PODCAST 52: Building Sales Coaching and Training Framework w/ Rob Jeppsen

This week on the Sales Hacker podcast, we interview Rob Jeppsen, CEO of Xvoyant and host of the Sales Leadership Podcast. Rob is a longtime sales veteran and is incredibly passionate about both the profession of sales but, more importantly, the importance of investing in your team through sales coaching and training.

If you missed episode 51, check it out here: Approach Sales with Gap Selling w/ Keenan

What You’ll Learn

  • How to build a sales coaching environment.
  • Why PDA on the sales team is a good thing.
  • Key mistakes a sales manager will make when trying to build a coaching framework.
  • Metrics to track to drive your win-rate.
  • Why sales coaching will drive up sales retention and not just revenue.

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Show Agenda and Timestamps

  1. Show Introduction [00:09]
  2. About Rob Jeppsen: An Introduction [02:19]
  3. Sales Coaching Is about Offense, Not Defense [07:02]
  4. Core Coaching Principles [10:56]
  5. PDA [16:01]
  6. Taking the Leap [36:17]
  7. Living an Authentic and Productive Life [41:26]
  8. Inspiration [43:11]
  9. Sam’s Corner [46:52]

Show Introduction

Sam Jacobs: Hey, folks, it’s Sam Jacobs. You’re listening to the Sales Hacker Podcast. We’ve got a fantastic show today. We’ve got Rob Jeppsen, CEO of Xvoyant and host of the Sales Leadership Podcast. He is a longtime and well-respected sales leader, and he’s going to talk to us about the importance of sales coaching, which is so important and so critical. Much of the time we don’t do a good job at it, or we’re doing the wrong things, focusing on activities, not the rep. Rob encourages us to focus on PDA, which is purpose-driven activity.

Before we do that, we’ve got a new sponsor. Showpad. Showpad is the leading sales enablement platform for the modern seller. Showpad’s all-in-one platform empowers sales and marketing teams to engage buyers through industry-leading training and coaching software and innovative content and engagement solutions. Using the most comprehensive data on successful sales interactions, Showpad fuels AI to discover, replicate, and automate what works for top performers.

Our second sponsor is Outreach.io. They are the leading sales engagement platform. Outreach supports sales reps by enabling them to humanize communication at scale and by automating the manual work.

About Rob Jeppsen: An Introduction

Sam Jacobs: We’ve got an incredible guest today. Rob Jeppsen is the founder and CEO of Xvoyant, a sales leadership tech platform committed to helping organizations develop world-class sales leaders. Before forming Xvoyant around three years ago, he worked at HireVue as senior vice president and general manager. He was SVP of sales for Zions Bank where he led 700 salespeople across seven lines of business, organized over 50 sales teams, and was responsible for sales targets over three billion dollars.

He’s received a ton of awards, including 15 gold and silver Stevie Awards from the American Business Association. In addition to that, he received the first Salesforce Surfboard Award as the sales leader who best used Salesforce to win new business in a large enterprise category. Rob, welcome to the show.

Rob Jeppsen: Thanks for having me.

Sam Jacobs: Tell us about Xvoyant. Walk me through the name and a little bit of background on the company.

Rob Jeppsen: I founded this company because I was a sales leader who had a lot of reps. We were geographically dispersed. I didn’t feel like I had a clear line of sight on what my managers did differently. I needed them to be just as equipped as my reps were. Everybody’s equipping reps; we aren’t equipping managers. So I did it. We got to the point where 76% of our team was hitting goal. We set six records in a row. Salesforce told me, “You should start a business around this.” Today, I have a tool that transforms Salesforce from a system of record to a system of action, system of improvement. I built it because I needed it.

The name of our company is a play on words. Clairvoyant is a magic person who can predict the future. But I believe there’s no magic required to predict the future in sales. If you understand execution, you can predict it and create what we refer to as an Xvoyant system.

Sales Coaching Is about Offense, Not Defense

Sam Jacobs: Walk us through how we’re supposed to be coaching.

Rob Jeppsen: Consistency is the key. Everybody should have a weekly one-on-one. Frequency is the first place that we miss. We also get inconsistent on focus. What do you do with your guys who are crushing? What do you think the natural inclination for a large majority of sales leaders would be?

Sam Jacobs: Leave them alone.

Rob Jeppsen: I see that all the time. Coaching is not about who’s good or who’s bad. It’s not about being a fixer. The one-on-one is about that individual’s development. I love to ask my leaders, “Think about all the meetings your reps have. How many of them are 100% about them and where they want to take their performance and their career?” The answer is very few.

Here’s the second thing that I see. Too many times the one-on-one is looking backward. Ninety percent of the time in a one-on-one should be about the future, and only 10% about the past. We ambush people with data, we make them feel like they have to defend what they’ve accomplished. This should be a strategic planning session that’s about getting where the company wants them to go, getting where they want to go, and creating individual plans for individual people.

Anybody that tells you, “Work smarter, not harder,” is full of shit. Work smart and hard. The one-on-one should be the time where you sit down and collaborate and say, “How good can you really get? And let’s get there together.”

Core Coaching Principles

Sam Jacobs: What are the processes or philosophies or systems that you’ve built into Xvoyant to help managers do that?

Rob Jeppsen: Here’s a simple way to start. I call it RASR. Start with results. It’s really easy. We use results to identify what we should be talking about. Are you on track for what the company wants? It’s an easy yes or no. Use a tool to identify how far ahead or behind you are, so it’s not a defensive conversation. It just is what it is.

That leads to the second results oriented question: are you on track to accomplish your personal goals? If yes, then we have to quantify process, and our tech quantifies process. Are you hitting what the company wants? Are you hitting what you want?

The structure then turns into this how good can you get? Maybe it’s time to start fishing in different holes and going to larger deals. Maybe instead of 5.3 starts in a week, round that to six? What is that worth to you? You’ll be blown away how much the stars appreciate someone taking them away from the intensity of the things they’ve got to do for the day and saying, “This is what it’s worth to make a small change.” The how-good-can-you-get conversation is the funnest one and is most often missed because when someone’s saying yes to all those things, sales leaders think, “I’m just going to leave them alone,” which makes it really easy to quit.

Let’s go back to the results. If any of those are no, we immediately say, “Let’s look at the process.” Process can be strong or process can be weak. Here’s what we’ve modeled that eliminates 80% of the variants of sales, anything that’s B2B. You can calculate the number of dollars that a rep should have in the pipeline by saying, “Goal divided by win.” That tells you how many dollars you should be chasing. Then if you divide that dollar amount by their average deal size, you also know how many deals should be in the pipeline. And then you should use tech to derive what their cycle times look like from start to close and by stage. So we can say, “You’re either greater than or less than what you should be on dollars to the pipeline. You’re either greater than or less than in deal flow to the pipeline. And you’re faster or slower than where you need to be.” If you get those three things, dollars, deals, and speed right, it eliminates 80% of the variants in sales. There’s still 20%. Shit just happens.

If someone has a great engine working for them we’re going to tune their deals, and the way we do that is by focusing on verifiers, rather than sales activities. And what you find is you have three coaching conversations: how good can you get, tune the deal, tune the engine. And it makes every coaching conversation 100% relevant to getting where they want to go, not just where the company wants them to go.

RELATED: How to Turn Your Sales Managers into Effective Coaches


Sam Jacobs: We talk in numbers, win rate and sale-cycle length, and all of these things. Numbers are a reflection of a set of embedded behaviors. How do you change behavior to affect all of the output metrics?

Rob Jeppsen: Data doesn’t make people change. People do. So we surround those numbers with the activities that drive it, and the skills. Every outcome that you track is driven by an activity that you do like dials, emails, or demos. Those are going to be effective or not effective based on the skills that you exhibit during that activity. That’s a thing that can be done in coaching because they can look at the way the delivery was on different things and you’ve coached to the skills to make it sure that the skills become more effective. Numbers give you content, but the coach creates the context.

You start creating what we call Purpose-Driven Activities or PDA. Don’t just go through motions and fill out Salesforce forms, have a purpose. A great one-on-one should inspire someone to say, “I have reason to want to be better than I am.” And if you do those things, you’re going to be blown away by how much adding purpose to an activity can change the result.

Let’s pretend we have six sales stages. A salesperson will say, “Well, I do these three or four activities in stage one and then I get to go to stage two and I do these three activities. Then I go to stage three. Then I do these. Then I go to stage four, etc. And I’ll get to the point where I have a deal that they keep saying is in commit. It’s going to close. It never freaking closes.”

Only 46% of forecasted sales deals closed last year. The odds in Vegas of winning at craps are 49%. So your chances of winning in Vegas are higher than getting your commits to close.

What we help our customers build is customer verified outcomes, or verifiers. Think of it as a toll booth where the toll has to be paid by the customer. They have to get this from a customer and it’s got to be something that you can say, “Here it is.” And when the salesperson emails them their part of the close plan, their win rates change.

The best reps make sure that before they’re done talking, the prospect knows what’s going to happen next and they’ve organized it before they go. So it’s not, “Hey, I’ll call you.” It’s, “Get your calendar open now, so we’re scheduling when that follow up conversation’s going to be. Here are the things that I’m going to be sending you. I’d like to get on the phone and walk them through with you and if there are any questions, you can ask me then.” That is an awesome best practice.

Taking the Leap

Sam Jacobs: You’ve started a technology company. I take it you’re not an engineer?

Rob Jeppsen: Dude, I’m the opposite. My dad is one of the engineers who invented the first laser jet printer for Hewlett-Packard. My dad thinks he failed as a father because he has a son in sales. I’m like, “Dad, if it’s not for guys like us, your printer means nothing.” And he’s like, “Without our badass product, you guys don’t have anything to sell.” So we go back and forth.

Sam Jacobs: How’d you do it? What do you attribute your success to?

Rob Jeppsen: I wanted to start the company for years, but I was afraid to make the jump because I didn’t know who’d build the product for me. I was fortunate enough to get introduced to someone and I said, “Let me tell you how big this market is. Let me tell you what this does.” This man made a prototype for me and I looked at him and I said, “Let me see if I can sell it.” And so I went and I sold it to people, even though it was ugly and limited. But because I speak with our customers’ voices because I am that market, we were able to attach it to key problems, dollarize those problems, and give them a crazy deal if they did it. We funded our company on a couple of those deals with some big customers, and then I went and raised two million dollars of seed funding.

We believe a manager’s job is to help a rep do their very best work, so they can live their best life. If you’re not doing your best work, you’re not going to live your best life. And so our people bought into that mission. We love sales leaders because if they do it right, they change more than companies and teams. They become legendary in the lives of people they lead. And our company got behind that. Our developers are researching and reading every study on sales coaching and the state of the sales world. They know as much about this stuff as a sales leader does.

Living an Authentic and Productive Life

Sam Jacobs: You sound totally inspired, totally passionate, totally motivated. Do you regiment your life in a certain way?

Rob Jeppsen: Lots of caffeine. I have a responsibility to my investors and I have a responsibility to my team members to give them all I got. I owe them my A game every single day. I owe my customers my A game every day. I owe my family and myself my A game. And that’s tough, to make sure that you have A game wherever you go. And so it has to be intentional. I try to get sleep. I try hard to feed the soul. I love my family, love my children. I’m a voracious reader. Reading inspires me. I read three types of books: I read things around my profession, sales, I always want to know what’s going on in the sales world, the latest thinking: I read a lot about leadership because I work with leaders and I want to make sure I can lead my team; and I also read success stories because I believe what you think about is what you’ll do. So I fill my head with success.


Sam Jacobs: Give us three books that you love that we should read.

Rob Jeppsen: Shoe Dog, Phil Knight’s story of Nike. When he started selling shoes, they were just flying out of the truck. Not because the shoe was the best, but he said his passion was contagious and irresistible. And that’s what I love about that book. Keith Rosen’s newest book, Sales Leadership is great. My all time favorite leadership book for salespeople is Cracking the Sales Management Code by Jason Jordan. And then on sales, I think everyone should read Gap Selling by Keenan.

Sam Jacobs: He was on the podcast recently, and we were talking about Gap Selling.

Rob Jeppsen: It’s a great book. I endorse it all the way.

Sam’s Corner

Sam Jacobs: Hey, everybody. It’s Sam Jacobs. Welcome to Sam’s Corner. Another great conversation, this time with Rob Jeppsen. You can feel Rob’s passion and enthusiasm for the art and science of sales.

Things We Learned:

  1. How to build a sales coaching environment.
  2. Why PDA on the sales team is a good thing.
  3. Key mistakes a sales manager will make when trying to build a coaching framework.
  4. Metrics to track to drive your win-rate.
  5. Why sales coaching will drive up sales retention and not just revenue.

Don’t Miss Episode 53

If you wanna check out the show notes, see upcoming guests, or play more episodes from our incredible lineup of sales leaders, visit gtmnow.com/listen/. You can also find the Sales Hacker podcast on iTunes or Stitcher. If you enjoyed this episode, please share it on LinkedIn, Twitter, or elsewhere.

If you want to reach out to me, you can find me on LinkedIn. If you have any interest or curiosity in learning more about the show, please reach out.

Thanks so much to our sponsors. The first is the Showpad. Showpad is the leading sales enablement platform for the modern seller. As well as Outreach.io. Outreach is the leading sales engagement platform. I’ll talk to you next time.

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