Selling Windows Phone: Microsoft’s Ben Rudolph on why iPhone and Android users will love and buy his device

Ben Rudolph might have the toughest job in technology.

Not only is he fighting two massive market leaders that together control the mobile market, he’s also fighting public perception. Android and the iPhone currently own 95 percent of the U.S. market for smartphones. Windows Phone is the almost-invisible little line in circle graph, with 2.7 percent. At least it’s now in third place, as RIM’s BlackBerry continues to fade.

Rudolph relishes the challenge, and he’s thrown himself fully into the fight, talking to literally thousands of iPhone and Android users in campaigns like Microsoft’s Meet Your Match viral videos, where he meets ordinary people and shows them how Windows Phone meets — and maybe exceeds — what their current phones do.

It’s odd to see Microsoft as the underdog, but that’s the reality in mobile. And according to Rudolph, that’s what makes it fun.

I chatted with Rudolph during his long Seattle commute home. Here’s the interview:

VentureBeat: Give us the 30 seconds on what you do…

Ben Rudolph: My official title is very long. It’s director of Windows Phone evangelism. Effectively, I spend my time helping people to find the perfect device. I oversee a lot of the experiential marketing stuff and all the smoked-by-Windows, which was the competitive ad campaign we started about a year ago.

I do a lot of stuff for social, Twitter, Microsoft’s and Windows Phones’ Facebook pages. I talk to a lot of people.

VentureBeat: So in other words, you have a pretty fun job.

Rudolph: I think I have arguably the best job in the company — I play with all the new toys before they come out and awesome stuff just randomly appears in my office for me to fiddle with. It’s like Disneyland for me.

VentureBeat: Let’s talk about Windows Phone. What are some of the most surprising features of Windows Phone when people see it for the first time?

Rudolph: The single biggest surprise is how different it looks and feels. I mean, it’s not a hidden feature, but it’s really that Start screen with the tiles. If you’re used to an iPhone or an Android phone, or even a BlackBerry, you’re used to the same sort of U.I. where you have all these little apps, and you go into an app and you do something, and you close the app, and you go into another little app, and you do something else.

So having a screen of tiles, when people see, they’re like, wow, there’s a lot of stuff going on. And then you put it in their hand, and you show them how their stuff comes alive on it, how their favorite people can be pinned to the Start screen, how their restaurants or movies can be on the Start screen, how everything’s flipping over with real information … all of a sudden when it’s in their hands it makes sense to them.

It comes alive, and it feels like the most fun jigsaw puzzle you’re ever going to put together. Because it’s the pieces of your life, it’s the stuff you care about: Your favorite sports teams, the news sites you go to. Your favorite people. Your favorite color. All that stuff comes together on that Start screen.

So it’s a very different way to do a smartphone. But when people see it, they dig it.

VentureBeat: One of the most interesting things about Windows Phone, and maybe the new Windows 8, too — I’m not a Windows guy; I use an iPhone and have an Android as well — is that it’s a differentiated operating system with a kind of different … ethos. That’s what makes Windows Phone interesting to me, actually.

Rudolph: I think you’re right. It was a completely different way of looking at how to build a smartphone. Not this app-centric model. Apps are great. They’re important. We’ve got lots of them — like 125,000 or something like that — but to be able to put it together in a way that makes sense around the experiences and the stuff you actually do, rather than just the apps you want to use — it’s just really cool.

And I love the fact that now with Windows 8 and Xbox, we’ve got this consistent look and feel across the whole company.

Now you pick something up — you pick up a Windows 8 PC — and it looks like the phone. You pick up the phone, and it looks like your Xbox dashboard. You play the Xbox, and it looks like your desktop. It’s all coming together, and it’s a really neat thing.

VentureBeat: So a phone is probably the most personal device, right, of all the electronics that you’ve got. Is it hard to get people to switch to a new type of phone?

Rudolph: I don’t think it’s hard to switch. Like anything else, when you try something new, you got to learn it, explore it, find all the settings. But what’s interesting, I find, is that people who are switching, or even getting a smartphone for the first time … because it’s built around the stuff that you want to do and the stuff you care about, it’s very intuitive.

I don’t need all of Facebook all the time; I just want to be able to see what my wife and my best friends are up to. So I pin my wife to my Start screen. I pin a group of my best friends, and I just get those chunks of Facebook.

So once you break out of that paradigm model of using apps for absolutely everything, once you understand that that’s not the only way you have to do something, the tile starts to make a lot of sense, and you start pinning and unpinning, and you’re off and running.

VentureBeat: So who’s the most resistant? Is it someone who’s maybe a feature phone owner or an iPhone owner who’s been an Apple user their entire life, or is it an Android owner?

Rudolph: It’s funny. Feature phone users are actually very receptive. If they’re ready to buy a smartphone, they’re ready to buy our smartphone.

There are a lot of people who have a very heavy emotional attachment to their phones, but it’s not specifically to the phone, it’s what the phone does, and the things that you accomplish with it.

So I’ll use iPhone as an example, because there are people who bought iPhones when they first came out and bought every iteration since then, and they’re like “I love my iPhone. I’d never leave my iPhone.” And then I ask why, and they show me all these apps and pages and pages of games, and all these little icons on their screen, and then I stop and I say “OK, you love all those things,” and they go “Oh, yeah, I love them all. It’s really important to me.”

Then I ask, “What do you do on your phone. What do you actually do?” And they say, well, “I e-mail. I talk to my mom. I use Facebook. I take pictures of my kids.” And then I say — what if I could show you a phone that can do all those things, but easier and better?

And generally speaking they’re like “I don’t know … I’m kinda used to this.” And then you show them something like the camera button on the Windows phone. You just hold the button and the camera turns on. Or you show them that you just want to look for a restaurant, you just hit the local scout button, and it pulls all that stuff up. You don’t have to learn anything or do anything — you just tap a button and then go — that’s pretty cool.

And the camera on the Lumia 920 is a perfect example.

You show someone the quality on that and they go, well, I want that one. I took this great picture of my son, next to his jack-o-lantern. It’s basically dark outside, but you can see his pajamas, and the funny face he’s making, and you show people that and they say: I want to be able to take pictures like that on my phone.

VentureBeat: So this is kind of a new challenge for Microsoft, isn’t it? For so many years, even decades, Microsoft has been in the dominant position — still is, in the desktop world — but now its an underdog. That’s a different challenge for Microsoft. How’s that work? How does that feel, to come in as the newcomer, the challenger?

Rudolph: It’s actually a lot of fun, primarily because the product is so good.

What we’re realizing is that a lot of people haven’t seen Windows Phone yet. And if they’ve seen it or heard about it, they haven’t touched it. So it’s a really interesting challenge where we’ve got this tremendously good product that gets amazing reviews — the experts get how good the operating system is and we get awesome reviews — but for ordinary people, it’s an interesting awareness challenge: How do we get more people to understand that that there is a Windows phone, that the Windows phone is different, and that when they try it they’re going to love it?

So for me it’s all about getting phones into people’s hands, because from personal experience — and I’ve personally interacted with thousands of Android and iPhone users — they’re all skeptical when they first walk up, and they all leave going: that sounds pretty cool.

So it’s a big challenge, but that’s what makes it fun.

VentureBeat: So on a device level there’s a lot to like. What about the ecosystem level, where Apple and Google and maybe even Amazon have these amazing rich ecosystems — what’s the view like from the Microsoft side on ecosystems?

Rudolph: We built our business by building a great ecosystem. That’s one of the reasons that Windows continues to be the dominant force in the PC market; we work with developers really really well, and developers like working with us, with over 125,000 apps now.

And we’re building a consistent experience across all the devices.

Office is on our phone, and it can be on your PC, and can get it as a service. SkyDrive works across everything now, Xbox music … so we’re building an ecosystem that’s very tightly integrated where you can get your stuff anywhere you are but still retains the soul of Microsoft, which is that we built this amazing platform, and you can build amazing things on top of it.

There are lots of people building really, really cool stuff, just for Windows Phone.

VentureBeat: Anything else?

Rudolph: Not really, but do you have a device to play one, a Windows Phone?

VentureBeat: No, I don’t.

Rudolph: Well, then we need get one to you. Because once you touch it, once you play with it, and get to know it, then I think it’ll make a lot more sense to you.

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