When Vincent Mudd first began making sales calls, he was given a territory and a book of business that had previously belonged to other sales reps. It did him little good; the contacts either refused to do business with him or found cheaper alternatives. Mudd called on them all year and got nowhere … until Halloween.

As the owner of Edmond, OK-based Mudd Print & Promo (asi/278114) recalls, he stuffed his six-foot-six, 240-pound frame into a Tigger costume with a “who-hoo-hoo-hoo” sound box and spring-loaded tail. He then visited all the clients who had refused to give him their business or who were particularly hostile to sales reps visiting them. “While I wasn’t 100% successful in winning everyone over,” he says, “I did generate new business from formerly dead accounts and elicited laughter and group photos everywhere I went.”

He continued the tradition for 10 years until, mysteriously, his Tigger costume went missing. So he purchased a new outfit, Mr. Incredible from the hit Pixar movie The Incredibles, which turned out to be even more successful at breaking down the resistance of front-office personnel. “Sure, sometimes the buyers were skeptical of my professionalism, me being dressed like a superhero,” Mudd says, “but after we created notepads to hand out with our superhero persona on the cover, even that resistance faded.”  

The costumes at Halloween were a surefire hit until 9/11 when, says Mudd, businesses would no longer allow masked-characters to enter the premises. “To this day, I haven’t found a more successful tool for getting past the stubborn front-office resistance that had plagued the reps before me,” he concludes. “I do dress up as Santa now at Christmas time, handing out chocolates to all our clients as I visit them, but I still haven’t had the success that Tigger and Mr. Incredible generated!”

Working in sales can be a constant struggle for survival. And in the quest to “always be closing,” salespeople will occasionally resort to the most daring, crazy, foolish and innovative attempts to win the deal. Taking risks and gambling on themselves is etched in their DNA.

But there’s a fine line between calculated risk and complete desperation, and walking that line is essential to finding sustained success. “You can put in the long hours, make the presentations and pitch multiple times before you make traction toward a sale,” says Zack Friedman, founder and CEO of personal finance company Make Lemonade and author of The Lemonade Life, which offers advice on the changes people can make to drive success in their lives. “What you don’t want is to appear desperate. It’s easy to recognize someone who is. The desperate salesperson is an unsuccessful salesperson.”

Persistence Pays Off

As the cliché goes, the definition of insanity is doing the same thing over and over again and expecting different results. By that logic, salespeople can be certifiably insane for the persistence they demonstrate in trying to win a client.

For years, Rollin Nelson, sales guru at Eau Claire, WI-based Impact Advertising, had been trying to land his electric company as a client. When he paid his monthly bill, he included his business card with a note that said “Please have Cindy (the marketing manager) call me.” Then, he dropped off spec samples and sent “checking in” emails, only to get no replies. He continued to send his card with fun notes for 10 months. Finally, the bill processor said to Cindy, “For Pete’s sake, call this poor guy!”

“She called, we met for coffee and the rest is history,” Nelson says, who discovered that he worked at a car dealership with her husband when Nelson was 19. Now he counts the electric company as a great client, and Cindy has given Nelson some orders that, with a double dose of Wisconsin metaphors, “are netting some serious cheddar.”

“There’s no set time limit when a salesperson should give up on a potential sale,” says Friedman. “Some sales take longer than others. Too often, the question is: How can I make a sale? The better question for salespeople to ask is this: How can I build a relationship and help this person? If you first lead by giving and helping others, you will demonstrate that you’re more trustworthy and others will be more willing to cooperate with you.”

In an ideal world, your ideas and expertise are enough to get you in the door and secure an order. In real life, there are often massive hurdles just to get to the buyer. But by listening and paying attention, you can break through.

“To this day, I haven’t found a more successful tool for getting past the stubborn front-office resistance that had plagued the reps before me.” Vincent Mudd, Mudd Print & Promo

Marty McDonald, president and CEO at Windsor Heights, IA-based McDonald Imaging Solutions Inc. (asi/522770), struggled for months trying to schedule an appointment with a potential client. It was nearly impossible getting to the decision-maker because there were several gate-keepers standing in McDonald’s way. Luckily, he acquired some useful information during a casual conversation.

“I heard that the CEO is a big hunter and even goes on safaris,” McDonald says. “I was at a promo show and saw a mug with a lid that made it look like a bullet. I ordered a personalized sample with the CEO’s name and the name of his company. I had it sent to my office and then put a handwritten note in the box. I FedEx’d it to the company and addressed it to the CEO.”

After a couple weeks, McDonald says he followed up with the executive secretary, who told him the CEO loved the gift and had even walked his name and card down to the vice president of marketing. McDonald scheduled an appointment with her, bringing a few samples of new products that fit their industry. She liked one of them so much, McDonald says, that she placed an order on their first sales call.

“Sometimes just listening to what your client wants, and delivering that, makes all the difference,” says Jim Gano, owner of New Jersey-based Crown Trophy of Flemington (asi/381147). Gano had been in negotiations for weeks, but his potential client had yet to commit to a deal. As he was talking with the buyer, Gano mentioned that he was traveling to Chicago in the next few days. The client just so happened to be from the Windy City and recommended local pizzeria Lou Malnati’s.

“I asked him what his favorite pie is, and he said the sausage is the best,” Gano says. “I told him ‘if you give me the contract, I will have two sausage pies shipped to you.’ He said, ‘I’ll bet.’ The next day he called me somewhat dumbfounded and said, ‘My wife just called and told me there’s a box from Lou Malnati’s that was delivered to my house and the packing slip says two sausage pies. My mouth is watering waiting to get home. I don’t know how you pulled that off, but you’ve got the contract.’”

Throwing a Hail Mary

Taking chances is essential to growth, as Top 40 distributor American Solutions for Business (ASB, asi/120075) can attest. After responding to an RFP for promotional hard goods, ASB was invited to make a formal presentation. During discovery, the distributor determined the prospect also had significant spend for apparel and print. However, ASB was told many times to only focus on the hard goods.

“As we developed the presentation, we decided we were going to tell the entire ASB story because it might be our only chance and we knew we could do everything better,” says Taylor Borst, ASB’s head of communications and public relations. “The spend in each category was significant and it was worth the risk.”

The ASB team making the presentation consisted of employees from different departments, creating a mix of men and women of various ages. As a result, the team decided to wear apparel decorated with the prospect’s logo – human models rather than mannequins. Each garment was different and incorporated a wide range of decorating methods. The team developed story boards showing apparel collections and brought racks with more apparel, in addition to a selection of customized hard goods that the prospect was initially interested in.

The day of the presentation, Borst says the team showed up at the prospect’s corporate office and went to the reception desk. “The attendant looked at our clothing, called the meeting host and said there were five employees in the lobby she had never met,” Borst says. “The clothing had made an impact. When the prospect kicked off the meeting, she shared the comment from the reception desk and her team laughed. Even though they kept reminding us the meeting was only addressing promo hard goods, they said everything we were showing was nicer than their current product.”  

“Sometimes just listening to what your client wants, and delivering that, makes all the difference.” Jim Gano, Crown Trophy of Flemington

Borst says the marketing director closed the meeting by telling them nothing would happen for a few weeks, as she was leaving on vacation immediately after the meeting. But before the team was left alone to pack everything up, the prospect asked to keep many of the samples, including some of the shirts literally off their backs. “Then they said they had a quick meeting while we were packing up and had decided to award ASB with ‘all’ their business in ‘all’ product categories,” Borst says. “Boom. Risk rewarded.”

Of course, not every outside-the-box strategy is going to pay off. Even thriving business owners have experienced some blunders on their way to high profitability.

In the early days of San Diego-based Team Phun (asi/342550), Jesse Goodwick, founder and principal owner of the company, took some calculated approaches to promoting the brand. His brother Jamie and friend Nick Moyal pounded the pavement, knocking on doors and posting Team Phun stickers on every stop sign near the beach shops in San Diego. “We gained really good traction in our local market, but we really wanted to land an account with one of the chain surf shops,” Goodwick says.

Multiple emails, samples, missed connections and a variety of guerilla marketing techniques led the startup nowhere. So Goodwick ended up giving his friends free merchandise to walk into multiple stores and ask the sales associates if they carried the Team Phun “Sunday Phunday” tanks, which were the company’s top seller at the time.

Then, Goodwick would go into the stores the next day and try to give them his sales pitch. “We thought this would give us leverage in sales,” he says. “To our dismay, it didn’t!” It took a few more years until Team Phun would do private label work for most of those accounts, Goodwick says, which they continue to service today.

It’s important to remember that if you don’t take the bat off your shoulder, you’ll never hit a home run. Of course, you may strike out, as in Don Gardiner’s case.

In 1979, the current creative marketing team manager at Bloomington, IN-based Winters Associates (asi/362390) had sold Chicagoland Chevy Dealers on the promotional idea of giving the first 25,000 fans at Comiskey Park a Jimmy the Greek Baseball Handbook. This 64-page guide to baseball – published by now-defunct promo supplier The National Research Bureau – featured scouting reports on all major league teams, both major and minor league schedules, ballpark layouts and ticket information. The front and back cover would highlight Chevrolet cars and area dealers.

Gardiner’s final task was to clear the promotion with then-Chicago White Sox owner Bill Veeck. By that point, Veeck had carved a remarkable trail of promotional ingenuity and infamy, from exploding scoreboards to team uniforms with shorts to coaxing a reluctant Harry Caray into singing “Take Me Out to the Ballgame” (which became synonymous with the broadcaster’s legacy). “I knew a little of his history and had figured he would love this idea,” Gardiner says. “After all, he was a man who took chances.”

Gardiner met Veeck in a small room by the Sox press box. At the time, Veeck was 65 years old with a splintered wooden leg, wearing a wrinkled shirt and glasses held together with white tape. (The title of his autobiography was Veeck, As In Wreck.) He liked the handbook’s wealth of information, as well as the idea of promoting local businesses, Gardiner says. But Veeck had one issue with the promotion: “Recently, we had a little problem with gambling around here and I don’t think the boys over at Major League Baseball will allow me to be associated with Jimmy the Greek.”

Gardiner was confused because although Jimmy the Greek was known for sports betting, he wasn’t aware of any recent controversies with the Sox.

“Surely, Don,” Veeck replied, “you remember the 1919 Black Sox scandal!” In that scandal, eight players were paid off by New York gambler Arnold Rothstein to throw the World Series.

“That was 60 years ago,” Gardiner replied.

“Love the idea, hate that Jimmy’s gambling reputation will nix the deal,” Veeck said in closing. Gardiner had to smile even though Veeck had wrecked the promotion. 

Eight men were out because of that scandal. Now it was nine. 

John Corrigan is a staff writer for Advantages. Tweet: @Notready4Radio. Contact: jcorrigan@asicentral.com