I saw this topic How far can outsourced development take a startup on Quora yesterday. This is indeed quite tricky question. Smart IT outsourcing can be a matter of life or death for startup company.  Some interesting insights and advises you can read below.

Adapt your communication processes (lots of google hangouts, hipchat, skype, shared google docs etc) and your development processes (borrow heavily from the open source community). If you do all of these things, you’ll build a long lasting, high performing team that will create true competitive advantage.
Stephane Kasriel
SVP Product & Engineering at ELance-oDesk

It is important to consider whether the company has someone who drives technology or product in house such as a VP Engineering, CTO or Head of Product.  If a company is technology enabled with a head of product and selects a great outsourcing partner, then they can scale the company with an outsourced team. Most firms will build small in house development teams as they scale or often will buy out the outsourced team. A great example of this is how Fab was able to scale up their business with an outsourced team.
Randy Rayess
Cofounder @VenturePact.

Intellectual property
The documents must be written very well but more importantly the legislation in the country where the outsourcing activity will take place must protect intellectual property. Even better if the country has the same laws as the country of the stratup. For example two countires from the European Union.

Transparency / Visibility
There must be project (PM) and account (AM) managers assigned to the startup who will inform it about the advancement of the tasks. Moreover, PM tools such as Jira and Kanbanize will show the progress of the entire project and of every iteration.
Stoyan Mitov
Business Development Director in Dreamix & Datakite

Treat your outsourced developers as part of your team. They *are* part of your team, get to know them, stay in touch on a near-daily basis (through short checkins and weekly meetings)
Stephan Orme
Product Design – CPO Oppsites

Some additional links that can be helpful

What is your opinion?

ps. The we outsourced the comic strip to lifesacomicstrip.blogspot.com :-)