Sales and the Art of Whale Hunting

Call me Ishmael…because this is a tale of modern-day whale hunters — that special breed of salespeople who build their numbers reeling in really big fish.

Now I realize whale hunting is out of fashion in a sales world that’s all about bottom trawling. ‘Sales velocity’ is all the rage and transactional selling is becoming the norm. Obsession over workflow, process and the latest CRM-bolt-on tools are viewed to be the keys to increase bookings. With all of that, the slow, methodical sales approach of coaxing a leviathan up from the deep has become a lost art.

As much as I’m transfixed by a beautiful dashboard in SFDC, and appreciative of algorithmically scored leads that identify the 20 best prospects for a BDR to dial tomorrow, there is nothing that compares to the awe I all feel when a huge deal closes. The admiration for the persistent whale stalker who has spent quarters, not days or weeks or months, getting a behemoth deal into the boat is a feeling like no other. So in honor of the fisherman of old toiling in oceans for a goliath of the deep, let me share the methods of four salespeople — whale hunters all — who have influenced my own approach these past 20-plus years.

Whale Hunter #1: The Engineer

On my second day out of college and my first day as a sales professional at ADP I met Jerry Hall. Even back then, Jerry looked as though he’d stepped out of Glengarry Glen Ross. He was unassuming, his suits were ill-fitting and out of fashion (in all fairness to Jerry, I’m now the guy in the office described this way). The outward appearance did not matter, because everyone in the sales pit knew one thing for sure — Jerry had it where it counted and that made him the alpha male.

I got my first glimpse of Jerry’s power on Tuesday of my first week. At 4 pm, the ritual of Roll Call commenced. Before CRMs, before e-signature orders, hell, before email, this was the weekly put up or shut up meeting where reps announced sales for the week. We’d go around the room and our VP of Sales, Bill Mellon, would call out names and each quota carrying replied with the dollar amount of sales. Let’s just say that public praise or embarrassment was (and still is) a big motivator to getting ink to paper.

At 4:20 Jerry enters the pit, strutting like LeBron James walking onto the court — despite the fact that Jerry was disheveled, soda in one hand and papers falling out of his briefcase in the other. Bill Mellon’s eyes lit up and thought, Is Jerry going to save my ass this week? “Alright, Jerry,” Bill said, “What d’ya got?”

Jerry was riffling through his paperwork, adding on the fly and saying, “Ah, put me down for $12k but it might be $18,000 by the time we’re done with this meeting.” While the dozen other reps were doing small-ball deals, Jerry’s slaying whales and closing deals five times the average.

With an urgency to refill my bank account that was days away from overdraft, having rented an apartment and bought two suits from Nordstrom’s in the 24-hours since graduating college that preceded my first day of work at ADP, I approached Jerry at the end of the first week asking, “Mind if I ride along with you on Monday?” Shockingly, he agreed. The following Monday I met him in the parking lot, climbed into his four-door, white Mercedes and thought, Whatever this guy is doing, I need to be doing the same. So began my tutelage under a whale hunter.

Jerry’s success doesn’t spring from any Jedi-mind trick of convincing buyers to part with tens of thousands of dollars, but rather, Jerry possesses incredible domain expertise combined with an engineering-level understanding of the product. Jerry understands the payroll space; even knows IRS code. He used his knowledge to do what we call the Challenger Sale today. His domain expertise enables him to speak with authority, expand the prospects’ view of the world and help them understand the risks they are exposing themselves to by managing payroll in-house, effectively making any decision other than outsourcing look absolutely insane. And why could Jerry speak with such authority? Because he knew the product he was selling better than the folks that built it and more deeply than those that implemented it. Jerry runs the product at redline. The sales engineers know that whatever he asks them to do can be done…they also know they’ll bust their asses doing it. But Jerry gets the deals, and you bet he delivers.

Whale Hunter #2: The Trusted Advisor

I’m pretty sure Cesar Enciso was one of the first in his family to graduate college and I’m also pretty sure he didn’t graduate with honors — all of that doesn’t matter because he’s the biggest whale hunter I know. I saw Cesar land deals 10–20x the average — and that was when he was just learning how to wield a harpoon. The secret to Cesar’s success? He applies the highest emotional intelligence quotient (EQ) I’ve ever seen in a business person. Cesar has the uncanny ability to read a customer, often understanding them more than they understand themselves. Cesar uses his EQ not to simply help a C-level executive solve a business problem, but also see how that person can personally benefit from the project. I have watched Cesar close some incredible deals while also advancing countless peoples’ careers by leveraging his high EQ.

Cesar’s ability to slay whales and help people climb the corporate ladder has had an interesting consequence — he wins customers for life. He’s that good. Cesar has such a strong relationship with his customers they end up taking him with them from job to job. And, equally impressive, as Cesar has gone from company to company, those buyers have moved their vendor relationships to follow him. Cesar has created the ultimate symbiotic relationship. I’m still not sure who’s the whale and who’s the barnacle — but the roles in the metaphor don’t matter. What I do know is that Cesar and his clients have mutually benefited from the long-term relationships they’ve fostered.

Whale Hunter #3: The Consensus Builder

Heather Welborn is a strikingly gorgeous woman. But instead of walking the runways of Paris, she went into sales. I have to say that Heather is not one of the best business women I’ve ever worked with; she’s one of the best business people I know.

I met Heather in the late 1990s working for a conference calling company, InterCall, which was in the middle of transitioning its products to the Internet and digital age. While InterCall had hundreds of reps busy pursuing the transactional model and scooping up minnows in the SMB market, Heather saw an ocean of whales. You can imagine my befuddlement when my team of over 60 people was consistently outsold by her three reps slaying whale after whale.

Heather was so successful at harpooning a bunch of finbacks that she convinced our CEO to let her create a national account division and teach others how to do what she does better than anyone else: work the dozens of stakeholders in the food chain — across divisions, across countries and across budgets. She’s second to none at herding cats and getting people, even adversaries within the same company, to find common ground on a project. A long time ago, I affectionately nicknamed Heather “Squirrel” because of her habit of going around collecting people like acorns, using information and relationships as power. She finds the acorns scattered across corporate forests that others ignore because seemingly they aren’t important individually. But by the time Heather collects enough acorns, she has a feast.

Heather’s ability to rally disparate business units and functions behind a joint solution is what wins her business and puts her in the whale hunter category. She’s a consensus builder who orchestrates people to work together for the common goal — the project and the sale.

Whale Hunter #4: The Buyer’s Friend

And this article wouldn’t be complete without my good-old-boy buddy, Jim Reiss. This Okie who now hails from Texas relies on his folksy southern style to create familiarity and gain trust before helping solve a business problem.

Jim is friendly and personable, but his real charm comes from his ability to turn a phrase. His speech is filled with some of the most incredible colloquialisms, metaphors and unusual connections of ideas that anyone has ever heard. Listeners are first thinking, what the heck did he just say? But after a moment’s cogitation, they’re doubled over laughing. Gems like, “It’s hotter than a billy goat’s ass in a pepper patch” or “I am as nervous as a long tail cat in a room full of rocking chairs” fits genuinely into Jim’s sales conversation. Although these phrases might be commonplace on a porch sipping sweet tea in the Lone Star state, they sure do create a lasting impression in Silicon Valley. Combine the side-splittingly funny sayings, southern twang and folksy charm — you can’t help but love Jim Reiss. Most buyers want to share a beer or break bread with Jim long before they’ve figured out if he deserves a P.O.

As disarming as Jim’s prose might be, don’t let that down-home humor fool you. Jim is one serious business guy. Jim’s the man with a one-two punch, behind the charm is the focus of a former military man. He’s sharp, hardworking, cool under pressure and comfortable deferring gratification while committing to a long-term goal. I’ve seen Jim connect on a personal level with a CRO just before he pivots to explaining how the best thing for that buyer to do is lay off a dozen under-performing sales reps and replace them with a mid-six-figure technology platform that was more reliable at helping that CRO reach his quota. Did he just say that? Really? Are you kidding me? You can’t tell someone how to do their job without first having related to them and earned their trust in the process.

You might not know it by who’s talking louder or more often, but Jim Reiss is usually the smartest guy in the room. But that’s all below the surface. Jim creates a real friendship before he turns a prospect into a customer.

Portrait of a Whale Hunter

Let me leave you with a list of traits that the whale hunters I’ve known share. Although not all illustrated above, the below qualities are an expanded list of what it takes to harpoon your Moby Dick. All of them are individually attainable, and the combination might elevate you to world-class whale-hunter status.

A whale hunter…

  1. Possesses insightful problem-solving skills.
  2. Has communication skills that rival Shakespeare.
  3. Is a domain expert that understands his/her product and industry better than developers, engineers and most of the product management staff.
  4. Orchestrates prospect relationships second to none. A whale hunter knows and does not fear the fact that to position and then ask for a BIG order requires building big trust. Big orders won’t close unless trust and confidence between the salesperson and the buyer isn’t abounding.
  5. Develops long-term relationships with customers who love them. Whale hunters might be aggressive but achieve a careful balance so that the aggressive nature is viewed as a benefit to the customer, not adversarial or parasitic.
  6. Works better and higher within their customer’s organizational charts than their peers. While most reps are selling to directors of IT, whale hunters are selling to CIOs and CTOs. And they’re able to stand toe-to-toe with them.
  7. Has the ability to inspire buyers, who often take big risks betting that the whale hunter will deliver for them, both professionally and personally.
  8. Displays incredible work ethic and is noticeably more motivated than most reps.
  9. Shows great resilience and bounces back from adversity. They don’t hear ‘no’ but rather ‘not yet’.
  10. Lastly, a whale hunter most often lets the numbers speak for them. Most whale hunters aren’t showy or flashy. They are strategic, methodical, analytic and humble in how they ply their trade. After all, it’s often a solitary existence navigating a vast ocean in search of the great whale.

Like Ernest Hemingway’s old man, there’re still a few sales professionals surveying the seas and thinking, “My big fish must be out there somewhere.” Consider hiring a few to hedge your bet against that high velocity sales machine you might be building. I can tell you from personal experience that there is nothing sweeter than hearing one of those whale hunters exclaim, Thar she blows!

First published on the HG Data Blog.