The Cheat Code & Friends

In Revenue Capital
  • 5.0 (6)
  • BUSINESS
  • UPDATED WEEKLY

Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you. Game over.

  1. 23H AGO

    Christmas, Chaos and GTM - Season 4: Episode #80

    It’s the Cheat Code Christmas Special! Join the hosts for an always colorful, yet never without value, conversation with Craig Rosenberg and Scott Albro on what actually works in go-to-market right now and why most founders are getting it wrong. If you’re trying to break through buyer apathy, build a brand from scratch, or rethink how you go to market in 2026, this episode will challenge a lot of assumptions. In a world defined by the attention economy, economic uncertainty, and buyer skepticism, Craig and Scott break down why traditional GTM playbooks are failing and what’s replacing them.   The conversation goes deep into why founders, especially technical ones, tend to dismiss go-to-market, how ABM has evolved (and why it’s far from dead), and what differentiated outreach really looks like today. They also explore where AI actually adds value, why productivity gains aren’t enough on their own, and how strong points of view and charismatic leadership can cut through noise in even the most crowded markets. Chapters 00:00 Introduction and Holiday Cheer 02:59 Understanding Go-To-Market Strategies 06:02 The Attention Economy and Market Dynamics 08:55 Differentiated Marketing Tactics 12:10 Navigating Economic Uncertainty 15:09 Building a Brand in a Crowded Market 18:01 The Role of Founders in Go-To-Market 20:50 Unscalable Tactics for Scalable Success 23:56 The Importance of Brand Recognition 26:23 Understanding Dismissiveness in Founders 28:09 The Role of Charismatic Leadership in Go-to-Market Strategies 30:06 Risk-Taking in Brand Building 32:10 The Evolution of Account-Based Marketing (ABM) 34:44 Leveraging Vertical SaaS for Targeted Marketing 36:10 Innovative Outreach Strategies in Sales 39:01 The Importance of Understanding Your Buyer 41:43 Transforming Sales Teams for Success 44:19 Addressing Buyer Apprehension in SaaS 45:54 Navigating AI in Go-to-Market Strategies References in the Show: https://www.forbes.com/sites/forrester/2025/11/05/navigating-2026-key-predictions-for-b2b-leaders/  https://synapticincorporated.com/all/customer-acquisition-strategies-for-2025-the-latest-trends/  Quote of the Show: "I think the crazy observation for me around what I'm seeing in the market is that buyers are really apprehensive. There's two things that drive that. One, is SaaS over the last 10, 15 years, I think, burned a lot of people with a lot of promises and not a lot of results that they could point to. And it may have put them on the hot seat to a certain extent. Then the other side of it is this massive acceleration of AI that they don't even understand. They can't wrap their head around it.” - Josh Wagner Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    52 min

  2. 5D AGO

    Data, Leverage and Leadership - Season 4: Episode # 79

    Tune in for a conversation with Kyle Norton, Chief Revenue Officer at Owner.com, on how modern revenue teams are using AI, data, and systems thinking to do more with less. Kyle breaks down how Owner built a highly efficient go-to-market engine by combining deep customer understanding with proprietary data, machine learning models, and relentless operational rigor.  The hosts dig into why today’s CRO must think like a systems engineer, how to evaluate AI tools without chasing silver bullets, and what founders get wrong when they expect AI to fix broken sales motions. They also explore the future of CRMs, agentic workflows, and why disciplined execution, not flashy tools, is the real competitive advantage in an AI-powered sales world. Chapters 00:00 Introduction to AI in Revenue Generation 03:54 Leveraging Data for Targeting in Vertical SaaS 10:16 Building an Outbound Engine: Strategies and Results 13:13 Attention to Detail: The Key to Sales Efficiency 18:00 The Evolving Role of Sales Leadership 22:04 AI Integration: Balancing Top-Down and Bottom-Up Approaches 24:52 AI in Sales: Understanding Market Dynamics 28:12 Evaluating AI Tools: Testing and Implementation Strategies 32:53 The Future of CRM: Disruption and Integration 39:57 Architecting AI Solutions: Master Agents and Context Management 43:03 Organizational Design for AI: Building Effective Teams References in the Show: https://www.revenuebrew.com/stories/2025/10/06/why-cros-are-rising-in-popularity https://www.hansonsearch.com/articles/sales-marketing-chief-revenue-officer/  Quote of the Show: "You have to combine art and science. Like you can't just tell a model, hey, tell me what my ICP is. You have to bring nuance to it. And you have to have a very in-depth and intimate understanding of the types of customers that you feel like you can win and serve really well and try to get hyper-targeted with it. And all the AI tools can help tremendously to do that refinement and then eventually do the scraping, enrichment, scoring and targeting. But it all starts with a really clear understanding of ICP.” - Kyle Norton Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    46 min

  3. DEC 5

    Signals, Saturation and Shift - Season 4: Episode # 78

    Join the hosts for a conversation with Jon Miller, co-founder of Marketo and one of the most influential minds in modern marketing, on how AI, tactic fatigue, and buyer anonymity are forcing marketers to evolve faster than ever. Together they explore the cracks forming in legacy marketing automation and the rise of signal-based journeys. Jon breaks down why the next decade of marketing won’t look anything like the last. This episode explains why marketers must shift from tactics to context, how AI can streamline operations without sacrificing creativity, and why sales and marketing alignment is still so painfully hard (and what might finally fix it). Jon also digs into the innovator’s dilemma facing big MarTech vendors, the resurgence of niche vertical plays, and the new skills marketers will need to thrive. If you’ve ever felt like your marketing is losing its edge, this episode will redefine how you think about innovation, AI, and the future of go-to-market. Chapters 00:00 Thanksgiving Reflections and Family Dynamics 02:59 The Evolution of Marketing Technology 06:01 The Impact of AI on Marketing Strategies 09:06 Tactic Fatigue and the Tragedy of the Commons 11:59 The Role of Specialization in Marketing 15:00 Training AI: The New Marketing Operations 19:59 Future of Marketing Jobs and Operations 20:34 The Role of AI in Marketing Operations 23:08 Evolving Skills in Marketing Operations 24:52 Sales and Marketing Alignment Challenges 27:05 Leveraging AI for Content Creation 30:19 Insights from Market Mapping 31:41 The Future of AI in B2B Marketing 34:27 Innovator's Dilemma in MarTech 39:22 Pricing Innovations in the AI Era 42:09 Personalizing Buyer Journeys with AI References in the Show: https://chiefmartec.com/2025/05/beyond-ai-assistants-how-ai-is-being-more-deeply-embedded-in-marketing-and-martech-stacks/  https://martech.org/the-three-forces-that-shaped-martech-in-2025/  Quote of the Show: "Can your average field marketer now come along and just say, hey, AI, go make me a new webinar for this audience and for this segment? And it actually does it the right way.” - Jon Miller Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    42 min

  4. NOV 21

    Hiring, Grit and Risk - Season 4: Episode # 77

    If you’ve ever underestimated the power of hiring, this episode will change the way you think about growth. Join the hosts for a conversation with Dr. Heidi Ojha, Founder and CEO of Aware Health, on how no-nonsense hiring can make or break your growth story. From identifying organizational gaps to building scalable hiring processes, Heidi shares what it takes to grow a team in one of the toughest sectors: healthcare. She explains why founders should approach hiring like a marketing campaign, the traits that define true high performers, and how onboarding and culture influence long-term success.  Listen in as they discuss startup realities, flexibility, career pathing, and why founders should spend nearly half their time recruiting.  Chapters 00:00 Introduction and Energy Check 01:57 The Importance of Hiring in Growth 06:10 Identifying Gaps and Roles 09:51 Hiring for Clinical and Non-Clinical Roles 13:56 Qualities of High Performers 17:53 The Hiring Process as a Marketing Campaign 21:52 Onboarding and Setting Up for Success 23:24 Revamping Onboarding Processes 27:15 The Importance of Team Integration 30:31 Flexibility in Roles and Responsibilities 32:45 Career Pathing and Growth Opportunities 39:11 Vision and Future Planning in Startups References in the Show: https://www.forbes.com/advisor/business/recruitment-strategies/  https://vettio.com/blog/startup-hiring-practices-the-ultimate-guide-for-founders/  Quote of the Show: "If they're lukewarm in the beginning, that's probably not a good recipe for them working out and being a really strong team fit. So, I think it's a bummer sometimes because I'm like, oh my gosh, this is a perfect candidate, and they're like, eh. So I'm like, nope, I'm going to be eh and pass on them because I want somebody who's like, this is what I want to do with my life.” - Dr. Heidi Ojha Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    45 min

  5. NOV 7

    Talent, DNA and Trust - Season 4: Episode # 76

    Tune in for a conversation with the man, the myth, the legend, Bill Binch, Operating Partner at Battery Ventures and former sales executive at Marketo, on what it really takes to build high-performing sales teams in today’s AI-driven world. From hiring for the right sales mindset to building customer-focused teams and scalable sales processes, Bill shares hard-earned lessons from decades of leading and advising top SaaS companies. He breaks down how founders can make smarter sales hires, why continuous learning separates great leaders from the rest, and how AI is reshaping the future of selling. Chapters 00:00 Introduction and Overview of the Conversation 03:05 A Day in the Life of an Operating Partner 05:57 Sales Hiring Challenges and Strategies 11:37 Identifying the Right Sales DNA 17:50 The Importance of Value Selling 23:52 Building a Sales Process in Early-Stage Companies 29:47 Adapting to AI in Sales 35:42 Success Signals for New Sales Hires 41:37 Navigating Stale Deals and Customer Relationships References in the Show: https://www.businessinsider.com/microsoft-layoffs-salespeople-relationship-guy-ai-solution-engineer-investor-2025-7  https://hbr.org/2025/09/how-successful-sales-teams-are-embracing-agentic-ai  Quote of the Show: "I wish I could write the one-size-fits-all book on your first sales hire or your first five sales hires and what order they should be. Should it be a sales rep? Should it be a sales leader? Should you have sales engineers? What should you have? What shouldn't you have? But I don't think that exists because it really depends on a number of different factors.” - Bill Binch Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    48 min

  6. OCT 24

    Disruption, Revenue and Relationships - Season 4: Episode # 75

    The world of sales is changing fast and the playbooks that fueled growth a few years ago aren’t enough anymore. In this special hosts-only episode, Justin, Josh and Sean break down what today’s shifting startup and sales environment really means for go-to-market teams. From evolving buyer expectations to the rise of AI-driven strategies, they explore how top performers are adapting to meet customers where they are and where they’re going next. You’ll hear insights on the new role of full-cycle AEs, why post-sale engagement is the key to long-term growth, and how marketing and thought leadership can drive meaningful differentiation in a crowded market. They also zoom out with an investor’s view of the market: why Series B and C rounds are getting squeezed, how bridge-to-profitability funding is on the rise, and where private equity rollups in verticals are reshaping go-to-market. Tune in to get an inside look at their perspectives and how modern sales leaders are redefining growth in a more complex, connected, and customer-centric world. Chapters 00:00 Introduction and Market Landscape Overview 02:47 Startup Growth and Benchmarking Insights 05:44 Challenges in Sales and Buyer Expectations 08:38 The Evolution of Sales Models 11:40 The Role of AI in Sales Dynamics 14:30 Consolidation Trends in Various Industries 17:39 Navigating the New Buyer Landscape 20:31 Reimagining Sales Strategies for Success 23:13 The Evolution of Information Access 25:34 Marketing Strategies in a Changing Landscape 27:23 The Role of Executives in Sales 29:38 Sales Hiring Trends and AI Impact 32:34 Building Strategic Relationships 35:38 The Importance of Post-Sale Relationships 38:34 Navigating the Investment Landscape 41:29 The Future of Sales and Marketing References in the Show: https://jurassiccapital.us19.list-manage.com/track/click?u=e3cbd001231a704e4826ed17e&id=28024b7e6d&e=781361f180  https://www.inc.com/brian-contreras/inc-5000-companies-ceo-survey-growing-sales-teams/91222802  Quote of the Show: "It's hard to hire salespeople because everyone says they're great at relationships. ‘Tell me where you've done that and show me what those results have been,’ should be the follow-up question to that. And then go talk to the parties that are involved within that story or that analogy, and you'll find out really quickly who did what.” - Justin Gray Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    46 min

  7. OCT 10

    Compensation, Culture and Accountability - Season 4: Episode # 74

    Tune in for a conversation with Mark Schopmeyer, Co-Founder and Co-CEO of CaptivateIQ, on how incentive compensation can make or break the success of an early-stage company. From the critical role of founding AEs to the delicate balance between keeping plans simple and aligning them with big-picture goals, Mark explains why no single model works for every business. They dig into the importance of trust and transparency in compensation plans, how leadership choices shape performance, and why cultural alignment is just as powerful as equity when it comes to motivating teams. You’ll also hear highlights from CaptivateIQ’s latest State of Incentive Compensation report, filled with trends and best practices that modern companies can’t afford to ignore. Chapters 00:00 Introduction and Team Dynamics 02:51 Incentive Compensation Overview 05:49 Founding AE Concept and Compensation Strategies 08:49 The Importance of Simplicity in Compensation Plans 11:44 Leadership and Organizational Culture in Compensation 14:47 Equity Packages and Early Stage Hiring 17:28 Balancing Risk and Reward in Startups 20:30 The Role of Accountability in Startup Success 27:40 Building a Long-Term Vision 30:42 Incentivizing Performance: Equity vs. Compensation 32:20 Understanding the Bigger Picture in Startups 32:54 Unlocking Outsized Performance through Trust 34:25 The Role of Culture in Compensation 36:07 The Relationship Between Ops and Frontlines 39:02 Building Trust in Compensation Plans 42:21 The Value of High Performers 43:48 Behavioral Insights in Sales Performance 45:20 Integrating Performance Culture Post-M&A 46:28 Incentivizing Beyond Traditional Roles 51:25 The State of Compensation Report References in the Show: https://www.captivateiq.com/resources/captivateiq-2025-sales-compensation-benchmarks-report?  https://www.hrdive.com/news/2026-raises-to-hold-steady-compensation/759671/?  Quote of the Show: "If there's anything I've learned working with startups and early stage companies and early stage founders, there's no correct way to do [things]. There's just a lot of methods to the madness. And I think founding AEs is no different.” - Mark Schopmeyer Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    54 min

  8. SEP 26

    Strippers, RTO and Sales - Season 4: Episode # 73

    A former single mom, stripper, and felon turned two-time author and VP of Innovative Disruption at Lift Enablement, Dr. V lays out hard lessons and simple truths on resilience, sales talent, and reporting—without the euphemisms. In this episode, we talk about what most teams tiptoe around: who you hire, how you build culture, and why “return to office” means nothing if the office isn’t safe. This episode is candid, occasionally spicy, and packed with immediately usable hiring and enablement takeaways. Chapters 00:00 — Cold open & why “Dr. V” 03:00 — From single mom & felon to author and executive 06:10 — Sales lessons from the club: price floors, personas, and conversion 14:20 — The RTO debate: safety, reporting, and retaliation 28:30 — Are remote teams less productive? Training vs. environment 33:40 — Hiring beyond pedigree: what hunger looks like on a sales team 46:30 — What “disruptive innovation” work actually is (and isn’t) 53:10 — Founders: take calculated risks on people References in the Show: https://www.cdc.gov/niosh/violence/about/index.html#:~:text=Quick%20facts%20and%20stats&text=Of%20those%20victims%20who%20experienced,5%20days%20away%20from%20work  https://drvboykin.com/pages/fix-your-face-the-book  https://stopstreetharassment.org/our-work/nationalstudy/2024metoostudy/  Quote of the Show: “Well, I'll be happy to return to work when the workplace becomes safe. What does that mean? Well, women aren't safe in the workplace and they're not free from sexual harassment. 38% of women have reported experiencing sexual harassment. That's one in seven women who have left a job or declined a job because of sexual harassment. 60% of women have said they'd experienced unwanted sexual attention in the workplace. And in some industries, more than nine out of 10 women say they've been harassed sexually. So if you want me to return to work, and 85% of people don't who have experienced sexual harassment don't report sexual harassment, yet we still have these numbers attached to it from a 15% reporting sample. Why would I want to return to work when you haven't made it safe to do so?” - Dr. V Ways to Tune In: Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190 Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912 YouTube: https://www.youtube.com/@CheatCodePodcast

    53 min
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5
out of 5
6 Ratings

About

Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you. Game over.

Information

  • Creator
    In Revenue Capital
  • Years Active
    2023 - 2025
  • Episodes
    80
  • Rating
    Explicit
  • Copyright
    © 2023
  • Show Website
    The Cheat Code & Friends