Proactive Office 365 chatbot that targets AD users with set messages at set times

As a change management consultant I need a better solution for communication departments to inform colleagues on business updates rather then sending out one way news letters. Therefore, I would like to create a chatbot for Office 365 users that has 2 differentiating capabilities: - Similar to [login to view URL] it is able to ask questions and record answers like a survey in chatbot format. - The chatbot is self able to open up conversations to defined audiences on Skype for Business / Microsoft Teams users with pre configured content at set times. More info in the documentation. I am eager and willing to improve this if necessary before getting started. Send me your feedback and questions! Main question is: Is it possible at al to have a chatbot that opens up conversations at set times? I have an intention to set up a long term relation. I want to start with a solid MVP that really is able to proactively ask questions and record answers in chatbot format. I really really appreciate real feedback on things that are and are not possible. I will need advise in this project so I want you to think along. I am more interested in your opinions and feedback than your quotes. It is more important to create a good solution rather then being cheapest. Things I need advise on: !!! - Will we be able to create a real proactive chatbot at all? - !!! - Should we make a CMS ourselves or make use of SharePoint? - If SharePoint; how do we update templates and chatbot features? - Should we create an Office Appsource app or just a loose solution with installation instructions? - How can I keep track on how many users are getting targeted? - Can you provide me install instructions as part of the solution?