[sclitheroe]

The most important consideration, and the one that nobody has mentioned here yet, is how the employer plans to support the employee machines at the remote end. The connectivity technology is easy - you have Citrix, SSL VPN, RDP, Skype, Microsoft OCS, Sharepoint, Exchange Unified Communication, etc...literally more technology than you can shake a stick at. VOIP telephone is relatively easy too (so I’ve been told, not my area of expertise)

But all of this is useless if the employees are unable to sufficiently maintain their machines to be able to make use of the remote access. Who is looking after their desktops, internet connectivity, keeping AV and patching up to date, etc. What happens if a machine breaks and is out of warranty? What happens if a machine is stolen or lost? What if they suddenly can’t print? etc, etc.

Unless you have technically savvy employees that can take care of getting connected themselves, these are the most important issues that have to be planned for, otherwise it’s not going to work, or not going to work well enough for the remote staff to be productive and happy.

Edit: these issues become even more important if the employer needs to be PCI compliant, is SAS70 compliant, etc. Securing the internal network and processes is straightforward, but you need to provide compliance out to the remote end points too, otherwise you have exposure and will fail your audits.