"I can tell you that former military officers are generally well-received, though the warmth of that reception can vary radically from organization to organization.
For example, certain companies have historically had a strong preference for hiring ex-military officers. Oracle and many of its offshoots such as Siebel and Salesforce.com are great examples of this. One of my friends, a former Army Ranger and company commander, has spent nearly his entire career working for Tom Siebel, for example, with great success.
Other companies are not particularly military-friendly—places like Facebook and Twitter, for example.
As a general rule of thumb, companies that place a premium on discipline and execution are military-friendly; companies that emphasize creativity and off-the-wall unpredictability are less so.
Ex-military officers are stereotyped as disciplined, hard-working, and aggressive leaders. They are typically not thought of as creative or innovative. As an example, I have a number of friends who are generally thought of as creative wild men—people are always shocked to learn that they are ex-Marines. They certainly don’t look the part, having left behind their buzz cuts for long hair and stubble.
A super early stage startup is unlikely to hire an ex-military person as their first hire unless that person has already proven themselves in the Valley. Startups stink at training, personnel development, etc., so they focus on hiring finished products. But startups that want structure and discipline seek them out."
Chris Yeh – Chris has been building Internet businesses since 1995. He has been a founder, founding employee, or seed investor in almost a dozen startups, and advises a wide array of startups ranging from network equipment makers to vertical search engines. He is the VP Enterprise Marketing for PBworks, the world’s leading provider of on-demand wikis and collaboration software. He was on the founding team of pioneering Internet companies such as United Online Services (Nasdaq: UNTD) and Merrill Lynch's Intelligent Technologies Group. Chris is a much-quoted thought leader in the field of interactive marketing; his research and publications have been incorporated into the Harvard Business School curriculum, while his projects have received press coverage in Fortune, SmartMoney, TechCrunch, and the Financial Times. He writes a monthly column on entrepreneurship for SitePoint, and has written over 25 other articles on entrepreneurship, marketing, and sales for publications such as ClickZ. Chris earned two degrees from Stanford University and an MBA from Harvard Business School.