I just left Pocketsmith after 6 years. My suggestion is to set up the calendar so it can take up the whole real estate AND show the upcoming bills on each date.
What Pocketsmith does is take your budgets (spending plans) you've created and place them on the calendar. You can color code them or whatever. Now you see your whole month "at a distance" and know what's coming up rather than scrolling up and down the whole page.
Create functionality to allow clicking on a specific spending plan and it takes you to a listing of all your transactions. (Like what you do today in a different UI context currently)
So why did I leave Pocketsmith? They changed their backend to where you can't even see pending transactions. Which as far as I'm concerned, makes the product worthless for me and messes up all the numbers. They also don't have predictive analysis of what you're going to spend based on Big Data. Simplifi does that currently when you create a spending plan to a degree.
But how can we make it better? What if you allowed the user to let Simplifi automatically adjust each spending plan based on predictive analysis of what you spent in each month or day or week?
We humans are predictive creatures. We tend to take vacations at the same time. We pay our bills on the same dates (usually). The list goes on.
What if Simplifi on the backend said, "This user spent X amount of dollars on a category called "Vacation" every year for the past three years in October and April. What if we automagically give him/her the option to plan for that so we help the end user actually learn how to budget their money because we know that history pretty much always repeats itself? Or what if we know for the past two years they show this particular spending habit trend? What can we do to help automatically budget that money for them so they are accurate in their forecasting?"
Think of what that would acheive.
