Does it meet how you do business? This is important but you've need to be cautious here. Sometimes the way you have been using ACT! and conducting your business may not be the most efficient. ACT! allows you to commit all sorts of database sins. It is probably one of the most undisciplined databases around. This is fine when you don't care about analytics or consistency across your users -- but you should NOT expect this from your new CRM. Most modern CRMs are designed to help you do things like analyze your data and understand things like how effective your sales campaigns have been – this cannot happen without consistency.
Cost. Cost is certainly a relevant consideration, but it shouldn’t be the only one. Most ACT! users don’t take into account the costs of managing an in-house database like ACT! With a cloud-based solution, those costs go away. You also need to consider your "opportunity costs". If managing your database takes time away from selling and managing your business, those costs need to be considered too.
Don’t get oversold. Most vendors have multiple levels/editions of their products. Each level providing more features at a higher expense. What they don't tell you is that if you find that you have chosen a level higher than you need, downgrading can be costly. In some cases, you need to go through a complete migration process again.
Company stability. In the last 10 years,
hundreds (probably thousands) of new CRM providers have come and
gone. The new guy may
have some slick features at a lower price.
They may have committed support staff to help you.
But what happens when their venture money goes away.
Ask the hard questions about migration. Some companies will offer “free” migration services if you buy more than 5 licenses. Here you can expect to get what you pay for. This rarely includes things like custom fields, notes, histories – it’s the very basics. Definitely work with a trial before you buy. Try the things the salesperson told you were easy. If you get stuck, try contacting the tech support. Remember, if you can't communicate with tech support during the trial phase -- it's not going to get any better.
Work with a consultant. Selecting a CRM and moving data around between different platforms is not easy. It's a complex technical process. Each vendor has their own pitfalls. A consultant can help you through the process. While the upfront cost can seem to be more than you'd like to spend, the end result will probably pay for itself many times over. Some things are best left to those with the experience and proper tools. You wouldn't consider doing your own root canal.