I'm starting with the obvious. A key to having a successful CRM implementation is selecting the right CRM system.  There are plenty to choose from Salesforce, Microsoft Dynamics, NetSuite CRM, Goldmine, Zoho, Act!, SugarCRM, Oracle Sales Cloud, Hubspot, etc, etc, etc. The list is long and varied.

Consider what you need based on the size of your organization. 

Some are great for small businesses, some are expressly designed to be more of an ERP system for large corporations. Some are designed to scale, some are not. So be forward thinking, are you growing? Slowly or Rapidly? The last thing you want to do is outgrow your implementation in a year or two and have to switch again. That costs time and money. And don't forget to buy a crate of aspirin for all the headaches.

Consider your functionality needs.

Some, like Highrise,  are designed to offer very basic CRM functionality, others, like Salesforce, are designed to be a development platform, where you can build your entire business on it, CRM, mobile apps, Customer Communities, Sales, Marketing, inventory Management, operations, etc. Some work well with other Technologies. Zoho, for example, works well with Google Apps. Microsoft Dynamics obviously ties in well with the Microsoft Ecosystem. Salesforce ties-in well with both, and their Open API allows for integration with thousands of other 3rd-party Applications

Consider what you can afford.

Most CRMs are cloud-based so the main thing you need to consider is the monthly subscription costs. For locally hosted CRM software, you need to consider the cost of hosting in addition to the sticker price. In both cases you need to consider the cost of training. You should take into account the cost of an in-house IT resource for continued modifications and maintenance of your hardware if you're hosting the solution. Or the cost of a consulting resource if you don't need full-time support. And don't just look at the price tag, consider the opportunity costs. What will your ROI be based on the software you select?

Consider the Product's track record.

The internet will give you hundreds of reviews at the click of a button. But often these are shallow and mostly comparisons of pricing and features. Dig deeper, find third-party consumer reports and reviews. Do they have a proven track record of positive ROI. How's their support? Are they easy to use? Do they have a good track record of user adoption (although that depends largely on you)? Talk to other companies, what do they use? What do they recommend? Also ask them what they learned from the implementation. That will go along way to avoiding similar pitfalls.

Consider Ease of Use and Configuration.

If it's not easy to use then forget about it, if your users have to jump through hoops to get data in and out of the system it will just collect dust. Some systems are complex and still easy to configure, and others are harder than advanced calculus, and will always require a dedicated resource to modify. So take that into account before you buy.

To thy own self be True.

Only you can determine what your needs are, what you can do, what you will need help on, and what you can afford. Do a little soul searching. And if you're still unsure, hire a consultant to help you to do a needs assessment. I know, I know, it's another expense. But spending a few thousand dollars up-front could save you Tens-of-thousands of dollars in lost costs of picking a bad software. Not just the cost of the software, but the cost of a failed implementation, and lost productivity. Picking the right one could mean the difference between hundreds of thousands of dollars in realized opportunities and millions.

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