Carry That Quota: Sales Tactics and Stories By the Rep For the Rep

By Jesse Rothstein

In Carry That Quota, Jesse Rothstein provides an insider's account of how to succeed in sales. Drawing on more than 15 years of sales experience across multiple fields and continents, Rothstein unpacks numerous essential topics. Chief among them are how to determine if a career in sales is right for you, how to cultivate productive relationships with clients and co-workers while still ensuring one's professional development, and how to leverage a diverse set of tactics as the field evolves. Underpinning Rothstein's argument is the belief that sales is a craft—not dissimilar from a doctor performing surgery or a lawyer prosecuting a case—that demands a complex skillset and knowledge. Whether you are just beginning your career in sales, a seasoned executive, or a professional in another field looking to hone your brand, Carry That Quota will equip you with concrete strategies to help you sell yourself and/or service more effectively.

• Language: English
• Publisher: BookBaby
• Release date: Sep 22, 2020
• ISBN: 9781544514741

Book preview

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Copyright © 2020 Jesse Rothstein

All rights reserved.

ISBN: 978-1-5445-1474-1

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To Jen and Matilda

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For the sellers

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WD>WS

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Contents

Author’s Note

Foreword

Introduction

1. Sales as a Craft

Section One: Know Thyself

2. Is a Career in Sales Right for Me?

3. Self-Care

Section Two: Relationships

4. Customers

5. Coworkers

6. Professional Development

Section Three: Tools and Tips of the Trade

7. Time Management

8. Communication

9. Tools and Tricks of the Trade

10. The Future of Sales (Epilogue)

Quick Reference Guide

Acknowledgments

About the Author

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Everything comes to him who hustles while he waits.

—Thomas Edison

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Author’s Note

Carry That Quota is based on my experiences as a salesperson. All of the stories are real, though I have modified some details (including people’s names) to protect their privacy.

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Foreword

I recall the first time I heard about Jesse Rothstein in mid-2013. The most experienced and successful seller on my team approached me to tell me about someone different and special at his prospect account whom we should strongly consider hiring.

Which company? I asked, always on the lookout for top sales talent.

Staples, replied my seller.

The office furniture and office supplies company? I responded. Why would we hire someone from there? Thanks, but no thanks—doesn’t sound like the right background for us.

Within a few weeks, I had thankfully eased my position and had the opportunity to meet Jesse—over email and then in person—and got to experience firsthand what being sold to by Jesse felt like. His job was to rid me of my misconceptions that he wasn’t a fit to be an enterprise seller at LinkedIn. After extremely crisp and concise interviews, an exemplary role play, and strong background and reference checks, I decided to take an intelligent risk on Jesse to join the team.

Fast-forward to the year 2020. I’m confident to say that hiring Jesse has been one of my best business decisions to date. Hopefully through reading Carry That Quota, you will come to know and appreciate both him and the sales profession as I do, but let me first indulge some of my favorite attributes of our author.

Jesse makes everyone around him better. He is a leader by action, and those around him take notice and emulate his behaviors and attitude. He comes into work every day with purpose, conviction, and focus to help solve the problems of both his customers and his teammates. In fact, one of the C-level executives of his customer emailed LinkedIn’s former CEO Jeff Weiner directly to ensure that Jesse remained attached to their account. It’s the reason that his colleagues seek him out almost daily for deal-strategy sessions and general guidance.

Jesse is a student of the game. This shows up in his distinct style of salesmanship—the perfect combination of old-school and new-school sales tactics. He’s taken more traditional approaches like handwritten notes, personalization, and deep relationship building and made them core to his approach to modern selling. I’ve personally received roughly ten handwritten notes and gifts from Jesse in our time as friends—a relevant book, a letter of encouragement, a note of gratitude—that have always inspired me. It’s in these moments that I’ve been truly in awe of his ability to connect with people in meaningful ways.

But he’s not lost on the power of automation and technology and the scale and efficiencies gained by using the modern tools of today and was our best practitioner of applying modern selling approaches.

Finally, Jesse is a challenger. In almost all of life’s endeavors, there are few things that come without blood, sweat, and tears. Jesse is someone who shows up daily with an insatiable commitment to his company, his colleagues, and his customers. He is intent on making the lives of these people better. It’s as if the question, How can I help? is forever ingrained in his thoughts and actions.

I’ve led sales teams on multiple continents for almost fifteen years at some of the fastest-growing and most successful technology companies in the world. In that time, I’ve partnered alongside thousands of salespeople and experienced the ups and downs of the sales profession.

However, not until I met Jesse had I experienced a sales professional who cared so deeply about helping others succeed. He marvels in the art and science—as well as the history and future—of the sales profession. In many ways, Jesse has been a mentor to me these past few years and is the perfect person to showcase the opportunities that come from a career in the sales profession.

I hope you take the time to read Carry That Quota and share it with others in your network. The words in this book have application for everyone in the sales profession.

—Matt Loop

Head of Asia, Slack Technologies

December 2019

Sydney, Australia

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Introduction

Whether we realize it or not, we are all salespeople.

Most people don’t realize this. Sure, not everyone sells professionally for a living. But we all represent a brand and attempt to get people to invest their time in us and our ideas. Instead of appreciating that fact, however, salespeople are often viewed with disdain. Have you ever been reticent (even ever so slightly) to tell a stranger or a family member what you do for a living? How many times have you encountered an obstacle with a client because of the caricature of the snake-oil salesman or the overly aggressive used car salesperson? Anecdotes and metaphors like these contribute to the sales profession having a negative connotation.

I see sales very differently. From my point of view, sales is a craft—not dissimilar from a doctor performing surgery or a lawyer prosecuting a case—that is both applicable to a wide variety of people and integral to helping people solve problems. When framed that way, sales takes on a whole different meaning. Although there might never be a movie made about the noble hero salesman, we contribute to the world in a meaningful way. I am motivated by my belief that the sales profession is often undervalued.

I’ve sold my entire professional career, and I love the profession. As a result of fifteen years in the field, I’ve attended hundreds of meetings and taken thousands of pages of notes. I’ve also read the many wonderful sales books on the market and highly recommend that you read them, too. Nonetheless, Carry That Quota is designed to fill a particular niche. No one has written a book that is for the rep and by the rep and a relatively young sales rep at that. My hope is that by providing insights while I’m in the trenches, I can offer a unique perspective on the sales profession.

This book is designed for young salespeople who can learn from my first fifteen years in the field. However, I also hope it proves valuable to all salespeople, regardless of their age and experience, and to a broader audience. Because ultimately, the intention of this book is simple—I want to help salespeople get better at the profession. I’m not proposing that every idea in this book will be relevant for everyone in sales, but my experience tells me that great salespeople should always be looking for an edge, an extra piece of information, or a way to do their job better. That is what this book is designed to do—to provide little tidbits or ideas that may help salespeople get better at their jobs. The book is a collection of ideas and things that have proved valuable for me in the last fifteen years of sales. I hope they help you as much as they have helped me.

This book is also part of my legacy. It’s been brewing in my mind since 2015, after a meeting with Jamie Stone, a client and friend with whom I was working at the time. I have immense respect for Jamie. He is an exceptional businessman (he would later become CEO of one of New Zealand’s largest banks). But more importantly, Jamie, like many New Zealanders, places a tremendous emphasis on legacy, the idea that your life directly connects to what the generations before you did and that you have an obligation to bestow this knowledge and these experiences to the next generation.1 Jamie suggested that I think more deeply about my legacy. What about doing something that will be around when you are long gone? he asked. Have you ever thought about writing a book?

It was the first time that the idea of writing a book entered my mind. But here we are, and I tell the story because, as you’ll come to see from this book, I see sales—and work in general—in the broader context of our purpose in life and what we leave behind. Thus, the title of this book, Carry That Quota, is not just about exceeding a sales target but also about the quota we carry in life. What I mean by this is that there should be a sense that we all stand for something. To me, that means embracing the concept of leaving a place better than we found it, in our lives and at work. I care deeply about my legacy and want to share what I’ve learned with you. I’ve felt the pain from preventable failures and can give you strategies, so you don’t have to make those mistakes. I’ve hit the road long and often and want to make it easier for those who come after me. I’ve carefully crafted a work-life balance that helps me be more productive during my on hours so I can enjoy my off hours more. So, I amassed my notes to share all of these things and more with you. I hope my ideas and experiences improve not only your work but also your life.

Whatever your motivation for picking up this book is, I can’t wait to help you improve so you, too, can carry that quota.

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1 For more on the importance of legacy in New Zealand, see James Kerr, Legacy: What the All Blacks Can Teach Us about the Business of Life (London: Constable & Robinson, 2013).

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Chapter One

1. Sales as a Craft

I knew it was an oh shit moment.

I was fourteen years old and working at Yellow Shed Antiques, a store in my hometown of Mahopac, New York. The store was full of everything from jewelry to furniture to stamps—it was a unique retail setup with decades of antiques all under one roof. The owner was Larry Moore, a close family friend and skilled businessman. One of my jobs was packaging and moving goods that customers had purchased, and on a cold evening in early December 1997, that meant working with my friend Jacob, Larry’s son, to move a sizable dresser with a large mirror. Larry had given us very specific instructions when handling furniture like this—we were supposed to remove the mirror and the drawers and transfer everything piece by piece.

Well, on this night, we were acting like overconfident teenagers and didn’t want to take the extra twenty minutes to remove and reattach the mirror.

You can probably guess where this is going.

The mirror was attached to the base of the dresser, and, sure enough, when we picked it up, we clipped a light fixture, and the mirror quickly came unhinged, fell, and shattered. Breaking glass is never a pleasant sound, but this time it was just horrific. I closed my eyes and clenched my fists in frustration. I wanted to scream, but I knew better and held my emotions in check.

Soon, I picked up on a sound that, at least at that time, was even worse than glass shattering—I heard footsteps. Seconds later, Larry appeared. Sporting slacks with a cardigan and dress shirt and reading glasses hanging around his neck, he calmly asked us to clean up the broken glass and begin the process of ordering a replacement mirror for the dresser. There was no screaming fit and no lecture. We knew what we were supposed to do and had gotten lazy. The cost of the mirror would come out of our paychecks, and we would be expected to reassemble the furniture with a new mirror.

I would have felt better if Larry had screamed at us.

I had started working at the Yellow Shed Antique store because my parents felt it was important for me to get a job in high school and learn what it meant to balance a part-time job with my studies; I think they wanted me to experience working with my back (physically) so that I would see the benefits of working