Podcast: How Can Entrepreneurs Develop a Stellar Sales Pitch?
Skip to content
The Insightful Leader Live: What to Know about Today’s AI—and Tomorrow’s | Register Now
Entrepreneurship Leadership Jul 6, 2022

Podcast: How Can Entrepreneurs Develop a Stellar Sales Pitch?

On this episode of The Insightful Leader’s “Ask Insight,” two seasoned entrepreneurs share wisdom from the trenches.

Based on insights from

Carter Cast

Craig Wortmann

Listening: Ask Insight | How Can Entrepreneurs Develop a Stellar Sales Pitch?
0:00 Skip back button Play Skip forward button 9:55

As an entrepreneur, how can you increase your sales—especially if you don’t have a product to sell yet?

On the second of our two-part edition of Ask Insight, we once again turn to our experts—Carter Cast and Craig Wortmann—for answers. Cast is a venture capitalist for Pritzker Group and Wortmann is the founder and director of the Kellogg Sales Institute. Both are clinical professors of innovation and entrepreneurship at Kellogg.

In this episode, we look at how to develop a strong sales pitch, and our guest faculty improvise how to approach an unexpected opportunity to sell.

Podcast Transcript

[PROMO – music fades UP]

Laura PAVIN: Attention The Insightful Leader listeners. Our podcast will be taking a little break for most of July. But we’ll be back in August with something really new and exciting. It’s ​​our first ever podcast miniseries…called: Insight Unpacked: Amazing Brands and How to Build Them. That series will feature many of our favorite Kellogg professors explaining how to build a brand from the ground up. And it’s honestly a lot of fun. You’ll be able to catch that in this same podcast feed when it drops in August. So stay tuned!

[music fades OUT]

[music fades UP]

Hey there, it’s Laura Pavin. You’re listening to Ask Insight…a special feature on The Insightful Leader…where we get Kellogg faculty to answer YOUR questions about management and business.

Last week, we had a conversation about leadership...how to retain talent and how to manage up and across. This week, we’ll hear the second part of that discussion…on entrepreneurship and—specifically—on getting STARTED as an entrepreneur.

Our experts are once again Carter Cast and Craig Wortmann, both clinical professors at Kellogg. Carter Cast’s specialty is entrepreneurship and leadership. He’s a former CEO of Walmart.com. And Craig Wortmann is our resident sales expert, and is the founder and director of the Kellogg Sales Institute.

Now, Carter and Craig have somewhat similar voices, so…know that, after we ask the first question, Craig answers first.

Okay, I’ll let our host, Insight Editor In Chief Jess Love…take it from here.

[music fades OUT]

LOVE: We have a listener question about increasing your sales as a startup. But before we get to that specific question, I want you to lay out some groundwork, if possible: if you’re leading a relatively new company, how should sales factor into your strategy? What do you need to consider at the very earliest stages of developing your sales strategy?

WORTMANN: “Start now” would be my first bit of advice. And that’s only partially tongue in cheek. One of the mistakes that I made as a newly-minted entrepreneur a long time ago was I carried a really dangerous and sort of arrogant assumption into my first business. I didn’t know how to be an entrepreneur, but I knew how to sell. And it turned out I was completely wrong because I was a professional salesperson for IBM and other places. And then I became an entrepreneur and I thought, “well, that’s one thing I know how to do.” And it turns out that entrepreneurial selling is fundamentally different than professional selling. It is so much more grit and discipline required…and resilience…because you don’t have anything yet. You don’t have a strategy. You don’t really have a product. You have a, maybe at minimum, viable paper napkin with a drawing on it. And now you have to go sell that to somebody? Or you have to raise money on that? And so when I say, tongue in cheek, “start now,” what I mean is really start finding the language by which you’re just…you’re trying to describe what you’re trying to do, the change you’re trying to make in the world, why that’s important, why you’re the one to do it. And as you do that, find the stories that you can tell that resonate with people, that land on them, that recruit them to your mission, to your vision.

The biggest mistake that I made in my first business was that assumption that I knew how to sell. And then I thought, “well, okay, before I start selling, let’s see if we can get this right. Let’s code the software. Let’s make sure it all works. I know what customers want.” And I sort of metaphorically went in the cave and we built all the software. And then we emerged from the cave and everybody kind of went, “yeah, that’s not what we want.” I said, “what do you mean?” What I should have been doing is just saying, “hey customer X, here’s our vision for this. Not sure it’s right. Here’s why we wanna do this. And here’s what we think you need.” And then using that 15 second or one sentence articulation of the value proposition…”does that resonate with you?” And then iterate, test and iterate.

[to Cast] What’s your thought about this?

CAST: One thing I’ve learned partly from you and partly from just being in these entrepreneurial jobs is…everyone is in sales.

WORTMANN: Bless your heart for saying that.

CAST: When you’re an entrepreneur, you are in sales. You have to do a very good job of being concise and clear about what you’re selling, which takes real discipline. So Craig worked me through a process that I found very interesting of…starting off by explaining your product’s value proposition in a minute, then explaining it in 30 seconds, then explaining it in 15 seconds, then actually doing a tweet and then doing a hashtag…taking it all the way down. And learning to be disciplined on being more and more concise about landing the description of what you’re selling right off the bat is really hard.

So, just so you know, I have not prepared what I’m about ready to do with Craig.


CAST: So I’m in the Admirals Club, and you’re sitting next to me, and it’s terrible weather and our flight’s delayed.

WORTMANN: I love this situation. This is a sales situation.

CAST: I look over at you and I say…so nice to meet you. I’m Carter.

WORTMANN: I’m Craig. Nice to meet you, Carter.

CAST: Nice to meet you. So what do you do?

WORTMANN: What I do is I run a company called Sales Engine, Carter. What we do is help companies build and tune their sales engine.

CAST: Oh, that’s interesting. So are you a consultant or are you a business owner? And who do you sell to?

WORTMANN: Yeah! Both. So we help companies understand the sales process that they’re using, that their people are following…the tools they used to support the sales team and the knowledge, skill and discipline of the team itself.

CAST: How quickly did Craig just do that? Ten..fifteen seconds? You have to be ready when you’re selling to be that clear and that crisp.

LOVE: It sounds almost like a little bit of a chicken and egg issue: you’re not sure what you want to produce until you know what they want you to produce. So are these earliest conversations…if things are going well, are you actually getting a sale or is that not really your goal out of those initial conversations?

WORTMANN: It’s such a great question, Jess. At time zero—and I’m curious Carter, what you think about this—at time zero, I think so much of it is…you’re asking for advice. You’re not necessarily asking for a sale because at time zero, there’s nothing to sell. Like I don’t have anything yet. Maybe I could sell a little bit of expertise, right? Carter could sell…you know…”hey, before we have the product, we could come in and do some consulting work for you.” And that’s a chargeable thing. But at time zero, there’s so little definition around your company, and your product, and your solution, and what problem you’re solving, and even the value prop…that you’re asking for advice. You’re saying, “hey,” in a very humble way, “may I just talk to you about what I think this value proposition is and see how this lands on you, and whether you would value it in your company, and it would solve a real problem for you?” That’s what you’re actually asking, but I characterize that as selling. That’s selling.

LOVE: Okay, let’s say you have your product, or what you think is hopefully going to be your product. You’ve got a really tight budget. What are some of the most cost effective things that you can do to increase your sales?

WORTMANN: Make lots of contacts with potential customers. And that usually lands on people as some tough love—and it is. The hardest part of any sales process for any company in the world, generally, is the beginning because you’re looking at a white piece of paper or an empty database and your job is to fill it. That’s the job of sales, at least at the beginning. And so, you know, if you’re on a shoestring budget, the best thing you can do, if you have a phone, is to pick up the phone, is to go to networking events to the extent that you can afford it and talk to as many people as you can. That is cost-free or a very low cost. And here’s, again, the tough love: so many entrepreneurs…so many huge sales organizations…don’t do that. Why? Because it’s hard and it’s awkward. Because you’re walking up to people who don’t know you, and we humans, we like to be comfortable. And sales, at the least at the beginning, can be dramatically uncomfortable.

LOVE: Alright: Craig, Carter—we covered a lot of ground with you today. Thanks for joining us.

WORTMANN: Thank you for having us.

CAST: Yeah, thanks. I really enjoyed talking to you.

[music fades UP]

PAVIN: It’s Laura Pavin. And that’s a wrap on our Ask Insight two-parter with Carter Cast and Craig Wortmann. This edition was produced by me, Laura Pavin, and Jess Love. And it was mixed by me. Special thanks to Carter and Craig.

Got a question about business, office dynamics, the economy, management or leadership? Give us a call at 847-859-9534. That’s 847-859-9534. Leave us a message with your name, your question and a callback number or email so we can reach you. Or you can email us at insight@kellogg.northwestern.edu. We might just have the right person to answer your question…either on our podcast, an email, or in another form!

[music fades OUT]

Featured Faculty

Michael S. and Mary Sue Shannon Clinical Endowed Professor; Clinical Professor of Strategy

Clinical Professor of Marketing, Founder and Academic Director of the Kellogg Sales Institute

Most Popular This Week
  1. What Went Wrong at Silicon Valley Bank?
    And how can it be avoided next time? A new analysis sheds light on vulnerabilities within the U.S. banking industry.
    People visit a bank
  2. How Are Black–White Biracial People Perceived in Terms of Race?
    Understanding the answer—and why black and white Americans may percieve biracial people differently—is increasingly important in a multiracial society.
    How are biracial people perceived in terms of race
  3. What Went Wrong at AIG?
    Unpacking the insurance giant's collapse during the 2008 financial crisis.
    What went wrong during the AIG financial crisis?
  4. Will AI Eventually Replace Doctors?
    Maybe not entirely. But the doctor–patient relationship is likely to change dramatically.
    doctors offices in small nodules
  5. Podcast: "It's Hard to Regulate U.S. Banks!"
    Silicon Valley Bank spectacularly collapsed—and a new analysis suggests that its precarious situation is not as much of an outlier as we’d hope. On this episode of The Insightful Leader, we learn what went wrong and what should happen next.
  6. Which Form of Government Is Best?
    Democracies may not outlast dictatorships, but they adapt better.
    Is democracy the best form of government?
  7. Marketers, Don’t Be Too Hasty to Act on Data
    Don’t like the trends you’re seeing? It’s tempting to take immediate action. Instead, consider a hypothesis-driven approach to solving your problems.
    CEO stands before large data wall
  8. Why Do Some People Succeed after Failing, While Others Continue to Flounder?
    A new study dispels some of the mystery behind success after failure.
    Scientists build a staircase from paper
  9. What Happens to Worker Productivity after a Minimum Wage Increase?
    A pay raise boosts productivity for some—but the impact on the bottom line is more complicated.
    employees unload pallets from a truck using hand carts
  10. Why Well-Meaning NGOs Sometimes Do More Harm than Good
    Studies of aid groups in Ghana and Uganda show why it’s so important to coordinate with local governments and institutions.
    To succeed, foreign aid and health programs need buy-in and coordination with local partners.
  11. How Has Marketing Changed over the Past Half-Century?
    Phil Kotler’s groundbreaking textbook came out 55 years ago. Sixteen editions later, he and coauthor Alexander Chernev discuss how big data, social media, and purpose-driven branding are moving the field forward.
    people in 1967 and 2022 react to advertising
  12. How Much Do Campaign Ads Matter?
    Tone is key, according to new research, which found that a change in TV ad strategy could have altered the results of the 2000 presidential election.
    Political advertisements on television next to polling place
  13. How Peer Pressure Can Lead Teens to Underachieve—Even in Schools Where It’s “Cool to Be Smart”
    New research offers lessons for administrators hoping to improve student performance.
    Eager student raises hand while other student hesitates.
  14. Understanding the Pandemic’s Lasting Impact on Real Estate
    Work-from-home has stuck around. What does this mean for residential and commercial real-estate markets?
    realtor showing converted office building to family
  15. Immigrants to the U.S. Create More Jobs than They Take
    A new study finds that immigrants are far more likely to found companies—both large and small—than native-born Americans.
    Immigrant CEO welcomes new hires
  16. Leaders, Don’t Be Afraid to Admit Your Flaws
    We prefer to work for people who can make themselves vulnerable, a new study finds. But there are limits.
    person removes mask to show less happy face
  17. Executive Presence Isn’t One-Size-Fits-All. Here’s How to Develop Yours.
    A professor and executive coach unpacks this seemingly elusive trait.
    woman standing confidently
  18. 5 Research-Backed Strategies for Building an Ethical Culture at Work
    An annual training session isn’t going to cut it.
    person displaying a powerpoint with a halo above infographics
  19. College Campuses Are Becoming More Diverse. But How Much Do Students from Different Backgrounds Actually Interact?
    Increasing diversity has been a key goal, “but far less attention is paid to what happens after we get people in the door.”
    College quad with students walking away from the center
Add Insight to your inbox.
More in Entrepreneurship