5 Things I’ve Learned From the World's Best Sellers

The $1M commission check. The 7-figure deal closed on the deck of a sun-drenched yacht. The massive quota dwarfed by the inevitable attainment to follow.

These are the results of the best sellers in the world.

My journey to find the faces behind these legends has led me from the unexplored depths of cryptocurrency sales to Silicon Valley’s fastest-growing tech companies. To sellers with $11M quotas, closets full of luxury watches, and walls of golden plaques chiseled with their names.

Speaking with them has unraveled a wealth of knowledge and revealed untold secrets to sales success.

I’m Karli Stone and these are the five things I’ve learned from the best sellers in the world.

#1: Be More than Customer-Centric. Be Customer-Crazed.

You’ve heard it a million times…

“Put the customer first!”

The general consensus will tell you this means pinpointing customer problems, asking relevant questions, and listening to the client’s needs.

Which is all fine and dandy, but for the best sellers in the world, these are just the table stakes. 

Care and attention for the customer run deeper.

Megan Wilson, Global Client Lead at Palo Alto Networks (now selling at Cloudflare), devotes every ounce of her energy to creating premier buying experiences for her customers.

So much so that she hits her 8-figure quota without ever having to glance at how she’s pacing.

Megan goes above and beyond by:

• Building end-to-end product plans that work back from her customer’s end goal
• Pushing back on superiors when they rush agreed-upon timelines
• Hopping on a plane to buy her clients a beer and sit down face-to-face
• And genuinely treating her customers like she would a friend

In this way, sellers become trusted consultants and valued partners.

#2: Any task that can be automated — should be

The best salespeople in the world are more productive than humanly possible.

When Nick Sanschagrin, Head of Sales at ChainStack, told me he sends between 2,000-3,000 outbound emails every two weeks – I didn’t believe him either.

“From cold emailing, I’ve met with 350 different prospects in the last six months, which translated to nearly one million dollars in net new revenue last year,” he told me all too casually.

His million-dollar strategy? Automating everything.

"I like to think 'How can I multiply Nick and reduce the effort that goes into getting a good output’."

Nick does a bit of his own research, schedules up to 500 personalized emails a day for the next two weeks, clicks a button, and voila!

He has time to focus on more “human” activities while the prospecting is done for him.

John Barrows, CEO of Sell Better by JB and trainer of over 100k sales reps, sees a sales future that’s completely automated.

But more from what I learned from John later…

#3: Your knowledge is a gift. Share it

Giving is one of the easiest ways to jumpstart a new relationship.

Kit Chandra sends stubborn gatekeepers fully-stocked edible arrangements. 

Megan Wilson will fly across the country to buy her client a drink.

These grand displays of attention are undoubtedly effective, but gifting also needs a strategy that’s scalable across the entire funnel.

Social selling guru Alex Boyd taught me that this can be as simple as sharing bits of knowledge.

“When you learn new things, talk about them,” he told me, “Pass on the knowledge, and don’t discount the value of what you know from your company and your customers.”

By consistently sharing his wins, losses, new learnings, and customer results across his LinkedIn, Alex has generated over $4.5M in revenue for his company RevenueZen.

He lists Sarah Brazier, another one of Apollo’s World’s Best Sellers, as a textbook example of how to publicly document your sales process and share your results.

Sarah does this by telling stories that inspire and delight her audience. She places her prospects at the center and makes them the hero.

“When you understand the structure of a story, and how the structure affects the audience's ability to absorb information logically and emotionally, sales conversations transform from stiff, robotic, interrogation sessions to an organic flow of ideas.”

From this idea, she’s created a LinkedIn lead generation flow that’s helped her amass 52k+ followers.

She's boiled down her advice into a simple way to get started, too:

1. Post something
2. See if anyone in your ICP engages
3. Check if they are a current opportunity
4. If YES, send them to the account owner
5. If NO, own the account
6. Create those conversations. (e.g. “Hey I saw your comment on my post, let’s talk about XYZ”)

#4: Curiosity closes deals

The best sellers in the world all agree on one thing: asking good questions and showing genuine curiosity is a salesperson’s biggest asset. 

In the age of AI and automation, John Barrows names it as one of the most essential skills sellers can have.

“No customer wants to be handed over 5x before they talk to someone who gives them value.”

Showing curiosity means not only uncovering what the buyer wants but why they want it. 

Joe Barhoum, a sales leader of 15+ years with a track record of closing multi-million dollar deals, leads with curiosity in every deal through his sales philosophy he calls The 4 Rules of Great Sellers.

“A prospect might say, ‘Give me a list of these 10 things’. Now, I could just build the list and hand it over, but there's a whole world in each one of those items. You’ve got to figure out why it’s important to them and if it meets their requirements or not and why.”

Human reasoning is infinitely complex and each of your buyers has an entire web of logic driving each decision (consciously or not). If you want to sell more and sell better, you need to untangle it.

Note: Speaking of curiosity, Alex Boyd has an awesome social selling strategy where he leverages customer curiosity by teasing them with just enough information to tempt them to reach out to him for more. Read about how he does it here.

#5: Growth opportunities aren’t always vertical

I’ve talked to salespeople enough to learn that their ambition goes farther than the commission check. 

It’s that next big career move — the promotion to AE, the big bump to team lead or sales manager, the inevitable rise to director, hell, why not CEO? — that keeps them picking up the phone.

But is success ever really that linear?  

Kit Chandra’s sales success story proves otherwise.

When he got fired as an AE, he made a horizontal move to customer success. He learned how to close in a safer environment, understand the entire customer lifecycle, and build genuine relationships. 

“The more you try to make a sale, the less you’ll make a sale,” Kit says. “The more you try to understand, the more you try to connect, the more you try to build actual influence based on logic and emotions, the better you end up doing.” 

He climbed the ladder as a CSM and went back to sales better and stronger, eventually becoming Twilio’s top-performing AE and a multi-million dollar deal closer.

He climbed the ladder as a CSM and went back to sales better and stronger, eventually becoming Twilio’s top-performing AE and a multi-million dollar deal closer.

I heard experiences like these echoed time and time again in my conversations.

Like Kaili Linville, who became Autodesk’s top seller because she learned how to get people using the product as a support person before pushing for a hard sell.

“Salespeople need to learn to find the connective tissue between the product and the company,” Jon Barrows says, “Promoting sales reps to CSMs helps sellers gather use cases and hear first-hand customer stories, while also helping them learn how to close in a safe environment.”

Moral of the story: look for growth opportunities outside of traditional career paths. Maybe they’re where you least expect them.