You will not fully understand all of the strengths and weaknesses of a SIS products when you evaluate it. SIS products are enormous, and even within a SIS company, they might not have all of the answers to your questions. That is ok as long as you know what they are good at as a whole.
Where is Their Focus?
With any SIS company, I want to know as much as I can about who bought their product. What other products do they sell? And most importantly, who are their main customers or where they originated from?
Government Schools
A SIS originating in the government space mainly has to meet the academic needs and so I should be confident that it can meet at least most of the academic needs of the school. Government schools are not as concerned about enrolments, billing, co-curricular, boarding, alumni and reporting requirements of independent schools and are areas that I would want to check closely for gaps. Sentral and Compass Education are a couple of examples of SIS that operate in the Government Space, but now also have some independent schools using their product.
Independent Schools
A SIS originating from the independent school space must initially meet financial and government reporting needs. Teachers' needs must be met, but without enrollments, billing, and government reporting, teachers don't get paid, and the school could collapse. To a lesser degree, you can consider co-curricular, boarding-specific needs, and alumni relations. So, if I select a school system that operates solely in the independent school sector, I can be confident that it will meet at least most of the needs of an independent school. This doesn't mean there won't be gaps; however, they are unlikely to be deal-breakers and might simply require an additional software purchase. The Alpha School System (TASS) and Veracross are in this catagory.
Custom Solutions - Platform not Product
Some SIS originate from consultants who see the potential to adapt big corporate products for other markets. To be successful, these systems must satisfy a limited number of high-end customers.
If you are in a school that refuses to compromise, you might consider these systems. They promise to adapt the software to the needs of the school, rather than requiring the school to modify its processes to fit the software.
These solutions hold the promise (if not the reality) that you can get exactly what you want, provided you are willing to spend enough money and time to make it happen. These tend to be costly solutions and are rightly met with some skepticism, especially when bold claims are made about how large companies intend to advance education. While they might aim to do so, the question remains: For how many schools and at what cost? Microsoft Dynamics 365 and Salesforce are a couple of these large platforms.
The orgins are a great place to start. If I want more clarity I might want to know:
What is the largest independent school that exclusively uses their product?
Who they integrate with?
Which conferences they attend (this will indicate where their business is focused)?
How do they interact with the community?
What is their reputation amongst schools. Is the company aware of their reputation? How do they deal with this?
How they present themselves publically (do they focus exclusively on education for instance, or is education a secondary market)
What are the backgrounds of the founders and their likely strengths that they brought to their product?
What is the age of the underlining archetecture. (Is it the titanic, or a sloop?)
For many people that is possibly too much. For me, all of that expands on my macro knowledge of the company and where its strengths and weaknesses are likely to be even before we get into the weeds. Context gives me a reference and lets me know where I need to focus most of my efforts, and questions before the demo is scheduled!
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