Sell to Win

The history of sales: A look back at the greatest salespeople of all time

Ashwin Balakrishnan
Contributor, Sell to Win
Ashwin Balakrishnan
Contributor, Sell to Win
the history of sales greatest salesmen of all time greatest salespeople in history

There are two types of people that history tends to remember favorably: pioneers and supreme talent.

Military commanders, athletes, and scientists are just a few of the professions where such achievement naturally attracts a place in the human record.

Sales reps…not so much.

But without question, the business of convincing others to willingly part with their money is one that takes incredible skill. And it certainly merits a trip through time to look at some of the businesses and individuals who did great things before or better than anyone else.

The oldest organized sales teams in recorded history

Our world is home to many businesses that have been operating for lifetimes; several in Japan and Europe have been doing business for more than a millennium. However, many of them served either a limited catchment area or a single royal client, or provided a necessary service that required no convincing.

The organized sales team—an intentional effort to increase revenue—is a relatively recent development. Our research indicates that the oldest one of its kind was that of the East India Company, famous for its less-than-ethical product procurement methods.

Founded in 1600, two years before their Dutch equivalent, the East India Company sold textiles, precious metals, gemstones, spices, tea, and medical and industrial products acquired through colonial expansion in Asia.

Their primary method of sale was a simple catalog—the names of products for sale printed on parchment—that wealthy member merchants used in procurement and while meeting customers such as aristocrats, monarchs, and foreign merchants.

In the United States—where the pursuit of happiness and the pursuit of wealth are often two sides of the same coin—one sales team has been around longer than any other. That distinction goes to the Philadelphia Contributionship, an insurance collective co-founded by Benjamin Franklin in 1752.

Using door-to-door pitches and community selling, these founding insurers were the first to provide fire insurance to American businesses before there even was a United States of America. They would place “the company’s symbol cast in lead, depicting four hands clasped at the wrist, fastened to a square pine board” to signify that a property was insured.

They weren’t just pioneers in sales, but in branding too.

The first successful inside sales team

The information age has changed how people sell. Developments like local SEO and chatbots have made it easier for customers to find and buy from your business with minimal active effort from you.

A profession that once relied heavily on efforts like door-to-door pitches and site visits has largely given way to inside sales—the act of making money from a fixed location, historically via telephone (known today as telemarketing).

The first inside sales team in the United States (and by all accounts, the world) dialed its first prospects in 1957 as employees of the Life Circulation Company, which would later become DialAmerica after the acquisition of Time Magazine’s phone subscription unit.

Interestingly, this team was made up entirely of women, but not for the right reasons. Rather than their personable demeanor or experience making people feel comfortable, women were preferred because they were paid 40% less than men.

Going back further, the concept of the lead list existed as early as 1903, when New York-based Multi-Mailing Co. stalked researched phone books in 13 states and found 600,000 viable prospects. All of them were pre-qualified by virtue of owning a phone, a luxury that put them among the “best classes in their communities”.

Those leads were used for catalog- and mail-based advertising, which denies them the right to be called the first ever inside sales team.

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Tech unicorns built on brilliant sales teams

Billion-dollar valuations are the gold standard in modern business, especially if your company is involved with any kind of technology. These businesses built their financial strength on the backs of great sales teams, and while not all of them have achieved unicorn status (yet), their approaches to sales make them well placed for continued growth.

Apple puts everyone and everything on sales

Between people who lined up to buy the first iPods and iPhones, and those who watched Jobs a few too many times, the story of Apple’s revival in the 2000s and its ascent to a $3 trillion valuation is fairly well known.

Steve Jobs deserves much of the credit for aligning every facet of Apple’s business around two things: world-class products and a universal approach to selling.

In the iPhone era, Apple turned every part of its business and every non-engineering employee into varying degrees of sales rep.

Copywriters, creative designers, Apple Store employees, and even executives were collectively responsible for creating an Apple culture and ecosystem that practically sold itself.

Xero turns top customers into top sales reps

When Xero achieved unicorn status in the late 2010s, much of the credit went to its ability to scale well at every part of the growth journey.

After opening for business in 2009, the New Zealand-based accounting software quickly reached 12,000 customers using a blend of direct sales and inbound marketing. Rather than sitting on incremental growth for several years, Xero turned to its customers.

Accounting professionals who used Xero were invited to a newly launched reselling program, which took the SaaS to 135,000 customers in three years. Most impressively, 60% of these new customers were attributed to the affiliate program.

Terminus practices what it preaches to improve personalizations

While not a unicorn (they closed Series C in 2021 at a $400 million valuation), account-based marketing platform Terminus is an example of what happens when a great sales team walks their talk.

For Terminus, personalization wasn’t just the game they endorsed; it’s the strategy they implemented themselves. They combined different pieces of their tech stack and account-based methodology to create a seamless prospect research experience.

The two key shifts were integrating Sales Loft with Sales Navigator, and changing from a high-velocity model to an account-based one. This allowed their SDR team to layer in a heightened level of personalization by making sure each account contained:

  • Only the contacts relevant to the deal (champions and decision makers)
  • Engaging those individuals with as much specificity as possible
  • Feeding further insights into Sales Navigator to improve the next step of the cadence

In one specific instance, a cold opportunity was identified as potentially warm again when one of the account contacts shared an article about account-based marketing. The SDR lead was able to quickly send over a personalized, highly relevant email that took the deal from cold to late-stage in a matter of days.

Overall, the SDR team was able to save hours each week, added $600,000 in pipeline during the third quarter of 2020, and (most importantly) made every prospect account feel like they were being attended to personally.

Related: The Complete Guide to SaaS Sales

Record-breaking sales reps of the last century

If companies chase billion-dollar valuations, sales reps aspire to million-dollar commission checks. Selling enough product to buy a house and a car from the same deposit is a dream for many, but a reality reserved for the very best of the best.

Businesses like to stay tight-lipped about revenue. Even those required to disclose their figures tend not to go into detail, like how much of their income is attributable to direct sales. But individual sellers love to talk about their prowess.

Here are five of the more astounding individual sales achievements of the last 100 years.

  • Everyone knows Jordan Belfort from the semi-historical biopic The Wolf Of Wall Street, but the real JB is one of the most accomplished sellers of the 20century.Belfort was a naturally gifted seller who set up a process (admittedly a rather naughty one) that allowed his company to manage over $1 billion in assets at its peak. Law enforcement might have caught up to him, but that doesn’t take away from his ability to make a sale.

  • Ben Feldman (not the Superstore actor) holds the distinction of selling more life insurance than anyone else in history. His lifetime sales for New York Life total over $1.5 billion in face value. Feldman once sold more than $20 million worth of policy in one day and $100 million in a year, allowing him to cash in seven-figure annual commission checks.

  • When Michigan native Joe Girard made a sale during his first day on the job, no one knew he would eventually hold the Guinness world record for most cars sold in a career. He was fired two months later when his co-workers complained that he was too good at his job, leading him to Merollis Chevrolet in Eastpointe, Michigan (now closed). It was there, between 1963 and 1978, that Girard sold 13,001 vehicles with a single-year high (1,425) in 1973.

  • China and ecommerce are no strangers, with the likes of Alibaba and JD.com calling the Asian super-economy home. So it comes as no surprise that some of the country’s top influencers are also ecommerce specialists—none more accomplished than livestream specialist Viya. In 2020 on Singles’ Day (the country’s biggest spending event), she sold 8.5 billion yuan ($1.3 billion) worth of inventory.

  • Selling a high-ticket product is a double-edged sword. The commissions per unit are higher than average, but sales are much rarer and take greater effort to close. That’s why Anita Krizsan’s record-breaking achievement is all the more impressive. In 2012, Krizsan sold £13 million worth of Bugatti Veyron cars at around £1.6 million per unit — a single-year sales record for automotive dealerships. While eight cars in a year might not sound like much, consider that Bugatti only manufactured around 45 units a year, which makes Krizsan responsible for around 18% of their 2012 sales.

There will always be a place for those who can sell

The world may never enshrine expert sales reps in the same hallowed halls as hall-of-fame athletes, rock stars, and inventors. Truth be told, it makes sense that selling products isn’t held in the same esteem as pushing the limits of the human body or developing life-saving medical procedures.

Nonetheless, great selling takes great skill.

The very best in the business spend years learning how to elevate it from a transaction to an art form. Empathy, psychology, and active listening all play a major role and aren’t easily developed; if they were, banks would be overrun with people cashing huge commission checks.

The bottom line: Selling is a talent worth celebrating. Society might not be able to appreciate its nuances, but those of us fortunate enough to see it in action every day certainly do.

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