It's hard to diagnose exactly what the issue is, without knowing more and/or seeing for ourselves....but the most likely scenario is that you just don't have enough flash power to fill the shadows.
Firstly, what aperture and ISO are you shooting at? Since you are limited by the max. sync speed, it's likely that you are having to use a low ISO and relatively small aperture. Both of those things will require the flash to use more power.
Then you are using an umbrella, which reflects some light, absorbs a little bit and diffuses (scatters) the rest. The result is that only a tiny fraction of what the flash is putting out, actually goes in the direction of your subject's face.
So with all of that going on, you simply don't have enough power/light from the flash to fill in the shadows on your subject's face.
Now, what exactly are you trying to do with your flash? The two usual options are creating a 'key' light or using it for 'fill' light. If you are using your flash as a key (main) light, then it has to be stronger than the ambient light. You would see shadows on your subject's face that are caused from the light coming from the flash. This is the scenario where using an umbrella is nice because it will help to soften the edges of those shadows. But if the ambient light is fairly bright, then you need A LOT of light from the flash...and/or it has to be really close to the subject. So as KmH mentioned, you would want to have your light/umbrella as close as possible to your subject. I'll also add that I prefer a soft box in this situation, because it keeps more of the light on the subject (less spillage).
The other option is simply to use the flash to fill in the shadows caused by the ambient light (raccoon eyes). In this case, it doesn't matter if the light is soft, so you can loose the umbrella. Also, it doesn't matter if the light is off camera, so you can loose the stand and just put the flash on camera. Note that flashes are designed with a reflector dish and zooming head so that they can constrain all of the light into a smaller angle. Usually the zoom of the flash will match the focal length (zoom) of the lens, to give you even coverage. But in this case you can zoom the flash head into a tighter beam, because you really only need it to light up your subject (maybe even just their face).
So using the flash directly pointed at your subject, without an umbrella and maybe even zoomed in....these will all help the flash put more light onto the subject...which means that your flash may actually have enough power, even at a low ISO and small aperture. It may even allow the flash to be used at a lower power level, which means you will have a faster recycle time and get more shots out of the batteries before you have to change/charge them.
So to recap, you really should decide whether you are using the flash for a key (main) light or just a fill. If it's fill, then all you need to do is put it on the camera and point it directly at your subjects. If you are using it for a key light, then get as close as possible and maybe switch from an umbrella to a softbox (something like
this).
And lastly, sometimes you have to realize the limits of your gear. Using a flash as a key light, outdoors in the daytime, takes A LOT of flash power....often more than the average flash unit has. That is why many photographers use studio type lights and run them off of a battery pack, or even a generator.
One last thing. There is an option that might help you in this situation...and that is high speed sync. Canon calls it HSS and Nikon calls it 'Auto FP'. In this mode, the flash pulses the light, rather than firing one large burst, this allows you to use any shutter speed, which allows you to control the ambient light and thereby use a larger aperture which makes it easier for the flash. But the trade off is that the flash range/power is very limited in this HSS mode....so it's really only a good option when you can get your light very close to your subject. And to use this feature with the flash off-camera, you have to have flash triggers (or cables) that are TTL compatible.