John McMahon on Building a Better SKO

Summary

Revenue Builders Podcast: John McMahon on Building a Better SKO

Date: May 31, 2026
Hosts: John McMahon (Five-time CRO), John Kaplan (Co-Founder, Force Management)
Main Theme: Best practices for running an effective Sales Kickoff (SKO) event—motivating sales teams, aligning around company goals, effective training, and avoiding common pitfalls.
Guest Focus: John McMahon shares his deep insights on what makes a SKO valuable and how to get the most out of bringing the sales organization together.

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Episode Overview

In this episode, John McMahon joins John Kaplan to break down the most impactful elements of a successful Sales Kickoff (SKO). The conversation covers the true purpose of an SKO, best ways to motivate and align teams, how to approach product updates, and the critical role of leadership communication. The hosts highlight tangible strategies, share hard-earned lessons, and deliver actionable advice for CROs, CEOs, sales leaders, and enablement professionals planning their next SKO.

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Key Discussion Points & Insights

The Core Objectives of a Great SKO

• Motivation is Fundamental (00:29)

  • “You’re going to get your whole sales team together...First and foremost has to be to motivate the sales team.” – John McMahon (00:29)
  • John emphasizes motivation as the central driver behind an SKO. He recounts how, especially in smaller organizations, frequent gatherings are used to keep energy and engagement high.

• Alignment with Company Goals (00:55)

  • Aligning the salesforce with the company’s yearly objectives and any shifts in strategy is crucial.
  • “Second is, you know, what do we need to achieve next year? So aligning the salesforce with the company’s goals and any changes to the strategy for the new year.” – John McMahon (00:55)

• Relentless Focus on Training (00:55–01:30)

  • “And then, most important is training, training, training and training them on knowledge and the skills needed so they can succeed in the coming year.” – John McMahon (00:55)
  • McMahon draws attention to the transfer of skills—both formal and informal—that happens at a good SKO.

The "Priceless" Transfer of Information

• The Hidden Value of In-Person Gatherings (01:30)
  • “It’s amazing the amount of information that gets transferred just between the sales reps...salespeople are training other salespeople. They’re trading ideas. So there’s this priceless transfer of information that...more than pays for the event.”—John McMahon (01:30)
  • The unique networking and peer-learning opportunities of SKOs are highlighted as often overlooked but critical to ROI.

How to Approach Product Updates

• Strategic Product Presentations (02:20–03:20)
  • Product updates and roadmaps can either excite or deflate a team depending on honesty and specificity.
  • “If you have something exciting...then you put the chief product officer up there...If you don’t have those things and don’t have them laid out, don’t present it. There’s nothing to present. Then just hope dreams.” – John McMahon (02:41)
  • Cautions against over-promising and under-delivering on products or features.
  • “Most sales leaders are very, very skeptical about when you are going to deliver that product...Don’t make promises that you really can’t keep because that’s one way to demotivate the salesforce.” – John McMahon (03:10)

Leadership Presentations: What Works and What Doesn’t

• Message Must Resonate on a Personal Level (04:04)

  • “Understand...what’s going on in the minds of those salespeople...Tell them why it’s going to be easier for them to do their job. Tell them why they’re going to be better at their job. Tell them why they’re going to make more money. And tell them why they’re going to be able to achieve their career aspirations.” – John McMahon (04:04)
  • Urges leaders to display real understanding and intimacy with rep challenges, not just deliver generic content.

• The "Platform of Opportunity" Concept (04:57)

  • “The reason I’m joining company A versus company B or C is because I want to stand on a platform of opportunity. And that platform...is going to take me up...when you define goals that say when we achieve these goals, you’re going to be a very special individual on a very special team.” – John McMahon (04:57)
  • Connects motivation, goal alignment, and personal development.
  • If hiring is right, most reps want to buy into this vision and go “all in.”

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Notable Quotes & Memorable Moments

On the True Value of SKOs

“It’s amazing the amount of information that gets transferred just between the sales reps...There’s this priceless transfer of information that in, in my experience, more than pays for the event.”
– John McMahon (01:30)

On Product Presentations

"If you don’t have those things and don’t have them laid out, don’t present it. There’s nothing to present. Then just hope dreams."
– John McMahon (02:50)

On Leadership Impact

“If you can’t explain those things because you’re not intimate...just standing up there giving a little bit of a tap dance as the CRO or the CEO, it’s really going to fall on deaf ears. You’re not motivating them.”
– John McMahon (04:20)

On Building Teams Around Shared Aspiration

“Anyone wants to be a special person on a special team...If you hired the right people, what I found is they want in and they want all in. Now tell me how I’m going to do that.”
– John McMahon (05:10)

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Segment Timestamps

• 00:29 – 01:30: Core themes: motivation, alignment, and training
• 01:30 – 02:20: The “priceless” peer-to-peer knowledge exchange at SKOs
• 02:20 – 03:50: Product updates: best practices and pitfalls
• 04:04 – 06:00: Advice for CEO/CRO presentations, creating a “platform of opportunity”

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Key Takeaways

• Motivation, Alignment, and Training are the pillars of a successful SKO.
• Peer-to-Peer Learning at SKOs often yields the highest ROI due to informal knowledge sharing.
• Honest Communication about product readiness is crucial—don’t damage credibility with over-promising.
• Leadership Must Connect their message to real rep experiences and aspirations.
• Creating a Sense of Opportunity with clear, achievable targets inspires high-level buy-in and performance.

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This episode is a masterclass for sales leaders seeking to maximize the value of their next Sales Kickoff, featuring candid advice and practical wisdom from John McMahon and John Kaplan.

Transcript

[John McMahon]

Foreign.

[Podcast Host]

Welcome to the Revenue Builders podcast with John McMahon and John Kaplan. This podcast is brought to you by Force Management. Force's solutions help companies meet the revenue goals that drive funding and higher valuations. How many of you will head up to your sales kickoff soon? Today, John McMahon shares his point of view on motivating reps at your sko. Jon Kaplan's asking the question,

[John McMahon]

an annual sales kickoff. And again, I think if we're talking about an enterprise software company, that's what you and I know. But the major themes have to be, you know, motivating your sales team. You're going to get your whole sales team together on an annual basis. Sometimes. I mean, as you know, I used to do it almost on a quarterly basis. If we were small, I definitely did it on a quarterly basis. But first and foremost has to be to motivate the sales team.

[John Kaplan]

Yeah.

[John McMahon]

Second is, you know, what do we need to achieve next year? So aligning the salesforce with the company's goals and any changes to the strategy for the new year. And then, most important is training, training, training and training them on knowledge and the skills needed so they can succeed in the coming year. One of the biggest benefits, though, that I think Most, let's say CEOs or CFOs don't get right about, and maybe even a lot of CROs haven't thought about, is when you get a bunch of people together and you're trying to train them, there's amazing transfer of information between different parties. And I think that's the priceless piece everybody focuses on. We're going to put everybody on an airplane, get them to a hotel, you know, spend a lot of money on food and drinks, but, you know, what do we really get out of that? And what I found is it's amazing the amount of information that gets transferred just between the sales reps. So it's not just about me and my team as a CRO training my salespeople, but salespeople are training other salespeople. They're trading ideas. So there's this priceless transfer of information that in, in my experience, more than pays for the event.

[John Kaplan]

Most people use, like these kickoffs to introduce product updates and roadmaps by chief product officers. This can either be really awesome or can really suck. Give me your. Give me your. Give me your experience and your insights here.

[John McMahon]

Well, you want to motivate the sales team. So if you have something exciting to talk about from a product standpoint, then you put the chief product officer up there or somebody else that can really explain what that product can do in the use case for the specific Persona you're going to call on and what the benefits are to that company and why we're clearly differentiated to sell that new product, you know, to that customer. If you don't have those things and don't have them laid out, don't present it. There's nothing to present. Then just hope dreams. Because in general, most sales forces and most sales leaders are very, very skeptical about when are you going to deliver that product. So if it's a calendar year and you say you're going to deliver the product in, you know, August of next year, they they think you're never going to deliver it next year. They think it's the year after. They just don't believe it. Because for the most part, products come out too late and then they typically don't do what they say they're going to do. So don't make promises that you really can't keep because that's one way to demotivate the salesforce when it comes to the products you're going to deliver.

[John Kaplan]

One of the big components you're always going to get the leaders, the CEOs and the CROs, they're going to get up and talk to the organization. What is the best advice that you give to these people?

[John McMahon]

Understand, though, you know what's going on in the, in the minds of those salespeople. Like I just said, you hit it with the word intimate. If you're intimate with them, you understand the daily, the weekly, the monthly, and the quarterly struggles that they go through. So tell them why it's going to be easier for them to do their job. Tell them why they're going to be better at their job. Tell them why they're going to make more money. And tell them why they're going to be able to achieve their career aspirations. And if you can't explain those things because you're not intimate, so you're just throwing up a bunch of fricking slides or just standing up there giving a little bit of a tap dance as the CRO or the CEO, it's really going to fall on deaf ears. You're not motivating them. That's the number one thing you have to motivate them. I always think that people are looking to stand on what I call a platform of opportunity. Right? Right.

[John Kaplan]

Yeah.

[John McMahon]

The reason I'm joining company A versus Company B or C is because I want to stand on a platform of opportunity. And that platform of opportunity, I believe, is going to take me up. And I think anybody wants to be a special person on a special team and when you define goals that say when we achieve these goals, you are going to be a very special individual on a very special team and that's how we're going to achieve this opportunity. Most people want in. If you hired the right people, they want in on that. If you hired the wrong people, they might not want in on that. But if you hired the right people, what I found is they want in and they want all in. Now tell me how I'm going to do that, which is what happens in the training, right? In the development. So it's a combination of giving them the right knowledge and then training them on the right skills to achieve that.

[Podcast Host]

Thanks for listening to today's episode. If you enjoy the content, please subscribe, rate and review the show to help us reach more people. This show is brought to you by Force Management, where we help companies improve sales performance, executing the growth strategy at the point of sale. Check out forcemanagement.com for more information.