What I learned about 7-figure sales .. from selling pizza

In my mid 20s, I opened a pizza restaurant in my hometown. Each week, the same people would come in. We’d talk about friends, weather, politics. I got to know their likes and dislikes — who wanted extra pepperoni and who hated onions. Even though I made a pretty decent Hawaiian pie, I’m convinced I made a lot of sales just by listening and talking.

Now, I sell software, not pizza. Hootsuite — we’re a social relationship platform — has 15 million users around the world, including 800 of the Fortune 1000 companies. The art of selling has undergone a technological revolution in the decades since my pizza days. It’s possible to blast out a “personalized” email campaign to thousands of prospects with a few clicks. Customer relations management (CRM) software to track client interactions is a multibillion-dollar-a-year industry. AI-powered chatbots have taken the place of small talk.

I’m not a Luddite. I know this is progress. But I also know it’s dangerous to confuse efficiency with effectiveness, especially in the world of sales. Email click-through rates, for example, can be abysmal. (2% is considered passable.) Chatbots are only as good as the algorithms behind them (at present, not great). In the the race to automate sales, we’ve lost a lot of the humanity and interpersonal skill that once went into the art of selling.

It’s easy to laugh at the cliche of the old-school sales guy — Rolodex crammed with notes on everything from clients’ birthdays and job promotions to their kids’ names. But there was something to the personalization and attention behind that approach — something that digital brute force, volume and automation alone just can’t match.

A return to “social selling”

And this is exactly where social selling comes into the picture. By now, social selling — using social media to find leads, build a dialogue and make sales — is already approaching buzzword status: the latest overhyped tool in the sales arsenal. But what all this buzz misses (and hides) is the fact that social selling isn’t anything new. If fact, it represents a movement back to a simpler, more human way of closing deals.

It’s also proving strikingly effective. A recent, comprehensive report from LinkedIn shows that 78% of “social sellers” outsell peers who don’t use social media. They boast 45% more sales opportunities than others, and are 51% more likely to hit sales quotas. On the other end of the transaction, three-quarters of buyers say they’re ready to have a social media conversation with providers.

I don’t think there’s any great mystery behind these results. People like to buy from people. They appreciate human interaction and genuine attention. They recognize when a salesperson has gone to the effort of doing her homework and building a relationship … rather than just cramming another automated drip email into their inbox. Trust, accessibility and accountability all translate to more sales.

The problem, of course, is that all this takes time. Salespeople are always up against the clock to meet quotas and make commissions. Scrolling through social feeds to learn about every prospect is time-consuming. Sharing relevant updates, finding and responding to comments, and keeping track of dozens, if not hundreds, of leads across multiple networks easily becomes overwhelming. You start to see the allure of just hitting “send” on a mass email and hoping for the best.

Staying human, at scale

But this is where I think technology does have a role to play — not to remove the human element from the equation, but to tackle some of the logistics that go along with social selling. It’s a quirk of the tech landscape that sales tools really haven’t evolved substantially in, well, decades. While the world of marketing technology has raced ahead, we’re still selling like it’s 1999.

CRM platforms, from Salesforce to Microsoft Dynamics, are useful systems of record, to be sure (though whether salespeople relish updating them is open to debate). But few are fully plugged into the living, breathing world of social media. There’s a huge gulf, in other words, between the tools we use to track customers … and the tools customers actually use to share their own thoughts and preferences.

The challenge becomes how to bridge those two worlds. Some steps seem obvious. There should be a way to pull in contacts from your sales database, for example, then automatically find their social media profiles and start following them. In 2017, doing this manually feels painfully slow.

At the same time, we need a way to automatically assemble all that information that used to be scribbled down on Rolodex cards, what salespeople call “buying signals.” Social media is full of rich data on life events like birthdays, job promotions and more. The right social selling tool would allow users to set “alerts” to catch these signals. A car dealership might track when its existing customers use the phrase “new car” on Twitter, for instance. Rather than having to scour feeds, salespeople would get pinged with an alert, then have a chance to start a conversation at the right time.

If it sounds like I’ve wrestled with this a bit, I have. My own company has a global salesforce working everyday to get in front of buyers. We needed a better way to do our own social selling. So we worked over the past year to put together an app that tries to solve some of these exact issues, for us and our customers.

Early signs suggest it’s working. One of my favorite proof points comes from one of our own veteran salespeople, who set up a custom alert for his existing customers. In the event that one of them mentioned the name of one of our competitors on Twitter, he’d get an immediate notification. The inevitable happened … and he was able to respond to his customer before our rival ever had a chance to steal business away.

Building a culture of social selling

Despite the potential, social selling remains more an aspiration than a reality in most companies. In fact, only 20% of organizations are actually taking advantage of social selling, according to Forrester.

The challenge, in no small part, is that selling this way is a deeply human experience — one that relies much more on building rapport and developing trust than in deploying the latest technological bells and whistles. It’s a skillset that an entire generation of salespeople are essentially having to relearn.

This reeducation, I believe, starts at the top. Leaders need to shift the perception of social media from distraction to serious business tool. Without buy-in from the C-suite, employees are reluctant to mix “social” with selling in the first place.

Getting employees up to speed is an equal challenge. For social selling to work, salespeople need to cultivate their own followings, from the ground up. There’s no magic bullet for this, other than consistently sharing updates that bring value to followers — that entertain, inform or enlighten. (The right employee advocacy tools, to help employees identify and push out great content for sharing, can help.)

One thing is for sure: plastering sales pitches across your Facebook news stream is the surest way to fail at social selling. Mining strangers’ personal feeds for sales fodder is as likely to end in public embarrassment as it is a sale.

The ultimate goal, as with any sales relationship — in 1917 or 2017 — is to build trust overtime: to toe that fine line between friend, trusted advisor and business associate. This takes commitment and a willingness to take the long view. It also takes something that may be hard for a generation reared on impersonal digital sales tools to swallow — a willingness to put yourself out there and actually care about people, one customer at a time.

Did you like this post? To receive my own weekly top picks — on topics like social media, marketing, leadership and tech trends — sign up for my newsletter.

Entrepreneur, investor, future enthusiast, inventor, hacker. Lover of dogs, owls and outdoor pursuits. Best-known as the founder and CEO of Hootsuite.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store