Using either DHCP or a static config (doesn't matter which)--AND assuming your wifi worked during install--make your /etc/network/interfaces look something like below (for wlan0 should match the name of your wifi card listed under ifconfig -a e.g. your detected wifi card could be nicknamed eth1 by the OS for all I know.):
auto lo iface lo inet loopback
auto wlan0 iface wlan0 inet dhcp
wpa-conf /etc/wpa_supplicant/wpa_supplicant.conf
To configure wpa_supplicant use the command (Referenced in the config above)
wpa_passphrase "YOUR_SSID" SSID_PASSWORD | sudo tee /etc/wpa_supplicant/wpa_supplicant.conf
Next, create a new executable script named iwconfig (you can name this script anything really, "iwconfig-default-ssid", perhaps?--I just made it short for the example):
sudo touch /etc/network/if-up.d/iwconfig && sudo chmod 700
/etc/network/if-up.d/iwconfig && sudo ln -s
/etc/network/if-up.d/iwconfig /etc/network/if-pre-up.d/iwconfig
Now edit /etc/network/if-up.d/iwconfig and add the SSID you want Ubuntu Server to connect to on startup:
#!/bin/sh
iwconfig wlan0 essid "YOUR_DEFAULT_SSID" mode managed
Now bring ifdown (if you haven't already), then ifup, and you should be golden now and when you reboot (as long as you're near your SSID.)
If you're out in public with your laptop with this config, you'll have to use: iwlist wlan0 scan, then sudo iwconfig essid "PUBLIC_ESSID" mode managed to connect with anything (and/or make a unique script for each place(s) you visit--just don't put any of these scripts under the 'if-up.rc.d' folder. /etc/network/interfaces can also handle location alias, so check the man/forums for help on this.)
Or you can try your luck with the CLI frontend for wicd when roaming about town:
sudo apt-get install wicd-curses