Sales Pro Shares Proven Techniques for Opening Doors and Crushing Quotas

Five in Five with Jonathan Jewett

By Stephanie Van Ness


In the past 20+ years, top sales performer Jonathan Jewett has sold tens of millions of dollars in enterprise software, and learned a few things along the way. In his book The 40 Best Sales Techniques Ever: Conquer the Leaderboard, Crash President’s Club, and Make More Money he offers proven strategies he and other successful sales pros use to beat their number.  

Last week he stopped by ViewPoint to offer insight relevant to our business and yours: how to create opportunities, understand potential customers and create a buzz around a brand.

1 You’ve had tremendous success and public failures in your sales career. How did those experiences inform the techniques you highlight in your book?

I’ve been on the front lines for many years. I’ve been a rep. I’ve been a manager. I still run a sales team so I’m always out there. I’ve learned that success in sales can be trial and error, since there’s no playbook. You learn when you win, and you learn when you lose. There are no college degrees offered in sales, and a lot of people who excel at sales didn’t choose the career but instead fell into it by circumstance.

I’ve discovered the most critical element that separates successful reps from those who are less so is execution. That’s why I wrote my book, which isn’t about sales theory. It’s about execution — giving people techniques they can implement right now to boost performance.

2  You’ve said, winners bring bold ideas to the table. How do you come up with the perfect idea to persuade a particular prospect?

There are no perfect ideas. But persuading a prospect is all about discovery — getting to know what is important to him. You need to understand his organization’s strategic goals and tie your value proposition to a key element of the company’s strategy. 

This is where big, bold thinking can really elevate your game. Don’t limit yourself by thinking only about the transaction in front of you.

Today is the age of disruption. Everyone is worried not only about the established competitors they’re familiar with, but startups that can shake up entire industries. Your prospect wants to know not only what these potentially disruptive companies are up to but how your prospect can compete. If you bring a bold, audacious idea that addresses this type of mission-critical, strategic concern your conversation will grow in importance.

3 Say I’m a salesperson. What’s the one piece of advice you’d give me to help me convince a new prospect that my product or service is the choice?

I’d say start by understanding how your prospect wants to buy. The hard sell — buy my product because it has these features and these benefits — isn’t necessarily the right tactic. In many cases, the less direct approach — showing a prospect you understand his issues, that you can relate — works best.

Here’s an example. I knew a rep at an outdoor equipment retailer who was far more successful than her fellow reps because she employed a more emotive sale. For instance, a customer carrying a perfectly functional backpack comes into the store, says he wants to replace it. Instead of simply directing him to the rack of new backpacks and rattling off the different features of the various packs, which would likely overwhelm him, she digs a little.

She asks him what he doesn’t like about his current pack. He says the straps chafe him on long hikes. Rather than immediately showing him packs with various strap configurations, she tells him about her last hike in Franconia Notch and how her pack annoyed her because the left strap kept slipping. She told him her hike experience wasn’t great because she ended the day with a very sore shoulder and back from constantly fiddling with the strap.

He could relate. And he now had confidence that she really understood and appreciated his problem and wanted to help him, not just make a quick sale. He left the store with not only a new backpack, but walking poles as well (upsell!) after she explained how they’d help decrease the impact on his shoulders and back from carrying a heavy pack.

The lesson? Create a relationship with your customer (based on shared experience, empathy etc.) and then offer something that will make a big impact for him.

4 How would you create excitement around the product or service you’re offering — generate buzz to intrigue your customers?

Salespeople must be great storytellers. They need to find ways to connect emotionally with customers and a great way is through stories. People remember stories long after they’ve forgotten about features and benefits. This applies to an individual sales rep selling to a prospect, as well as a brand marketing to its consumers. In both cases, the trick is to frame your story from your customer's perspective. Answer his most basic question: what will it (your offering) do for me?

Back to our backpack example. By sharing the story of her hike in the White Mountains the rep created a memorable narrative, rather than just spewing a laundry list of features. By then showing the customer her top three picks for his new backpack, the rep offered him a solution to his problem (chafing from the shoulder straps) that would make a big impact in his life (no more shoulder pain and the ability to comfortably enjoy much longer hikes). She probably also created a loyal customer because that hiker is likely to remember her and seek her out when shopping for his next outdoor excursion.

5 Change happens whether you’re ready or not. What advice do you offer to companies trying to create opportunity in a shifting landscape?

Be as informed as possible about what’s going on in your industry, and what’s happening with your customers and targets. Be visionary. Be well-connected. Technology can help. For instance, set up Google alerts so you’re notified about the latest developments with your target accounts and markets. Spend focused time on LinkedIn, learning about your customers and sharing information relevant to them. Find innovative ways to leverage your knowledge of important trends. Be part of the conversation. Don’t always look to sell. Look to build relationships.

Change is inevitable. But, don’t let it blindside you.

For more on Jewett’s sales tips, reach him at And, if you’d like to find out how your brand can leverage memorable storytelling to create a solid connection with your customers, get in touch with us here at ViewPoint at

Stephanie Van Ness

Assoc. Director of Marketing and Chief Storyteller at ICS, Boston UX and ViewPoint Interactive Solutions

An experienced copywriter with a Boston University J-school degree, Stephanie Van Ness writes about user experience (UX) design and innovations in technology, from self-driving vehicles to gesture-controlled medical devices. Her work has appeared in a number of industry publications, including Medical Design & Outsourcing, Mass Device, Connected World,Medical Device + Diagnostics, UX Collective and Prototypr.