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Sales Gravy: Jeb Blount

7 Oct 2026 · 11m · 6 chapters

Episode artwork

What Every New Salesperson Needs to Know to Succeed in Their First Year (Ask Jeb)

In short

Advice for new salespeople to succeed in their first year by following the sales process, building pipeline, and staying grounded in the present (not future pressure or past habits).

Guest

Kaylee Prindle, new to educational sales; sells curriculum to districts/schools/teachers in NY (excluding NYC) and CT (with some enterprise accounts). She previously was a high school English teacher (5 years) and then a high school assistant principal in New York (10 years).

Key claims

It takes about 9 months for sales to “click,” 1 year to sell, and ~2 years to crush results; focus on process goals (e.g., 40 meaningful conversations/week) and pipeline building—no money without prospecting.

Notable examples

her “disaster” pipeline early on; her manager’s coaching; the “future pressure doesn’t exist in the present” framing; using daily prospecting drills from Jeb’s 90 Days book.

Written by AI. May contain mistakes.

Chapters

0:47

Kaylee's Sales Journey

Kaylee Prindle shares her background and current experience in educational sales.

“but you went back and did year one again, what would you tell me?”
1:55

Sales Expectations and Challenges

Discussion on sales quotas, pipeline management, and the challenges of a new territory.

“I was a high school English teacher for five years.”
4:02

Overcoming Mental Barriers in Sales

Jeb shares his early experiences and the mental barriers faced by new salespeople.

“telling you, well, I'm not really good at this or this isn't going to work for me or I'm not getting it or what have you.”
6:05

Overcoming Mental Barriers in Sales

Jeb shares his early experiences and the mental barriers faced by new salespeople.

“If you're a golf fan or you know anything about golf, you play golf.”
7:53

Focusing on the Process

Jeb emphasizes the importance of focusing on the sales process rather than outcomes.

“But want to do what, want to be successful, where does that fit?”
10:09

Advice for New Salespeople

Jeb offers practical advice and encourages new salespeople to embrace the learning process.

“Every day you get up and you like read a little bit and you work a little bit and then you go to work and then you come back and then you've got that comfort of I'm going to go back, I'm going to do this again.”
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Transcript

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0:00Company spending is complex. Managing it should be simple. Amex Corporate connects cards, expenses, and payments to streamline the way you work. Built to simplify, designed to scale. This is Amex Corporate. Get started at go.amex slash amexcorporate. Terms apply. This is the Sales Gravy Podcast. Hi, I'm Jeb Blount, best-selling author, fanatical prospecting, objections, sales EQ, and inked, and I'm here to help you open more doors, close bigger deals, and rock your commission check. All right, everybody. Next up on the show, we've got Kaylee Prindle. Thanks for having me. I really appreciate it.

0:34Brand new to educational sales. I mean, when I say brand new, I'm ending my week seven right now. But really, you know, I'm a career shifter. So really, my question for you is like, if you could hold everything that you know with all of your expertise, but you went back and did year one again, what would you tell me? What would you do? Start with tell me what you sell. So I sell curriculum, basically, to districts, schools, and teachers. And my territory is all of New York State except New York City and all of Connecticut. There are a few enterprise accounts in there that I don't touch. How much of that is inside on the phone and on video?

1:11And how much of it is outside actually going into the districts and calling on your school? The expectation is 40 calls a week, eight in person, making that happen. I got a 1.1 million quota. My manager wants me to have 3.3 million in my pipe. This has been a real untapped territory, which I think she's trying to be supportive is like, hey, I don't want to scare you. And for me, I'm like, no, for me, that excites me because I feel like untapped means like, let's go. So that's a little bit of like where I'm at. But also I'm a millennial, but I'm a millennial of I like longevity. I'm not looking to bounce around.

1:46I like to find a work home and stay there. And so, you know, for me, it's like I want to be very good at what I do, but I don't want to burn out and make a mess. What did you do before this? I was a high school English teacher for five years. And then for the last 10 years, I was a high school assistant principal in New York. So you came out of the education space so you understand how schools work. What's your pipeline sitting at right now? I can't even answer that question for you because it's such a disaster. When you say 40 calls, can you tell me what y 'all define as a call? Yeah. So basically 40 calls is if I'm calling just to confirm an appointment, they ain't counting that.

2:20But if I'm calling to be like, hey, listen, I know you needed that quote that minute. I got you. I sent it to you. You got it. Cool. Awesome. Great. That would count. Even though like we did the email because the email, the LinkedIn, all of that kind of stuff, that's not counting right now. So it's 40 meaningful conversations. A couple of things to answer your question. Like what would I have told myself in your shoes starting off? Because I've already done a lot of these things. They're really lessons that I learned along the way. One of the things that I learned early on was that, like you, I got into a role.

2:53I really wanted to be successful. I'm really driven to win and be successful. And my manager was giving me the same advice that your manager is giving me. Sounds like you get a really good boss. I had the same thing. I had probably the best boss I ever had when I first started off in sales. And the problem was, is I didn't believe him. I mean, he was telling me things, but my brain couldn't connect. I can relate to that because I'm pushing up against, I have this school-based mindset. that. It's hard, right? Because you're coming from your experience and your boss is saying, do these things. And your brain's like, I don't believe you.

3:23It's not like you're defying your boss. It's just the interpretation. So like one of the things that Bob told me early on, he goes, it's going to take you nine months for this to click. She was like, you're so eager beaver. She's like, but you need to know one year to even get your head around this. Two year, you're going to feel like you're some type of God, but you ain't. And then three or four year, you'll start to get the hang of it. And I connected that to teaching because that's how I relate to teachers. First year, you're a mess. Second year, you think you're Superman. Third or fourth year, you start to learn the system.

3:52You're in your third month and you're slogging. Like I asked you, what's your pipeline right now? And you go, it's a disaster, right? And you don't feel like you're getting anywhere. It's not clicking. And so your mind starts playing games on you and it starts telling you, well, I'm not really good at this or this isn't going to work for me or I'm not getting it or what have you. I went through all that pain. And even though I explain this to people who come in and work for me as sales trainers, I'm like, it takes a year for you to get this. And it's going to take two years for you to really like start getting because my trainers are also sales people.

4:22I wish I could speed the process up, but we've done this enough times that we know exactly what this progression is going to be. At nine months, things started kicking. I mean, in a year, like, okay, I was selling. At two years, I was crushing it and making a lot of money. The thing is, is that a couple of times he had to pick me up off the floor because I was disappointed and I was down on myself. And if I could go back and do it all over again, I would say to myself, stop doing that. Like stop thinking that way. Just follow the system because the system's going to work for you. And that's what I would give you advice.

4:53Now you got a great boss who is explaining the process to you, work the process and set process goals and focus on the process and don't think about anything else because you've got a couple of things that are happening in your head right now. You're either living in the future for where you want to be. I want to get here, want to get here, want to get here. I'm eager to be there, I want to accomplish this. Or you're living in the past where you're bringing all of your educational background and those things in, right? And the thing is, the only thing that is real is where your feet are right now.

5:20And so you have to stay in the moment. And the way that you stay in the moment is process, right? You've got to focus on the process. Going into a follow-up call, I want every important note right at my fingertips, not buried somewhere in a scribbled stack of notes. And with Plod Notepin S, I always have them because it's a wearable, portable note taker that lets me stay present and focused on customers during every single meeting. Plod captures the conversation and turns it into organized summaries and action items so I can follow up faster. And if I need a specific detail, Plod's recall has that ready for me.

5:53And that's why Jeb Sr. and I and all of Sales Gravy trusts our Plod Notepin S. Try Plod and stay focused on the conversation while it handles all of your notes. Go to plod.ai forward slash Jeb. That's plod.ai forward slash jeb and use code JEB to get 10 % off your purchase. If you're a golf fan or you know anything about golf, you play golf. I don't play golf, but I watch Full Swing on Netflix and I'm obsessed with it. So I, yeah. Yeah. Okay. I love Full Swing too. But Ben Hogan, one of the six people to win the career Grand Slam in a book that he wrote that most golfers still read today. He said that if you want to get better at playing golf, you have to focus on the process of hitting the ball, not the outcome.

6:33So forget about where the ball goes, focus on the process. And the same thing with you, right? It was the best advice for golfers. It's incredible advice for salespeople. Focus on the process, focus on the process, focus on the process. If you listen to Sales Gravy every Monday, we've got a money Monday. I talk a little bit about that. But that's the thing that like when I go back and think about it, I wish that the young me had a known because under all that pressure and all that anxiety, and I know you feel pressure, right? Because you look at the people around you, right? The thing is, is that pressure doesn't exist in the present.

7:02Pressure only exists in the future that you're making up in your head. So if you're focused on the process, you focus on what you can control. Your actions, your responses to what happens to you in the world, and your mindset. Focus on that. That's it. Nothing else. And then your boss is telling you, do these things, follow the system, follow the process. Even though your brain is saying, do something else, right? My boss started saying, I bet you're starting to think about money. I bet you're starting to say one. And I was like, I'm not there. I'm going to be there very soon, but I'm not there just yet.

7:34And she's like, OK, well, we're going to have the conversation now. And she really revisited this whole piece of like, no money is coming to you unless you do all of the pipeline building and prospecting. Period. End of discussion. Especially when it'll be your territory. Especially I know what I know. There's no shortcut. And now, like you said, that pressure comes more from internally of like, yeah, I want to stroke. I want to do well. I want to be successful. And yeah. But want to do what, want to be successful, where does that fit? That's in the future. Pressure only exists there, but it doesn't exist in the moment when you're following the process.

8:06So the basics and fundamentals that your boss is laying out for you are always in play. They will work. Work the basics, work the fundamentals, work the system, do it religiously, and you're going to be okay. The past tells you, oh, well, in education, you have to do this or you have to say this or when I was a teacher, I would have done this. Right. I would have said that. Now you start projecting your past onto your present. Not helpful at all. Right. And the future is where all the pressure is right now. Be in the present. And in the present, you can be happy. Right. In the present, you can be content.

8:37You can feel good. Like every day I ran the process and I got a W. That's the advice I would have given myself. Yeah, it's really helpful. And also that connection of future, present, past, because eventually you've got to just bite the bullet and get out there and do it. You're the system, work the system, get the results. Like, I'm not trying to over-zealify this here. You know, it's Monday. You've got to make four meaningful conversations. Have four meaningful conversations in the morning and four meaningful conversations in the afternoon. In order to have those four meaningful conversations, you've got to make$20.

9:08That's it. Just one meaningful conversation at a time. But that's the key. You're an educator, right? I mean, at the heart, right? You're a teacher. This book right here, 90 Days to Level Up Your Sales Skills. This is a teaching book. It's one day at a time. So think about this, okay? We need to keep you grounded in the present. So you open it up, right? And you're on day 11, and day 11 is prospecting activity. This will take someone with your education level about one minute to read. And then there is a review or an activity on your prospecting activity for that day. What does this do? It grounds you back to what are you supposed to be doing every day?

9:42The grind. You go to day 25, we're talking about prospecting objections. We go day 52, there's qualifying methodologies. Every day you're getting a drip. And so for someone like you, like you're getting started, you've got all this excitement, you're eager, you want to win, you're selling in a very, very hard market to sell into. Because I don't know if you've noticed this, but selling to educators is freaking hard. So as you're going through the process, it keeps you centered on on just work to process. Every day you get up and you like read a little bit and you work a little bit and then you go to work and then you come back and then you've got that comfort of I'm going to go back, I'm going to do this again.

10:17And then you can run the whole thing again. Now, one more thing. Now, this is a gratuitous plug for the audience and for you. One thing that you might want to talk to your boss about is potentially bringing you and maybe some of your colleagues to the Outbound Conference, which is Sales and Leadership Training Conference. It's at a really cool resort in Las Vegas. Red Rock is awesome. But it's a really good conference where you get to network with a whole lot of people from different industries. You get to see what other people are dealing with. The entire conference is themed around breaking through buyer resistance, which is a big deal these days.

10:48And by the time you get there, you will be ready for breaking through buyer resistance because you're going to have built a full pipeline and have had some catastrophic failures fall on your face and you feel really bad. But this will show you that it's normal in sales, but it sounds like you've got a killer boss and you tell your boss there's a full day leadership conference. She can bring her sales team and then she stays for the leadership conference. But it sounds like your boss is awesome. I mean, I love hearing how she's coaching you. Tell her I said hello and you know what to do, right?

11:17Focus on where your feet are present. Very nice to meet you and stay in touch, okay?

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From the publisher

Starting a sales career is hard, and the first year will test your confidence before it rewards your effort.

In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers a question from Calee, a former high school teacher and assistant principal who is seven weeks into her first sales role with a $1.1 million quota and a pipeline she calls a disaster. Her question: if Jeb could do year one of his sales career over again, what would he tell himself?

His answer is simple, but not easy: stop worrying about outcomes and just work the process. Jeb explains why it takes most new reps months for sales to click, why pressure only exists in the future you imagine, and how process goals keep you focused on the work that builds pipeline today.

What You'll Learn:

  • What to focus on in your first year in sales to avoid early burnout
  • Why it takes months for a new sales rep to see results
  • How to set process goals that keep you focused on daily prospecting activity instead of quota anxiety
  • How to manage sales pressure by focusing on what you can control: your actions, your responses, and your mindset
  • Why career changers need to stop projecting past experience onto a new sales role
  • How to build a sales pipeline one meaningful conversation at a time
  • What golf legend Ben Hogan's advice on process over outcome teaches salespeople
  • Why following your sales manager's system pays off even when your instincts push back

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