Great discussion. I totally agree with @mattzito about the opportunity to sell at the business unit level. At the same time the points about getting IT buy-in remain critical. I've watched too many SaaS uses shut down or "banned" under the guise of security/compliance/etc for failing to engage IT.

The reality is that IT has always pushed to be more than the control point or network. Different organizations have different ways to execute on the use of ITs skills in business units. The complexities of large organizations (budgets, accountability) make this dynamic very localized to a company and why the role of the account manager is so critical.

My own experience at Microsoft was going from a consumer company to a business unit focused sales effort to a top down IT/C-suite sale. Office was a classic bottom up sale at the time which morphed into a strategic sale over the course of a decade. Many people forget that in the early 1990's Microsoft was always a big question mark in the world of the enterprise.

Regarding pricing, here's a post I did a while back on SaaS pricing. http://techcrunch.com/2014/05/16/the-price-is-right-for-earl...

--Steven