The Cheat Code & Friends

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. Chapters00:00 Introduction and Light Banter02:59 Sales Backgrounds and Early Experiences06:01 The Impact of AI on Sales11:51 Sales Management and Coaching Challenges18:00 The Future of Sales with AI19:38 AI in Sales Training and Onboarding22:29 Challenges in Mid-Market and Enterprise Sales25:15 Real-Time Coaching and Sales Skills27:16 The Importance of Human Connection in Sales30:01 Guiding the Buyer Through the Sales Process36:01 The Role of Marketing in Modern Sales42:54 Tech Talk: Insights from Matthew WhyattReferences 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

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.Chapters00:00 Introduction and Excitement for Snowboarding02:56 The Evolving Role of the CRO05:53 AI's Impact on Sales Processes09:04 Prospecting and Sales Strategies with AI11:53 The Future of Sales Leadership14:56 Implementing AI in Organizations18:01 Hiring and AI Proficiency21:04 The Changing Buyer Landscape24:03 Customer Experience and Sales27:11 Conclusion and Key TakeawaysReferences 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 DunlapWays 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

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.Chapters00:00 Introduction to the Podcast and Guest02:55 Navigating Chaos in Startup Land05:52 The Impact of AI on Sales08:49 Balancing Scale and Personal Touch in Sales12:06 The Evolution of Sales Roles15:06 Understanding Ideal Customer Profiles (ICP)17:53 The Importance of Coaching in Sales21:02 Rethinking Sales Development Roles23:59 Career Pathing in Sales27:10 The Future of Sales Teams29:46 Final Thoughts on Experimentation and AdaptabilityReferences 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 EitelWays 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

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.Chapters00:00 Introduction and Setting the Stage05:05 Understanding Titan X's Value Proposition10:29 The Shift in Sales Strategies17:14 Redefining Sales Development as an Ad Channel20:15 The Importance of Messaging and Targeting21:21 Understanding Messaging by Persona24:41 The Importance of Follow-Up and Data27:49 Dispositions and Their Impact on Sales30:46 Data Aggregation and Coordination Drag34:22 The Reach Rate and Cold Calling Strategy39:18 Identifying Skill Gaps and Data Quality40:05 Customer Success and Operationalizing Sales43:01 The Challenges of Product-Led GrowthReferences 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 GilkeyWays 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

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.Chapters00:00 Introduction to Growth Strategies02:56 Targeting Ideal Customer Profiles05:51 Internal Buy-In for Market Focus09:12 Team Structure and Talent Acquisition11:59 Implementation Challenges and Customer Success14:58 The Role of AI in Implementation18:13 Revenue Growth and Account Management20:56 Navigating Complex Sales Processes23:59 Hiring for Success in Enterprise Sales26:50 Conclusion and Key TakeawaysReferences 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 HuffakerWays 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

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.Chapters00:00 Introduction and Guest Background02:53 The Challenge of Hiring Marketing Talent04:04 Understanding Marketing Roles05:44 Evaluating Marketing Needs07:40 The Importance of Experience in Marketing10:48 Hiring for the Right Stage12:55 Setting Expectations and Goals22:29 Red Flags in Hiring24:46 Communication and Trust in Marketing30:09 The Distinction Between CMO and CRO34:12 The Importance of Marketing at the Executive TableReferences 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 GilmartinWays 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

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.Chapters00:00 Introduction and Holiday Cheer02:59 Understanding Go-To-Market Strategies06:02 The Attention Economy and Market Dynamics08:55 Differentiated Marketing Tactics12:10 Navigating Economic Uncertainty15:09 Building a Brand in a Crowded Market18:01 The Role of Founders in Go-To-Market20:50 Unscalable Tactics for Scalable Success23:56 The Importance of Brand Recognition26:23 Understanding Dismissiveness in Founders28:09 The Role of Charismatic Leadership in Go-to-Market Strategies30:06 Risk-Taking in Brand Building32:10 The Evolution of Account-Based Marketing (ABM)34:44 Leveraging Vertical SaaS for Targeted Marketing36:10 Innovative Outreach Strategies in Sales39:01 The Importance of Understanding Your Buyer41:43 Transforming Sales Teams for Success44:19 Addressing Buyer Apprehension in SaaS45:54 Navigating AI in Go-to-Market StrategiesReferences 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 WagnerWays 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

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.Chapters00:00 Introduction to AI in Revenue Generation03:54 Leveraging Data for Targeting in Vertical SaaS10:16 Building an Outbound Engine: Strategies and Results13:13 Attention to Detail: The Key to Sales Efficiency18:00 The Evolving Role of Sales Leadership22:04 AI Integration: Balancing Top-Down and Bottom-Up Approaches24:52 AI in Sales: Understanding Market Dynamics28:12 Evaluating AI Tools: Testing and Implementation Strategies32:53 The Future of CRM: Disruption and Integration39:57 Architecting AI Solutions: Master Agents and Context Management43:03 Organizational Design for AI: Building Effective TeamsReferences in the Show:https://www.revenuebrew.com/stories/2025/10/06/why-cros-are-rising-in-popularityhttps://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 NortonWays 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

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.Chapters00:00 Thanksgiving Reflections and Family Dynamics02:59 The Evolution of Marketing Technology06:01 The Impact of AI on Marketing Strategies09:06 Tactic Fatigue and the Tragedy of the Commons11:59 The Role of Specialization in Marketing15:00 Training AI: The New Marketing Operations19:59 Future of Marketing Jobs and Operations20:34 The Role of AI in Marketing Operations23:08 Evolving Skills in Marketing Operations24:52 Sales and Marketing Alignment Challenges27:05 Leveraging AI for Content Creation30:19 Insights from Market Mapping31:41 The Future of AI in B2B Marketing34:27 Innovator's Dilemma in MarTech39:22 Pricing Innovations in the AI Era42:09 Personalizing Buyer Journeys with AIReferences 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 MillerWays 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