluating Software Vendors

Brandon Gracey
October 27, 2014

“Our sales order management software isn’t what you’re used to. It’s easy to implement, won’t disrupt your business, and we’ll train your team on how to use it. Most companies see results a week or two from kickoff.” Our sales team is saying these words all day long here at Handshake, because the first thing everyone inevitably wants to know is the same: What’s it going to take to get this software up and running? This question often comes up before we even start talking about what Handshake does as sales order management software, and it’s understandable. For anyone who’s ever nursed battle scars from complex ERP integrations and CRM migrations where budgets and time frames were blown out by months or years, the war stories are enough to inspire fear in even the most seasoned IT professionals. The software landscape is dominated by products that can devour time, manpower, and money to introduce and integrate rather than making your life easier (which was the original goal, wasn’t it?). At the risk of sounding evangelical, it doesn’t have to be this way!

How Do You Know a Software Vendor is Right for You?

We may be a SaaS company (if you're not sure what SaaS is, or why it might be right for you, click here), but we’re also evaluating software vendors for our own business on a regular basis. Almost all of the software products we use at Handshake were very easy to onboard, use, and introduce to the team, and they all have a couple things in common:

  1. They are effectively focused on a specific, significant problem, rather than full of partial solutions for a jumble of smaller problems.
  2. The founders/creators have “lived” the problem first-hand and built their software with those pain points in mind. (Check out our post, "Breaking Up With Paper," for Handshake Founder Glen Coates's story).

Products targeted to your use case are going to be the most helpful. In these situations, the vendors developing the software will better understand your needs and how your business operates. Once you’ve discovered a product that you think meets these criteria, the next step will be quizzing the company to find out what’s involved in getting up and running. Having had many experiences on both sides of the phone, here’s a list of some of the best questions you can ask to get the ball rolling.

Evaluating Software Vendors: Questions to Ask

1. What’s your company’s story? Did they stumble on a problem and try to solve it, or did the company’s founders do it because they were sick of the problem themselves? The best answer would be more along the lines of the latter. A product that was thoughtfully designed and developed based on someone’s known experience of the same problem you’re currently experiencing is going to meet your needs much more effectively. 2. Who’s going to help me set it up? You don’t want to be stuck without support. Your SaaS vendors should offer a Knowledge Base that will help you address simple problems, ongoing flexible support options like live chat, and a skilled team of customer support professionals to help you move forward. 3. How long until all my users are fully active on this program? This question cuts right to the chase. A good answer depends on your expectations, but you generally want to hear that the solution is simple enough to be running within a few weeks, and intuitive enough for your team to adopt it quickly. Ask the vendor for a hands-on demo or free trial, so you can see for yourself whether or not it’s easy to use. 4. Walk me through your standard implementation. Get a comprehensive understanding of how the entire process will work. Be wary of non-specific answers. The vendor should also be asking you the right questions in order to determine your needs. 5. What was the most complicated installation you’ve experienced with a client? Onboarding can take a few left turns in even the most buttoned down processes, so do a bit of digging to get a feel for how your vendor manages them. 6. How do you integrate to X? This answer is the difference between an easy onboarding and a not so easy one. Ask whether your vendor has already done integrations with the services you have, and how they did it. You want to look for SaaS vendors that use open APIs to link to your current systems, if applicable. 7. Can we use this product as a standalone service if we don’t want to integrate it to another service? Not every product can stand alone; some SaaS solutions were built to use only in conjunction with other software. So if you’re looking for a standalone product, make sure to sniff this information out early. 8. What does my IT team need to know? Ask this early on. You should get a bulletproof answer. Every tech-related decision you make is going to get the attention of your IT team if you have one. Your software vendor should make that process easy and predictable for you.   Not every onboarding process will be easy, but you should definitely be able to see value quickly. Whether it's Sales Order Management software, CRM software, or an ERP, be sure to make questions specific to your company’s situation when evaluating software vendors. You may have more complex inquiries that far outreach the few above. Your potential SaaS vendors may not have the perfect answer, but they better have an answer. Salespeople with strong products to back them up will want to engage in these questions and show you how their product outstrips the competition.