Leadership in social media campaigns: big vs. small operations

When Teddy from Blue State Digital came in to speak to us, I asked him briefly how important he thought it was for the Obama social media campaign that Obama himself was tech-savvy. The answer was that (a) despite perceptions, he actually isn't tech-savvy and (b) this did not matter. I didn't have time to push him on this further but I think it raises a more interesting general question about leadership behind - and support for - social media campaigns in different settings.

It might not have been important for Obama to be tech-savvy or be familiar with online social networks because he had a plethora of tools, support, funding and people working for him who were effectively able to run the campaign for him. I imagine that this is similarly the case for many larger operations, whether they are campaigns, businesses or specific brands. But what about the smaller operation? For example, my brother owns a travel company based in Austria, France and Switzerland that is now 5 years old. They are really lagging behind in terms of utilising the potential of social networking. Neither my brother nor his business partner are particualrly tech-savvy and they have minimal administrative/support staff, preferring to concentrate headcount funds on on-the-ground operations. None of the current sales/marketing staff are comfortable/able to design a social media strategy for the business.

My question is how should smaller operations that may be constrained in terms of either headcount, expertise or both begin to kick-start and maintain a social media campaign? Is it feasible both in the short or long term? I'd be interested in any thoughts on this particular case or on the issue more geenrally.