The last thing you need is a document automation software product that's too difficult and technical to work with. In fact, it defeats the purpose of having it in the first place --- generating hundreds of error-free documents in seconds.
Choose a tool that easily integrates with your existing familiar applications like Word, Excel.
(FYI, Windward quickly integrates into MS Office as an add-in and there's no code-behind)
Ensure it can draw data from multiple datasources like Salesforce,MS Dynamics, SQL, MySQL, XML, JSON, Oracle, OData, and more (you can create documents by harnessing over 150 datasources when you choose Windward!).
Check that it renders in the output formats you require for easy sharing - DOCX, PDF, XLSX among others.
(Windward can pretty much do everything including direct to a printer)
You spend 90% of your time creating and designing the template(that has 100% information) needed to generate documents. You can significantly slash this time and speed up the whole process by ensuring the solution you choose has template formatting features like query wizards (to select data), conditional tags (to conditionally include content), drag and drop doclets (drag those saved doclets to drop onto a template to cut repetitive tasks and create complex documents in seconds)
(Windward has all these features and more to make your template creation and formatting process simple, fast, and easy).