The Cheat Code & Friends

In Revenue Capital

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. 2H AGO

    Gifting, Attention and Saturation - Season 5: Episode # 87

    Listen now: Digital channels are getting saturated, and AI is accelerating the noise. Kris Rudeegraap shares how that shift is changing the way companies capture attention and build relationships. As CEO of Sendoso, he walks through why email alone no longer works, how gifting and direct mail are being used across the entire funnel, and what makes certain outreach actually stand out. Kris explains how teams are combining channels, using data to personalize at the individual level, and experimenting with creative sends that drive real engagement. He also breaks down how AI is shaping the future of go-to-market, from smarter timing and messaging to autonomous agents that support sales teams.  Tune in for insights on acquisitions, scaling into new markets, and why human relationships are becoming more important as automation increases. Chapters 00:00 Introduction and Personal Updates 06:28 The Evolution of Sendoso and Gifting Strategies 12:27 Market Trends and Segment Adoption 14:29 Changing Buyer Behavior and Sales Strategies 14:57 The Power of Gifting in Marketing 18:10 Creative Use Cases for Gifting 22:00 AI's Role in Personalization and Gifting 24:17 Market Expansion and Customer Insights 28:01 Navigating Acquisitions and Integration Challenges 37:58 The Future of Sales with AI and Human Interaction References in the Show: https://www.giftbit.com/2026-trend-report  https://ddbricks.com/post/corporate-gifting-trends-2026-from-objects-to-experiences-why-budgets-are-shifting  Quote of the Show: “I still believe in email. I don't think email is dead. I just think you can't be email-only, which you could have been five years ago, 10 years ago. And so when you need to add other channels, one of the obvious ones that works really well is gifting a direct mail, and we're poised for helping a lot of companies since we've built the infrastructure and the data layer over the last decade.” - Kris Rudeegraap 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

    34 min

  2. MAR 27

    Coaching, Performance and Trust - Season 5: Episode # 86

    Bad sales reps have always had places to hide. AI is starting to remove them. In this episode, Matthew Whyatt shares what happens when sales teams finally see the truth: which reps are really performing, which managers are actually coaching, and where deals start breaking down. The conversation focuses less on AI hype and more on what sales leaders can do with better visibility, better data, and better training. Matthew gives his opinion on why strong sales remains a human-to-human skill, even as AI reshapes how teams prepare, practice, and improve. He talks through the role of discovery, the danger of over-explaining in demos, and why guiding the buyer is often just as important as pitching the product. They also dig into objection handling, onboarding, sales management, and the growing pressure on leaders to raise standards rather than rely on instinct.  Chapters 00:00 Introduction and Light Banter 02:59 Sales Backgrounds and Early Experiences 06:01 The Impact of AI on Sales 11:51 Sales Management and Coaching Challenges 18:00 The Future of Sales with AI 19:38 AI in Sales Training and Onboarding 22:29 Challenges in Mid-Market and Enterprise Sales 25:15 Real-Time Coaching and Sales Skills 27:16 The Importance of Human Connection in Sales 30:01 Guiding the Buyer Through the Sales Process 36:01 The Role of Marketing in Modern Sales 42:54 Tech Talk: Insights from Matthew Whyatt References in the Show: https://www.linkedin.com/pulse/ai-wont-replace-your-sales-team-itll-just-expose-lazy-matthew-whyatt-kpq9c/?trackingId=a%2BGQ6EiGSH%2BeaPS8yVR63Q%3D%3D  https://podcasts.apple.com/us/podcast/the-ceo-and-the-salesman-podcast/id1635865557  Quote of the Show: “AI is removing the nooks and crannies that crappy salespeople can hide in.” - Matthew Whyatt  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

    47 min

  3. MAR 13

    Bottlenecks, Buyers and AI - Season 5: Episode # 85

    This episode will change the way you think about sales leadership, buyer behavior, and what growth teams need to do next. Join the hosts for a conversation with Jake Dunlap, CEO of Skaled, on how AI is reshaping the modern revenue engine from the inside out. Jake breaks down why CROs are running out of time to treat AI like a side project, where most teams are misapplying it, and how the biggest opportunity isn’t in automating more noise, but in improving how sellers think, work, and create value. From prospecting and deal strategy to coaching, hiring, and customer experience, Jake shares a sharp perspective on what’s changing fastest in B2B sales. Listen in as he explains why buyers are moving ahead of most sales teams, why traditional sales playbooks are losing relevance, and why the future belongs to organizations that remove friction, move faster, and meet customers where they are. Chapters 00:00 Introduction and Excitement for Snowboarding 02:56 The Evolving Role of the CRO 05:53 AI's Impact on Sales Processes 09:04 Prospecting and Sales Strategies with AI 11:53 The Future of Sales Leadership 14:56 Implementing AI in Organizations 18:01 Hiring and AI Proficiency 21:04 The Changing Buyer Landscape 24:03 Customer Experience and Sales 27:11 Conclusion and Key Takeaways References in the Show: https://www.forbes.com/councils/forbesbusinesscouncil/2025/12/15/the-winning-ai-strategies-of-high-growth-companies  https://synoviadigital.com/insights/the-state-of-ai-in-2025-what-mckinseys-data-tells-us-about-2026  Quote of the Show: “AI is more of a shift in how we solve problems as humans, less of a new interesting technology.” - Jake Dunlap 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

    43 min

  4. FEB 27

    Handoffs, Experimentation and Agility - Season 5: Episode # 84

    Startup land can be complete chaos… shifting buyer behavior, distributed teams, tighter budgets, and AI changing how work gets done. In this episode, John Eitel, CRO at Orum, explains what it all means for modern revenue leaders and why agility is no longer optional. Together, the hosts and John explore the death of the linear funnel, the resurgence of outbound, and why what was “old” in sales is suddenly working again. John also dives into the real leverage point most teams ignore: coaching and how AI can finally make it scalable without losing the human edge. The conversation questions long-held assumptions about SDRs, role specialization, and career paths, pushing leaders to rethink how their sales org is actually structured. This is about building revenue teams that experiment faster, learn quicker, and adapt before the market forces them to. Chapters 00:00 Introduction to the Podcast and Guest 02:55 Navigating Chaos in Startup Land 05:52 The Impact of AI on Sales 08:49 Balancing Scale and Personal Touch in Sales 12:06 The Evolution of Sales Roles 15:06 Understanding Ideal Customer Profiles (ICP) 17:53 The Importance of Coaching in Sales 21:02 Rethinking Sales Development Roles 23:59 Career Pathing in Sales 27:10 The Future of Sales Teams 29:46 Final Thoughts on Experimentation and Adaptability References in the Show: https://www.sellingpower.com/23217/from-pipeline-to-prediction-the-ai-playbook-for-high-growth-sales-teams  https://www.forbes.com/sites/lilianraji/2025/12/31/your-2026-marketing-strategy-edge-email-education-and-authenticity/  Quote of the Show: “No longer do our buyers all come into an office and sit at a desk with a phone on it. They're in a coffee shop, they're in their homes. They're now moving targets that buy differently. And then you put AI on top of that. I think that really was the third domino in this effect. But I think probably, again, those things all coming together have really sent this thing into a spin of change here.” - John Eitel 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

    37 min

  5. FEB 12

    Dialing, Data and Discipline - Season 5: Episode # 83

    Joey Gilkey, CEO of TitanX, joins the show to tear down one of the most sacred ideas in go-to-market: that more activity equals more revenue. Joey argues that most sales teams aren’t failing because reps aren’t working hard enough. They’re failing because the system they’re operating inside is broken. Cold calling still works, but only if you stop treating every prospect the same. Most people will never answer the phone, and pretending otherwise destroys rep productivity, forecasting, and morale. By identifying who is actually reachable before a call is made, teams can radically change the economics of outbound. The conversation covers why SDR teams should be treated like a signal engine, not a meeting factory, and why founders keep defaulting to headcount when efficiency is the real constraint. By the end of the conversation, it’s hard to look at SDRs, outbound, or ‘activity metrics’ the same way again. Chapters 00:00 Introduction and Setting the Stage 05:05 Understanding Titan X's Value Proposition 10:29 The Shift in Sales Strategies 17:14 Redefining Sales Development as an Ad Channel 20:15 The Importance of Messaging and Targeting 21:21 Understanding Messaging by Persona 24:41 The Importance of Follow-Up and Data 27:49 Dispositions and Their Impact on Sales 30:46 Data Aggregation and Coordination Drag 34:22 The Reach Rate and Cold Calling Strategy 39:18 Identifying Skill Gaps and Data Quality 40:05 Customer Success and Operationalizing Sales 43:01 The Challenges of Product-Led Growth References in the Show: https://www.marketingbrew.com/stories/2025/12/18/cmos-on-overhyped-marketing-trends-in-2025  https://www.mckinsey.com/capabilities/growth-marketing-and-sales/our-insights/the-cmos-comeback-aligning-the-c-suite-to-drive-customer-centric-growth  Quote of the Show: "An ad doesn't give us feedback. An email doesn't give us feedback. It's why I love the phone. It's just conversational advertising. If we can activate an audience, not even around conversions and appointments and meetings, and instead we can uncover interest and intrigue and intent, the three I's, and we can take that intel, that could be the mitochondria, the powerhouse of the go-to-market cell, which is, I'm on the front lines getting information that no one else has from my SDRs.” - Joey Gilkey 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

    47 min

  6. JAN 30

    ICPs, Niche Markets and Expansion - Season 5: Episode # 82

    Mike Huffaker, CRO, Planet DDS, joins the show to share what actually drives real growth in a vertical SaaS market where “going broad” is the default trap. Mike explains why narrowing to a true ideal customer profile can feel terrifying, but becomes a growth cheat code once you commit: higher win rates, higher ASPs, clearer messaging, and less competitive deal cycles. He also gets candid about the part most teams underestimate after they move upmarket: implementation. In Mike’s dental niche, going live means data conversion, workflow change, training across roles, and real internal leadership from the customer side.  If you can’t deliver outcomes post-sale… none of the bookings matter. Chapters 00:00 Introduction to Growth Strategies 02:56 Targeting Ideal Customer Profiles 05:51 Internal Buy-In for Market Focus 09:12 Team Structure and Talent Acquisition 11:59 Implementation Challenges and Customer Success 14:58 The Role of AI in Implementation 18:13 Revenue Growth and Account Management 20:56 Navigating Complex Sales Processes 23:59 Hiring for Success in Enterprise Sales 26:50 Conclusion and Key Takeaways References in the Show: https://www.forbes.com/sites/jodiecook/2025/08/08/5-chatgpt-prompts-to-define-your-ideal-customer-profile/  https://www.entrepreneur.com/growing-a-business/how-defining-my-ideal-client-profile-transformed-my-business/498064  https://martech.org/the-biggest-ideal-customer-profile-mistakes-businesses-make-and-how-to-fix-them/  Quote of the Show: "We did a lot of modeling on what we were generating from an MQL perspective, what we expected we could do from an outbound motion as well. And we got everyone pretty comfortable with it. And it's turned out to be something where the team now appreciates not having to work through. I guess, for lack of a better term, things that just keep you busy that don't really drive results.” - Mike Huffaker 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

    39 min

  7. JAN 16

    Unicorns, Duct-Tape and Expectations - Season 5: Episode # 81

    Hiring marketing talent is one of the biggest blind spots for early-stage founders, and Jessica Gilmartin has seen the same mistakes play out over and over again. In this episode, Jessica (former CMO/CRO at Calendly) shares why “marketing” is actually multiple jobs, how to decide whether you need demand gen, product marketing, or brand, and why most founders hire the right person for the wrong stage. She shares real frameworks for setting clear expectations, building trust through communication, and avoiding the toxic ripple effects of a bad hire. The conversation also covers what the best early marketing leaders have in common (including the underrated value of entrepreneurial experience), why duct-tape marketing eventually collapses at scale, and why marketing needs a real seat at the executive table… not tucked under sales. Chapters 00:00 Introduction and Guest Background 02:53 The Challenge of Hiring Marketing Talent 04:04 Understanding Marketing Roles 05:44 Evaluating Marketing Needs 07:40 The Importance of Experience in Marketing 10:48 Hiring for the Right Stage 12:55 Setting Expectations and Goals 22:29 Red Flags in Hiring 24:46 Communication and Trust in Marketing 30:09 The Distinction Between CMO and CRO 34:12 The Importance of Marketing at the Executive Table References in the Show: https://www.entrepreneur.com/starting-a-business/the-5-mistakes-that-kill-startups/499868  https://hbr.org/podcast/2024/10/why-founders-need-to-focus-more-on-sales-and-marketing  https://www.linkedin.com/pulse/12-most-common-mistakes-made-building-your-first-sales-lemkin-ucw7c/  Quote of the Show: "I've never been sad that I have fired too early. I've only been upset with myself if I have fired too late. I think a bad hire or a bad employee is absolutely toxic to everybody else in the organization.” - Jessica Gilmartin 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

    40 min

  8. 12/24/2025

    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
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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 - 2026
  • Episodes
    87
  • Rating
    Explicit
  • Copyright
    © 2023
  • Show Website
    The Cheat Code & Friends