The Revenue Insiders

The Revenue Insiders
  • 5.0 (15)
  • BUSINESS
  • UPDATED WEEKLY

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

    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

    30 min
  2. The CRO Is Dead. Long Live the Chief Revenue Architect.

    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

    37 min
  3. The Outbound Pivot Every GTM Team Is Getting Wrong | Jason Bay

    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

    41 min
  4. Sales Leadership: Why Frontline Sales Managers Are Set Up to Fail

    APR 16

    Sales Leadership: Why Frontline Sales Managers Are Set Up to Fail

    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 the number, the people, the pipeline, the forecast, and the cross-functional relationships that make all of it work. And in most companies, they were given zero preparation for any of it beyond being really good at selling. In this episode, Tiffany and Kelly go deep on why the super rep pattern continues to dominate sales leadership culture in 2026, what it's costing go-to-market organizations, and what a better model looks like, from the structure of a frontline leader's ideal week, to the skill vs. will framework for coaching, to the real reason the AI-fueled push toward bigger team spans is a risk most boards aren't accounting for. And if you're looking for sales leadership coaching or frontline manager training, Kelly's program (run in partnership with Sarah Bedwell) is linked below. In This Episode: Why promoting top AEs into management without training sets them up to failThe skill vs. will assessment every frontline leader should be running on their teamWhat the "frozen middle" is and why your coaching time should center thereThe ideal structure for a frontline sales leader's week, Monday through Friday in detailWhy expanding team spans using AI tools right now is a serious organizational riskFollow The Revenue Insiders on Spotify and leave us a rating — it helps more GTM professionals find the show.Learn about Kelly's Sales Leadership Coaching Program: therevenueinsiders.com

    35 min
  5. If It Was Easy, Everyone Would Do It: AI Strategy for GTM Leaders

    APR 9

    If It Was Easy, Everyone Would Do It: AI Strategy for GTM Leaders

    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 companies in the country. He's spent over 20 years in B2B sales and has a front-row seat to what's working, what's failing, and what most leaders won't admit isn't working. In this episode, Jeff breaks down how he approaches AI as infrastructure. He built hyper-specific AI personas — a customer marketing expert, a strategic advisor, a pressure-tester — and stitched them into a collaborative system that elevates every project he runs. The foundation came first. The speed and quality of output came after. He also shares something most AI conversations skip: the discipline required to get the most out of these tools. Pushing back when the AI tells you what you want to hear. Running your Claude-built plan through a NotebookLM critique. Returning to your desk with notes and iterating again. It's a loop. And it works because Jeff treats it like one. If you're a revenue leader trying to figure out what AI adoption should actually look like — not what LinkedIn says it should look like — this is the episode. In This Episode: The AI employee framework Jeff built and how it mirrors a real team dynamicWhy LinkedIn is becoming a minefield of AI slop and how to protect your personal brandWhat enablement leaders are rightly doubling down on in a world of AI-assisted repsThe outdated playbooks still running in too many GTM orgsJeff's honest take on where AI impacts services companies vs. software companies differentlyFollow The Revenue Insiders and leave us a rating, it helps more GTM professionals find the show. Connect with Jeff Rosset: https://www.linkedin.com/in/jeffrosset | salesassembly.com

    36 min
  6. The Real Reason AI Can't Replace Your Best Sellers

    APR 2

    The Real Reason AI Can't Replace Your Best Sellers

    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 your prospect's LinkedIn activity, and generate a follow-up sequence in seconds. But when the conversation goes deeper and when a buyer actually engages, the sellers who close are the ones who can read the room, adjust in real time, and make someone feel like they're talking to another person, not a machine. Kelly Lewis and Tiffany Jones dig into the concept of engineered empathy, first introduced on the show by sales strategist Brynn Tillman, and why it's exposing a real gap in how GTM orgs are deploying AI right now. They also cover what this means for RevOps career paths, where enablement is headed as tool training gives way to skill development, and why Tiffany is making a major move, going full-time with The Revenue Insiders. In This Episode: Why engineered empathy is the biggest AI risk in outbound sales right nowHow senior sellers use AI differently than junior reps — and what enablement should do about itThe case for bringing back boot camp style skills training as SDR automation frees up budgetHow to think about RevOps and enablement career paths when the tools keep changingTiffany's announcement: leaving corporate and joining The Revenue Insiders full-timeFollow The Revenue Insiders on Spotify and leave us a rating — it helps more GTM professionals find the show.

    30 min
  7. LinkedIn's Algorithm Changed: What Every Seller Needs to Know

    MAR 26

    LinkedIn's Algorithm Changed: What Every Seller Needs to Know

    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 The Revenue Insiders, Kelly Lewis and Tiffany Jones sit down with Brynne Tillman, who has spent nearly two decades teaching sales professionals how to leverage LinkedIn for pipeline and revenue growth. Brynne unpacks LinkedIn's shift from a social graph to an interest graph, explaining how the new 360 Brew algorithm rewards consistency of message, intentional engagement, and value creation over volume and viral tactics. She introduces the concept of "engineered empathy," the icky phenomenon where AI-generated outreach fakes personalization but falls apart on closer inspection, and shares her CRISPY framework for building AI prompts that keep the human in the conversation. Whether you're an SDR trying to book more meetings, a sales leader building a social selling motion, or a RevOps professional designing the systems behind outreach, this episode delivers tactical, immediately actionable guidance for how to show up on LinkedIn in 2026 and beyond. Brynne also makes the case for giving away your best content freely, arguing that thought leaders who hold expertise behind a wall will lose business to those who don't. In This Episode: How LinkedIn's 360 Brew algorithm works and why it changes everything about content visibilityWhy "connect and pitch" behavior is now actively suppressed by the platformThe CRISPY framework for writing AI prompts that produce authentic, human-sounding outputHow to build custom LinkedIn feeds that ensure every minute on the platform is spent engaging your ICPWhy giving away your best content for free is the most effective trust and revenue strategyConnect & Subscribe:Follow The Revenue Insiders on Spotify and leave us a rating. It helps more GTM professionals find the show.Spotify: https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445YouTube: https://www.youtube.com/@TheRevenueInsidersLinkedIn: https://www.linkedin.com/company/the-revenue-insiders Guest Links:Connect with Brynne Tillman: https://www.linkedin.com/in/brynnetillman | https://socialsaleslink.com

    39 min
  8. The Fractional Revolution: Why Top RevOps Talent Is Leaving Full-Time

    MAR 19

    The Fractional Revolution: Why Top RevOps Talent Is Leaving Full-Time

    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 now in RevOps, sales leadership, and marketing is something different — experienced operators at the VP and C-level are deliberately choosing to work across multiple companies simultaneously, on their terms, with equity stakes and a variety of problems that no single full-time role could match. And the companies hiring them? Getting access to talent they could never afford full-time, compressed learning curves, and the kind of "looking around corners" expertise that only comes from someone who's built the playbook before. In this episode, Tiffany and Kelly sit down with Pedro Martins — fractional RevOps executive and LP in multiple VC and PE funds — for one of the most honest conversations we've had about what this model actually looks like from the inside. Pedro breaks down the four types of fractional engagements (and why most people confuse them), shares the financial case for equity-based fractional structures, and explains why product founders are often terrified of sales — and how the best fractional leaders meet them there. In This Episode: The four engagement models: consulting, advisory, fractional executive, and interim — and when each one is the right fitWhy LinkedIn fractional RevOps titles have more than doubled in the last four years, and what's driving itThe financial upside of equity-structured fractional engagements, and how to think about the long gameWhy context switching is a skill, not a problem — and how to manage it across multiple clientsThe one piece of advice both Pedro and Kelly ignored when they started — and what changed when they finally followed itConnect & Subscribe:Follow The Revenue Insiders on Spotify and leave us a rating — it helps more GTM professionals find the show. Guest Links:Connect with Pedro Martins: https://www.linkedin.com/in/pedromartins/

    36 min
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5
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About

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

Information

  • Creator
    The Revenue Insiders
  • Years Active
    2024 - 2026
  • Episodes
    59
  • Rating
    Clean
  • Copyright
    © The Revenue Insiders
  • Show Website
    The Revenue Insiders

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