I'd approach this by trying to craft a Makefile recipe to carry out the steps you want, including passing the binary to be tested as a command to ssh. Something along the lines of (note that this is totally untested and probably overly complicated):
SCP_CMD=scp
SSH_CMP=ssh
HOST_URI=pi@raspberrypi.local
HOST_PATH=/home/pi/bin/
LOCAL_PATH=./
OUTPUT=binary_to_test
.PHONY: transfer remote_execute test_on_remote
test_on_remote: $(OUTPUT) transfer remote_execute
transfer:
$(SCP_CMD) $(LOCAL_PATH)$(OUTPUT) $(HOST_URI):$(HOST_PATH)$(OUTPUT)
remote_execute:
$(SSH_CMD) $(HOST_URI) "$(HOST_PATH)$(OUTPUT)"
Obviously you'd need to add some rules here to compile your binary as well. Just typing make should then compile, transfer and run your binary. You may prefer to use rsync instead of scp if, for example, you had supporting files that need copying over as well as the binary to be tested.
A possible alternative to running the binary through ssh for testing might be to install gdbserver on your Pi and start it through ssh and then connect to it with the cross-compiler gdb on your development machine.