With regards to pricing: I think you may want to simplify that. In particular, from the perspective of an organization with 20 employees, there is no difference between an HR expenditure of $20 per month and $100 per month. $80 is rounding error on a single employee's overtime pay. (Seriously. Compare the cost of your system to, e.g., payroll systems.) However, you have four plans which attempt to make distinctions between non-distinct things.
Assuming you're in the right range on current pricing, I'd be thinking more along the lines of:
Free for 3
$20 for 10
$100 for 100
CALL for more
Now you only have to administer three options, and if you convert anybody with 20 employees you win much bigger.
Note the CALL option. There is an awful lot to be said for the CALL option in enterprise sales. Realistically speaking, price is not going to be what prevents your solution from being adopted at large corporations. However, and this might be a bit of a shocker for you, they might not deal with variable pricing that well. (It is easier to get my boss to sign off on 2 * $X,000 per year than to sign off on twelve payments which will average out to $X,000 per year. Think of how much extra work that makes for him in working the company bureaucracy. First he has to attach a projection. Then he has to document how he made the projection. Then he'll remember "Oh, shucks, if this ever materially changes I'm going to have to update the projection, but updating projections doesn't bring in my projects or get me my next promotion.")
Incidentally: you list a bunch of features, not benefits, on the front page. Nobody, not even HR drones, wakes up in the morning and says "You know what I want to do today? Create office holiday schedules!" Let me hum a few bars: decrease costs, increase compliance with company policies, reduce workplace conflicts stemming from miscommunication about leave.
I don't understand how you can say $80 is a rounding error, and then suggest pricing tiers that that have an $80 gap. My brain started clanging with cognitive dissonance!
Also, I think advising him to have a "Call for more" option is bad advice. Don't introduce that kind of friction at the 101st users - that's not right. Maybe, just MAYBE, he wants to say call for 1000+, but even in this case, I think it will be better to be transparent about pricing.
Sorry for the clanging. As I indicated, I think that the correct anchor for this pricing is "HR expenditures" (like payroll) not "cheap web services anybody in the organization can start using on their own initiative as long as they have a credit card". (Why do I think that? Because I think you need HR buy-in to sell any plan costing more than $20 / month, so you might as well charge them through the nose to let them know you're serious.) However, I was focusing on the need for simplification in that point, so I picked price points that they demonstrated they'd be more or less comfortable with charging for my example.
I would be interested in hearing your reasons why the CALL option is "not right". Here are my reasons why it is:
As it stands currently, they will not sell any plans whatsoever to companies with 100+ users. Not a single one. The reason is that when you get to 100+ users you have just won yourself a ticket aboard the USS Enterprise Sales. There are now a few hundred obstacles standing in front of the sale where there weren't when you were selling to a man who routinely invites all his employees over for dinner. If you haven't done Enterprise Sales before, you don't know what these obstacles are yet. So, let the prospective customers who you're going to crash and burn trying to sell to tell you what their objections are.
For example, hypothetically suppose one of my day job's customers was looking for a solution to this, and you took my advice and had them call you. Here's the first question they're going to ask: "What is your policy for compliance with the Personal Information Protection Act?" And the answer presumably sounds like "Umm... let me Google that." Now, let's be honest: you're going to totally crash and burn with that sales call. But you've learned something useful: a) there is a Personal Information Protection Act and b) somebody who was interested enough in my software to pick up the phone/send an email/etc asked about it first, which means that presumably my answer was important in making a buying decision. So, presumably, if you got it into your head "I really want to sell to Japanese universities" you'd a) research the law b) implement the technical and legal measures you'd need to comply with it and c) prominently say so on your website. Then, the next time someone called you and (having totally failed to read your site in a manner typical of all customers everywhere) asked about the Personal Information Protection Act, you'd have an answer ready to go, so you could get totally humbled by their second question this time.
Repeat a few dozen times and you might actually succeed in making Enterprise Sales.
(Edit: I had misremembered the English name of the law I cited.)
Assuming you're in the right range on current pricing, I'd be thinking more along the lines of:
Free for 3
$20 for 10
$100 for 100
CALL for more
Now you only have to administer three options, and if you convert anybody with 20 employees you win much bigger.
Note the CALL option. There is an awful lot to be said for the CALL option in enterprise sales. Realistically speaking, price is not going to be what prevents your solution from being adopted at large corporations. However, and this might be a bit of a shocker for you, they might not deal with variable pricing that well. (It is easier to get my boss to sign off on 2 * $X,000 per year than to sign off on twelve payments which will average out to $X,000 per year. Think of how much extra work that makes for him in working the company bureaucracy. First he has to attach a projection. Then he has to document how he made the projection. Then he'll remember "Oh, shucks, if this ever materially changes I'm going to have to update the projection, but updating projections doesn't bring in my projects or get me my next promotion.")
Incidentally: you list a bunch of features, not benefits, on the front page. Nobody, not even HR drones, wakes up in the morning and says "You know what I want to do today? Create office holiday schedules!" Let me hum a few bars: decrease costs, increase compliance with company policies, reduce workplace conflicts stemming from miscommunication about leave.