Some characteristics of plans that I don't like:
* Passing some arbitrary limit (# of contacts, # of users, # of files, etc) triggers a steep increase in price, rather than having the price gradually increase as usage increase. For Mailgun, usage is the number of emails sent. For us, it's the number of users on the account.
* Because of the steep price increases at arbitrary points, some users get a lot more value out of the software than others. With Highrise (another CRM) an account with 5,000 contacts pays $24, while an account with 5,001 users pays $49/month. Both accounts are getting roughly the same value, but one is paying twice as much as the other.
* Most SaaS companies with plans force users to choose which plan (or tier) they want when they sign up. How would a user know what features are worth paying for when they haven't even tried the software yet?
* Plans are often used to upsell existing customers after they're locked into your service. Salesforce has a plan that is cheaper than my company's price ($5/user/month vs. $10/user/month) but it is limited to the point of being almost useless. I've talked to many people who got suckered into a 1+ year commitment with them only to realize they'd have to pay $65-$250/user/month to get the functionality they needed.
* Customers have to monitor their usage to make sure they don't trigger the next tier. It's just one extra thing to worry about every day, and businesses have enough on their minds without worrying about unexpected price increases.
Having said all of that, I'm currently struggling with how I might go about offering more products than just a CRM without making it look like a tiered system. I don't consider it to be the same thing because they really will be additional products (project management, invoicing, etc.) which are generally completely separate subscriptions if you use a different company's products, but I want them to be integrated/bundled directly with the CRM to make the user experience as simple as possible. Still not quite sure how to pull this off. Pricing sure is tricky.