Getting leadership support
To run a successful red team program, it is critical to have active leadership support.
One of the big benefits of an offensive security program and red teaming generally is that they are there to keep everyone honest. Trust but verify. The support of the Chief Security Officer (CSO) is probably easy to get, but the support must be beyond that; it must include the other executive levels of the organization as well. This can't be stressed enough; if you do not have executive buy-in, the effectiveness and outcomes of the program will be limited. Getting long term buy-in might be achieved by using various strategies, including providing data and providing actual breach results, explaining how they impact the organization.
Convincing leadership with data
When looking at data, it is useful to look at the competitive landscape and analyze recent breaches that have occurred in the industry, and the associated impact they have had on organizations...