Member preview

5 Sales Lessons From a Sales Rep Turned CEO

By Steve Benson, founder and CEO at Badger Maps

Sales is the most important life skill I’ve learned. In any role or situation, at minimum, you’re selling yourself. You’re pitching an idea, an opinion, or your qualifications all the time.

Selling a product isn’t any different. You need confidence in the solution you’re selling (and your ability to sell it). Confidence comes from knowing exactly how your solution will improve the life of your buyer.

Learning the principles of sales improves every area of your life. But how do you learn how to sell?

The secret is to listen.

When selling anything, it’s important to truly know your buyer. Understand their business. What drives them? What metrics do they care about? When you know what they want to accomplish you’re able to help them.

Taking the time to understand what drives your prospect also helps you differentiate yourself from the competition. Listen closely and you’ll learn what’s most important to them and what they’re afraid of. That allows you to bring the relevant aspects of your solution into the conversation and make them feel uniquely suited to the challenges your buyer is facing.

Sales is ultimately about value — you educate people on how your product or service can help them by listening and understanding their problem.

Grit always wins.

Everyone assumes successful salespeople are charismatic, extremely likable and attractive — the cliche of the ‘Dazzling Sales Rep’. Actually, the sales reps who perform best on modern sales teams are the ones who are organized, efficient, hard working, and who leverage technology in their process. The ones who succeed have grit.

All of these characteristics amplify the results a salesperson is able to make. Being charismatic doesn’t hurt, but it only gives you a slight edge. A rep with grit and creativity gets ahead by doing more. They talk to more leads and work more hours — which leads to more sales.

You’ll face a million obstacles in life, and you need grit to pound your way through them. When you run into a problem, wrap your head around it until you have a solid strategy. Then execute it. People often avoid doing hard things, but you can’t ignore them in sales.

Sales is a team sport.

Sales is often seen as an individual role. Actually, it’s a team role involving many parts of your own organization, as well as using your influence to indirectly manage things at other organizations.

Great salespeople have the ability to play quarterback on a deal with a lot of moving parts. You need to work closely with everyone from Legal to Product Management. You never know who might influence a decision, so it’s important to treat everyone like they have a say in whether the deal closes or not.

Optimize your sales process.

In sales, your process is how you find and close your opportunities. Think of your sales process as one big lifecycle and break it up into many small steps.

Your leads, people who might do business with you, are at the top of the funnel. The next stage are engaged leads, people who show interest. Following that are prospects — interested people who are qualified to buy. Then they turn into opportunities, deals waiting to be closed. Finally, you have a customer.

You lose some people at each stage of the funnel. Not everyone is interested, and not every interested person is qualified to buy. It’s important to pay attention to where people are in your sales process. You can’t treat everyone the same, that’s how you get labelled a “sleazy salesperson.” Meet people where they are in their decision making process and you’ll have an easier time selling them.

Your customers are your best salespeople.

Finally, it’s important not to overlook the importance of customer success. Work with your current customers to make them very successful and happy with you and your solution. This increases your close rate, reduces cancellations, and leads to a higher number of referrals.

When your customers refer their friends and colleagues to you, it shows that they’re especially happy with their experience. They become your best salespeople and help you grow your business.

Sales isn’t easy. It takes dedication, empathy, and the drive to improve every day. But if you’re willing to put in the time to learn how to sell, you’ll see positive results in every other area of your life, too.


Steven Benson is the Founder and CEO of Badger Maps, the #1 route planner for field salespeople. After receiving his MBA from Stanford, Steve’s career has been in field sales with companies like IBM, Autonomy, and Google — becoming Google Enterprise’s Top Performing Salesperson in the World in 2009. In 2012 Steve founded Badger Maps to help field salespeople be more successful.

Like what you read? Give Yitzi Weiner a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.