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How To Buy Enterprise Software (Without Getting Scr3w3d) - Blog #2 in Series of 4

Updated on April 12, 2013

Don't Get Scr3w3d


In the previous blog, we discussed how businesses often buy overly complicated enterprise software, at excessive expense. The solution is to choose simpler enterprise software solutions that are adaptable, and to only buy what you actually need. We covered the concepts of Overkill, Don’t Just Go For The Big Names, An Ounce Of Preparation, and Ask Questions.

In this installment, we will discuss how to evaluate and choose the best enterprise software vendor for your company’s needs.

Avoid Unstable Startups

Startups have a sexy allure nowadays and people often forget that they are untested. While the media covers startup superstar companies that seem to race quickly to lucrative IPO’s, the fact is that many startups fail, despite the best of intentions.

Since you are making a large commitment in terms of money and time when buying enterprise software, you want to make sure you are choosing a company that will have longevity. If you need continued support or items down the road, you don’t want to discover that your once-hot vendor is now out of business.

In addition, whether they admit it or not, startups are usually still testing and continuously debugging their products long after they have gone to market. This is almost unavoidable due to the nature of developing software, but you don’t need this to become your problem.

The same goes for the company’s business processes and implementation issues. This stuff needs to be ironed-out before you come on board, or you are just a guinea pig for the vendor and subsidizing the vendor’s costs of development.

This issue is most critical if a vendor is only offering Software as a Service (SaaS). Be certain that you have the option to move the software in-house.

For the above reasons, it is critical to select a vendor that has been in existence for a long time and has demonstrated the value of its products.

Send Brief Requests For Proposals (RFP’s)

Don’t waste time initially sending out long, detailed RFP’s to lots of vendors you haven’t particularly vetted yet. Long RFP’s up front tax the sales representatives and, if the forms are too complex, the sales reps may not even get around to responding to you – they have other accounts that are easier to handle. Long RFP’s up front are not efficient, either, because you don’t need complex details from a lot of vendors who might not even be a close fit for your needs.

It is better to create a brief, concise RFP that lists the main issues you would like to address with the software. Your earlier list of most important goals for the software will inform you here. Your initial RFP should only take the sales rep about 30 minutes to complete.

Questions to ask the sales representative include:

1. What will the costs total over the next 5-10 years?

2. Will we need consulting to implement the system, and if so, how much?

3. Will any technical specialists be required to implement or run the software system?

4. Will the enterprise software cover all the needs my company outlined?

5. Can we see a demonstration of the product first?

Send In-Depth RFP’s To A Smaller List Of Targeted Vendors

Once you receive responses to your initial RFP’s, choose a target list of vendors who gave the best answers for your needs. Then you can send them longer RFP’s where you go into more detail about what you need and ask how long it will take to implement your system.

Let the vendors know they have made it to the second round in your selection process. That way they will be motivated to give you all the information you need as quickly as possible.


The above might seem like a lot of work, but it will pay off in saving you time, money, and a lot of headaches. In the next blog in this series we will discuss the importance of taking control of product demonstrations. We will also give more tips on how to research vendors.


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