We know what great salespeople do. Their methods, techniques, and best practices have been codified into internationally acclaimed books, podcasts, and webinars. As technology advances and the buying mindset changes, their continued insight proves more valuable than ever. (For the latest insight from the greatest sales professionals alive, watch SalesSummit.io, now on demand.)

Then there are the outliers. Salespeople who should not have been successful, but, against all odds (or perhaps with every single odd in their favor) found great success. From some of these, we can’t learn a whole lot outside of “be in the right place at the right time.” But from others, we can glean a life’s worth of wisdom. Here are their stories, as told by SalesSummit.io presenters - some of the most influential sales professionals in the modern era.

These are the tales of salespeople who should not have succeeded.

Right Place, Right Time, Right Printers

jill-konrath.jpgJill Konrath

When I worked for Xerox, new hire reps (often just out of college) were often sent to rural territories for their first year or two. While they did handle some bigger accounts, they primarily dealt with small business.

I’ll never forget when Jeff (not his real name) was assigned to work in a quiet Wisconsin community, home to a small military training center.

Shortly after his arrival in the territory, there was a situation in Cuba that triggered a mass emigration of people to the US. Over 100,000 crossed the ocean to the US a short period of time. Shortly after they started arriving, it was discovered that Cuba had dumped their prisoners and mentally ill on the US.

With people pouring into the country, the government ultimately set up “processing centers” to deal with all these immigrants. One place they chose was Ft. McCoy in Wisconsin. To handle all the paperwork, copier orders began pouring in. Dozens and dozens.

Young Jeff ultimately was the #1 rep in the region and one of the top 10 in the US that year. While he did a good job working with the military, he did nothing to create the opportunity. He just happened to be at the right place at the right time.

A Gutsy Proposition

brent-adamson.jpgBrent Adamson

A head of sales once shared the story with me of one of his best sales reps who’d been invited to compete with two other suppliers in an RFP. Upon submitting the RFP, each supplier was given an hour to present their submission and answer questions. 

In that meeting, the star-performing rep did something pretty remarkable. He walked in, sat down, and said, “Thank you very much for your time today. Since we only have an hour together, I’m not going to go over our submission step-by-step. You’ll find everything you need to know in there.” And he slid the submission across the table. 

Then he said, “Instead, I’d like to use our time today to share with you the three things that we were surprised to find not included in your RFP, why they matter so much for your business, and how overlooking them can create all sorts of problems for your organization.” 

And for the next hour, that sales rep proceeded to (diplomatically) dismantle that customer’s thinking to such a degree that they cancelled the RFP, asked the other two suppliers to return home without presenting, and restarted the entire process. Several months later when the customer had readied a new version of the RFP, it looked a great deal closer to that rep’s advice, and he easily won the deal.

To be sure, it’s a high-wire act. But it’s such a great example of what you might do when you’ve got nothing else to lose and were just going to wind up competing on price anyway.

The Elder Salesman

will-barron.jpgWill Barron

Sam is a sales professional that I use as an example on the Salesman Podcast all the time. He was "too old" to work in sales at 72, he "didn't get" the cutting edge video endoscopy equipment that we selling.

Yet, I'd invite him into my training sessions with consultant surgeons that I was selling to all the time. They would completely ignore me, circle around Sam and listen like little children, giggling routinely and on cue.

Sam had been wrapped up in the world of endoscopy sales since these now consultants were frightened 25 year old trainees. He knew all the times they'd screwed up, that they 'd been shouted at, and had more tales of debaucherous trips away on "surgical skills training" than you could count.

I sold hundreds of thousands of pounds worth of surgical equipment each year, not by pitching, social selling or anything remotely complex. By simply giving my prospects access to Sam and letting his relationships do my selling for me.

A Mother's Intuition

john-barrows.jpgJohn Barrows

My mom is about as far away from being a sales rep as it gets. Well, at least the perception of what most people think a sales rep is (Boiler Room, Glengary Glen Ross). What she did recently reminded me there is no real secret to sales success. It’s all about hard work and focus.

She works at a Performing Art Center in Virginia as an Executive Assistant and Board Liaison. A while ago she got an idea to leverage the Art Center to help support veterans. By combining the Arts Center, George Mason University, and the veteran community, she hoped to improve veterans' lives through music and the performing arts.

She started by working to gather all the relevant information about the various programs, funding, target market, existing resources, etc. and kept it all in a binder that she carried around with her. She then identified the major players/influencers that she would need to get involved to make something like this happen and thoughtfully reached out to each of them for their feedback and potential buy-in.

Because of her preparation and the homework she did, her message was directly relevant and interesting to each person she reached out to. They all responded and were more than willing to meet and during the meetings their feedback on her idea was overwhelmingly positive.

In order to help promote the event and find veterans and vendors to participate she did her research and developed a list of 200 potential influencers in the veterans' community. She then reached out to each one of them independently with a tailored message asking for their participation and support along with help spreading the word.

I remember talking with her the day before the event and she said she was expecting about 200 people to be there, including vendors and various event contributors, but had no idea how many actual veterans were going to show up. She hoped she would get more veterans than vendors but since this was a free/open house event with no registration she was going to have to wait until the event to find out how many would show up. They did- and in a big way. Over 500 veterans showed up to the event and it was an incredible success all the way around.

What Goes Around...

chad-burmeister.jpgChad Burmeister

There was a sales professional that I knew who would sell “shady” deals that were over-promised and under-delivered, because he was committing to things the company could not deliver. When I moved into enterprise software, a VP of Sales once told me “It’s my job to steal as much money from prospects as possible. I tell them on a Friday that we will deliver the feature requests in a month, when they sign, on Monday I tell them the truth that it will take much longer.”
They found success because the prospect they were working with did not know that they were over-promising. This type of selling has gone way down with the advent of social media. These sales people (and often sales leaders) who flat out lie to the customer get found out down the line. Just look at a few recent VPs of Sales who have moved from pretty well established companies. Their over-promising catches up with them.

Speak Softly, Make Great Sales

julie-hansen.jpgJulie Hansen

If you met Kevin you’d never guess he was the top sales consultant for a large biotech company. Soft-spoken and a bit of an introvert, at a cocktail party Kevin is more likely to be found near the door, waiting for an optimal time to leave, than trading small talk at the bar. In other words, Kevin contradicts the still prevalent belief that to be successful in sales you must be an extrovert.

Yet in the competitive world of medical devices, Kevin (and others like him) thrive. Why? It takes more today than an outgoing personality to sell complex solutions to savvy clients who have a number of degrees behind their name. While Kevin’s technical background makes it easier for him to gain a client’s trust and talk their language, knowledge alone doesn’t consistently produce the kind of results Kevin is getting.

Kevin is part of a new breed of technical sellers: they’re not just “product smart.” They’re also what I call, “presentation smart.” Like Kevin, they make sure their presentation or product demo is not just a dry data dump of features. They listen more than they talk. They know when and where to highlight value, and how to use discovery to align their presentation with their client’s needs, interests and level of understanding.

In the world of complex sales, introverts are the new extroverts.

Winning Friends and Influencing Prospects

mark-hunter.jpgMark Hunter

If you were to meet Ross (not his real name), you would say there is no way he could ever be successful in sales. He always was quick to say he wasn’t that smart, not organized and certainly not aggressive, yet the numbers he posted each month blew away everyone else in his company.

Although on the surface Ross didn’t seem like he could sell, he actually could because of one thing -- his personality. He led with his personality, whether it be on the phone, in a message or in person. His ability to remember personal information about others and the way he could relate to them was simply amazing.

The result was Ross was able to uncover information from customers that his competitors had no chance of ever knowing. His personality allowed him to be invited into customer meetings and literally handed the business. He won because of his ability to disarm the customer and his ability to be seen not as a salesperson, but as a trusted friend.

Saving Lives and Saving Sales

shari-levitin.jpgShari Levitin (from her upcoming book: Heart and Sell)

Tim never pictured himself in sales. He’d earned his helicopter pilot’s license in New York, his commercial pilot’s license in Michigan, and he’d graduated from nursing school in Seattle. He had flown hundreds of patients per year to emergency rooms by medical helicopter. He was proud of his work saving lives.

But Tim was frustrated: competitors in the medevac business were crushing his business. “How do I convince hospitals that our flight program is better than the competition?” he asked me. “We’re cheaper. In fact, we charge 38% less!” Tim was so convinced of the incredible value he offered, he pitched his services solely on price savings. After he told me this, I paused.

“Do you have any children?” I asked him.

“Yes,” he said. “My son is eleven.”

“Imagine getting a phone call. It’s terrible news. Your son has suffered a snowboarding accident,” I said. “It’s life-threatening. In the moment you receive that call from Ski Patrol, do you care at all about the price of emergency helicopter transport?”

“Absolutely not,” he replied.    

“Neither do your customers,” I told him. “They care about one thing: saving lives. You’re focusing on the wrong benefit.  What’s the real metric hospitals use to judge medical helicopter companies?”

“Survival rate,” he told me.

“Perfect,” I said.  “So what is your company’s survival rate compared to your competition’s?”

“It’s a million times better.”

“Really!” I exclaimed. “How come? What makes the difference for you guys?”

“We have much better medical practitioners,” he assured me. “We’re farther away, so it takes a little longer for us to arrive at the scene.  But the quality of care we provide more than makes up for the slight difference in arrival time.”

Tim told me a story about a high-school boy who was recently in an accident. “The competitor’s equipment broke down,” he said. “So we transferred the boy to our helicopter. We had to resuscitate him three times on the way to the hospital. But he arrived alive. We returned him to his family three days later.”

He continued, “Two weeks went by. I was sitting in a Starbucks when a middle-aged woman recognized me and broke into tears. She said, ‘You… you saved Brandon’s life.’”

After a bit of coaching, Tim changed his presentation. Instead of talking about price, he focused on the emotional benefits of using his company. He didn’t shy away from asking customers a very straightforward question: “What’s more important to you in choosing a provider--speed of arrival or number of lives saved?”

I spoke to Tim a month after our session. He’d just landed the biggest contract in his company’s history. How? He’d simply asked the right questions and told the story of saving the high-school student.

Wisdom of the Ages

jack-kosakowski.jpgJack Kosakowski

My grandfather was the most successful salesperson I ever know… That probably shouldn’t have been. He had to pay rent at 14 years old. He didn’t get past middle school graduation because he was working full-time at 14 years. He was a car mechanic and brick layer until his early 30’s. At 30 he took his first sales job selling pots and pans door-to-door. At 40 he was selling heat and smoke detectors knocking doors and making cold calls. 

He ended up becoming the most successful sales practitioner and leader at Masterguard until the day he retired. Nobody could beat him for many years.

He was successful and shouldn’t have been… Because he made a commitment to winning at all costs. He was committed to learning more than everyone else about his product. He was committed to giving the best buyer experience than anyone else. He was committed to winning more than anyone else. Commitment beats talent and hard work any day. When you are committed to winning… Winning is all you know.


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