As someone who has been in big outsourcing deals, and been responsible for both business strategy and IT strategy, I would say that medium-sized businesses need a good business-oriented IT manager rather than an "IT strategist". This person would work with those inside the firm to coordinate plans and priorities, and service providers to ascertain the best provisioning.
Before you do any outsourcing you need to get your own act in-house in order. Outsourcers make more money from a client's mess, that's a commercial reality. This internal challenge is often a harder challenge than simply "outsourcing" just because the CFO thinks it will save money. If you don't do it properly it will cost money.
I'm all in favour of outsourcing, as part of an IT services mix, but there is no such thing as a free lunch and the hard yards have to be done on the client's side to get the best results.
