The Revenue Insiders

The Revenue Insiders
  • 5.0 (14)
  • BUSINESS
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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. Sales Leadership: Why Frontline Sales Managers Are Set Up to Fail

    2D AGO

    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
  2. 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
  3. 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
  4. 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
  5. 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
  6. Your Post-Sales Team Is Your Real Revenue Engine with Alex Raymond from AMplify

    MAR 12

    Your Post-Sales Team Is Your Real Revenue Engine with Alex Raymond from AMplify

    **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 the teams responsible for 73% of annual revenue and 100% of profits. In this episode, Alex Raymond makes the case for flipping that equation. He walks through the economics of net revenue retention (hint: 119% NRR doubles your business in four years), explains why the concept of "recurring revenue" is a dangerous myth, and shares what active retention actually looks like in practice. Kelly and Tiffany bring their own experiences leading GTM strategy and revenue operations, creating a conversation that's equal parts strategic framework and tactical reality check. Whether you're an account manager wondering why your portfolio keeps growing while your support doesn't, or a CRO rethinking your org design, this episode gives you the data and the playbook to make the case for change. **In This Episode:** • Why 73% of revenue and 100% of profits come from existing customers, yet post-sale teams get 4 to 7x less investment than new business • The math behind NRR: how hitting 119% doubles your business and each point adds 12 to 18 points of valuation • What "active retention" means and how to build the same rigor into renewals that you bring to new deal reviews • Why the "360 degree AE" is one of the worst ideas in modern go-to-market and what org structure actually works • A smarter approach to account planning: ditch the 35 field template and ask five questions that actually matter **Connect & Subscribe:** Follow The Revenue Insiders on Spotify and leave us a rating. It helps more GTM professionals find the show.

    40 min
  7. The Biggest Threat to Revenue Isn’t Your Pipeline It’s Your Leadership Mindset with Dr. Debbie Qaqish, Creator of Revenue Marketing

    MAR 5

    The Biggest Threat to Revenue Isn’t Your Pipeline It’s Your Leadership Mindset with Dr. Debbie Qaqish, Creator of Revenue Marketing

    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 tools, AI platforms, and revenue tech stacks. But what if the real performance bottleneck isn’t your funnel It’s the nervous system of the person running it? In this powerful conversation, we sit down with Dr. Debbie Qaqish, founder of The Growth Factor and the original architect of the Revenue Marketing movement, to unpack: Why less than 30% of CMOs report credible financial impact despite incredible technology Why the biggest threat to revenue might be the leader, not the strategy How chronic stress rewires the brain and narrows decision-making Why AI is increasing stress, not reducing it The neuroscience behind fight or flight leadership Why marketing and customer success are the most underinvested teams in GTM What positive psychology actually means, and why it’s not “woo woo” Dr. Debbie explains how constant cortisol spikes impact performance, creativity, and revenue results, and why boards and CEOs must start thinking about psychological performance as a growth lever. For ambitious GTM professionals, especially those early in leadership or aspiring to it, this episode challenges you to think differently: If you were building your marketing or sales org from scratch What would your people need in order to thrive? This is not a soft skills conversation. It’s a performance conversation. And it may be the most important one we have this year. Listen if you care about: Revenue leadership Sales and marketing alignment Customer success burnout AI and the future of work Sustainable high performance in SaaS and B2B Subscribe to The Revenue Insiders and follow us on LinkedIn for weekly conversations designed to help you build your own GTM point of view. For more information on The Growth Factor: https://www.growthfactor.us/reset-revenueinsiders https://www.linkedin.com/in/dqaqish/

    32 min
  8. Reinvent SKO, Drive Reinforcement, and Maximize Revenue Impact

    FEB 26

    Reinvent SKO, Drive Reinforcement, and Maximize Revenue Impact

    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 like ours, everyone is either at SKO, recovering from SKO, or planning the next one. But here’s the real question: Are companies reinventing Sales Kickoff… or just repeating the same playbook? In this episode, Tiffany and Kelly unpack what’s changing in modern Sales Kickoff strategy and what revenue leaders must rethink if they want real impact. You’ll hear hot takes on: Why stand-and-deliver keynotes no longer work for revenue teams The ideal timing for Sales Kickoff (and why week three may be the sweet spot) When to roll out comp plans (hint: not three days before SKO) How to use pre-work and knowledge transfer before your in-person event Why small group executive Q&A is more powerful than big stage questions How to create intentional executive access moments Creative connection tactics like “speed friending” to boost engagement The shift from SKO as an event to SKO as a program Most importantly, they break down what happens after kickoff. Because the real ROI is not the energy in the ballroom. It’s the reinforcement that follows. Kelly shares how to: Programmatize post-SKO reinforcement into 5-8 week branded initiatives Layer manager coaching development alongside skill reinforcement Prioritize what to train first based on business impact Use leading indicators, confidence surveys, and behavior data to measure success Tiffany adds a powerful perspective on measuring “hunger” — how quickly reps engage with follow-up content, request transcripts, and seek more information. If you’re a sales leader, CRO, Head of Enablement, RevOps leader, or marketing partner thinking about how to make your next Sales Kickoff more impactful, this episode is your blueprint. Sales Kickoff should galvanize your team. Reinforcement should transform them. Subscribe to The Revenue Insiders and follow us on LinkedIn for more practical insights on sales leadership, enablement strategy, and modern GTM execution.

    24 min
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5
out of 5
14 Ratings

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
    55
  • Rating
    Clean
  • Copyright
    © The Revenue Insiders
  • Show Website
    The Revenue Insiders

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