Jeff Kirchick of ‘Next Caller’: “Prospecting”

Ask the person to tell you “no.” I mean, not literally, but it’s OK to be direct with people. A chapter in my book is called “The Customer Is Not Always Right.” We have this idea that you need to be deferential to people if you are selling something to them. Well, are you deferential […]

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Ask the person to tell you “no.” I mean, not literally, but it’s OK to be direct with people. A chapter in my book is called “The Customer Is Not Always Right.” We have this idea that you need to be deferential to people if you are selling something to them. Well, are you deferential to your best friend or your spouse when they offend you? Or do you stand up for yourself because you have built trust with them? Chances are, you emerge stronger in your relationship because you told them how they made you upset. Why is it any different in sales? Ask the customer if your solution is a priority for them or not, and let them know that you need to move on if it isn’t. If anything, this will force them to at least open up to you about what is going on. But if you just keep following up by essentially nagging the person without really laying out what is at stake for you or why your time matters, then why would you expect to get a meaningful response? You won’t.

As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Jeff Kirchick.

Jeff Kirchick is Vice President of Enterprise Sales for Next Caller, a Y-Combinator backed technology company based out of New York City. In his role at Next Caller, he has helped lead the company by managing the sales team while also selling to some of the largest companies in the world. What sets him apart has been his ability to build authentic relationships with his customers. He has led a successful sales career for over a decade and spends much of his free time mentoring younger sales professionals who are interested in sales as a career, particularly those who come from underrepresented backgrounds in tech sales.

Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

Sure. Growing up, I was all about playing sports. You could not take me away from a baseball and glove or a soccer ball, and I wrestled throughout high school and parts of college. My dream was always to become a professional athlete, and I can still remember running errands with my mom and me swinging an imaginary baseball bat in stores as I daydreamed about making it someday. Like most kids who have this dream, unfortunately, I eventually realized I would need to do something else for a career. I was fortunate enough to get a great education at Princeton University, but I had had no real vision of what I wanted to be because I was interested in so many things. I applied for teaching jobs, consulting jobs, jobs in sports, and so on. Eventually, I stumbled upon a sales role for a tech company in Boston. All that competitive sports stuff I had done growing up had helped me to become a very hard worker. I believed in myself and my work ethic and I liked the idea of “writing my own paycheck” in sales. So I took that sales job, and the rest is history.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

Early in my sales career, I somehow booked a meeting with the President of Las Vegas Sands. Me and my boss got escorted through the casino past all sorts of security desks and were led to this ridiculous office on a high floor of the Palazzo in Las Vegas. We were then led into a magnificent office with its own pool and all sorts of other amenities. The guy walked out and the first thing he did was fix my collar and said, “You went to Princeton and you can’t even get yourself collar stays?”, and then sat down. I felt like I just got kicked in the balls. In the moment, I kind of choked up. But looking back on it, that was just the way that guy was, he just had a special brand of humor. The takeaway here is that everyone puts their pants on the same way you do. Don’t psych yourself out with people. I ended up having a great meeting, because I recovered from feeling embarrassed for a little while. People are just people: don’t allow yourself to spin yarns in your own mind that they are any different than you.

Are you working on any exciting new projects now? How do you think that will help people?

Yes, I just wrote a book, Authentic Selling: How to Use the Principles of Sales in Everyday Life. It discusses the emergence of Machine Learning and Artificial Intelligence and how these new trends make our authenticity — really, our humanity — more important than ever. Not just because our authenticity separates us from machines and helps us to not be replaced by them, but also because people sense and appreciate authenticity in many different ways. We can sniff out honesty, accountability, empathy, etc. fairly easily. I hope the book will help everyday people to realize they are always selling themselves and being sold to, and that taking an authentic approach to relationships will just make them so much happier. Especially in today’s broken dialogue, I hope it can enable some positive change and encourage people to be more interested in listening rather than being right all the time.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

That would definitely be my high school wrestling coach, Steve Ward. He always did and said what he wanted to do and say whether it was going to be popular or not. And he never minced words. For example, if someone on the team was going to face an unbeatable opponent, he would call it a “bag of sticks match.” That is allegedly because snakes snap the bones of their prey before easing up their grip, so the idea was that you should bring a bag of sticks with you to snap and fool the opponent into easing their grip prematurely. It might seem cruel that he did that, but he was always funny about it, and if anything, it helped people relax because it kind of was a subtler way of saying, “Just go out there and have fun.” He would give out awards after every match, and one of those awards was called “The Gumba,” which went to the person who had the weirdest or funniest thing happen to them at the meet. He just made everything easy and accessible in that way. He was a great mentor to me who was always very real with me about everything, whether I was going to like it or not. I always remember how motivated I was to succeed for him. A good leader has that effect on people.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

Well, something I talk about in my book is the idea of Inception, which is really about showing rather than telling. In my experience, people do not like being told to adopt an idea, because then the idea is not theirs. People like coming up with ideas on their own. So I would hope that people might be affected by what they read in this brief interview in some way to hopefully feel on their own that I have some useful insights. But for those who want to get to brass tacks, I have been in sales for over a decade and I am currently the sales leader for a Y-Combinator tech company called Next Caller, and I have effectively grown the company by negotiating multi-million dollar contracts with several of the Fortune 500. I take a slightly different approach to my selling than what you might obtain in traditional sales training programs and have received tremendous feedback. The most important statistic of all, to me, is that we have zero churn amongst our customer base. And of course, I recently published the aforementioned book.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

Validate their feelings and assure them they are not alone. The times I have felt I suffered the most in my life were times when I thought that the suffering was unique to me. There are things that have happened to me in my life that are so awful that I am not prepared to even tell them to you, and yet those things have happened to other people too. There is actually a psychological element to feeling better knowing that you are not suffering alone. Think of when you buy a deal on Groupon, for example. Sometimes a certain number of people need to buy the deal in order for the deal to “tip.” They say there is no such thing as a free lunch, so when you get this amazing Groupon deal, part of you feels some satisfaction that a certain number of people are going down with you and the ship if it ends up being a hoax. That’s the psychological element that gets people to buy — the idea that they will not suffer alone if it is all a ruse. We are so eager to tell everyone these days how we feel or how they ought to feel. When someone tells you something — even if you disagree with it — at least start by validating the other person’s feelings, and reminding them that there are others out there who feel the same way. When you enable people to feel that only they have the ideas that they have, they will start to turn on themselves quickly and feel that there is something wrong with them.

I’d also encourage people to build routine. Look, our lives have no meaning unless we have problems to solve. I know that sounds counter-intuitive, but think about it — if you solved all of your problems, what would make you happy any more? We need to overcome something to be satisfied. A lot of people feel nothing but despair right now. Give them a new problem to solve and suddenly they are distracted again. I mean, I wrote a book during the pandemic. A lot of people thought that was impressive, but really, when would have been a better time to do it? I had lots of free time. Use it to do the things you told yourself you wanted to do. Encourage others to do the same. My brother and I teamed up to get my parents a Peloton for the holidays. Now they have a new problem to solve — figuring out how to use it.

Lastly, turn off cable news and social media as much as you can. I don’t want to sound like a wacky conspiracy theorist, but I think most people agree at this point that the media and social media companies have a financial interest in driving us apart and creating division. Spend some time in Meditation. Go for a run. Go for a hike. Do anything but consume the agenda-driven narratives of paid TV hosts who want to make you angry and sad for clicks, attention, fame, and money.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Negative stigma. I talk about this early in the book, but our brains have a way of telling us that the used car salesman is a sales guy but that the college admissions counselor is not. What really makes them any different? Great sellers are often great people, because they are capable of so much of what is missing in today’s dialogue: empathy. But we seem to associate “sales” with “persuasion,” and the two are not really the same. But even if they were, there is this idea that persuasion is all about getting someone else to do something that they really should not do. And that’s just false as a premise. Sometimes people need to be persuaded to do things that they simply do not realize are good ideas for them. I had a girlfriend in college, for example, who was so mean to me that all my friends tried to persuade me to break up with her — I just didn’t want to be persuaded. So I learned the hard way instead.

So I think our education system kind of turns a blind eye to the principles of selling for fear of the negative stigma. But really, we need this training more than ever. Our political dialogue is completely fractured to the point of normalizing political violence on both sides, we have a younger generation of people today that is obsessed with pushing out and selling fake images of self to the world because they do not understand how to sell themselves organically, and even contestants on “Shark Tank” do not seem to be able to take a simple “yes” for an answer. Frankly, our society should be embracing this subject more than ever. The way we talk to each other right now is unhealthy.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

This is a difficult question, and to some extent, I think it depends how you are defining those words, because we all have different ideas of what it means to be “salesy” or “pushy.” I guess my instinct would be to say that we should avoid these things, if anything else than for the connotations of those words. There is this idea in my book about inception, which is where the customer comes to the same conclusions as you but feels like they got there on their own. I associate being “pushy” with kind of forcing an idea down someone’s throat or really overtly pushing them towards that idea. Good selling is just letting people find out for themselves, you just act as the sherpa. There is a black man named Daryl Davis who has successfully converted 200 men from being KKK members to regular upstanding citizens in our society. Guess what? He didn’t give them any lectures or guilt them into reading White Fragility; instead, he just got to know them and he let them figure out for themselves that black people are deserving of much better treatment by them. They figured that out by realizing Daryl was a great guy, and he was black, so they made the connection on their own. I learned more about racism when I was pulled over for speeding with a black friend in the passenger seat, seeing his fearful reaction, and talking to him about it than I did from any of my friends who posted a black square on their Instagram after the death of George Floyd. Some selling is performative, overt, and in-your-face; really good selling is passive and oftentimes unexpected and/or unintentional.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

That’s easy — prospecting. I studied Creative Writing in college and wrote a book of creative fiction for my senior thesis under the tutelage of the esteemed author Edmund White. Most of my classmates — well on their way to Wall Street or cushy consulting gigs — scoffed at me for wasting my time with a meaningless English degree while I seemingly wrote poems in the library. Well, joke’s on them because I put that craft to good use. I sincerely enjoy figuring out creative ways to connect with people. There is a chapter in my book called “Weirder Than Waldo” in which I explain that effective cold outreach can involve, well, being weirder than Waldo. Waldo was a really weird guy with his red and white striped shirts and stuff but he was still impossible to find. If you really want to stand out from the pack, embrace your weird, authentic self. Weird is good. People actually like weird. What people don’t like is inauthentically weird people — people who are clearly acting out a version of themselves they are too uncomfortable to actually be just so they can attract some attention. Look what happened recently with the scandal with Alec Baldwin’s life pretending to be Spanish. She seemed interesting at first glance, but now she has effectively been canceled for pretending to be so interesting. Meanwhile, Dennis Rodman is a celebrity mostly for what he did off the basketball court rather than what he did on the court, and he was sincerely weird throughout his entire career. People loved it.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

Unfortunately, I have kind of a boring answer — I currently do a lot of the traditional stuff, like researching the right leads on LinkedIn or by looking at company org charts with some other tools we have. But something I have always tried to do in every industry I work in is become as knowledgeable as possible. People want to do business with people who they trust. And it is hard not to trust people who are smarter than you in a particular subject area. I may not always be the smartest person in the room, but I definitely want to be the smartest person in the room about whatever I am selling. It’s not a sexy answer, but thought leadership naturally will draw people to you if you are patient.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

Objections are challenging only because salespeople have an agenda in their interactions much more than they should. When your agenda is to sell a product, naturally you will feel disappointed the moment someone makes it more challenging to fulfill your agenda. I don’t want to weird people out, but we really have no idea why we are here on Earth or what our purpose is. If you really sit down and think about that and remind yourself that we are literally specks of dust in a universe we know virtually nothing about, it kind of becomes a lot easier to have some non-attachment to these things we feel will deliver immediate gratification to our lives. It makes it a lot easier to sit back and just enjoy the journey; to be empathetic and just to want to help put a smile on someone’s face; to just want to make an impact on the world before we die. I realize I am making this sound easy and trust me, I need to continue working on this myself, but we need to try to have more non-attachment to our own ideas. We’d be so much happier.

The best way to handle an objection is to put yourself in the customer’s shoes. Really try to understand how they got from Point A to Point B. You can’t really do that until you ask a few open-ended questions. Assume less, ask more. You might uncover something that salvages the opportunity. You might not. You need to be prepared to lose the sale if that is what is right for everyone — you need to have the right intentions about why you are doing what you do. Generally, in my experience, asking these open-ended questions exposes me to information that makes it more clear and obvious that there is still a place at the table for the product I am selling. But reflexively explaining that to a customer hardly ever works, largely because that is the opposite of how inception works.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

Honestly, the number one answer is pretty counterintuitive, and that is to just take “yes” for an answer. So many salespeople get excited about getting to the finish line that they keep talking or provide some sort of echo chamber for the customer about why they are making a good decision. Once you have done your job, just shut up and move on. The more things you say, the more objections you might introduce. When a customer gives me the green light, I don’t tell them how awesome they are or how awesome things are going to be, nor do I do any victory dances. The real work has yet to begin — making my new customer happy and delivering on all of my promises.

I think if you build a good relationship with a customer, you have a right to explain to them what is at stake for you if the deal moves forward. I certainly do this with my clients so they understand why I am trying to move things along. I think it is also important to remind people about what they stand to gain, and therefore, what they stand to lose by waiting around. This isn’t pushy, it’s just reality. Really, if the customer and you have built a good rapport, it should be simple enough to straight up ask what needs to happen for the deal to close, because now you are just two players on the same team. You cannot really get to the point of being able to ask these questions without seeming pushy unless you build strong, authentic relationships first.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

Ask the person to tell you “no.” I mean, not literally, but it’s OK to be direct with people. A chapter in my book is called “The Customer Is Not Always Right.” We have this idea that you need to be deferential to people if you are selling something to them. Well, are you deferential to your best friend or your spouse when they offend you? Or do you stand up for yourself because you have built trust with them? Chances are, you emerge stronger in your relationship because you told them how they made you upset. Why is it any different in sales? Ask the customer if your solution is a priority for them or not, and let them know that you need to move on if it isn’t. If anything, this will force them to at least open up to you about what is going on. But if you just keep following up by essentially nagging the person without really laying out what is at stake for you or why your time matters, then why would you expect to get a meaningful response? You won’t.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

Considering that almost all interactions are sales interactions, I would say nothing is off the table. But even in more overtly professional settings like my field, everything you listed here is in play for me. One thing we did recently was start to use Cameo, a website that allows you to pay celebrities to give shoutouts to people in a short video. We have had a few prospects get excited about meeting with us because we found someone topical for them who they admired to give them a special shoutout. Really though, I try to build strong enough relationships with my customers that I can just text with them the way I text with any of my other friends. If we can build that kind of bond, I can level with them and explain sincerely what it means for me if they move forward. Honestly, business doesn’t even seem like business at that point, it’s just kind of a part of our relationship and intermingled between other things we have going on in our lives. This kind of happens organically.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

One of my motivations to write the book was to try to inspire better dialogue. Listen, I didn’t expect to write this book and then get invited onto Joe Rogan’s podcast or something and then abruptly change the world. I’m a relative nobody who has been awfully discouraged seeing the way people talk past each other; the way people make silly memes to often willfully mis-characterize what their political opponents are saying; the way people justify violence — as long as the offenders agree with their own ideas. I think we ought to be ashamed of ourselves. This is a collective responsibility and it is high time we stop blaming everyone else but ourselves for why it has come to this. We need to up our empathy game, myself included. If I could start a movement, it would be a movement about empathy. It would be a movement about recognizing that other people might have views that seem reprehensible to us on the surface, but that they are coming from a completely different background and upbringing with a different set of information than we are. We need to get to a point where we can strongly disagree with people but at least understand why they are the way they are without resorting to the explanation that they are simply evil. Like any other human being, I struggle with this. But I take pride in my accountability to my own struggle, and I hope others will find the pursuit worthwhile. Quite frankly, in the absence of dialogue, you can only have violence. And I am pretty sure that very few people want to have violence.

How can our readers follow you online?

I have a website,, where I post a new blog once every week or two. If people want to keep up with my writing or just want to contact me, that is the best place to start. I love meeting new people and being exposed to new ideas, so I’d be excited to hear from some people.

Thank you for the interview. We wish you only continued success!

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