Best way to implement this flow

There is something I am trying to accomplish and I’m not sure if the best way to make it happen. It’s actually a couple of things that are somewhat related. I am trying to come up with a roadmap on how to accomplish the end goal but don’t know the best way to get there.

First, we are a charity working with a group of volunteers. Volunteers are required to sign each policy through BoldSign. I need to archive these signed policies for each volunteer.

Here are my options and concerns.

First, I have a list of all volunteers set up as Items. Each policy is then set up as its own column. I could just attach each policy to the matching cell of the volunteer and cell. This would store the document on Monday.com. There is a status column for each volunteer and each policy that shows whether it’s signed or unsigned. It’s easy to see at a glance who needs to sign which policy.

I’m not sure I like this due to space limits and backups, etc. I wouldn’t want to lose everything if Monday,com closes shop. I don’t foresee that happening but you never know and it’s best to be ready for that.

Another option is to store the documents on Google Drive (we have workspace). Each volunteer has their own folder in GD. Instead of attaching the signed policy to the volunteer in Monday.com, there could be a link to that policy in their GD folder. Again, the status would have to be updated when it’s signed.

I am not sure which way is best. And which makes the most sense for automation. There is no direct integration between Monday.com and BoldSign…same with Make.com. But, BoldSign emails the signed document and can be set up to automatically send it to a GD folder.

For total automation, this is what I was thinking. Please help me determine if I’m on the right track.
Use Make.com to monitor the BoldSign folder for incoming files. Have it search for a name that matches the volunteers name on Monday. When it matches, either move the document to the volunteer’s GD folder or automatically attached to their name on the board. I’d also need the status to automatically be updated.

The other option to this is similar to the previous, but have make monitor mailbox for messages with attachments. Have it monitor and search for a name. When a match is found, move that attachment to the volunteer’s GD folder or add it to the Monday board

So, lots of typing here and I apologize but wanted to lay it out. What do you think the best option is for these scenarios? Do you have better suggestions?

Ultimately the goal is I have A LOT of documents that require organization. It would also have to be documented what volunteer has signed what policy. This all done manually takes a lot of manpower and can be automated to an extent. How do I reach that goal?

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