We're concerned about the 3rd party fear, but there seems to be some recent precedence here. Gmail and Hotmail have seen a lot of adoption by schools and there are a number of medium to large schools which host Blackboard for smaller local schools. If this proves to be a serious blocker to adoption, we can talk about inside firewall installs.
As for the finer details of the monetization scheme, we are open to suggestions. Our current line of thinking is to offer a freemium model to teachers at a price subsidized by enterprise sales. We've got some ideas for features which will only be activated when a school buys into the system for all of their teachers and students, as well as some features that would benefit from being hosted and linked with other schools.
As the other poster suggested, teachers might not want to pay for your product. To really break [into] this market, you might have to make it free and look for other ways to monetize (which might open other doors of opportunity here..).
At least from my perspective, teachers don't pay for anything. Most of the education IT market here targets schools (in the UK), with price points to match.
I agree most solutions are fairly complicated (dashboard, moodle). A lot of UK schools are starting VLE (virtual learning environments) with this kind of functionality (albeit more complicated).
I agree about data protection issues although this must be possible to circumvent (probably with the school's consent). Students are typically blocked from accessing outside email at schools.
Selling in to the UK publicly-funded system is a pain. Distributors and VARs may help.
Yeh your potentially revenue model was what lost me a bit :)
My mother is a primary school teacher and so not quite what your after but her experience would probably scale to higher level education. So hopefully my ideas count as semi-insightful :)
I could see this being adopted by university professors in certain circumstances - but the idea of shelling out for it will definitely put them off (trust me - our lecturers claimed for EVERYTHING :D). Plus many universities already have custom portal software that the lecturers have to use (for whatever reason: usually in case of disputes etc.).
Same probably applies to (UK) secondary school (US = high school) level teachers (i.e. they wont want to pay). BUT in their case getting the school to pay for it on "expenses" would be next to impossible (budgets are super tight atm). As I see it this is probably your target market (definitely in the UK anyway) so if you can market it to the schools themselves you might have more success.
Some ideas for you (I apologise I only briefly scanned your app so they could be in place already :) plus some of this is relevant to UK schools and I have no idea how it works in the US - though I would bet it is similar). This also assumes your interested in grouping teachers by school :)
Firstly allow collaboration. In schools usually assignments are designed by one or more subject heads/organisers. If you let said co-ordinator upload all the assignments to somewhere all of the subject teachers can access and send them out to their students this would probably get you a lot of interest. Mostly because if the teachers / subject heads change the historical data is already there to make use of :)
One other idea is to allow some kind of grouping of gradings for a specific email address. One of a teachers BIGGEST gripes is collating reports for their students. If they could see all the awarded grades by subject in one click I bet you would get piles of "we love you" email.
But yes: the main way I see of selling this is pitching it as a "whole school" thing. Individuals, of course, might make regular use of it (perhaps this is your freemium model - free individual, pay-for school-wide collab features) but it is to schools I think you have to pitch it.
Sorry to ramble - it's too hot again :) hopefully something there is useful.
As for the finer details of the monetization scheme, we are open to suggestions. Our current line of thinking is to offer a freemium model to teachers at a price subsidized by enterprise sales. We've got some ideas for features which will only be activated when a school buys into the system for all of their teachers and students, as well as some features that would benefit from being hosted and linked with other schools.
How would you approach it? Why?