The Revenue Insiders

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 level * The go-to-market levers frontline managers control (and the ones they don't) and why knowing the difference changes everything * How to build an operational cadence that protects your coaching time and eliminates the "booked 6am to 6pm" calendar trap * The delegation framework that got one manager hours back in her week while making her reps stronger closers * What second and third-line leaders should be inspecting to find out if their frontline actually has a plan 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/1g4cKcEX9pIDnzBxxJzUvL [https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL]Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445 [https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445]Watch on YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88Cg [https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88Cg]Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders [https://www.linkedin.com/company/the-revenue-insiders] Connect with Sarah Bedwell: https://www.linkedin.com/in/bedwellsarah [https://www.linkedin.com/in/bedwellsarah]

Why Your Brand Sounds Like Everyone Else's AI Slop with David J. Ebner | Content Workshop

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 company adopted generative AI at roughly the same time, trained it on roughly the same data, and now entire industries sound like they were written by the same machine. David J. Ebner has spent 13 years building Content Workshop into one of the most respected B2B content agencies in the country, with a deep niche in cybersecurity, one of the most skeptical buyer audiences in the market. He's also the author of King Makers, where he argued long before it was popular that writers and creatives are the real kingmakers in B2B. In this episode, Kelly and Tiffany dig into what AI actually does well in the content creation process, where it falls apart, and why curiosity, emotional intentionality, and human discernment are the skills that separate brands that win from brands that blend in. David J. Ebner also shares his framework for deploying AI at the right steps of the process, why "speed to quality" beats "speed to publish," and how anyone, including job seekers building a personal brand on LinkedIn, can create content that actually makes people feel something. In This Episode: * Why the gap between "passable" and "good" content has grown wider as AI made bad content disappear * How to deploy AI in the content creation process without diluting your brand voice or creativity * The difference between content that informs and content that educates, and why only one builds trust * Why "the hero of your brand story is the audience, not you" is the most forgotten rule in B2B marketing * How job seekers and GTM professionals can build a personal brand that stands out in a sea of AI content Connect & Subscribe: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/1g4cKcEX9pIDnzBxxJzUvL [https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL]Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445 [https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445]Watch on YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88Cg [https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88Cg]Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders [https://www.linkedin.com/company/the-revenue-insiders] Guest Links:Connect with David J. Ebner: https://www.linkedin.com/in/davidjebner [https://www.linkedin.com/in/davidjebner] | https://contentworkshop.com [https://contentworkshop.com] | https://chatteragent.ai [https://chatteragent.ai]

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 going * The reason most AI rollouts in sales orgs stall, and why enablement (not IT) should own the adoption * How to use AI as an objective coach for your own EQ blind spots * Why the over-empathetic leader trap hits new managers hardest, and how to push past it * From great seller to great coach: the leadership skill that just became non-negotiable

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 it * The "Too Good to Ignore" methodology: Disqualify, Offer, Provoke * The martini glass pipeline and why the classic funnel is dead * Where AI actually belongs in your outbound motion (and where it does not) * Why frontline sales managers are the real unlock for any outbound pivot Connect & 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/1g4cKcEX9pIDnzBxxJzUvL [https://open.spotify.com/show/1g4cKcEX9pIDnzBxxJzUvL] * Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445 [https://podcasts.apple.com/us/podcast/the-revenue-insiders/id1767256445] * Watch on YouTube: https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88Cg [https://www.youtube.com/channel/UCNCx_Fge5kxBbKHev1C88Cg] * Follow on LinkedIn: https://www.linkedin.com/company/the-revenue-insiders [https://www.linkedin.com/company/the-revenue-insiders] Guest Links * Connect with Jason Bay: https://www.linkedin.com/in/jasondbay [https://www.linkedin.com/in/jasondbay] | https://www.outboundsquad.com [https://www.outboundsquad.com] * Free Outbound Masterclass: https://www.outboundsquad.com/masterclass [https://www.outboundsquad.com/masterclass]

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 fail * The skill vs. will assessment every frontline leader should be running on their team * What the "frozen middle" is and why your coaching time should center there * The ideal structure for a frontline sales leader's week, Monday through Friday in detail * Why expanding team spans using AI tools right now is a serious organizational risk Follow 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