There have been many of these over the last few years… none all that successful. The problem (as I see it) is that you don’t know when or why you’ll need to call one of those annoying toll free numbers… and at that point it is too late for the application/service.
That being said… as someone who worked with Fortune 500 companies building those annoying IVR (interactive voice response) systems – I have to ask… when will you learn? They should be for the customer – they should offer what the customer wants and needs, not what you want them to do. The problem is the standard IVR pushes what the company wants you to do and hides what you really want to do…
It is simply poor design. What I’d love to hear about is the companies that have really well designed VUI(s) (Voice User Interfaces) that their customers love to use. Or, is that simply not possible using voice?

Add this to your list of must have iPhone applications. Direct Line (iTunes link) is a service that helps you automatically navigate phone trees to get right to an operator (exactly what companies don’t want you to do).

Install the application, browse of search the included companies, and select the one you want. Direct Line then calls the number and preselects the appropriate choices to get you to an actual person.

The service operates much like Bringo, which we wrote about in 2007, but since it works directly from your iPhone it saves you the extra steps. In my testing it mostly worked, although it failed to get me through to operators at two companies (Air Canada and AT&T). No worries, though. Just send creator Michael Schneider an email at support@thisistech.com and he’ll update the database.

It’s well worth the $0.99. Direct Line joins DataCase on my list of must have productivity apps for the iPhone.

[From Direct Line Saves iPhone Users From Automated Call Hell]

From Seth Godin – this is how communications applications create value.

“My computer will call your computer…”

Lisa points us Fonolo, a company in beta that spiders phone trees at big companies and promises to make it easy for you to go straight to the spot you want. Then it calls you when the phone is answered and records the call so you can keep a record.

Bringing symmetry to asymmetrical relationships is a huge opportunity for a technology company. I think there’s room for a union of top high school students, for example, to give some leverage in the recruiting process. And of course, stubhub took the power away from ticket scalpers.

[From Deep dialing]

Now the question is what will people pay for it. Different things value and price.

The trick is to create solutions that have more value than a nominal price. Does Fonolo do that? I’m not sure. Perhaps if the price is having to view or listen to ads…

So here is the question:

Would you trade ads for navigating a phone tree?