Best way of getting users to buy premium features

A client has a website for a service and the service is free. The client wants to introduce a number of subscription schemes so that users can use premium features.

Question: how do we get users to buy features? Give them away for a couple weeks and then force an upgrade? Give them a choice at registration? Prompt at appropriate times during usage of the system “hey, did you know you can also do this for £xx”

Does anyone have a background in this and what advice can you offer? What works best? What did you learn?

My first question would be are the customers consumers or business? If the latter good luck - four years later we are still trying to figure this one out.
In our experience our customers are restricted from purchasing by a number of factors:

  1. They are the ones who need and will use the new feature but they have no purchasing authority.
  2. The purchasing authority does not use our product.
  3. Those customers who work for larger companies have a lockdown policy on purchasing software. That includes online plugins for a web app that does not affect their locked down desktop in any way. You have to go through a rigorous seven step process involving IT Security, Application Review Teams etc. etc. to seek and be granted approval for your purchase. In this case an online process simply does not work as one of the steps requires direct face to face presentations from the seller.
  4. I have met many of our customers who have told me because of step 3 they long ago gave up trolling the web or going to the conference exhibit floor to see what is new. As one customer put it “this is the 21st century - I use what I get from IT”.
  5. Smaller companies that do not have this restricted policy are too busy to be looking online for new product that will help them do their jobs better. “Unless one of your account managers sends me an email or a phone call, my staff and I are too busy working to peruse your site for new features” It should be noted this includes clicking on ads for new features that are placed next to our log in for our main web app.
  6. Customers have learned to use the features of our apps that they need to complete their work. They will not search out a new feature that is available because they have no perceived need for it. This could be because we are not their 24/7 365 day workday tool. We are a supporting tool that they use when necessary.

All that being said in my past life when the world was less busy and not so restricted by purchase paths we found that the one month free trial was the key to selling wide into an organization. This still required the personal contact to start the process, but after that we found that if customers found value in the product they did not want to lose all their work artifacts they had created. Hence they paid for it and then word of mouth took over. Their colleagues would see Joe getting his work done in half the time and asked why. And then they would get a free trial and eventually word would reach senior mgmt. which could lead to a company wide purchase.

But in summary its a tough world getting customers to part with their money. We certainly need to do some work on our end to make it easy for our customer to give us their money. Problem is it’s not their money, aka a consumer product. They are spending their companies money and their purchasing rules are very prohibitive.

This is helpful, especially the second last paragraph.

Our product is for business and we have good contacts that can introduce potential clients to our software. Your point about a free trial is certainly something we’re looking at.

thanks for the great comments

c

This was very helpful to me.I expect like this post again!

OK, a wee bit more about the problem

Our system is for submitting applications to government.
Sales are insisting on 5 different types of payment plan for multiple applications, single applications, certain application types, monthly usage etc (cringes) but there’s no way on earth a user can make an informed decision about which one to buy without using the service first, besides, don’t you think 5 plans is too much choice? Oh, and there’s a basic free plan, 'natch.

So what do we do? We need to get users using the system and once they do maybe pitch the pricing plans. But I’m not sure how to communicate all this on the homepage because its going to confuse the hell out of everyone.

Complexities:
Sales are not going to budge on the 5 plans (they’ve already come down from 7)
The plans don’t match the personas we researched

Simply put on your page “We have a variety of different pricing options to suit your budget. Please contact your account representative to discuss”
Wait till you actually sell something first before you start defining complex pricing plans.
Enjoy the problem of defining different pricing plans when sales proves the need is there.