First step is to understand their need. Forget about the software, what business problem are they trying to solve? What issues do they have?
Once you understand the need, try to figure out what plans they have in place to try and meet those needs. Some might have projects in place already, some might not have any clue what to do.
If they are actively trying to solve some of their business problems, try to understand their timeline for addressing those problems. This will give you a little insight into when you might actually make a sale. Use that timing as a way to layout a high level “project plan” for them to evaluate the solutions you may offer. Give them that plan, discuss it with them.
Also, don’t just call and ask for stuff, that gets annoying really quick. Are there articles that would point out similar problems for other school districts that would be worth sharing? Do you have press releases? “Dig the well before you are thirsty” is the old saying. You always have to provide some value in each contact with your prospect. If all you ever do is ask them for information, you will quickly be put on the ignore list, even though you have the exact solution to their problem.
Finally, you need to really understand the approval process for each prospect. Who needs to be involved in the decision? Who actually makes it? Who is the main person that influences the person that makes the decision? Whose desk do the required approvals have to sit on for signature? Do you need to present to the School Board? Do you have to be registered with the districts before you can do business with them?
Good luck in your endeavor. Be valuable to your prospects before you ever ask them for their business. And it is a numbers game, don’t give up easily. Scratch and claw. Most of the work of a good salesperson is done between discussions with the prospect. There are no magic words or phrases that will get the job done.
What he said.
Without telling us too much, how does your software solve a transportation problem? Do the schools that you are talking with know what their problem is? Does your solution save money, increase safety, enable students to learn more/better/faster, does it help teachers, does it help parents? Once you can answer some of these questions, you can start to develop a strategy to get your software into their school or district.
Depending on the answers to my above questions, you will need to identify who the buyer(s) and influencers are. If this is a solution that helps parents, teachers or kids, then you need to get parents or teachers involved. The parents or teachers won’t be the one signing a PO, but they will have influence.
You need a value proposition.