The Revenue Insiders

The Revenue Insiders
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The Revenue Insiders bring you relevant topics around B2B Go-To-Market Strategy to help you create your unique go to market point of view, elevating your presence in your next meeting. This podcast focuses on Sales Operation, Sales Enablement, Sales Leadership, B2B Sales, GTM, Go-To-Market, Annual Revenue Planning, SKOs, Revenue Strategy & Career Growth

  1. 4d ago

    AI Is Exposing Your Pricing. Is Your Revenue Team Ready? with Todd Caponi

    TLDR: Your end of quarter discount isn't speeding deals up, it's teaching buyers to wait. Todd Caponi, author of Four Levers Negotiating®, shows sales leaders and revenue teams a transparent way to negotiate that protects deal value and builds trust past the signature. Todd Caponi is the founder and principal of Sales Melon, a seven time sales leader, and the author of The Transparency Sale, The Transparent Sales Leader, and Four Levers Negotiating. Kelly Lewis and Tiffany Jones sit down with him to unpack the moment he discovered his model: a Houston conference room in 2008, a procurement team asking for 35% off, and four words on a whiteboard. As Q4 discounting season kicks off, AI is exposing pricing models, and peers are comparing notes on what they paid, Todd makes the case that old school negotiating is running out of road for sales managers, RevOps, enablement, and go-to-market leaders. Tiffany brings the buyer's side as a RevOps leader who owns the software budget, and pushes Todd on how any of this works with AI consumption pricing. In this episode: The four levers every B2B pricing model already runs on: volume, timing of cash, length of commitment, and timing of the dealWhy fake expiring discounts slow deals down, and what to do insteadWhat happens when an executive "closer" undercuts the rep at the finish lineHow the model holds up under consumption and usage based pricingThe question every revenue team should answer: what do we give up to be great at our core? Follow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.Subscribe on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLSubscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/id1767256445Watch on YouTube: https://www.youtube.com/@TheRevenueInsidersFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders Connect with Todd Caponi: https://www.linkedin.com/in/toddcaponi/ | https://toddcaponi.com

    AI Is Exposing Your Pricing. Is Your Revenue Team Ready? with Todd Caponi

  2. Sep 24

    Is AI Quietly Breaking Your Annual Planning? A GTM Midyear Check

    TLDR: Eight months into 2026, Kelly Lewis and Tiffany Jones put their January predictions on trial. AI isn't coaching your reps, most companies aren't running the agents they told their board about, and annual planning is about to get messy. Season 3 of The Revenue Insiders opens with a midyear reckoning. Kelly and Tiffany revisit the go-to-market predictions they made in January and test them against what is happening now: sales manager span of control creeping toward 15 reps, SDR promotions falling off a cliff, the gap between companies that have deployed AI agents in RevOps and the ones that just say they have, and consumption pricing hitting annual plans nobody built for it. They also get into the Seismic and Highspot merger, what an OpenAI hiring post and the EU ban on emotion recognition in hiring tools say about EQ in sales, plus why governance is still unsolved in revenue operations. If you lead sales, RevOps, or enablement, or you are early in your sales career, this is your 2027 planning prep. In this episode: Why AI coaching inside the tools isn't the same as a manager developing a rep, and what happens when finance plans for 15 reps per sales managerThe RevOps "haves and have nots" of AI agents, and why so many boards are being told a story that isn't trueHow AI assisted annual planning goes wrong when it's built on bad data and ignores the people, the buyer, and the go-to-market realityWhat consumption and outcome based pricing mean for comp plans, forecasting, net dollar retention, and the role of the CSMThe future of enablement after the Seismic and Highspot merger, and why cutting your enablement team for AI is the wrong ROI mathFollow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.

    Is AI Quietly Breaking Your Annual Planning? A GTM Midyear Check

  3. Jun 11

    Salesforce's Contentful Buy and the Future of GTM

    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 4,800 brands including roughly a third of the Fortune 500. The headlines filed it under martech. On this episode, Kelly Lewis and Tiffany Jones turn it into something far more relevant for go-to-market teams: a preview of what happens when your content becomes structured data that AI can assemble on demand. They unpack the strategic logic of the deal, the eye opening down round from a 3 billion dollar valuation in 2021, and why this fits the broader pattern of Salesforce buying its way toward an agentic, headless future. Then they get practical. What does this mean for the enablement leader, the RevOps team, and the seller on the front line? This is a candid, occasionally spicy conversation about clean data, content governance, the consolidation versus best of breed debate, and the human skills that get more valuable as AI takes over more of the revenue motion. In This Episode: Why the Contentful deal is a sales and enablement story, not just a marketing oneThe data readiness problem and why garbage in still means garbage out, only fasterWhether enablement platforms like Highspot and Seismic still have a role, and what survivesHow the enablement job shifts from making content to governing the truthWhy critical thinking and discovery are the durable skills for every sales careerThe line in the sand: what should never be handed fully to AIConnect & SubscribeFollow The Revenue Insiders wherever you listen and leave us a rating. It helps more sales leadership, RevOps, and enablement pros find the show.Subscribe on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLSubscribe on Apple Podcasts: https://podcasts.apple.com/podcast/id1767256445Watch on YouTube: https://www.youtube.com/@TheRevenueInsidersFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders

  4. Jun 4

    Why This AI Company Is Growing Enablement w/ Melina Giakas from Clay

    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 team and deliberately pumping the brakes on automation? In this episode, Kelly Lewis and Tiffany Jones sit down with Melina Giakas, who leads GTM enablement at Clay, for a conversation that challenges almost everything you're hearing about AI in revenue right now. Melina shares how her team uses AI to compound competence instead of skipping it, why she makes go-to-market engineers prove a skill by hand for a quarter before automating it, and how Notion agents quietly handle content governance in the background. It's a practical, contrarian look at where AI actually belongs in modern sales enablement, RevOps, and the broader GTM motion.In this episode: Why Clay is growing enablement headcount while the market cuts itThe "prove it before you automate it" rule for go-to-market engineersWhy AI roleplay keeps failing (and it isn't the technology)Moving beyond the LMS to measure behavior change, not course completionsUsing Notion agents for content governance with a human in the loopConnect & SubscribeFollow The Revenue Insiders wherever you listen and leave us a rating, it helps more GTM professionals find the show.Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLApple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88CgMore: https://www.therevenueinsiders.comConnect with Melina Giakas: https://www.linkedin.com/in/mgiakas/ | https://www.clay.com

    Why This AI Company Is Growing Enablement w/ Melina Giakas from Clay

  5. May 28

    The AI SDR Lie Every GTM Leader Needs to Hear

    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 product is selling. The first ten clients came in on founder charisma and deep product knowledge. Then the business needs to scale, and suddenly the founder is the bottleneck nobody wants to name. Gearoid Cox built SalesPipeline to solve this exact problem. His firm hires, trains, and runs sales and marketing teams on behalf of small companies that have outgrown founder-led sales but aren't yet ready for a full in-house GTM org. In this episode, Tiffany Jones sits down with Gearoid for a candid conversation about the gap between founder selling and scalable selling, what gets lost when founders pitch features instead of mapping buyer journeys, and why the new-logo obsession is robbing most revenue orgs of the easiest growth available to them. They get into the AI conversation honestly: where AI is genuinely changing the game inside sales orgs (reporting, dashboards, enrichment), and where the AI SDR pitch is over-promising and damaging buyer trust at scale. If you're a founder, a fractional GTM operator, a head of revenue, or a RevOps leader trying to make sense of the moment, this one has receipts. In this episode: Why founders cling to sales and what to do about itThe difference between a sales process and a founder in their headBuyer journey thinking versus features-and-benefits sellingWhy AI SDRs are great products pointed at the wrong use caseWhere the real revenue lives (hint: it's not new logos)What "graduating" from outsourced sales actually looks likeConnect & SubscribeFollow The Revenue Insiders wherever you listen and leave us a rating — it helps more GTM professionals find the show. Guest LinksConnect with Gearoid Cox: https://www.linkedin.com/in/gearoidcox/| https://sales-pipeline.io

    The AI SDR Lie Every GTM Leader Needs to Hear

  6. May 14

    The Go-to-Market Levers Your Sales Managers Don't Know They Have w/ Sarah Bedwell

    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 calls, and still trying to figure out where their number is going to come from. But here's the problem: most of them have never been walked through the actual strategic planning process that turns a territory into a business they can run with confidence. In this episode of The Revenue Insiders, hosts Kelly Lewis and Tiffany Jones sit down with Sarah Bedwell, a seasoned revenue leader and sales enablement consultant with 20 years of experience spanning her time as employee number 70 at Tableau through building go-to-market programs across industries. Sarah breaks down exactly what it means to operate like a CEO of your own sales business, from identifying the go-to-market levers you actually control to building an operational cadence that gets you from spending 15% of your week on deals to 40%. If you manage a sales team or lead people who do, this one is packed with frameworks you can put to work immediately. In this episode, you'll learn: Why most sales managers miss quota because they don't understand their own individual ICP at the territory levelThe go-to-market levers frontline managers control (and the ones they don't) and why knowing the difference changes everythingHow to build an operational cadence that protects your coaching time and eliminates the "booked 6am to 6pm" calendar trapThe delegation framework that got one manager hours back in her week while making her reps stronger closersWhat second and third-line leaders should be inspecting to find out if their frontline actually has a planFollow The Revenue Insiders wherever you listen and leave us a rating — it helps more GTM professionals find the show. Subscribe on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLSubscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445Watch on YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88CgFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders Connect with Sarah Bedwell: https://www.linkedin.com/in/bedwellsarah

    The Go-to-Market Levers Your Sales Managers Don't Know They Have w/ Sarah Bedwell

  7. Apr 30

    The CRO Is Dead. Long Live the Chief Revenue Architect.

    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 DescriptionThe shape of the revenue leader job is changing faster than most go-to-market orgs are willing to admit. AI is collapsing the work RevOps used to spend quarters on. Forecasts that took 18 months to build are getting rebuilt in two weeks. Dashboards, deal scoring, account research, even some of the coaching prep work — it's all being compressed. So what's left? The human stuff. The coaching. The connection. The ability to walk into a forecast call and read the room instead of running an interrogation. The ability to develop a frontline sales manager who was a great rep three months ago and has no idea how to lead a team today. This is the conversation we get into with Dannii Mathers, senior consultant and coach at SBR Consulting and co-host of the Growth Workshop podcast. We talk about why most AI rollouts in sales orgs are failing (hint: the head of IT is delivering the training), why enablement is the function actually built for the AI moment, why emotional intelligence is a measurable, buildable leadership skill, and why the leaders who self-rate their EQ highest are almost always the ones with the biggest blind spots. We also get into one of the most useful AI use cases we've heard for sales leaders: feeding your own meeting transcripts into an agent and asking it to flag where you're talking over your team, invalidating input, or skipping curiosity. It's an objective feedback loop that no 360 review will give you. If you're a CRO, VP Sales, VP RevOps, VP Enablement, or a senior operator headed into your first leadership seat, this one will land. In This Episode Why Gong renamed CRO to Chief Revenue Architect, and what it tells you about where the role is goingThe reason most AI rollouts in sales orgs stall, and why enablement (not IT) should own the adoptionHow to use AI as an objective coach for your own EQ blind spotsWhy the over-empathetic leader trap hits new managers hardest, and how to push past itFrom great seller to great coach: the leadership skill that just became non-negotiable

    The CRO Is Dead. Long Live the Chief Revenue Architect.

  8. Apr 23

    The Outbound Pivot Every GTM Team Is Getting Wrong | Jason Bay

    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 replaced by AI agents overnight. And a whole generation of AEs was hired with the promise they would never have to prospect, only to get told last quarter that outbound is back on their plate. Welcome to the hardest outbound environment in a generation. In this episode, Kelly and Tiffany sit down with Jason Bay, founder and CEO of Outbound Squad and one of the most trusted voices in B2B outbound sales. His team has worked with 250+ sales teams and 20,000+ reps at companies like Gong, Zoom, Shopify, and monday.com. Jason walks through his new methodology, the first of its kind built for the AI era of pipe gen: Disqualify, Offer, Provoke. We cover why the predictable revenue model created a generation of AEs who resist prospecting, why shame is the real block for frontline managers, where AI actually belongs in your outbound motion, and why the best sales orgs are narrowing their focus instead of casting wider nets. If you are a CRO, VP of Sales, RevOps leader, enablement pro, or a sales manager staring at a pipeline gap, this one is a must-listen. In this episode: Why the predictable revenue era is over and what replaces itThe "Too Good to Ignore" methodology: Disqualify, Offer, ProvokeThe martini glass pipeline and why the classic funnel is deadWhere AI actually belongs in your outbound motion (and where it does not)Why frontline sales managers are the real unlock for any outbound pivotConnect & SubscribeFollow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show. Subscribe on Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvLSubscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445Watch on YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88CgFollow on LinkedIn: https://www.linkedin.com/company/the-revenue-insidersGuest Links Connect with Jason Bay: https://www.linkedin.com/in/jasondbay | https://www.outboundsquad.comFree Outbound Masterclass: https://www.outboundsquad.com/masterclass

    The Outbound Pivot Every GTM Team Is Getting Wrong | Jason Bay
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The Revenue Insiders bring you relevant topics around B2B Go-To-Market Strategy to help you create your unique go to market point of view, elevating your presence in your next meeting. This podcast focuses on Sales Operation, Sales Enablement, Sales Leadership, B2B Sales, GTM, Go-To-Market, Annual Revenue Planning, SKOs, Revenue Strategy & Career Growth

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  • Creator
    The Revenue Insiders
  • Years Active
    2024 - 2026
  • Episodes
    64
  • Rating
    Clean
  • Copyright
    © The Revenue Insiders
  • Show Website
    The Revenue Insiders