Is the conjugate base of pyrrole resonance stabilised?
There is like you assumed no reasonable amount of resonance stabilisation. However, the aromatic &pi;-system contributes to the stability of &sigma;-skeleton.

Below you can find the MO of pyrrole and its N-deprotonated anion (click it to enlarge). You can see that in MO 17 the electron density is shifted further into the centre of the ring, accounting for the larger negative charge on the nitrogen. It is a bit more difficult to see, but that is also true for MO 18 and 14 (pyrrole), which becomes 15 (anion). The most significant change is that the upon deprotonation resulting lone pair becomes much higher in energy (12 to 16), and it is as you note perpendicular to the &pi;-system in a &sigma;-type orbital. Note that the image only shows the trend and has no information of the actual orbital energies, apart from that they increase from bottom to top.