April Challenge: Match Last April's Sales in a Single Day

April is traditionally the worst month of the year for my online planbook business. So far this year I'm seeing about 4x increase over the same month in 2010. So I could just accept that April will get a nice bump, but still only be 1% of my yearly revenue (I had to round up to get to 1%). Nah, forget that.
The Challenge
In April 2010 there were 14 sales totaling $280. I've already had 16 orders in the first 4 days of the month, so just beating that isn't enough. My goal is to beat that revenue number in a single day.  It can be any day of the month, so that gives me 30 chances...well 26 chances since the month is already 4 days old and I haven't done it yet.
Since there is a 14 day trial it's hard to predict exactly when people will upgrade to the paid version.  This is a good thing, since it prevents me from targeting a single day. The best case scenario is I complete the challenge and also have a bunch of really great days as well.
No Coding
None of the things I'm trying involve adding new features to the site. I know there are features missing and as coder it's tempting to try to build the site by adding features. The purpose of this challenge is to force myself to concentrate on marketing and sales skills.
History
Getting 15 or more orders in a single day isn't unprecedented. I've done it 30 times before. But every one of those days was in the busy August to October period.
The Plan
Gather Intel
One of the first things I want to do is learn. The two pieces of information I want to learn are:

  1. From those who signed up, what is the single greatest benefit.
  2. From those who didn't, why?

This information will be used to help focus the content on the landing page.  I hope this will help with conversions.
As an incentive I'm going to randomly select one of the responds from each group and give them a $25 Amazon gift card.
For these type of surveys I generally don't use any special tool. The user just has to hit reply and type their thoughts. I do it this way because replying to an email is easier then going to a 3rd party site and filling out a form.
Also I want free form responses. Say I select 5 possible benefits and an other option where a user can type in a response, most users will select from the list. By doing that I've already corralled them into selecting from what I believe the benefits are. 
There won't be so many response that I can't just go through and read each individually to gather the data. I don't need any fancy reports here.
Raise Price
About a week ago I bumped the price on the homepage to be $25 per year from $20 per year. I didn't actually change it in the system, which allows people who signed up for the trial before the bump to still get in at the $20 amount. I'll change the price in the system to match in the next few days. This is a permanent change - not just for the month.
Buy More Ads
Notice I said the challenge was to beat the revenue number. I'm willing to shave off a few points of profit to get this done. Now because of the 14 day trail I really need to be driving new signups in the beginning half of the month.  If someone signs up on April 25th they probably won't upgrade to premium until May and that doesn't help me here.
I should mention I cheated planned ahead and bumped my AdWords budget to $40/day around mid March. The result was 883 new signups, which is my 3rd best month of all time.
Discounts
There is a group of users that access the site regularly, but never upgraded to a premium account, instead sticking with the free version. I'm going to send an email to these users with a $5 for 6 months promotion. I'm not sure how big this group is just yet, but roughly 300-500 users I believe. The day this email goes out will probably be my best chance to eclipse $280 in a day.
I will have to do a bit of coding for the 6 month plan. I figure this isn't a new feature, so I'm not breaking any rules. I'm going with 6 months because it has a "less commitment" feel to it, plus it will cover the end of this school year and the beginning of the next school year.
SEO
I do pretty well for a lot of keywords, but I've never really tracked my Google performance. As part of the AppSumo Lean Startup bundle I got 4 months of Ginzametrics, which is a keyword tracking tool.  My plan is to pick 5 words I already rank well for and 5 other words that I wished I ranked better for and track those.  Then using the intel gathered from the surveys mention above I'm going to rewrite some of the content to target the 5 keywords I want to improve on.
I probably won't get much of a boost from this this month, but it's something that could payoff down the road.
Press
Although I've gotten mentioned on the national teacher's union website and Mashable that wasn't my own doing. I didn't even know about the articles until users started clicking through.
In the past when I've reached out to education blogs and had little success. I realize the success rate for these cold emails is low. I still feel there is room to refine my approach do better.
My plan here is to pick out 5-10 education blogs/news sites I really want to get mentioned on and put together emails for each one.
I'm also going to put together a press pack, which, in theory, makes it easier to write about my site.
Track My Progress
I'll be making posts as I tackle each of the parts above so make sure to sign up for my RSS feed of follow me on Twitter.