There is a 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. 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 including how to determine if a career in sales is right for you, how to cultivate productive relationships with clients and coworkers while still ensuring one’s professional development, and how to leverage a diverse set of tactics as the future of sales evolves.
Whether you’re 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.
Drew Applebaum: Hey listeners, my name is Drew Applebaum and I’m excited to be here today with Jesse Rothstein, author of Carry That Quota. Jesse, I’m excited you’re here, welcome to the Author Hour podcast.
Jesse Rothstein: Thanks for having me Drew.
Drew Applebaum: You’re welcome. First, can you tell us a little bit about your background?
Jesse Rothstein: I am sort of a career sales professional. I have been in the profession 15 plus years and have worked in sales across a number of different places around the world, for a number of different companies. I pride myself on doing it in a way that maximizes the relationships on both sides of the sales equation. Both the customer as well as the seller.
Drew Applebaum: What inspired you to write this book?
Jesse Rothstein: Yeah, it’s a good question. I think it’s a couple of things, I would say, for me, I’ve had the opportunity to experience a number of different things in my life through work, through family, through friends. And throughout the years and as I’ve gotten older, I’ve thought a lot more about the concept of legacy. The idea and the notion of what will be around when I, or you, or we all are not around anymore.
This book is a manifestation of a number of things. But it’s primarily around this idea of creating something that can help others, specifically, salespeople, get better at their craft. And something that will be around as part of my legacy when I’m no longer here.
Drew Applebaum: You mentioned that this book is for sales reps. But I think it goes beyond that, do you see other industries being able to read this book and take some tips and tricks away from it as well?
Jesse Rothstein: Yes, in the book, there are some very specific tactical things that are related to what I would call just basic productivity in the modern world. Many of them can be applied to salespeople but almost all of them can be applied to people that are not necessarily salespeople by trade.
How you communicate, how you manage your time, how you follow through, how you research, these are things that all apply to many different professions, not just sales.
Drew Applebaum: You start the book with a quote, “Whether you realize it or not, we’re all salespeople.” Can you explain this thought to us?
Jesse Rothstein: Yeah. Throughout our lives, whether it’s at work or at home, I’m sure we’ve all been in situations where we’ve had to sell an idea or a concept. I have vivid memories of trying to persuade and to sell my parents when I was little why my brother and I should be able to stay up late if there was a movie or a game we wanted to watch. Or, my wife tells me stories of how she would always try to sell her older brother on why she should tag along with him for his newspaper route and why that was a good idea.
What I’m getting at is, selling an idea and communicating an idea and getting a person or a group of people to understand that and to reason with you is a skill. I think in all of life’s endeavors, trying to sell or persuade someone comes up all the time, it’s just not always called sales.
Drew Applebaum: Yeah, totally agree with you there. One of my favorite parts of the book is you tell a lot of personal stories in there including some of the early lessons you learned about how to conduct sales the right way. Can you tell us about learning sales the right way?
Jesse Rothstein: Yeah, I’m a big believer in the currency of business and the life of relationships. I think relationships are really founded upon this idea of building trust and showing value. When you’re trying to establish trust and show value, I think you really need to realize that you only get one chance to make a first impression. Your brand follows you forever, your personal brand follows you forever. I think when sales is done the right way, it’s done in a way that both the seller and the customer feel that there was trust built and there was mutual value that was gained from the interaction.
I think that when it’s done the right way, there’s a feeling that the seller can always go back to the customer and maybe ask for a referral. And the customer or the buyer feels so inspired and good about the interaction that they’re willing to provide a referral or a recommendation to that seller. I think when it’s done the right way, it’s a really beautiful thing.
Drew Applebaum: For a lot of folks, a sales position is their first job and they’re excited about heading to work but a lot of them burn out quickly and they’ll start looking for another position soon. Talk to us about the question’s folks should ask themselves to know if a career in sales is right for them.
Jesse Rothstein: I think the first thing that I would say is sales requires a tremendous amount of self-awareness. I think, depending on where people are in their maturity level, self-awareness comes for people at different ages. I’ll be the first to admit, I was very insecure at a young age and still to a certain extent at times am insecure about certain things.
I think as I’ve gotten older, I become more self-aware. But I think people need to realize in sales, you’ve got to be self-aware. Why is that? Well, you’re going to hear and know a lot, you’re going to get rejected, you’re going to hear people tell you that they’re not interested, you’re going to hear people basically push back on you and say, “Hey thanks, but no thanks.” And I think, if you are okay and comfortable in your own skin, you’re confident, then by hearing “No,” and being rejected more and more, you’re going to bounce back and be more persistent, which is a big part of sales.
I think the other thing is, to a certain extent, you’ve got to like interacting with people and you’ve got to have energy for interacting with people whether it’s virtually or in person. Not all salespeople are extroverts, many great salespeople are introverts but sales is a people-oriented profession. If you like doing work in research and more introspective type stuff, sales may not be right for you, but you’ve got to factor in that extrovert or interaction type of calibration, that’s part of the profession.
Successful in Sales
Drew Applebaum: Yeah, are there certain personality characteristics that you found are helpful to be successful in sales?
Jesse Rothstein: There are. I think sales often gets a bad rap. I think society often thinks that salespeople are not intelligent. I would argue that being intelligent, being sharp, being organized, being unbelievably maniacal, and conscientious with your time, those are just a few things in terms of personality traits. I also think you’ve got to have a tremendous motor, you’ve got to have a tremendous level of energy to not only do it well over the course of an hour or a day or a couple of days but you’ve got to have a tremendous level of endurance and stamina to do it over time. Because it’s a very up and down type of profession.
Drew Applebaum: Talk to us about some of the main pros and cons and essentially the pros should outweigh the cons to decide if this career is right for you.
Jesse Rothstein: Starting with the pros, the ability to learn. My favorite thing about the profession is that it’s essentially this unbelievable, never-ending learning journey. Whether it’s learning about people, the companies these people work at, the industries they’re in, what other companies are doing, how their companies are reacting to things going on in the world.
You get this exposure to learn literally every single day. I think, as people stay hungry and they want to learn, I just think that’s a really healthy kind of life skill. The second thing that’s a pro, I think, is sales offers this ability for you as the seller to compete with yourself. You know, it is a relatively competitive profession, but I find the best salespeople have this competitive drive with themselves where they always want to get better. I think from a human nature standpoint, that’s a really healthy thing.
On the con side, I eluded to this before, Drew–the ups and downs are taxing, it’s a very roller coaster-ish type of profession. It’s not always going to work out in your favor. A lot of times, you’re selling into a company and that company is going bankrupt and you’re not going to sell anything because that company is not going to be around anymore. Or you get lucky, right? You have companies expanding their business and they need a bunch of products and services and you happen to be there at the right time.
You didn’t do any work, you basically just were the salesperson who was the recipient of the order. The ups and downs can wear on you. I think the other thing that can wear on people is just the fact that it’s not easy to generate conversations with people on a consistent basis. Even though technology has expanded and there’s been a proliferation of ways to get in touch with people–you can call, you can text, you can reach out on social media, you can email–it’s still hard to get a conversation going with a new company or a new person. It’s getting harder and you hear and know a lot and you don’t get a conversation or a meeting schedule. It’s hard and it’s a really tough thing to deal with rejection on a consistent basis.
Drew Applebaum: Yeah, you actually use the analogy that sales is like running a marathon. Tell us why you compare the two?
Jesse Rothstein: On a personal level, I run marathons, I’ve been doing it the past 10, 15 years as a way to kind of counter-balance–have a little bit of an outlet outside of work. The reason I draw the parallel is that, the marathon itself and the discipline required to train and run the marathon is unbelievably challenging. When you’re actually in the marathon and you’re running, you’ve got to be at a fitness level where you can really go 15, 20, even to a certain extent, 23 miles before you feel the pain.
I’ve got a friend and a colleague and a mentor who always tells me, “When you think about sales, and you think about marathoning, you’ve got to seek the pain cave when you’re training for a marathon.” You’ve got to replicate the point in your training where you don’t think you can go anymore and then you have to keep going. And that’s a lot like sales because sales, like a marathon, just keeps going and going and going and you feel like it’s never going to end.
But if you can get to a mental point where when that pain cave hits, and you can get through that, you could do anything, whether it’s in a marathon or in sales.
Drew Applebaum: Absolutely, I totally agree with that. We all know life on the road is hard for a salesman and you spend time speaking about how self-care is extremely important. Can you identify some of the strategies that you use to make sure you’re staying your best self and keeping healthy while on the road?
Jesse Rothstein: This doesn’t get talked about enough in the sales profession or, quite honestly, I think in business in general. You think about self-care and there’s a lot of things that are involved in that from a sleep standpoint, from a nutrition standpoint, from an exercise standpoint. I talk about it in the book, how I learned about this the hard way and I had an experience where I was very sick with the flu and a fever while I was on the road. It was not a good situation.
I think that people really need to think about self-care and manifest self-care when on the road but also when they’re not on the road because it becomes part of their routine. Getting the sleep that their body needs, eating the right way, exercising, and doing other things to escape the day to day of the work. It helps them obviously be better when they’re on and working.
That requires planning, it requires time management and to a certain extent, the mental discipline to do it consistently. Because if you’re not consistently practicing that self-care, every day, every week, you’ll burn out.
Drew Applebaum: You mentioned that being successful in sales has a great deal to do with building relationships. You use a quote in the book, “Relationships rule the world.” Tell us about those challenges and the most important steps a salesperson can take when building a long-term relationship with their clients?
Jesse Rothstein: Yeah, when I think about building relationships with clients, I think about differentiation. I had a client years ago who is now a friend and to a certain extent, a mentor, share with me very early on in my career that if you’re just like everybody else, you’re just like everybody else.
That really hit me hard. I was in my mid-20s, when we had this conversation. I think really good people in society in general, they’re different, they’re unique. They bring something to the table that makes you want to see them again, you want to interact with them, they’re inquisitive, they’re interesting, they’re doing things to help you as a person. When it comes back to sales and comes back to relationships, you have to remember, most people that are dealing with salespeople, they make the stereotype that all salespeople are the same and there’s no differentiation.
So, if you as a salesperson can differentiate and show that you’re different, you can set yourself apart. Now, that takes time, you don’t do that in a 30-minute phone conversation. But when people realize that you are different and you can add value and you’re not just all about the sale, then it often leads to a very fruitful relationship.
Drew Applebaum: You also mentioned an important skill is just getting in the door with the client. I’d love to hear a personal story of yours, about the time you went above and beyond to get into the door with a client.
Jesse Rothstein: Drew, I would say that this is one of the hardest things to do in business. It’s “I,” or “We,” or “My company” wants to talk to this person or this company or this group of people–and we want to get in and have a meeting or have a call and it’s hard. It is really hard because people often don’t respond to cold phone calls, cold emails, cold outreach, it is really hard.
I’ll share a story where I wanted to get in front of a very senior executive, that was the senior executive that the customer that I was doing work with. I had never been able to put a face with a name of this executive and I actually found out that this executive was going to be doing a charity event around a very large kind of community endeavor. I got involved early with the same community endeavor and I knew that the executive was going to be at the event, at that time, on that date and I wound up connecting my schedule. I figured out his schedule so that we were essentially going to have what he thought was a serendipitous type of interaction. But I knew was happening months in advance.
That interaction, that handshake, that face-to-face contact then led to the initial stage of a relationship being established. Now as time has gone on, we always talk about that initial time we met. I have told him the story about how I knew that he was going to be involved at that event and that is how I got to him. I learned that information by listening on the news, on social media, and other channels to know that this senior executive happened to be involved with this particular organization.
Drew Applebaum: And now that you’ve established that relationship, how do you build trust with that client?
Jesse Rothstein: Building trust is something that takes a lot of time. I think it requires a lot of consistency. I think the level of transparency that I bring to relationships, both client relationships and also personal relationships is something that I pride myself on. I’ll be the first to tell a client that they may not need the product or service that we’re selling. I will also tell the client what I think they should do in certain situations even if that means talking myself out of a sale.
I am not afraid to do that because I think about building those relationships, not just for that moment in time but for the length of the lifetime or the relationship. So that in five or ten or fifteen years if that client is in a bind and they need some advice on something, they feel that they can call me or email me anytime to get that perspective. I often will approach those relationships with a 30, 40, 50-year lens and that I want this person to see value in me and my brand, and my company not just for that exact transaction or that moment but for a very long time.
Drew Applebaum: You have a chapter in the book about coworkers and we all know that in a sales environment it’s a team effort within a company and there are many hands needed to deliver. Navigating those relationships is really tough so how do you build strong relationships with coworkers?
Jesse Rothstein: Yeah, so that is a valid point. We talk about it a lot in the book. I would say, the way I look at relationships with coworkers is the way I look at relationships with a lot of people. We talk about this in the book, but I think it hits on this point. In the world, in the business world and the personal world, I firmly believe there are two types of people in the world: “The ones that get it done and the ones that don’t.”
We all know this. There are people that you are going to meet and interact with that are going to follow through. They are going to do what they said they were going to do. And there’s others that won’t. They’re flaky, they don’t reply to your email, they don’t reply to your text message. They are just not going to get it done.
I think when you are talking about this in the context of coworkers, you’ve got to do your best to understand what makes these people tick. Often, you don’t necessarily have the same scorecard. You often don’t report to the same manager. You have different goals, different perspectives, different things you’re striving towards. I think finding out what that coworker’s ‘why’ is as quickly as possible helps you not only establish trust but helps you get things done with that coworker. So, following that kind of framework I think is extremely important.
Again, not to sugarcoat it, there are some coworkers who are fantastic. They are the ones who get it done. They care, they want to do the right thing, they follow through. And there are others that don’t and that’s just the world we live in.
Drew Applebaum: In the book, you talk about in order to grow as a salesperson you need to seek out challenges, training, and learning opportunities. Talk about these challenges and then the opportunities that sales reps can find.
Jesse Rothstein: Training and learning and overall personal development–I have found, over my last 15 plus years, it all starts and ends with you as the salesperson. You can’t rely on your company or your learning and development department or your sales effectiveness department to own how you want to get better. You have to have this intrinsic motivation and you have to delegate the time and the energy and the resources to get better.
That often means doing things on your own. Whether it is reading books, listening to podcasts, potentially taking some courses online or at some local universities. But my experience is that if salespeople want to get better at a skill or whatever it might be, they’ve got to be willing to do it themselves. You just can’t rely on anyone else.
Drew Applebaum: You spoke of this earlier in the interview about time management and that it is really important for sales reps. Can you give us some tips and tricks to keep salespeople focused?
Jesse Rothstein: So, time management I think is the single most important skill that a salesperson can and should master–full-stop. I am absolutely so shocked and so surprised at how companies do not allocate time and energy and resources and training to teach your salespeople how to manage their time better. I think it is so important, it demands a lot more time and attention that the people give it. The way that I think about it is time management actually starts with you as a salesperson allocating your time to manage your time.
It sounds a little weird but let me explain it in more detail. I find that when you allocate an hour or two, very early in the week or in some cases later in the week, to plan your time and plan your calendar so that what it is you should be doing and where you should be and all of the things that go onto your schedule, that in of itself provides a tremendous opportunity for you to be more productive. So that is tip number one–allocating time to plan your time.
The second thing is having the ability to block out time in your calendar for free form thinking. And what I mean by that is allocating time, whether it is in the middle of the day or early in the day, whenever it is best for you. We often don’t allocate time just to think and try to be creative. Then I think people need to do this because in the world we live in, you are being pinged and messaged–all the time you are wired in. If you don’t de-wire yourself and have some free moment of thought, you can’t be creative and you can’t think.
Then the third tip, which is very, very specific for salespeople, is to color-code your calendar and allocate a color for the revenue-producing client-oriented type of activities. Pick another color code that is what I would call internal non-revenue producing activities and make sure each week, you’re taking a look at that to maximize the amount of time you are spending on revenue-producing type of activities that are client-focused.
Too often, and this is quoted in the book and there is a lot of research on it, most salespeople today only spend about 25 to 30% of their time selling because they are bombarded with internal bullshit and things that are not relevant to sales. So, you, as a salesperson, can combat that by looking at those color codes and making sure that you are spending the majority of the time with the proactive revenue-producing type of activities.
Drew Applebaum: Now, you put all of these in the calendar. Give us some tips to develop a system of execution to make these ideas happen.
Jesse Rothstein: So, the tips that I follow and the methodology that I follow is actually rooted in something that has been developed called the Action Method. It was started by a company by the name of Behance, which was ultimately acquired by Adobe. I had a close friend who founded this company and who came up with the concept of the Action Method.
The action method essentially is a method in place where, whether you are at a meeting, with a client, or whether you’re talking to a college, you have a bulletproof system to mentally take notes of the action items that you have to get done. Then how, ultimately, you’re going to get them done as part of your own routine. In the book, I go through my own personal ebb and flow about how I capture action items and notes and how I put them into practice and then allocate them on the calendar.
I think that the main take away is every single interaction, every meeting, every conference call, every webinar–whatever it is you’re doing requires both prep time and follow-up time. And if you don’t allocate prep time and follow up time on the calendar, you’re not going to get the action items or the follow-ups done because you don’t have the time allocated to do them.
The Future of Sales
Drew Applebaum: Now towards the end of the book, you talk about the future of sales. What do you see the sales landscape looking like in the future?
Jesse Rothstein: First and foremost, there will always be a need for salespeople. Companies seeking to solve problems, in some cases very complex problems, will need salespeople–intelligent, smart, weathered salespeople to help navigate those challenges and make those decisions. I also think that the sales profession can and will shrink. This has obviously been researched and proven by companies like Gartner and the Corporate Executive Board.
I do think the profession will shrink because I think more and more companies can buy commodity-oriented services online. There’s just not as much differentiation because there’s so much that people can seek out online in terms of products and services, especially if they are commodity-oriented. I also think that sales will continue to move into a collaborative team-pack oriented activity. I think the days of the lone wolf salesperson–one salesperson covering one territory or one salesperson covering one account, I think those days are over.
I think that the challenges that companies and people are facing are much more complex and I think that there is going to be a need for more team and collaborative type of selling. Companies are responding that way because there’s just so much information out there, no one can really be a specialist in anything.
Drew Applebaum: Finally, which sale are you most proud of, or which connection that you’ve built are you most proud of?
Jesse Rothstein: You know to me, the sale and the signing of the contract is fun, it is exhilarating. And it’s, to a certain extent, a manifestation of a lot of hard work. I think for me the thing that I am most proud of and the connection, so to speak, that you allude to, that I am most proud of is the fact that I can go back to my current clients and my former clients and I can pick up the phone or send them a message and strike up a conversation or provide a referral or just reconnect with them.
That, to me, is really the stuff that I am most proud of. I pride myself on how I deal with people and I believe very firmly that the currency of business and life are relationships. That is the stuff that I am most proud of, those connections, those relationships that I have built and maintained over years. Almost more so than the sales themselves.
Drew Applebaum: Well, writing a book is no joke. So, first of all, congratulations and if readers could take away one or two things from your book, what would it be?
Jesse Rothstein: I would say that the title of the book is, Carry That Quota, that is a very kind of sales or business type of title. A sales quota, so to speak. But I believe we all stand for something bigger. I think each of us has the ability to carry something in our own lives, whether it is our work lives or our personal lives.
We carry that quota and each quota for all of us is a little bit different. I think people should take away from the book that whatever it is they’re doing, at work or at home, they should do it with a sense of sincerity and genuineness and a sense of follow-through. That they themselves are carrying their own brand. And in essence, their own quota. I think if we all did that and took pride in what we did, I think both at work and outside of work, the world would be a pretty good place in terms of how people operated.
Drew Applebaum: Jesse, this has been such a pleasure and I am excited for people to check out this book. Everyone, the book is called, Carry That Quota. You can find it on Amazon and besides checking out the book, where can people find you, Jesse?
Jesse Rothstein: Yeah, so I am available on LinkedIn, Twitter. I’ve got a newsletter on Substack that is available for people to follow. And I share thoughts and that is really the best way to get a hold of me, LinkedIn, Twitter, and Substack.
Drew Applebaum: Awesome, well thank you so much for coming on the Author Hour podcast.
Jesse Rothstein: Thanks for having me, Drew.