People will always consider a primary investment much more carefully than a secondary one. They can be price-sensitive if they haven't bought from you before. So, you need to make it appealing for users to complete that initial purchase, and then nudge them to upgrade to a more comprehensive plan.

After taking on board some advice from a user, Soapbox changed their smallest payment plan to $5/month for the first 5 users.

Within the same month of implementing the new payment plan, they saw customer conversions increase 4x higher than the monthly average.

When users see the ROI and gain value from the product on their initial payment plan, they're more likely to upgrade.

One thing to bear in mind is that your starting deal size will go down. You have to aim to increase the volume of purchases of that initial product. You also have to help users continue to upgrade once they've seen the value your product can provide.