PODCAST 126: How to Book a Meeting with Nearly Anyone in the World with Jeff Winters

Today on the show, we’ve got Jeff Winters, the founder and CEO of Sapper Consulting, one of the top 10 people in the world who can get a dream meeting — a meeting with virtually anybody in the world. We also announced a contest on this episode, so give it a or read our blog.

If you missed episode 125, check it out here: The Power of Authenticity and Emotional Intelligence in Sales with Mykal White

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Show Agenda and Timestamps

  1. Show Introduction [00:10]
  2. Who is Jeff Winters and what is Sapper Consulting? [02:00]
  3. How Sapper Consulting built REGIE [07:20
  4. Why outbound prospecting is difficult [11:45]
  5. How to create emails that get read and responded to [15:57]
  6. Ways to use technology to help you sound less automated [26:01]
  7. Jeff’s recommended resources [32:47]
  8. Sam’s Corner [35:24]

Show Introduction [00:10]

Sam Jacobs: Today on the show, we’ve got Jeff Winters, the founder and CEO of Sapper Consulting, one of the top 10 people in the world who can get a dream meeting — a meeting with virtually anybody in the world. We also announced a contest on this episode, so give it a or read our blog.

Now, we want to thank our sponsors, and Sapper Consulting is one of those sponsors. Sales enablement is easy. All you’ve got to do is create perfectly targeted content, stay informed on email best practices, drive more engagement quarter over quarter, spend less money, oh, and do all of this with less time, okay? It’s not that easy, but Sapper Consulting has built REGIE to keep the promise of sales enablement alive and keep your team doing what they do best, which is winning.

REGIE uses artificial intelligence to create entire outbound, inbound and even follow-up sales campaigns faster. Using over 1 billion rows of performance data across 75 industries, REGIE uses your targeting to inform your campaigns, decreases the time your team spends creating campaigns, and because the campaigns are structured on email best practices, your campaign warm-up period will shrink. The result? More sales meetings. Start creating better sequences faster. Visit go.regie.io.

Our second sponsor is Outreach, the number one sales engagement platform. Outreach revolutionizes customer engagement by moving away from solid conversations to a streamlined and customer-centric journey, leveraging the next generation of artificial intelligence. Everybody’s using artificial intelligence these days. If you’re not using artificial intelligence, why are you even alive?

The platform allows sales reps to deliver consistent, relevant and responsible communication for each prospect every time, enabling personalization at scale. Never before possible. Previously unthinkable. You couldn’t even think about it because it wasn’t thinkable. It was unthinkable. Anyway, check them out at www.outreach.io.

Now, without further ado, let’s listen to this interview with Jeff Winters.

Who is Jeff Winters and what is Sapper Consulting? [02:00]

Sam Jacobs: Hey, everybody. It’s Sam Jacobs. Welcome to the Sales Hacker podcast. Today on the show, we’re honored and excited to have Jeff Winters. Jeff is the founder and CEO of Sapper Consulting. Sapper helps over 600 clients supercharge their top-of-funnel. From his kitchen table, Jeff has led Sapper to be the 170th fastest-growing private company in the United States and employs over 125 people. It’s a bootstrap company, so that’s an incredible stat. He’s also an expert on sales and sales engagement, and he’s been named one of the 20 Speakers You Shouldn’t Miss The Opportunity To See in Forbes Magazine. Jeff, welcome to the show.

Jeff Winters: Sam, thank you so much for having me. Excited to be here.

Sam Jacobs: What does the company do, in your words? Give us the opportunity to learn more from the founder.

Jeff Winters: We do one thing three ways. We supercharge the top of your funnel. That’s the one thing, help you get more sales meetings, drive more pipeline, and we do it in three ways.

The first is we do it for you. You come to us, you want to have us get more meetings and put more appointments on your calendar. Our team does it stem to stern. We send out the messages; we put the meetings on your calendar. Your sales team, your AEs, whomever, show up at the end of the day with a calendar full of meetings with prospects they want to talk to.

The second way we do it is done with you. Like you said, we’ve done this. Right now we’re doing it for 600-plus customers. We’ve got a lot of knowhow, a lot of best practice. We’ll have customers come to us and say, “Look, we don’t need your people. We’ve got infrastructure, we’ve got the sales tech. We just want your best practice and your knowhow.” We do a pretty standard consulting engagement and we do it with them.

Then last is do-it-yourself, and we’re really excited. We launched REGIE, our product, back in February, but we’re releasing the new and improved REGIE now. Basically what REGIE will do is you can log in to REGIE and tell it the buyer persona that you want to meet with, and it’ll spit out emails, 10 emails in under three minutes. It’ll give you all the touch types for the campaign, so email, phone calls, social, et cetera, and now it’ll do it with tone in mind. It’ll customize or help you customize the tone of your outreach to a specific buyer persona, so one thing, done three ways. Do it for you, do it with you or do it yourself.

Sam Jacobs: That’s amazing. Let’s learn more. What’s your background? I think you’ve been doing Sapper for 10 years. Walk us through your background, how you came to start Sapper, where you all are based. Give us a little bit more about the company and the origins of the company.

Jeff Winters: Sure. I’ve actually been doing Sapper for seven and a half years. Been in startupland, I guess, for 10, and I’ll give you the other two and a half. I started Sapper, like I said, seven and a half years ago. The origin story is this. I took a job. Just prior to Sapper, my job was basically to go in and be the head of sales at a different startup. I got there on the first day and I’m all excited. I’m 26. I feel like the CEO has found me out of obscurity. He sees in me all the potential my mother always told me I had.

He sits me down on my first day and he goes, “Look, Jeff, we’re really excited to have you. There’s a few things you ought to know. Number one, the product’s great, but it hasn’t technically been sold to anyone. Number two, I really only want you to sell it to chief human resources officers at Fortune 1000 companies, but we’re super excited to have you. Good luck.”

At that point, I realized that I have not been found because of my amazing potential. I’ve been found because this is going to be a really hard job, and maybe some other people didn’t want to do it. Nonetheless, I’m up for a challenge, so I spent six months. I can’t get a hold of anybody, I mean nothing.

Finally, I’m thinking: should quit or not? What I decide to do is, I start waking up in the middle of the night, like two, three in the morning, and sending funny emails. I’m not kidding you, I got 170 meetings in one year and I’m flying around the country. I’ll never forget. There was one at Morgan Stanley that sticks out. I go to the 500th floor of this enormous edifice in New York, and I walk in.

It’s a conference room full of people, and the chief human resources officer walks in. He goes, “We’re excited to see the software. Thanks for coming. How in the world did you get this meeting? How did you get this meeting? I can’t believe that we are all here to meet with you,” which was highly insulting, but also the start of the business, because I realized at that point that if I could get meetings for this company with these people, I could get meetings for anybody with anybody. I quit, and Sapper was born.

Sam Jacobs: What were the funny emails?

Jeff Winters: I’m worried you’re not going to think they’re funny, definitely not by today’s standard. Basically what it said was, “My name’s Jeff Winters. I am the head of sales for a startup company in a basement office in the Silicon Prairie of St. Louis, Missouri.” Then in parentheses, it says, “I know you’re jealous.” Then I went into what we do and how we did it, and that was it.

I know your audience isn’t cracking up and saying, “Oh, my goodness, that’s the most hysterical email I’ve ever read,” but you know what? It worked like a charm, because at the time people just weren’t using humor in emails and that was the humor I used, and it just got a crazy response at two in the morning.

How Sapper Consulting built REGIE [07:20]

Sam Jacobs: Wow. Tell us a little bit more about Sapper. You quit after this amazing meeting at Morgan Stanley. You start the company, and what happens from there?

Jeff Winters: The first couple of years were really hard. For all you out there who are working at your kitchen table … I guess we’re all working at our kitchen table now … for those of you that were working at your kitchen table because you had no office pre-coronavirus, I hear you. I was there. My brother and I, in my kitchen for a year and a half or so, until he scratched the floor with a chair and my wife kicked us out. That’s the great, exciting story for two years. I’m sure some of your listeners are there now. To them, I say like, “Keep going. Keep going. Keep persevering.”

In terms of the technology, I don’t have the ability to build this technology. Tell you how it came about. We were, for so long, sending so many outbound communications to clients across a broad spectrum of the universe. Every ICP, every buyer persona, we were working on behalf of. Our team started thinking like, “We probably have a unique treasure trove of data that would be very hard to have. We know, by persona, by ICP, how people respond to what, for a long period of time, and how we can, more specifically, get meetings with these individuals,” because that was the name of the game.

We brought in this brilliant CTO who’s got a PhD in informatics. I mean, the guy is just a genius. We got together and he said, “I think that we can figure out how to tap into this data, a couple billion rows of data, and triangulate what’s going to work by persona.” I was like, “I can’t believe it,” so that’s the mission we set out on.

He’s done an amazing job at giving us this. He gave us this differentiator inside of our business. This is what our team uses, and why we’re special and why we’re different as a company. Then, like so many other companies before us, you start telling people about your differentiator and they go, “Well, wait a minute. What if we just want to buy your differentiator? What if we just want to buy REGIE? We want to buy the secret sauce,” and so we built it.

We built it and we launched it, and it’s a first-of-its-kind tool. It’s great in that it enables teams who are stuck that are using sales engagement, who are stuck and not getting enough meetings to get unstuck. It’s great in that it allows teams who were writing tons of different messages and emails to write them in mass and do it a whole lot more quickly. It’s great for folks who want to get a leg up, who haven’t used sales engagement before. It’s got these awesome utilities. That’s how we got to REGIE.

Sam Jacobs: That’s amazing. Any fun or interesting examples of the differences in terms of communication style or preferences by persona?

Jeff Winters: I think the big thing that’s emerged is how little individuals take into account tone by persona and what personas care about. To me, that’s the big aha. Some emails need to be shorter, some need to be longer, some need to be more fact-based, some need to be more story-based. Those are all things you would probably assume, and if I told you, you wouldn’t be wowed by it. A director of IT is not going to respond in the same way as a director of HR. We’re talking about very different personality types.

I think the key takeaway here is how much individuals underindex on their audience and the personality of their audience. That to me is the big takeaway that, as we go on in our conversation, we’ll hit on why it’s so important, especially in light of how difficult outbound prospecting is today and how difficult it’s going to get in the future.

Why outbound prospecting is difficult [11:45]

Sam Jacobs: Let’s talk about that. Let’s just focus on that last sentence. You mentioned it’s difficult and it’s getting more difficult. Tell us how it’s getting more difficult and what we need to do to prepare.

Jeff Winters: First of all, I’d say if you’re an outbound prospector, today is the easiest day of doing your job you’re ever going to have going forward. Tomorrow is going to be harder, the next day is going to be harder, and the next day’s going to be harder than that. I’ll give you the data and I’ll give you the reasons why.

First of all, quality conversations, down from eight on average in 2010 to five. Attempts per prospect, up from 4.7 in 2010, now near 10. Nearly half of all salespeople say that prospecting is the hardest part of their jobs.

Now let’s just zone in on COVID. Since March, sales email volumes have increased 60%. Reply rates are down 25%. There should be no doubt. I guarantee you, for your listeners, nobody’s sitting there going, “That’s BS. It’s not getting harder.” It is getting harder. Let me just list for you a short list of the companies and institutions and governments that are making it harder. I’m not saying they’re doing anything wrong. I’m just going to give you a list, okay?

Apple, in terms of helping from their phones, like marking things as spam callers. Google and Microsoft, who are doing spam in the inbox. The Continent of Europe with GDPR, the State of California with privacy regulations. I’m not saying that these are wrong, by any means. I’m just saying think of the headwinds there that you’re dealing with. Some of the most brilliant, well-capitalized companies in the history of the world, continents, states and governments, are all making it harder for outbound prospecting, and nobody’s talking about it in those terms.

I wanted to bring light to this conversation here, and also to share that the winners and losers of outbound prospecting future are going to be determined by how well they’re preparing now and the steps they’re taking now. It’s awesome for anybody who’s listening and cares about this, that they care enough to want to be a winner and want to take steps to mitigate how difficult this is going to be.

Sam Jacobs: You mentioned that you’ve got a cold outbound future-proofing checklist. What is the checklist, for people that are aware that the world is conspiring against them, it’s getting harder to do outbound prospecting and they need to prepare themselves? Go through that checklist for us.

Jeff Winters: The first is deliverability, and it’s everybody’s favorite wonky topic. We know companies who have gone from getting hundreds of meetings a month to literally zero in a blink of an eye because their email domain had a problem. The first thing on the checklist is getting deliverability down, and also preparing for if you don’t. From a deliverability standpoint, for all those who aren’t super familiar with deliverability, it’s just the idea that I can get an email into your inbox. I can get an email into your inbox, because these are table stakes. This is a must-have.

A couple of tips for listeners. First is make sure that you have backup domains, and that you’re getting them ready now. If you’re a big outbound prospecting shop, you should have a couple of extra domains that you’re warming up in the background, that you are getting interaction on, in case you need them to do more outbound prospecting.

Sam Jacobs: Domains would be like a .biz or something like that for your company, or some modification of spelling? Is that what you mean?

Jeff Winters: That’s right. That’s exactly right. Some modification that you’re using, obviously within proper guidelines of best practice, that you are using to make sure that your domains, if you run into an issue with your domain for whatever reason, that you have others that you can use.

RELATED: The 4 Most Important Cold Call Statistics for Sales Success

How to create emails that get read and responded to [15:57]

Jeff Winters: You’ve got to have list perfection. List perfection is the order of the day now. Having a good list, a prospect list that’s 85% accurate, 90% accurate, is unacceptable. You’ve got to rule that out of your vocabulary. You have to have 100% accurate lists, and here’s why. Because if you don’t, Google and Microsoft … who, look, they have a black box of how the spam filtration works, but here’s what we know. We know that detection is based and foldering is based in some measure on interaction.

If we are not sending to the perfect list, we’re going to have bounces, we’re going to have lack of interaction. It’s totally unacceptable. You’ve got to adopt the Santa Claus method. You’ve got to make the list, you’ve got to check it twice. Very tactical, you need to be running your list through at least one other checkpoint, and you’ve got to dial the stringency on that checkpoint up. If you’re using certified, NeverBounce, things like that, you’ve got to make sure that the stringency’s dialed up a lot.

Third tip is around the email content you’re using. Email content has to be persona-based. The tip I would give here, I know there’s all sorts of discussion and ethos around personalization and hyper personalization. I go against that a little bit, because to me, a lot of the talk around personalization and hyper personalization is really meant for major, enterprise-focused businesses, AEs and SDRs, because for so many of us, it’s just not possible. It’s just not scalable.

There’s got to be some happy medium between sending a ton of emails to the universe and making sure I’m hyper personalizing everything and spending eight, ten minutes in email. I’d say to the audience here, and I think this is super important, to find that happy medium. The way that you do that is three things. First, you have to make sure that that email does not look automated. You have to say something in the first sentence of that email that grabs the reader’s attention and they go, “Oh, this isn’t automated.”

Sam Jacobs: Give me a great example.

Jeff Winters: A great example here would be something like, “Hey, just picked up the kids from school and had a second, and wanted to shoot you a note.” “Hey, just finished dinner. I was looking through my inbox and I’ve got to talk to you.” “Hey, just got back from a job and wanted to reach out.” Things like that, because so many emails you get today go, “Hope you’re well, I hope things are good.” That’s what every automated email starts with. I’m looking at the preview content and I’m going, “This is automated.”

Sam Jacobs: “In this unprecedented time, I hope you’re safe and sound,” or something like that. Not good.

Jeff Winters: That is absolutely 100% automated all the time, and I’m never opening it. Even if I’ve gotten over the deliverability and even if I’ve got a perfect list, now I’m hitting you with, “I hope things are well.”

Sam Jacobs: What do you think about subject lines? Any points of view on subject lines? I used to have a theory that a question mark in a subject line got better open and reply rates, but I don’t know if that’s true anymore. What do you see, as one of the world’s gurus?

Jeff Winters: Thank you for saying one of the world’s gurus.

Sam Jacobs: Well, 600-plus clients.

Jeff Winters: What I see is you can go one of two ways. Version one is a one-to-three-word subject line that is generic. “Connection,” “Quick question,” “Introduction,” things like that. Method two is to give a little tidbit about what you’re going to say that doesn’t sound spammy. Number two is a lot harder, but if it works it’s better, in my opinion, because someone is opening with the intent to be interested, opening with the intent to be interested. Those are my two points of view on subject lines.

Sam Jacobs: The generic one might get more open rates, but to the point it’s less qualified, in a way?

Jeff Winters: It can be. Yeah. Back to the point, the preview text, I would argue, is as important or more important than the subject line. That’s the key. Make your first two sentences to let them know this is coming from a human.

On email content, the number one email content tip is making sure the writing style is not automated. You’ve got to write in the style and tone of the buyer. We talked about that. Then last, and this is sort of unconventional, is the best email content is accompanied by phone and LinkedIn touches.

The best email content is accompanied by phone and LinkedIn touches. Yes, there’s great data that it increases reply rates, but more than that, it’s all about continuing to humanize what you’re doing. If I see your face, I’m less likely to think that you are sending this out to a zillion people. If I hear your voice, I’m less likely to think you’re sending this out to a zillion people. Those are the three tips.

Sam Jacobs: I like it. You said in the past, “No lazy bumps.” Tell us what you mean by that.

Jeff Winters: We see these all the time. “We’re bumping this to the top of your inbox.” “Want to make sure you saw my last message.” Those are okay if they’re accompanied with some value, with a great article that you think would be interesting for that person, with a case study, with a white paper. No lazy bumps means you’ve got to add value in the bump email, because the bump email, like anything else in this world, once it gets to be a best practice, it’s not a best practice anymore. We’ve got to be more creative and add value with our bumps.

Sam Jacobs: Fair enough. Okay. We’re going through the future-proofing list. The first is deliverability. The second is list perfection. The third is email content. Anything else that you want to go through in terms of this checklist? Because I think it’s fantastic.

Jeff Winters: I’ve got one more. The last thing on email content is you have to refresh your sequences. You have to. Your emails need to be refreshed at least once a quarter. Otherwise, the algorithms are going to track the types of messages we believe. You’re going to have spam issues. Also, you want to be fresh with the content, so refresh once a quarter.

The last piece is around channel specialization. To me, in the future world you’re going to have experts at each company … and some of these will be by committee … in terms of social channel engagement, email engagement and phone engagement. One thing that I cannot understand right now is how we are expecting SDRs to write amazing prospecting emails in addition to all the things that they do with their day. I see this online all the time. They go, “For SDRs, you’ve got to hire for great writing ability.”

Seriously? We want these people to make phone calls, accept rejection, track to be an AE, make sure they’re using sales engagement, make sure they’re using CRM, oh, and they’ve got to write like Shakespeare. These are different people. I don’t understand how the expectation could be there, that this is one person. SDRs are amazing, incredible, the lifeblood of so many companies. You can only do so many things at once, and you can only be great at so many things.

This is something I would focus on and we recommend to our clients, is making sure that email content is written by a committee, and then tested and then put into practice. Make sure that your phone scripts are done by a committee. We don’t want individuals going off. We want people innovating, of course, but we want, broadly speaking, there to be best practice within the organization.

As fast as things are moving, we need specialization across these different channels in order to make sure that if one becomes less effective, we’re ready. We’re rock stars on the phone. If email is not working as well, we’re rock stars on the phone. If phone’s not working as well, we’re rock stars on social media. You can only do that with focus.

Sam Jacobs: One of the issues in the past that I’ve seen when other people write emails is that it comes out of some marketing meeting/focus group where it just doesn’t sound like English anymore. It is so feature-heavy, and it is a bunch of buzzwords that don’t even make sense.

That’s sometimes the fear that I have with other people writing SDR emails, which is they just came out of some brainstorming session where they’ve listed all of the key, defining, differentiating attributes of themselves that they see relative to competitors, but they are using weird technospeak that nobody actually uses. That’s one of the ways that I can tell that something is instantly automated, because it just reads like a user manual.

Ways to use technology to help you sound less automated [26:01]

Jeff Winters: Totally agree. Sales messaging and sales campaign messaging is totally separate and distinct from marketing messaging. I’m sure I’m the millionth person to say that, but I think as you start to think about how do you then craft your sales messaging, you jumped to, “Have marketing do it.”

That’s not what I would have said. If you’d said, “Jeff, how would you do it,” I would not say, “Oh, kick it to marketing and let them do it.” Not at all. What I would be using is … I’m biased, obviously. REGIE for us is the tool that helps us write this awesome persona-driven content.

If you’re not using REGIE or a tool like REGIE, then what you’re doing is you have a committee, and that committee is made up of practitioners, folks that are either on the front line or have recently been on the front line, who are not writing in the theoretical, who are writing in the practical, and who know what it takes to take awesome sales messaging … which is different from marketing messaging in my opinion … and get it to work. That to me is the difference. It’s the who, not the what.

Sam Jacobs: Makes a lot of sense. One topic I want to make sure we cover is this idea of a dream meeting, the perfect person, the chief HR, the CHRO, if you’re selling HR software, the CFO, the CRO. How do you do it? What are your insights there?

Jeff Winters: You asked me a question in the prework, and the question was, “Name one thing in the world that you’re top 10 at,” or something. It’s an impossible question, right? I thought about it and thought about it and thought about it. Finally I was like, if you put 10 people in a room and I was one of them, and they were all the best at this as well, if you put the top 10 in the world in one room and you said, “All right, I want you guys to get a sales meeting with X person.” By the way, I’m not saying this is the greatest thing to be good at. I’d rather be good at a zillion different things, but this is mine.

Sam Jacobs: It’s a pretty good thing. It’s a lucrative thing.

Jeff Winters: I think I’d be very competitive in this. I’ll give you my favorite story, and then I want to share a little test. I was working with my first client. This guy is a mental toughness coach. He’s amazing. It’s my first client after I’d quit my old job. He said, “I want to get a meeting with Nick Saban of the University of Alabama football team, and I want to be their mental toughness coach,” okay?

Do you think a lot of people want to speak to the University of Alabama football team? If you look at the roster of people that speak to them, a couple of weeks ago was Michael Jordan, a couple of years ago it was Kobe Bryant. Not just anybody gets to speak to the University of Alabama football team. This is my job. This is what he tasked me with.

I’m poring through Nick Saban videos, and all of a sudden I get to this video. It’s Saban at a press conference, and a reporter goes, “Nick, why do you drive so hard to be great at what you do,” and Saban snaps back at him. He goes, “Why do you drive so hard to do what you do?” He doesn’t let the reporter answer, and he paraphrases a Martin Luther King speech.

He says, “The reason is because that’s who I am. If I were a street sweeper, I’d be the best street sweeper in the world. I’d sweep streets like Michelangelo painted the Sistine Chapel. I’d have a street sign that said, ‘The best street sweeper in the world lives right here.'” That’s what he said, and so I got this idea. We send Saban a 50-pound street sign that says, “The best street sweeper in the world lives right here.” Okay?

We start calling to follow up, and his assistant tells us that it’s hanging in his house, okay, in his recruiting room where he takes recruits. Swear to God. Then, to my client’s credit, he followed up for a long time after, and he remains one of the mental toughness gurus at Alabama to this day as a result of that.

As I was thinking through that story, and thinking through the top 10 in the world and listening to your podcast, I feel like people say that but they don’t get checked on it. Nobody checks them on their top 10 in the world. Here’s what I was thinking. I want to do a dream meeting challenge for your listeners, to check my skills on this, so put my money where my mouth is. I want to start the Dream Meeting Challenge for one of your listeners. Here’s what I want to do.

If you comment under the LinkedIn announcement of this podcast, if you tag me, @JeffWinters, and you write REGIE, the name of our awesome product, I’m going to select three individuals, do a quick interview to make sure that everybody’s doing it for the right reasons, and I’ll select one person and I will work with you, and I will get your dream meeting. I will follow up with Sales Hacker and let them know when it’s done. It’s not going to be instant, it’s not going to be overnight, it’s going to take awhile, but I want to put my skills to the test and benefit somebody in your audience.

Sam Jacobs: That’s fantastic. The Dream Meeting Challenge, folks. You heard it here. This is live, recorded, live to tape. The first-time announcement. This is going to be amazing. Okay. We’ll take you up on that, Jeff. That sounds exciting. All right. The Dream Meeting Challenge. You’re going to get it, whoever it is. Could be Angela Merkel. Doesn’t matter.

Jeff Winters: Well, we’ve got to be reasonable. We’re going to have some qualifications.

Sam Jacobs: You’re already backpedaling.

Jeff Winters: Yeah, I know. It’s got to be a business. It’s going to be reasonable, but I promise you, somebody’s going to get an awesome, amazing meeting that they never would have otherwise got, and we’re going to make it happen for them.

Sam Jacobs: I’m excited for that. We love that. That’s going to be great. Folks, if you’re out there listening, make sure you hop on LinkedIn when you’re listening to this episode. Find Sales Hacker. I’m sure Jeff will have retweeted or reposted this episode. Put your name in the comments @him, so that he knows that he’s been tagged. He’ll reach out and schedule, and we’ll see if we can get you a dream meeting for whatever it is that you’re selling.

Jeff Winters: Yeah, @JeffWinters and then the word REGIE. Do not @ the person you want to get the dream meeting with. That’s going to screw the whole thing up. @JeffWinters and the word REGIE.

Jeff’s recommended resources [32:47]

Sam Jacobs: Jeff, it’s been amazing having you on the show. One last question for you before you go. When you think about people that have influenced you, that have had a huge impact on you, books you’ve read, podcasts you’ve heard, who are some people or one person that comes to mind that you think we should know about besides you, as we’re making our way along the road of life?

Jeff Winters: I’ll give you a person, and then I’ll give you a couple of books that have just really disproportionately impacted me. This person is Henry Schuck, the CEO of ZoomInfo, and I’m not saying we’re close by any means, but I’ve met with him a few times and I’ve just been so inspired.

Pre-IPO, just so inspired by what he did with that organization. Myself as a customer, how we’ve been treated, the product evolution, and just the amazing strategy that he put in place through organic growth and acquisition and fundraising, how he weaved it all together. Look, I got a view of it from a million miles away and three hours worth of conversation, but that’s just somebody who’s had a profound impact on me in my life and how I run the business.

In terms of books, I love books in two categories, for me. I love philosophy books, and I love business books that are encyclopedic, like Chapter 1, Verse A, Type 2, like there. In those categories, I love the Ryan Holiday books around stoicism. Principles by Ray Dalio is one of those that I just think is the greatest.

Sam’s Corner [35:24]

Sam Jacobs: Hey, everybody, Sam’s Corner. Loved that conversation with Jeff Winters, one of the world’s gurus in terms of getting a meeting.

The whole point here is that the job of outbound sales is going to get harder and harder and harder, and you can’t just be a robot. You can’t just be doing it the same old way. You’ve got to evolve, you’ve got to adapt. Here’s the checklist that he mentioned, just so you have it in front of you.

First, you’ve got to be testing different email domains in case yours gets jammed up. Deliverability is the number one key for future-proofing your outbound email. The second is getting a great list, list perfection, because you’ve got to be able to get into the email inbox. To get into the email inbox, you need accurate email addresses, or you’re going to be marked as spam and get kicked off. Great email content, and remember, written in the tone and the style of the buyer. Don’t be lazy about it.

Remember the email preview. That part cannot look like a robot, even if it was written by a committee, right? That part needs to have something interesting, something different, something personal. He mentioned, “I just got back from a job.” “I’m sitting down to type you this email after dinner.

If you send one of those emails, make sure it is after dinner that you send it. Don’t send it in the morning and say, “I was just thinking about you as I got out of my evening bath.” Also that would border on creepy, and he says don’t be creepy. We learned about that in Friday Fundamentals.

The point is email content has to be on point, and you’ve got to be thinking about it. You’ve got to refresh this email content at least once a quarter, and then you need channel specialization, and he says by practitioners, by a committee of practitioners. Meaning the social channel, meaning your messaging on LinkedIn, should probably/definitely be different than the messaging you have on email. That should be different from the voicemail that you leave, and all of it should be memorable, personal and interesting. I thought that that was a great conversation, because those are highly actionable insights in terms of how to make sure that you’re able to get a meeting.

Remember the Dream Meeting Challenge that Jeff mentioned. When we promote this episode, in the comments of the promotion, put @JeffWinters and then put REGIE, R-E-G-I-E, and he’s going to look through and he’s going to select three people to interview. One of those people, you just tell him who you want to meet with. He will get you that meeting, and that Nick Saban story is fantastic. It’s going to take creativity, it might take a little bit of persistence, but Jeff will get you that meeting, as long as it’s not Angela Merkel. I don’t know what he has against her, but apparently something.

Don’t miss episode #127

Thank you again to Sapper Consulting for sponsoring the Sales Hacker podcast. Make sure you do check out REGIE. REGIE is using artificial intelligence to create entire outbound, inbound and even follow-up sales campaigns faster. Go to go.regie.io for more information on how to do that, so that you can be sending the right message at the right time to the right person using tone, using nuance, and using the things that are valuable to that persona, all by using REGIE.

The second sponsor is, of course, Outreach. Outreach is the number one sales engagement platform. Check them out at www.outreach.io. If you want to reach out to me, you can. You can email me at sam@revenuecollective.com, or you can go on LinkedIn.

Other than that, folks, talk to you next time.

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