Your Best Salesperson Isn’t a Salesperson

This is part 3 of our content series “Adapt: Strong Advice for POS Resellers,” powered by Vend

As a young cash register salesman, Lefty Monson did everything by the book. Every day he would put on a pressed suit, tighten his necktie, stand up straight, and walk into a merchant establishment confident about selling them a new machine. Problem was when the business owner spotted Lefty on the sidewalk, he or she would run to the office in the back of the store and slam the door shut. Nobody wants to get cornered by a salesperson, and they’ll climb through thorn bushes to escape from one.

Undeterred, Lefty kept trying. Unconvinced, owners kept running. Until one day some customers’ cash registers needed swapped out and a technician wasn’t available. The job fell to Lefty, so he put on his baseball cap, a collared shirt and jeans and headed to the merchant locations. This time, the owners didn’t run away – they actually greeted him with a smile and warm “hello!” Lefty, being the helpful, friendly, kind-hearted person he’s always been, struck up conversations with them. Many of the owners even agreed to a new product demonstration the next time Lefty was in the area.

Partway through that day, Lefty had an epiphany. What if he kept his suit and tie in the closet and dressed casually for all his calls so he would present like the helper he naturally was as opposed to a stereotypical sales rep? More conversations would lead to more sales, right? His theory proved correct. Lefty never took off his baseball cap, casual shirt, and jeans, and for decades until his recent retirement, he was considered the POS channel’s greatest salesperson and sales trainer. Lefty was inducted into the RSPA (Retail Solutions Providers Association) Hall of Fame in 2012 because of his stellar work and influence on others.

Lefty Monson is a one-of-a-kind person, but his dilemma and his solution are not an aberration. I’ve learned from leading resellers that the best salesperson isn’t the one with the most hair gel, the strongest vocal cords, the most confidence, or the most sales tricks.

It’s the person who can genuinely empathize with the merchant owner, understanding pain from their perspective before offering an appropriate solution. It’s the person who is primarily focused on solving customer problems, not on hitting their own Q3 sales quota. It’s the person who is perceived by the merchant as a partner, not a product pusher.

There are two main sources where you can find this talent. The first is to recruit managers from merchants in the vertical you want to sell into. For example, to increase your sales in specialty retail, seek to recruit a retail manager (who is likely stressed by long hours) and pitch them that they can have their evenings and weekends back in a role with your company.

Pitching a job directly can be awkward – you don’t know them well enough, them saying “no” immediately seems rude, them saying “yes” seems desperate – so, instead, present the opportunity in general terms. Say something like, “We have an opening in a business development role. We’re looking for a friendly person with retail experience who would enjoy helping merchants run their business better. Do you know anyone who might be a good fit for that?”

Also, your job board postings should change dramatically. Don’t list the opening in Sales looking for prospectors and closers. Post in the Retail Manager section with the message “Looking for a change?”, hoping to attract someone with retail management experience. Your listing should focus on normal working hours, reclaiming evenings and weekends, and collaborating with fellow retail managers. Those are likely to be the points your target audience cares about most.

The second source of talent is inside your own company. Many resellers I’ve worked with have found success when they transform a technician into a Sales Engineer role. Think how powerful their experience would be when talking with a merchant. Instead of requiring your salesperson to memorize second-hand anecdotes, the Sales Engineer can simply interject, “I’ve run into this before and here’s how we solved that …” You might have to invest time training a tech-turned-Sales Engineer on some finer points of communication, but that’s often more manageable than teaching a sales lifer how to connect with a merchant.

One of my favorite books on this subject is The Trusted Advisor by David Maister, and my favorite section in that book is Maister’s list of 22 traits trusted advisors have in common. Among those attributes are “they don’t try to force things on us, they help us think things through, they always seem to have our interests at heart, and they act like a real person, not someone in a role.”

Always be on the lookout for naturally helpful, friendly people who could contribute to your organization in business development. I know a company who was attending a college job fair with hopes of hiring a well-dressed business or econ major to fill a sales opening. When the company recruiter arrived on campus, she couldn’t find a local newspaper to purchase. Several students and faculty walked past her. But one student sensed she was lost, offered directions, and he walked with her to find a paper.

Since he was a graduating senior – and because he was so helpful – the recruiter offered him a chance to interview for the sales job, even though his only work experience was cleaning offices in the evening. That conscientious student got the job and turned out to be one of the company’s best-ever Account Executives. His unassuming, inquisitive, low-pressure approach to prospects was endearing and allowed him to gather facts that helped him make the sale.

Your best salesperson isn’t a salesperson. They’re just someone who’s trying to help.

Adapt: Strong Advice for POS Resellers is powered by Vend. Used in over 25,000 stores around the world Vend is the point of sale of choice for inventory based retailers. Through our reseller program, we partner with ISOs, dealers, agents and merchant level salespeople to help our partners and merchants sell more, save more and make more. Learn more about our program.

Don’t forget to visit Vend at RetailNOW if you’re attending the conference later this month. They’re at booth #228, hosting a workshop on Hijacking Customer Success on Tuesday morning (July 30, 10:30am in Meeting Room 301), and one of their leaders Jake West will be joining a panel on VAR & ISV Secrets to Maximizing Your Vendor Partner Relationships on Wednesday (July 31, 10:40am in Meeting Room 302).

Adapt Part 1: 5 Fundamentals of POS Reseller Marketing

Adapt Part 2: Content Marketing Shortcuts for POS Resellers

Channel Business Advisor Jim Roddy works with high-initiative, growth-oriented point of sale VARs, ISVs, and MSPs to help them uncover their blind spots with customers, employees, and business best practices. Then he applies his 25+ years of business management experience, executive leadership, and retail IT industry expertise to help them get better. Jim can be reached at