The Revenue Insiders

TLDR: Salesforce just acquired Contentful, and everyone is calling it a marketing story. Kelly and Tiffany make the case that it is actually a sales, enablement, and RevOps story about content becoming AI ready data. Here is what it means for your team before a Salesforce rep calls you this fall. Full Description: Salesforce signed a deal to buy Contentful, a content platform used by more than 4,8...

TLDR: While enablement teams everywhere are shrinking and the whole market is racing to automate, Clay is doing the opposite. Melina Giakas explains why her AI-forward enablement team makes reps earn the shortcut before any automation gets switched on. Enablement is supposed to be the first thing AI replaces. So why is one of the most AI-forward companies in go-to-market growing its enablement tea...

TLDR: Founder-led sales got you to seven figures. It won't get you to eight. Gearoid Cox, founder of SalesPipeline, joins us to unpack why most founders can't let go of sales, why AI SDRs are more brand damage than productivity gain, and what it actually takes to architect a sales motion that scales without the founder in every seat. Full Description: Every founder hits the same wall. The...

TLDR: Everyone tells sales managers to "be the CEO of your business," but nobody actually explains what that means. Sarah Bedwell does, and the gap between what most frontline leaders are doing and what's possible is staggering. Sales managers have some of the hardest jobs in any go-to-market organization. They're managing seven to ten reps, sitting in on deals, running forecast...

TLDR: AI made content faster. It also made everyone sound exactly the same. David J. Ebner, founder of Content Workshop and author of King Makers, breaks down why the gap between "passable" and "good" content has never been wider and what GTM teams need to do about it before their brand disappears into the noise. The AI content crisis isn't coming. It's here. Every B2B...

TLDR ; Gong just renamed the CRO role to Chief Revenue Architect. That's not a branding exercise. It's a signal that the top of every go-to-market org is being rebuilt around systems, AI, and the human skills your team can't fake. This week, Dannii Mathers (SBR Consulting) joins us to call out what's actually changing and what every revenue leader needs to do about it. Full Descrip...

TLDR: Outbound is harder than it has ever been. Jason Bay, founder of Outbound Squad, breaks down why the predictable revenue era is officially over, why AI is exposing every average seller in the market, and the methodology GTM teams need to survive the "too good to ignore" era of sales. Full description: Reply rates below 1%. Nobody picks up unknown phone numbers. SDR teams are being r...

TLDR: Your best sellers are getting promoted into leadership roles with no real training, and both they and the business are paying for it. Tiffany and Kelly break down why the frontline sales manager is the most underdeveloped role in go-to-market and what actually fixing it looks like. Frontline sales leaders are carrying one of the heaviest responsibilities in any revenue org: accountable for t...

Jeff Rosset didn't just start using AI tools. He built an internal system of AI employees inside Claude that do specialized work for his business. The way he got there is a masterclass in how to actually adopt AI without losing what makes human revenue teams irreplaceable. Jeff Rosset is the founder of Sales Assembly, a peer community for revenue leaders at some of the fastest-growing B2B tech...

TLDR: AI is changing how buyers experience outreach, but the sellers winning right now aren't the ones who automate the most. They're the ones who know when to be human. This episode breaks down engineered empathy, what RevOps leaders should actually be doing, and why boot camp style skills training is making a comeback. AI can write the email. It can personalize the subject line, pull you...

TLDR: LinkedIn's new 360 Brew algorithm just changed how your content gets seen, who sees it, and what gets suppressed. Brynne Tillman, CEO of Social Sales Link and the LinkedIn Whisperer, breaks down exactly what sellers and GTM leaders need to do differently starting today. Full Description: The rules of LinkedIn just changed, and most sellers haven't caught up yet. In this episode of Th...

TLDR: The fractional executive model isn't a workaround — it's becoming the career path of choice for senior GTM operators. Pedro Martins spent 15 years at Salesforce and DocuSign before going fractional, and he breaks down exactly how it works, what surprised him most, and what you need to know before making the leap yourself. The gig economy was just the beginning. What's happening n...

**TLDR:** Your post-sale team probably drives most of your revenue but gets a fraction of the investment. Alex Raymond , founder of Amplify and author of The Growth Department, joins Kelly Lewis and Tiffany Jones to break down why the smartest companies are treating account management as their primary growth engine. Most revenue leaders still chase growth through new logos while under-investing in...

TL;DR: Your revenue problem might not be pipeline. It might not be your strategy. It might not even be your tech stack. It might be leadership stress, burnout, and mindset. In this episode, Dr. Debbie Qaqish, creator of the term “Revenue Marketing,” breaks down why psychological safety and neuroscience are the next frontier of GTM performance. We spend billions on sales methodology, enablement too...

TL;DR: Sales Kickoff is not a 3-day event. It is a revenue activation strategy. In this episode, Tiffany Jones and Kelly Lewis break down what makes a modern SKO successful, how to move beyond stand-and-deliver presentations, when to schedule your kickoff, and how to design reinforcement programs that actually change seller behavior. It’s kickoff season — and if your LinkedIn feed looks anything l...

TL;DR: You can’t always “leave politics at the door” anymore. In this episode, Kelly Lewis and Tiffany Jones talk about what happens when world events show up at work, why psychological safety matters more than ever, and how leaders can support their teams without turning the workplace into a debate stage. We typically don’t talk politics on The Revenue Insiders. But after a Super Bowl halftime sh...

Most companies overlook the secret to dominating cloud marketplaces—and it’s not what you think. As tackle.io CEO John Janke reveals, understanding how AI will reshape go-to-market strategies is the game-changer that can catapult your revenue and valuation in 2024. In this eye-opening episode, John shares lessons from a decade of navigating the complexities of B2B software sales, acquisitions, and...

TL;DR Sales enablement pioneer Roderick Jefferson joins Kelly Lewis for a raw, deeply human conversation about the evolution of enablement, why revenue teams are still missing the mark, and the life-altering stroke that forced him to redefine success, leadership, and self-care. If you work in enablement, revenue, or leadership, this episode is required listening. What happens when the person who c...

TL;DR: Leadership does not mean choosing between empathy and authority. In this episode, returning guest Raheela Nanji joins Kelly Lewis and Tiffany Jones to break down feminine energy in leadership, why empathy is a learnable skill, and how strong leaders hold boundaries without becoming pushovers. What does it really mean to lead with feminine energy and why does it still feel uncomfortable for...

Guest Megan Fletcher: @CRMbestie on Tiktok & Instagram Summary In this engaging conversation, Tiffany Jones and Kelly Lewis interview Megan Fletcher, a TikTok sensation known as CRM Bestie. They discuss her journey in creating content focused on RevOps and sales, the challenges of balancing a corporate career with family life, and the unique perspective she brings as a woman in a male-dominate...

Revenue Insiders host Tiffany Jones sits down with Anders Krohn, CEO and founder of Kernel.ai, to unpack how “agentic company data” is transforming RevOps at high-growth companies like Navan, Gong, and Mistral by finally fixing broken CRM data at scale. They dig into why most revenue leaders don’t trust their Salesforce or HubSpot account data, how Kernel’s AI-native alternative to Dun & Brads...

L;DR: Kelly Lewis and Tiffany Jones kick off 2026 with bold go-to-market predictions: AI agents become a “shadow RevOps team,” ICPs get dynamic and constantly refreshed, pricing shifts away from seats toward consumption and outcomes, hiring prioritizes EQ over resumes, sellers enable champions to sell internally (especially to CFOs), and digital sales rooms evolve into AI-powered deal command cent...

Summary In this episode, Beth Yehaskel, a seasoned revenue architect and go-to-market advisor, shares her insights on building effective go-to-market systems. The conversation delves into the importance of connective tissue in organizations, the challenges of decision-making in smaller companies, and the role of empathy and communication in successful go-to-market strategies. Beth also discusses h...

TL;DR: If you have ever been told “you need to be more strategic” with zero useful guidance, this episode is for you. Kelly and Tiffany break down what strategy actually looks like in your day to day work, how to respond when you get that feedback, and how to rebuild your brand inside the company. In this solo conversation, Kelly Lewis and Tiffany Jones unpack one of the most frustrating pieces of...

TL;DR: Author and speaker Ravi Rajani joins Kelly and Tiffany to unpack his recently release book, Relationship Currency —how deep listening, empathetic leadership, and conscious questions build trust, influence outcomes, and shape careers. Tactics for sellers, enablement, RevOps, and rising leaders inside modern GTM teams. What does it really mean to invest in relationships at work? In this conve...