I am a small business owner from Methuen, MA. My partner and I are committed to helping other small business owners maximize their bottom line by providing effective tools at low cost. Our first venture is a an online scheduling program called HeresYourSchedule.com. We have many more ideas ready to go!
First, it is important to know if you have done an analysis on what your competitors are charging, both for hosted and .exe versions. This is a crucial piece of your pricing strategy.
Next, are you calling out your features nice and strong vs. your competitors? It is important to give your customers are reason to enter their payment information other than just on price alone. The worst differentiator for any company is price - because it is very easy for a competitor to drop a price and wipe you out.
With that said, Would you consider dropping the download version all together for bit and try and all hosted pricing scheme? Personally, I feel your price gap is currently too high, $360/yr online or $99/yr to download. It seems like a no brainer that I would just download.
Offer a monthly subscription price, your current at $29.99 if it is in line with your competitors.
Also offer a yearly subscription, that offers a good discount and reason to purchase. Say $250/yr. That is still giving you a double the revenue per subscription than your current download option. You can always increase the price as you make the software more robust.
I hope this helps.
Thanks for the advice Rick and Scott! Sorry it took me so long to get back on, I have lost power due to the snow storms in New England and just got it back Saturday.
Anyways - My biz partner and I are working on creating tools that large companies typically use and pay a bundle to use for small businesses at low costs. Our current tool is an online work schedule program. It is currently a free product because we want to build a following. Even as a free product, adoption started slow, but we have had many new subscribers sign up this week.
We will look for ways to monetize this site soon and we are already working on the next web based software - I can't wait to launch it!