Play #21: Tactics dictate strategy. 
I sell for startups, so my sales strategies are unorthodox by necessity. When I read Benioff's book recently, I started to nod whenever he described a tactic that worked once as the inspiration for his most successful strategies. That's how it works for me too. Here is what I mean:Personal Invitation to Meet with Customers
What if you invite the prospect to join some other customers for bourbon and cigars in a couple weeks? You would be amazed what happens when you make that kind of personal invitation. You can make this invitation by phone, email, comment on their blog, handwritten note - whatever works. Or maybe you invite prospects who will be attending an event in your area to catch a demo over lunch. Or you invite them to sign up for a free test account. When you find a channel and invitation that works once, you may have the basis for a campaign. The handwritten note is an antique sales tactic, for example, but when you find a call to action that works you can create great lead gen campaigns.
Help Prospects Qualify Themselves
What if your prospects could set appointments with you on a self serve basis? Not these complicated lead gen forms you have to fill out for a white paper or a webinar - just your super geeky service as a filter, and then a registration page that allows anyone to schedule a consultation by providing their name, company name, and their phone number. This won't work that well if the consultation is simply a sales pitch. Or if it's hard to find. But if you actually focus on establishing your credibility as a resource, you will generate truck loads of goodwill. Once you find reliable sources of high quality consultation orders, you're in business.Establish Your Own Credibility
Create a presence on the web that attracts prospects and proves your expertise in your area. This could be a social media strategy (e.g., blog/twitter/facebook/For
, etc). But it could also be a live event strategy backed up by online scheduling and personal invitations. You can call CEOs to follow up on a referral from a mutual connection, or you can dial media planners directly. But before you can sell them, they have to buy you. Strange but true. When you prove your own value first, you can sell the value of your product or service much more easily.Map the Terrain in Front of You
In other words, you can work top down and bottom up and you can't forget that you sell to people instead of brands or departments. While you call the CEO, you should also be emailing the relevant executives and commenting on the blogs and messaging the Quora accounts of the women responsible for the right projects or functions. If you don't know who the right people are - and what they're working on - then you haven't done your homework. You need a map before you can start digging. If you don't know whether they answer their phones, respond to their email, read their snail mail, or whether they use one of your competitors everyday - same problem. Map it out first by experimenting. When you strike pay dirt, then you dig. Work the Matrix
Come up with target communities, tactics, and a budget. Then test systematically. When you get results with one tactic/community pair, start looking for ways to leverage that success further in that community. When you find a bunch of related tactics that work, you have a successful sales strategy. Then you mine the terrain in front of you. Then you move on to the next community.
Unorthodox sales requires discipline and creativity. You can't succeed without both. And if you're not going to sell to the enterprise, then you're going to talk to fewer people and the maps are going to be a lot simpler. But these ideas still apply. Trust me. I've done it both ways.
Update: I didn't have time to respond fully earlier. Hopefully, this update is not as cryptic as my initial answer.