March Salesness Championship: Who’s the Best Salesperson In Pop Culture

Pipedrive Fictional Salesperson March Madness

At the same time as NCAA’s March Madness is playing out on basketball courts across the country, another competition — unlike any you’ve seen before — will play out in boardrooms, limousines, cafés and luxury condos.

Ladies and gentlemen, here is the Pipedrive March Madness for Salespeople.

Editor’s Note: This is a multi-part series. Those who have read round #1, round #2 and the Final Four, skip to the championship 

Round 1: Game On!

Pipedrive Salesperson March Madness

Gordon Gekko vs. Dwight Schrute

Gordon Gecko vs. Dwight Schrute

  1. Gordon Gekko — Wall Street

Greed personified. A wealthy, unscrupulous corporate shark. A slick-talking inside trader. An archetype, he projects confidence and values money over everything. Gekko is a relentless head case who sells his ideas like no other. But can he take on the former Dunder Mifflin receptionist?

  1. Dwight Schrute — The Office

Uncouth and unhinged, this salesman is also unstoppable. He lives and breathes selling. A sales sage, check out this quote from Dunder Mifflin’s best salesman: ““Pre-sale, take this time to get your mind and body ready for the fight of its life, because sales is a brutal street fight. The price points will be your brass knuckles. And customer service, when backed into a corner, might just be your Molotov cocktail out there. Get focused.” But will he be strong enough to battle against of Wall Street’s most feared and revered titans.

Jordan Belfort vs. Jim Halpert

Jordan Belfort vs. Jim Halpert

  1. Jordan Belfort — The Wolf of Wall Street

Though a con artist and a womanizer — let’s just ignore those imperfections for a moment — this guy can give a sales pep talk that will bring the house down. However, he got busted and did some time. But now that he’s back, is in he in good enough shape to take on a seemingly mild-mannered salesman?

  1. Jim Halpert — The Office

Ahhh, Tuna. Jim, the hilarious and lovable prankster who just wants Pam’s love. Oh, and to embarrass his sworn enemy Dwight Schrute every chance he can get. After rising to regional manager at Dunder Mifflin, Jim started his own sports marketing company named Athlead and then struggled with clients and life/work balance. Las Vegas bookies have his nice guy at 6-1 against Wall Street’s most loved shyster/salesman/motivational speaker.

Don Draper vs. Jamie Randall

Don Draper vs. Jaime Randall

  1. Don Draper — Mad Men

Mysterious. Brusque. Charismatic. This advertising guru’s skills in sales have less to do with action and more to do with embodying an image. While a certain type of understated egotism goes a long way, it’s uncertain if his old-school charm will be enough for the modern lover who is Jamie Randall.  

  1. Jamie Randall — Love & Other Drugs

This particular salesman, who bedded woman left, right, and center, once experienced a bout of erectile dysfunction with his new girlfriend, the first woman he ever really cared for. So what did he go out and do? He convinced his boss that he’s the best man for the Viagra account. That’s the kind of hardcore commitment that he brings to the sales table every day. Soon thereafter, he was Pfizer’s number one salesman. Some pundits predict that Randall will eat the big man from Madison Avenue for lunch.

Moira Brown vs. Jim Young

Moira Brown vs. Jim Young

  1. Moira Brown — Fallout 3

Known for being a bit on the eccentric side, Moira sells things that you need most during your travels through this popular video game. Watch your step though — and your wallet. If you click into her store intending only to buy energy cells and missile launchers, don’t be surprised if she cross-sells you combat armor and frag grenades. In her virtual world, she’s that good. However, she’s never gone up against a ruthless vulgar stockbroker like Jim Young.

  1. Jim Young — Boiler Room

According to this arrogant liar, there’s no such thing as a no-sale call. Young made his name by masterminding a “pump and dump” scheme in which he and his crook coworkers created artificial demand for stocks of companies that didn’t exist, cold called people, and then pocketed exorbitant commissions after duping people into becoming investors. His gift for the gab and fiery phone tactics got him this far — but it’s yet to be seen how he’ll fare against a digital opponent as powerful as Moira Brown.

Chris Gardner vs. Elmer Gantry

Chris Gardner vs. Elmer Gantry

  1. Chris Gardner — The Pursuit of Happyness

This man and his son were homeless for a year while he struggled to break into selling stocks. His story is about integrity, rejecting rejection, how a positive outlook can pay off, and working harder than you thought possible. He’s the opposite of Elmer Gantry.

  1. Elmer Gantry — Elmer Gantry

Kicked out the seminary, this flawed preacher became a traveling salesman, selling everything from shoeshine to vacuum cleaners to religion. A narcissistic, womanizing drunk, Brother Gantry’s belief in the power of faith pulled him through. In a way, he’s the all-American salesman — he’d believe in anything if it helped him sell it. It’s this gumption that fuels his popularity on social media. But will it be enough to burn down Chris Gardner?

Jeannie Van Der Hooven vs. Ricky Roma

Jeannie Van Der Hooven vs. Ricky Roma

  1. Jeannie Van Der Hooven — House of Lies

Up for doing whatever it takes to make it in the advertising world, Jeannie is merciless. She’s also got huge goals, knows what she needs to do, and isn’t afraid to do it. If anyone were to be the spiritual successor to Blake in Glengarry Glen Ross, it would be Jeannie Van Der Hooven.

  1. Ricky Roma — Glengarry Glen Ross.

A master salesman whose strategy is to gain the trust of a potential buyer, anticipate their rejections, and then jujitsu the entire experience so that the buyer thinks they’re in control and acting of their own volition. Deservedly so, he won the Cadillac Eldorado. But does he have enough chutzpah to win against Jeannie?

Tommy Calahan vs. Jay Pritchett

Tommy Calahan vs, Jay Pritchet

  1. Tommy Calahan — Tommy Boy

Tommy’s ability to successfully sell people auto parts has little to do with natural ability. His appeal as a salesman is all about his relatability and naive honesty. Easy to read with no pretense at all about him, he’s the epitome of a trustworthy guy who just happens to be selling you car parts. He’s a sales fan’s dream, but few think he poses Jay Pritchett — a salesman’s salesman — a threat.

  1. Jay Pritchett — Modern Family

In an old advertisement for his closet company, Jay’s slogan was: “Closet? You’ll love it!” It was supposed to invoke the saying, “Like it? You’ll love it!” But nobody got it. Oh well. Notwithstanding Jay’s lack of slogan-writing abilities, he’s a consummate salesman.

Al Bundy vs. Willy Loman

Al Bundy vs. Willy Loman

  1. Al Bundy — Married … With Children

Underdog. Crass. A lowly shoe salesman. Never an outright winner, on the surface, Al Bundy seems to lack the charm and personality to sell anything. But that’s exactly what he — as the dark horse in this competition — wants Willy Loman to think. 

  1. Willy Loman — Death of a Salesman

This salesman, approaching the end of his career and struggling to come to terms with his life,  eloquently illustrates the darker side of being a salesman. Sure, he’s a cultural icon. But one day, every icon must meet his iconoclast — will today’s match against Al Bundy be that day?

It is game on. Check back later this week to find out who made the Elite Eight in the Pipedrive March Salesness for Salespeople.

Round 1 Results & Round 2 Matchup

There were some huge upsets in the first round of the Pipedrive March Madness for Salespeople. For one, the goody two-shoes of sales Jim Halpert knocked out the bad boy of sales Jordan Belfort with a convincing victory. In some matches it was hard to distinguish the favorites from the underdogs.

With the next round fast approaching, what qualities and traits will enable one salesperson to outsell their opponent? Will it be problem-solving skills or people skills? The ability to multitask or the ability to listen? Impeccable communication skills or a lust for winning?

We’re now down from 16 to eight salespeople.

Here’s the Elite Eight.

March Salesness elite 8

Dwight Schrute vs. Jim Halpert

Pipedrive March Madness Dwight Schrute vs. Jim Halpert

For some salespeople, the road to the championship is paved with overselling, losing sight of the goal, and believing price will solve the client’s problems. But not Dwight and Jim. These two quintessential salesmen are far too seasoned and professional to make those kinds of sales mistakes. In this contest, will Dwight’s tenacity and passion for selling paper products be enough to get him into the Final Four? Or will Jim’s slow but steady approach to sales put him over the top?

Don Draper vs Moira Brown

Pipedrive March Madness Don Draper vs. Moira Brown

This matchup will be about much more than just closing deals. Touted as a battle of the sexes, it pits a man who epitomizes workplace sexism against a feminist who embodies gender equality. In this bout, Brown, will need to bring her A-game if she wants to take down the main man from Mad Men. Draper’s insatiable desire to win and his creative sales strategies are partly why he’s thrice won the most valuable salesperson award.

Chris Gardner vs. Jeannie Van Der Hooven

Pipedrive March Madness Chris Gardner vs Jeannie Van Der Hooven

When Gardner started interning as a stockbroker, even though he was homeless — a fact that he kept secret from co-workers — he still called 200 prospects each day. And it paid off. Not only did he get the job, it was his optimism in the face of adversity that shaped him into the confident salesman he is today. Van Der Hooven took a different route to the top. Unscrupulous, she burned many bridges on her way to becoming a high-powered management consultant — perhaps that’s why her firm is being investigated by the feds.

Jay Pritchett vs. Al Bundy

Pipedrive March Madness Jay Pritchett vs. Al Bundy

In this matchup, we’ll get to experience a classic salesman throwdown that has been brewing for years. Seeing these two charismatic yet flawed characters go head-to-head will prove once and for all that Pritchett is not just Bundy in the witness protection program. Pritchett, the more sophisticated of the two, is expected to sweep the floor with the less civilized Bundy, who many sales fans still can’t even believe has made it this far in the competition.

It’s game time! Come back next week to find out who made the Final Four in the Pipedrive March Salesness for Salespeople! 

Round 2 Results & the Final Four

In the Elite Eight of the Pipedrive March Madness for Salespeople, four phenomenal salespeople were eliminated — Jim Halpert, Moira Brown, Jeannie Van Der Hooven and Al Bundy.  

Here are the Final Four!

March Madness Final Four

Dwight Schrute vs. Don Draper

Dwight Schrute vs. Don Draper

Despite being somewhat deficient in common sense and social skills, Dwight Schrute is a highly effective salesman who puts everything he’s got into his current and future clients. There’s no denying he’s passionate about selling and loves what he sells (even though it is just paper). But this weekend when he goes up against the formidable and dapper Don Draper, will Schrute’s wacky pre-meeting warmup routine of shadowboxing and playing heavy metal air guitar be enough? Surely Schrute knows that, in terms of money and cultural cache, Draper’s sales skills far eclipse his. Indeed, Draper’s clients are American icons, including Hershey’s, Kodak and Chevrolet.

The result of this matchup — like much of sales in today’s cutthroat business climate — will come down to who wants to win more. And as always, anything can happen on game day.

Chris Gardner vs. Jay Pritchett

Chris Gardner vs. Jay Pritchett

In this matchup, you can be sure that neither Chris Gardner nor Jay Pritchett will rest on their sales laurels, not even for a second. Gardner, famous for being without a home but never without hope, might break out some of his high intensity optimism that inspires salespeople and non-salespeople alike to achieve their full potential.

In the other corner is Pritchett, a self-made millionaire who might use some of his old school sales techniques that are still effective in today’s digital age — such as getting the foot-in-the-door and taking prospects out for free meals — in order to get the upper hand on his opponent. Which one of these ridiculously successful businessmen and proud fathers will come out victorious is anyone’s bet.

Today, four salesmen are still standing. By Monday, there’ll be only one. Come back next week to find out who is the champion of the Pipedrive March Salesness for Salespeople!

The Championship!

Pipedrive March Madness Championship

In basketball, the saying goes that you miss 100% of the shots you don’t take. In sales, you likewise miss 100% of the deals you don’t chase. But that’s not to say that to be successful in sales, all you need to do is turn up and start pitching prospects. Unfortunately for some salespeople, even working hard doesn’t guarantee favorable outcomes. Talent plays a part. So does luck. But what is interesting about today’s championship match is how it proved that working harder and smarter can lead to more deals, bigger deals, higher speed and higher conversion rates.

Don Draper vs. Chris Gardner

Chris Gardner vs. Don Draper Salesperson March Madness

In the championship round of Pipedrive’s March Salesness for Salespeople, Don Draper and Chris Gardner went head-to-head in a fierce battle. Draper’s suave sales pitches initially put him way ahead of his opponent. Then Gardner made a resounding comeback by continually evolving his sales process, living by a code of ethics, and helping others succeed.

And the winner is …

Chris Gardner!

Gardner, who ended up beating Draper to be named by Pipedrive as the best salesperson in pop culture, personifies many of the qualities and behaviors that Pipedrive — as a company and a sales management tool — believes are the true source of sales success. Two of these qualities, among many, include focusing on key sales activities and being aware of how activity goals drive sales. Gardner does this by being tenacious about contacting high value prospects — even going so far as to cold call CEOs — and by efficiently using every moment of every day to reach his goals.

Thanks for following Pipedrive’s March Salesness! We’ll leave you with this memorable Gardner quote: “The future was uncertain, absolutely, and there were many hurdles, twists, and turns to come, but as long as I kept moving forward, one foot in front of the other, the voices of fear and shame, the messages from those who wanted me to believe that I wasn’t good enough, would be stilled.”

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Lee Black

Lee Bob Black has been writing about innovation, creativity, entrepreneurship, sales, education, media, and finance for over ten years.

  • Richard

    Good Freaking Choice! YAYAY!!!