How to whip a struggling sales team into shape, startup-style

By Timo Rein , written on January 10, 2014

From The News Desk

In the 1992 movie adaptation of "Glengarry Glen Ross," Alec Baldwin gives an oft-quoted speech to his real estate agents. I've heard no fewer than ten accounts of sales, PR, and marketing people having had this speech used as a paragon of sales prowess. "You know what it takes to sell real estate?" Ricky Roma, played by Alec Baldwin, asks. "It takes brass balls."

The problem is that much of sales does require some level of balls -- perhaps another heavy metal, but there's little support. One can be aggressive, successful and a hard worker, but everybody has off days -- and even the most hesitant salesman can be turned into a killer deal-machine. They just need to know they can do it -- and that it’s not all about superficial bluster and talking.

Most people see sales as a guy on a phone who just wants to take money from you. The reality is that most salespeople have a product and an email account (or a phone) and they're told to get to it. The result? Those who don't care about hounding people do well, and those who feel bad are often given the choice -- lose the worries, or lose your job.

It's been like this for a while. Back in the late 90s (and beyond), salespeople were effectively left with a bunch of leads and Lotus Notes. They had to log their calls, their hours and would get measured on how many calls out they made. Many still do. And that’s not the way to make a great salesforce. Just because you log a call doesn’t make that call worthy of being logged.

At the turn of the millennium, Salesforce rumbled slowly out of the gate, taking the focus off of leads and onto the now-dreaded buzzword of "CRM" -- Customer Relationship Management, where salespeople knew that leads had hearts, brains, mothers and fathers. Since then, Salesforce has grown to a multi-billion dollar company, with its own conference and an entire platform ( With that followed an entire hundred-billion industry of CRM suites -- a paradoxical industry of creating better and better ways to enter in and save data about customers. It needs to be a combination -- focusing on leads combined with data and having really great conversations.

The obsession has become about quantifying and managing data, about easier ways to enter data, and we're almost back where we started: Except now assholes can be *lazy* assholes and email 400 people at once. We're back to square one, with a more intricate call-down list. And everyone will happily blame the salesperson.

Silicon Valley commonly "fixes" industries by streamlining paper-borne processes. Practice Fusion fixes medical data. Zillow brings housing information to the masses. Amazon stops you having to go to the store. If sales was purely zeroes and ones and not people making sales, that’d be great.

Much of the innovation in sales has been fixing the wrong problem. On the front page of Intuit Quickbase, the quote is telling: “Siebel was so difficult: we couldn't get our managers to use it. QuickBase is so simple, I can require use. And, it's less expensive.”

Great. Your quote that you just put on a website says that your managers are too stupid or lazy to use Siebel, and so you finally found something simple enough for them to use. Just because something is easy-to-use doesn’t make it efficient or effective.

Salesforce, Zoho and others have become excellent at categorizing which customers live in which place, and what deals started or had calls on what particular dates, but lacked anything to do with the momentum, mood, emotional context or well-being of the salesperson.

In short: The valley has been predominantly missing the obvious problem: Sales*person* management.

Many people managing sales teams  will talk in vague sporting analogies -- full-court press, hail mary pass, and so on -- but they fail to realize that in this case the salespeople are the athletes -- they’re the ones with their egos and jobs on the line each day, worrying about whether they’ll close a deal (or in your sporting analogy, put points on the board). Just like athletes (though, sadly, not quite as well-paid or as attractive), they're emotional, they get hurt, they get tired, they need to know the game is winnable and they need to be given a pep talk.

Sales organizations aren't always able to do that. Even great managers can't. So this is why sales software has begun to fill that gap. Here's how:

Emotional support (and hope)

Sales is an immensely emotional career. One hour (or even five minutes) can include massive success and dismal failure. A "no" can be in your hands in milliseconds. You can lose a sale without them even having to look you in the eye. You can be told horrible things in a moment because the person doesn't need to connect to you. The Internet has created a world where a salesman can be totally ignored with as little effort. You don’t even have to end a call.

Sales software should understand and cradle these emotions and help temper the disappointment with little dopamine injections. ToutApp, for example, has a little trickle of successes to deliver to you - hope in an otherwise dismal day. It'll tell you in a live feed when people read your emails, where they read them and what time. Even if you're not getting a sale in a day from a particular client, there's an actionable trail of hope to work off of.

Functionality needs to exist that reminds the salesman that all hope is not lost. While we as an industry like to celebrate the world of the salesman that is ‘killing’ or ‘crushing’ it, we’ve yet to create a world that attempts to get the salesman that’s being crushed or killed by a bad few days the support he needs to keep going. We need to accurately telegraph a sales cycle over simply saying that eight calls have been logged.

A carrot to go with the stick

The very idea of the commission -- or a potential "gift" for hitting a target -- is great, but fails to be cost effective. It's also tough to do well -- if you're giving them out too much, you're going to lower the bar. If you're giving them out too sparingly, you're going to knock the wind out of your sales team.

While deeply connected to emotional support, sales teams also need motivation beyond simply making money. Rewarding avariciousness is going to make managers unhappy, salesmen unhappy, and eventually get people who only care about money further. Small victories can keep people going on so many levels -- especially when the going gets tough. Small milestones, small amounts of progress -- numbers of demonstrations you’ve made, for example, makes someone focus on making a great demo, and thus a great (eventual) sale -- and prove that you’re working even when you’re not selling.

One format -- though we're slightly past the trend -- is the gamified sales company that based their business on fantasy football. Salespeople effectively play a "game" based on metrics, and managers can even "draft" particular players. Bringing any form of silly levity to an otherwise very demanding career -- and bringing in a way to reward managers is rather ingenious, and leads to my next point.

Enabling great management

My final point is that most people see sales organizations as one of those ancient sales barges with one large bald man whipping a crew of sad, hard-working men. The reality is that every organization -- sales and otherwise -- usually has some form of middle and upper management that sees the world as a series of numbers that their salespeople put out. This is actually inefficient -- by turning your salespeople into numbers, you're losing what makes it worth having salesPEOPLE versus a little duck that hits the "enter" key every two seconds.

It's actually very difficult to find products that directly deal with this problem: managing a team is challenging, especially with sales. CRMs need to integrate (or entirely consume) companies that encourage direct team interaction (versus Yammer's "feed") and emotional status. For example, a CRM with built-in video chat/live chat between teams and the ability to share (as crazy as this sounds) emotional statements and situations might help bolster a team. Then again, it could also attract catty shark-types who want to bring another member down.

This is where great management comes in -- giving managers the ability to directly coordinate with remote and in-person teams using CRM is necessary. Perhaps highlighting great metrics beyond simple sales (EG: This person has only made 3 sales, but in a market we've barely touched!) and letting them share with an internal content management system how they did it might be immensely rewarding.

The crux of my argument is simple: CRM and sales software is the stepping stone to making great salesmen more common. It's our industry's job to create things that kill cold-calling, brainless sales zombies dead and reward those with heart and knowledge.

The next generation of sales software should foster and empower greatness and on potential greatness over those who can simply call 85 people a day. The greatest salespeople are not human data-entry machines, and as long as we make that the norm, we're going to keep creating terrible salespeople.