You’ve got to hand it to Salesforce: The big battleship of Cloud CRM is remarkably adept at turning its boat around to make war against the startups aiming torpedoes at its hull.

First, it was Yammer.

Flash back to the 2008 TechCrunch50: Yammer enters the market with a bold play: Build an enterprise collaboration app around the status update and newsfeed mechanic, give most of it away for free to let individual teams test it out, and then acquire enterprise customers from the bottom up. Once you’ve got the users and the attention of their bosses, (so the logic goes), you leverage what you’ve launched into a platform that can support a wide range of apps. Some of these apps you build yourself, some you open up to third parties.

Salesforce CEO Marc Benioff, judging the competition, saw Yammer on stage and said, “I really like this company the best”.

Fast forward one year to Salesforce’s Dreamforce 2009 conference, and Benioff is announcing Chatter, a status update and newsfeed app that integrates with Salesforce CRM but otherwise looks an awful lot like Yammer.

Fast forward again to this year’s Dreamforce conference, and Yammer is handing out free Starbucks coupons outside Moscone Conference Center and making a big deal about its new ability to integrate with Salesforce.

Whether or not Salesforce’s entry has made a meaningful dent in Yammer’s enterprise-domination ambitions is an open question, but it seems that Chatter was a depth charge intended for Yammer’s submarine.

This time, it’s Asana.

At the beginning of this month, after almost three full years in development, Asana (a startup founded in 2009 by Facebook co-founder, Dustin Moskovitz, and early Facebook employee, Justin Rosenstein) launched to the public with an ambitious but now familiar play: Build a team collaboration app (this one around to-do lists and projects), give most of it away for free, acquire enterprise customers from the bottom up and leverage that foundation into a platform that can solve a wide range of businesses’ needs.

Fast forward to literally five days later and Salesforce is announcing Do — a simple collaborative to-do list for teams and projects that integrates with Salesforce’s CRM and looks an awful lot like … Asana.

Yet again, Salesforce heard a ping on its radar. Yet again, the battleship shifted course to attack the enemy submarine. But with Asana, Salesforce now finds itself up against an entirely different, more menacing foe, one whose capabilities are a more dangerous threat than those of the one it faced before.

The thin edge of the wedge.

If you’re wondering how some project management app — even one built by Facebook rockstars — could possibly represent even a minor risk to the master of cloud CRM, consider this brief history of Salesforce.

When Salesforce launched its automation app in 2000, it was essentially a content management system for sales contact records. Armed with this core, Marc Benioff’s marketing genius, and the advantages of the cloud, Salesforce pushed its way into the enterprise through the sales department’s door.

From there, the company has tried hard to take its original product and use it as a platform to launch new applications and empower third-party developers to launch even more. (This is what Chris Dixon cleverly coined thin edge of the wedge strategy: You slide your way into the market’s cracks with one thing, than push on that edge until you’ve busted the whole market wide open.)

One problem Salesforce faces with executing this strategy is that the thin edge of CRM does not abstract particularly well into other problems. Sure, you can bolt things on (like tasks or a social newsfeed) but when it comes down to it, you’re dealing with a core framework that was built to handle customer record data and metadata and not much else.

Salesforce CRM, after all, is basically just a browser-based version of software that originated long before the Web became a full-fledged platform and way, way before the Web went mobile. You can push the CRM framework from its roots in sales into customer support, but if you try to push it much further, you’re going to start crashing into walls.

The other problem is that, as even diehard Salesforce fans will point out, the underpinnings of Salesforce’s user experience are a relic from the early days of the cloud. “Wouldn’t it be great”, you can’t help but say to yourself as you wait for a screen or interaction in Salesforce to load, “if something came along that cracked the core problems of CRM but whose interface didn’t slow me down?”

Enter Asana, stage left, with arguably the quickest, most adaptable project management app on the Web. Behind the surface of Asana’s collaborative to-do list is a real-time interface and a tremendously ambitious vision: To make collaboration so fluid, effortless and fast that the software eventually becomes the standard conduit between humanity and the work it needs to get done. Underpinning Asana is a highly-flexible data model constructed entirely around managing tasks.

Unlike customer records (or social sharing plus manual status updates, for that matter) tasks form the core of everything we aim (or should aim) to do at our jobs. Unlike CRM, you can abstract a properly-designed task framework across every function and every line of work. Among other things, you can go after ticket management for customer support, applicant tracking for HR, bug tracking for IT and, of course, CRM for sales (indeed, there are already companies using Asana for some of these things).

If you want to find a thin edge that can expand into the entire enterprise, collaborative task management is a great place to start. The founders of Asana know this, which is why they are doing what they are doing.

Which brings us back to Salesforce’s Do. Do is the first Salesforce app built on Heroku, coded in Rails and written in HTML5. Thanks in part to the platforms it’s built on, Do works well on mobile devices and is generally much faster and more responsive than the mainstay Salesforce apps built on Force.com. But despite these advances, Do’s design is less carefully considered than that of Asana; its interactions less meticulously crafted; its interface not realtime.

When you play with both apps, it becomes clear that Asana’s team has devoted more time thinking through the problems surrounding collaboration and building the intellectual and technological horsepower necessary to tackle these problems head-on.

In co-founders Dustin Moskovitz and Justin Rosenstein, respectively, Asana’s got Facebook’s original architect and the guy who has us pressing “Like” buttons all over the web. In Kenny Van Zant, Asana has the man who built Solar Winds’ bottom-up marketing strategy and knows how to penetrate the enterprise with freemium models like the back of his hand.

Despite Salesforce’s agility and the best sales and marketing machine in tech, it’s going to be hard for Do to win. The app is up against a killer team with an expansive vision, a solid product foundation, and a deep understanding of the problems at hand. If Salesforce wants to protect its core business from Asana’s eventual, inevitable assault, the CRM juggernaut will have to empower Do’s team to do remarkable things, up to and including the cannibalization of Salesforce CRM. So the question becomes: Will the Salesforce battleship, facing down an upstart nemesis, have what it takes to defend against the Asana submarine?

The question is a big one, so break out your popcorn: The war for the future of enterprise software is officially on.

This post originally appeared in TechCrunch. About eight months after writing it, I left Twilio and joined Asana as the first full-time marketer.

 “History shows that popular technology is often supplanted by entirely new models.”

That simple observation, presented in a letter from Google Chairman Eric Schmidt to the Senate Subcommittee on Antitrust, Competition Policy, and Consumer Rights, summarizes Google’s single best line of defense against the blunt instruments of government regulatory dismemberment. You don’t have to fear our power, Google says, because something will inevitably come along and take it from us.

Well, that something may finally be here. Her name is Siri.

While Siri is not the sole figure in the classical tragedy that ends with Google’s disruption—a play whose large cast includes heel-nippers like Blekko, vertically-targeted engines like Kayak, richly populated databases like Yelp and pretty much everyone else in consumer software—it is hard to read Schmidt’s letter without a sense that he knows that Apple and Siri are Google’s key antagonists.

Apple’s newest plaything appears about 15 times in Schmidt’s letter. Siri, Schmidt writes, is “an entirely new approach to search technology,” one that represents a “significant development.” He points to MG’s piece about Siri’s potential to make his case. (For more on how this impacts search, see my post about Siri & Quora).

Schmidt’s argument—a highly cogent and persuasive piece of propaganda—is dead-on: In the narrative arc of Google’s story, Siri is indeed a significant development. In fact, Siri is arguably the most significant development in Google’s story since, well, the advent of Google.

Sure, this story includes Facebook, the social web juggernaut that Google failed to see charging towards it on the distant horizon, and the Bing/Yahoo nexus that Microsoft assembled at magnificent cost. But in the retrospective view of of 3-5 years from now, these developments—while major—will likely pale in comparison to that fateful April day when Apple acquired Siri.

This is because Siri transforms computers from “passive” participants in the search process to “active” ones and in so doing attacks Google’s model head-on. Instead of taking queries and then passively delivering 10 blue links—which you then have to mine for the correct information—Siri actively goes and gets the correct information, herself. If you don’t give Siri the input she needs, she’ll ask you directed questions until you do. If the goal of your search is a specific action (like buying a movie ticket, reserving a table or calling a taxi), Siri can skip all the steps Googling would require and just do it.  At least, that is the idea.  Siri is still quite limited in what it can do, but the writing is on the wall.

When a technology comes along that eliminates the need to follow previously-required processes, we call it disruptive. There’s no other way to slice it.

Many classical tragedies have sad twists at their center, and this one is no different: When they launched Android against the iPhone, Google and Schmidt attacked Apple’s homeland and turned a longtime friend (Steve Jobs) into a mortal enemy. And now, with Siri, Jobs will have his posthumous revenge. Because make no bones about it: despite Jobs’ original claims that the Siri acquisition was not about search, Siri and the ecosystem of Siri-optimized APIs sure to evolve in its wake represent a bigger mortal threat to Google’s search business than anything Google has ever faced.

So Microsoft, you can can stop bankrolling the anti-Google lobby in Washington. Feds on the subcommittee, you can put away your knives: the weak have little to fear from Goliath.

In technology, at least, someone always comes along with a rock and a slingshot.

I originally posted this on TechCrunch.

If you are a marketer who has spent the last 10 years mastering the art of capturing and converting customers on the desktop web, the rapid rise of smartphones and the iPad might make you nervous.

You’ve built businesses on paid search, written essays about optimizing lead forms and studied the ever-changing subtleties of SEO. Using cookies that follow us around the web, you’ve turned display advertising into a performance medium. But just as you were beginning to wrap your heads around the whole social thing, along come the iPhone, Android and the iPad and with them a whole new reality: the post-PC world.

The post-PC world is radically different from the world in which most marketers honed their skills. Here, horizontal keyword search is losing ground to vertical-specific apps like Yelp and Hipmunk and a stream of recommendations from Foursquare, Twitter, Facebook, Pinterest and maybe Path. Along its frontiers, touch- and voice-driven interfaces write most of the laws. This landscape is unfriendly to lead forms. It rejects traditional tactics like SEM and SEO. In the post-PC world, the marketing methods of the last decade will be on their way out the window. Marketers and businesses that can’t adapt will be on their way out the door.

But there is good news for those ready, willing and able to evolve: Post-PC consumers – like generations of consumers before us – will still want ways to entertain our senses, engage our imaginations and stimulate our minds.

The future of marketing in the post-PC world is not about showing up high in search results. It is about reputation and spontaneous discovery. It is about weaving yourself into the feed. This is an evolution of what is known these days as inbound marketing. It involves creating awesome content that makes you relevant and then leveraging your overall awesomeness to establish a relationship with your target customers and maintain it over the years.

When you do it right, your customers want to find you. They need to find you. Your existence delights them because you are exactly what they were looking for – whether they knew what they were looking for or not.

But post-PC consumers are not patient. When we want to engage with your business, we expect you to respond in an instant, on the communications channels we prefer to use. Responding to our emails in a few hours or days just ain’t gonna cut it: depending on our demographics, we are either overloaded with email or hardly use email at all.

But we do consume almost every text message (SMS) that we receive. When we’re in info-gathering, entertainment or transaction mode, we tap on links that seem enticing and follow push notifications into our favorite mobile apps. And if your business offers a frictionless way to contact you, many of us will even call.

This is where cloud communications comes in.

Cloud communications democratizes telecom, making it easy for anyone with access to programming chops to create applications that historically required tons of expensive telecom hardware, big contracts with telecom carriers and a slew of esoteric telecom skills. Cloud communications abstracts these challenges away, making things like interactive voice response, automated outbound dialing, two-way SMS, text-to-speech and even mobile VoIP as simple to implement as a few lines of code.

In practice, this means embedding SMS tools into your CRM, email software or whatever else you want to use. It means using call tracking to gather metrics on phone calls or sending voice and text messages to notify sales reps about new leads in real-time. It means creating “tap-to-call” capabilities that instantly connect smartphone or iPad users via VoIP to your sales or support agents with a tap on a link in a mobile app or an ad. And for these agents, it means taking calls straight from an iPad – not locked down in some office or call center, but anywhere that wireless internet can go.

If what you’re selling is weaksauce and your content is boring, you will find the post-PC era to be a cold, cold world. But if you can produce products that incite our passions and generate content that resonates through an ever-more-insane degree of noise, you’ll have a shot at becoming part of our feeds. If you do these things while creating new ways to engage us when and where we want to be engaged, the future will be yours.

So what are you waiting for? The latest iPad is selling like crazy and it’s time to think different.

The post-PC world is almost here.

I originally posted this column in TechCrunch.

With the rise of Google+, the decrease in controversial posting activity by famous tech people and the allure of other shiny new things, the majority of tech press has turned the focus of their gazes away from Quora, my favorite startup of 2010.

Well now that Apple has gone and integrated the most sophisticated piece of AI to ever to see the light of the consumer market into its iPhone 4S, I thought it was time to brush some dirt off of Quora’s shoulder and shine a light on what the future of the company could hold.

What most people who don’t get Quora miss when they write it off as “another Q&A site” (or whatever it is they say then they write it off) is this: When they first launched Quora in the Fall of 2009, Quora’s founders and their first hire-designer Rebekah Cox-created the core of the most impressive “subjective knowledge extraction” machine ever constructed. (Yes, Wikipedia deserves its credit as the first juggernaut of this space, but Quora is positioned to eventually seize its mantle. Meanwhile, you could argue that the whole internet is the most impressive subjective knowledge extraction technology ever constructed, but that’s just semantics).

By combining an answer voting mechanism and a reward addiction loop (upvotes are crack) with a strict identity requirement and a one-to-many follower model, Quora started solving the problem of extracting high-quality experiential knowledge out of humanity’s collective head and getting it into structured form on the internet. What’s more, Quora is also using humanity’s collective wisdom to rank it.

With this engine, Quora is building a database of human experience that could eventually contain the answers to a lot of questions people carrying the iPhones of the future might have.

Which brings me back to Siri.

For those of you who haven’t thought through it yet or haven’t played with the iPhone 4S, Siri is a game-changing technology: The thing knows how to translate the garble of human language into targeted API calls that subsequently pull out the correct information from a potentially ever-expanding set of databases (assuming that Apple one day integrates other databases into Siri, which I’m confident it will). The main thing standing between Siri and the best answer for our likely questions is that the database that contains these answers is still a work in progress.

That work in progress is Quora, which is probably why I heard the rumor that some massive search and advertising company that shall go unnamed until the next paragraph allegedly offered to pay upwards of $1B to acquire it.

If that rumor is true, it means that Google looked at Quora and understood the magnitude of the threat. If it’s not true, it means someone making high-level strategic decisions at Google is not paying attention. As I wrote in a post about Quora and Google in March:

Consider an internet on which the best answers to the majority of our queries come not from the vast, increasingly noisy expanses of the world-wide-web but from the concentrated knowledge and experience of its most articulate experts. Here, you no longer filter through 10 blue links (or hundreds) to find what you seek; you simply input your query and are delivered the top response. Should you find yourself asking a question no one has asked before, you merely add it to the stream, where it makes its way to the people who can answer it best.

Take Siri as the primary interface for these queries and that just about wraps it up: If Quora’s brilliant team successfully navigates the chasm between its passionate early adopters and the rest of the articulate set, their company could eventually, along with Siri, become an existential danger to the core of Google’s business.

I originally posted this column in Techcrunch.