I hope all is well. I have had a lot of these conversations with customers over the years, and I have found that the answers vary company to company, as the business needs that have to be addressed are always specific to the operational environment of the company.
Start by looking at the following link, which lists all of the pfSense products currently available and provides a nice table that allows you to see what the most likely product for your organization would be. Link is:
I would find one or two products that you think fit your usage profile and then click on the
More Details button to see a deeper overview of each, including features available/offered for each product.
I have found that the quickest way to a
C Level executives' heart is via a comparison that links business requirements, strategies, and / or risk mitigation to features that provides a tangible one to one mapping that can be seen.
To that end... find some of the features that the pfSense product offers and map them to things that you are being asked by the business to secure and protect. Discuss those things with your boss as proof of what the pfSense solution can do, and do the same, to the extent possible, for the ISP provided infrastructure.
See if there are any gaps that standout one way or the other, and highlight those as you make your presentation, or during your next conversation.
Remember to take cost ( $$$ ) into account as part of your presentation, as you will have to pay more for the pfSense solution, but it may provide tangible benefits that are worth the cost. You have to make that comparison and value readily apparent to your boss if they exist.
Hope that helps to get you started. Please feel free to follow up with me directly if you have any questions as you proceed. My e-mail is: firstname.lastname@example.org
Good Luck !!