An investor, administrator, and a former teacher walk into a startup pitch… how does that one go again? Not sure, but I’m guessing the punch line involves a learning management system. Anyway, that is the premise for an interesting panel I attended Wednesday at the (deep breath) NewSchools Venture Fund-Aspen Institute Summit on Education Innovation, the annual gathering of educators, researchers, thought leaders, investors, and entrepreneurs. (Read more about it here.)

Of course, just because those people are together, doesn’t mean they are hearing each other. Entrepreneurs don’t always know what schools need, or they can’t garner influence with district-level purchasing power, or they fail at both of those things, which means they probably don’t have a lot of money. To fix that disconnect, one conference session pitted three entrepreneurs against a panel that represents each step of the education startup continuum: an investor, a (former) teacher and principal, and a district administrator.

Each entrepreneur, all of whom were participants in venture capital firm Imagine K-12’s startup incubator program, had five minutes to pitch and then faced questions and feedback from the different stakeholders. (This is a format used at various education startup events, including Startup Weekend EDU and others I’m sure to get tweets about.) There were winners, and there were losers.

The judges:
Shawn Carolan, managing director of Menlo Ventures, which has invested in companies like Siri (on your iPhone) and Tumblr (your teenager’s blog).

Hae-Sin Thomas, CEO of Education for Change Public Schools, a charter management organization in Oakland, and a former teacher and principal.

Tim Cawley, Chief Administrative Officer at Chicago Public Schools.

The pitch:
Socrative, a simple, mobile classroom assessment tool for teachers, based in Silicon Valley. Teachers can use it for in-class assessment and quizzes, pushing questions to students mobile devices and receiving real-time feedback on answers and performance.

The questions:
How do the questions get into the tool?
Teachers can upload, or share questions with other teachers, said Michael West, Socrative’s Chief Technology Officer.

What is the price point?
So far, 50,000 teachers have used Socrative (for free) and it signed a three-year, $94,000 contract with Forsyth County Schools, in Georgia. The cost for districts is roughly $3,000 per school, West said.

Can it be integrated with other assessment tools?
Not yet, but Socrative is working on it.

The feedback:
Carolan: Teachers shouldn’t have to rely on students having devices. The large assessment market— $1.8 billion, according to West—becomes much smaller when limited to 1-to-1 classrooms.

Thomas: Any tool that makes teachers’ lives easier is a good one, but it needs to tie in with whatever assessment tools are already being used in the classroom.

The pitch:
Instagrok, a search engine for education. Search results can adapt to grade-level and be presented visually, allowing students to curate the results into presentations and keep journals of their activity. (Similar to Wolfram|Alpha, the computational search engine I’ve written about.)

The questions:
How does the leveling work?
Founder Kirill Kireyev: The student inputs his or her grade level and the search algorithm can filter and censor appropriate results based on content.

How do you make money?
It’s a free tool with a paid version that is ad-free and offers additional functionality. There is also an enterprise version for institutions.

The feedback:
Cawley: “Based on the way it will have to spread, it has to be a killer product. I don’t see a way that it will ever be mandated or chosen by a district or a school.”
Carolan: Need to pick a business model. Can’t market a free, a paid, and an institutional product.

The pitch:
Hapara, a dashboard and management tool for Google Apps for Education, which include email, documents, calendars, Blogger, and YouTube. Google Apps are widely used in schools—18 million active students— but are difficult to manage in real-time, said Jan Zawadzki, the company’s founder. Hapara has 35,000 paying accounts.

The questions:
Do teachers have to “feel the pain” of Google Apps before they want to use this?
Districts as large as 10,000 students have signed on, so, no, Zawadzki said.

Why doesn’t Google do this on their own?
Education isn’t a revenue-generator for Google, it’s a “wonderful p.r. and marketing program,” Zawadzki said.

The feedback:

Carolan: “You win my blank check of the day award.” (As Cawley noted, don’t get excited, that means the signature is blank too.) It’s a great market and it’s easy to use.

Thomas: If you implement data analysis—showing teachers what kids are doing and learning in the applications—”you’d have an amazing product that everyone would buy.”

Hapara seemed to impress the most, while Instagrok had some work to do. Some teachers in the crowd were hesitant to crown any of the companies a winner, because all seemed to overlook professional development. The entrepreneurs, along with Carolan, suggested that the product needed to be so easy to use that professional development wasn’t needed. “You have to have a business model that works before you invest in teacher training,” Carolan said. (Zawadzki explained the professional development issue a bit more in the comments section.)

As Thomas pointed out, the tools aren’t as effective if teachers don’t know how to analyze the information they are getting out of them. So, let’s not close the entrepreneur-teacher gap just yet.