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no, I haven`t actually
For schools, the reputation of the manufacturer is very important. If you can get the trust of schools, everything else is minor.
No, I haven't worked in the Education Software industry. But in my opinion, just like trying to sell any new product, this field will have the either the same or a lot more challenges in comparison to other industries, due to tight budgets, in comparison to other businesses, as educational institutes are generally not considered a business entity, but an institution providing service to the society.
In today's world, even though schools are running it like a business, by charging exorbitant fees, not much investment in updated technology will be seen in this field.
For eg: An Indian oriented school might not show favourable response in comparison to an English oriented school, due to the huge difference in fees collected from students. No offence to any naionality. But this is the reality, for which we cannot really blame anyone, as upgradation of school equipments & software is definitely costly, which might not be feasible.
Therefore, such practical problems definitely poses a challenge for a salesman who is trying to sell education software, as it might not be at an affordable price or a real advantage to using the software.
If a salesman has to be successful, he will have to sell customised software to schools at very reasonable price, to attract educational institution attention.