I frequently make a cake that has fresh strawberry and lightly sweetened whipped cream filling. Start with 1 cup of heavy cream, whip with 3-4 tb sugar and 1 tsp vanilla. When it is just getting stiff I whip in 1 pint of chopped strawberries. Continue to whip just until it turns light pink and forms stiff peaks. Use this promptly; it will get looser over time.

Fresh always tastes best. Dried usually tastes more intense. Jell-o might stabilize the cream but is likely to have a "commercial" flavor and texture.

I think fresh strawberry cream would taste good with vanilla. I'm assuming you mean a cream custard/"pastry cream" filling (i.e., with eggs), rather than a true cream filling, because the filling should have a distinct texture from the whip. The trick is balance. I wouldn't want to have an intense strawberry flavor in the cream that overwhelmed the vanilla of the pie filling. Puree the strawberries and run them through a sieve, and add to the whipped cream with a quarter teaspoon sugar to stabilize. Add a little sugar to taste if needed.

Stabilize the whipped cream -

1/2 t unflavored gelatin powder

2 T cold water

1 C whipping cream

2 T powdered sugar

Sprinkle gelatin over cold water in small bowl to
soften.

Scald 2 T of the cream in tiny pan on stove; pour
over gelatin, stirring till dissolved.

Refrigerate until consistency of unbeaten egg white. (This takes about 10-15
minutes.) Then, with a whisk, beat until smooth.

In a stand mixer with a whisk attachment, or with a hand beater, whip
remaining cream and sugar just until soft peaks form; whip in the smoothed
gelatin mixture, stopping to scrape the bowl twice. Whip until stiff peaks
start to form, but be careful not to over beat. 10-20 seconds more.

Fills and frosts top of 2 8" or 9" cake layers; or frosts 10"
angel
cake or sponge cake. Tops one standard 9" pie with some left over to enjoy
from a spoon.

Stands up well, even in warm weather.

Fold in the strawberry freeze dried - about 1 T. Taste and add more.

Place fresh strawberries around the edge.

Thank you all for the comments. I'm going to use the strawberry freeze dried powder. If it was strawberry season I would have used the fresh strawberries.

Also as many posts as I have read concerning whipped cream I have never seen someone suggest the Dr. Oetker Whip It (Stabilizer for whipping Cream).

I use it always when making whipped cream. It holds up excellent. One packet of Whip It per one cup of heavy whipping cream. If you can find it, buy it. You won't be disappointed.