Revenue Rewired

Jay Feitlinger and Sarah Shepard

Reimagine how you approach marketing, sales, and revenue growth with the Revenue Rewired podcast. Hosted by StringCan Interactive’s CEO Jay Feitlinger and COO Sarah Shepard, this podcast dives into the biggest challenges mid-market B2B companies face. Weekly this dynamic duo breaks down complex strategies into actionable insights to help you align your business, maximize ROI, and drive measurable growth. No jargon (ok maybe a lil), but mainly just straight talk to fuel your revenue engine. Tune in and take your business to the next level.

  1. 4D AGO

    Ep 58: Why Playing Hardball With Your Sales Team Is the Smartest Marketing Move You're Not Making

    If you think marketing's job ends when a lead gets handed off to sales, this episode will flip that assumption on its head. Jay Feitlinger and Sarah Shepard dig into why the smartest B2B marketing strategies are built from the inside of a sales conversation, not from brand guidelines or analytics dashboards alone. From a networking call that sparked a 16-year-old realization, to how AI tools are quietly reshaping the buyer journey, Jay and Sarah get real about what it actually takes to close the gap between sales and marketing. The insight hiding inside your sales team's daily calls might be the most underused content strategy asset you've got. Your sales team is sitting on a goldmine of buyer insights that your marketing strategy desperately needs, and most companies are leaving it completely untouched.The "playing hardball" mindset isn't about conflict. It's about marketing having the courage to ask hard questions and build a bridge that helps everyone win faster.AI tools like Claude and Fathom aren't replacing relationship-driven roles. They're handing salespeople a superpower if they're willing to pick it up.The buyer journey is splitting in two directions at once, and the marketing teams that don't see it coming are going to feel it when their sales team starts struggling downstream.You don't need a paid AI subscription or a massive tech stack to start. One honest prompt about your biggest work frustration might be the thing that finally gets your team aligned. EPISODE CHAPTERS 00:01 - The $20 a Month Wine Education That Started It All00:42 - A Networking Call That Asked the Question Jay Had Never Heard in 16 Years02:18 - Why Sales Insights Are the Marketing Data Nobody's Tracking 06:36 - Treating Revenue Like a Fitness Metric: The Analytics Reframe Your Team Needs08:23 - Is the Buyer Journey Splitting Into Two Completely Different Conversations? 12:23 - Why Keyword Stuffing With AI Is the New Quickest Way to Wreck Your Website 16:43 - What Happens When Even Gen Z Doesn't Trust AI Yet 19:25 - How Note-Taking Tools Like Fathom Can Stop the "I Don't Get Anything From Sales" Problem 23:42 - When HubSpot Starts Telling You Where You're Losing Deals Before You Ask 25:41 - The Frustration That Made Jay and Sarah Early AI Adopters 28:05 - The One Prompt That Can Start Your Whole Sales and Marketing Alignment Journey ABOUT THE HOSTS: Jay Feitlinger is the CEO of StringCan Interactive and a lifelong entrepreneur who built his philosophy on the power of sales and marketing working as one unified team.  Connect with Jay on LinkedIn: https://www.linkedin.com/in/jayfeitlinger/  Sarah Shepard is the COO of StringCan Interactive, known for her no-nonsense approach to marketing strategy, analytics, and the sometimes uncomfortable conversations that drive real revenue results.  Connect with Sarah on LinkedIn: https://www.linkedin.com/in/sarahshepardcoo/  About Revenue Rewired and StringCan Interactive Revenue Rewired is a podcast built for B2B marketers, sales leaders, and business owners who want to grow revenue with strategy and purpose. Hosted by Jay Feitlinger and Sarah Shepard of StringCan Interactive, each episode tackles the real conversations happening at the intersection of sales, marketing, and innovation. Website: www.stringcaninteractive.com Email: podcast@stringcaninteractive.com  Get the Revenue Rewired book on Amazon: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ  Newsletter: https://www.linkedin.com/newsletters/revenue-rewired-7423414515779936256/ B2B sales and marketing alignment, sales and marketing podcast, B2B demand generation strategy, AI tools for sales teams, HubSpot marketing automation, buyer journey 2025, content marketing strategy B2B, LLM content optimization, GEO AEO SEO for B2B, sales insights for marketing, Fathom notetaking tool, B2B revenue growth podcast, StringCan Interactive, Revenue Rewired podcast

    29 min
  2. APR 23

    Ep 57: The Real Reason AI Isn't Clicking for You, And the Easy Fix

    You've sat through the webinars. You've read the threads. You're still not sure AI is actually working for you. That's not a knowledge problem. It's a starting point problem. Jay and Sarah skip the productivity playbook and go personal. They share the real ways they started using AI for themselves first, from decoding MRI reports to building a compound interest app at the dinner table, and why that's the move that actually builds confidence to use it in business. No framework. No course. Just honest reflection from two operators who've been in the AI weeds for three-plus years. If you're burned out on AI hype but still haven't found your version of it, this episode's for you. KEY TAKEAWAYS • Why starting personal beats starting professional? The fastest path to using AI in your business is using it for something you actually care about first. That low-stakes repetition is what makes the business application feel obvious later. • What "building on sand" actually costs you. Don't design your workflows around a single tool's features. Platforms shift overnight. The goal is AI fluency, not AI dependency. • How your personality should drive which LLM you use. ChatGPT, Claude, and Perplexity aren't interchangeable. Try them before you commit. Your cognitive style matters more than the feature list. • Why the privacy risk is smaller than you think. Sarah's filter: if you wouldn't mind anyone seeing this information, you don't need to be nervous about putting it into an LLM. That reframe removes paralysis without removing caution. • What happens when your team experiments out loud? AI literacy spread at StringCan because leaders shared what they were trying, not just what worked. That culture of experimentation is what drives client conversations now. EPISODE CHAPTERS 00:00 Welcome and Sarah's Paris trip 02:17 Why we're done talking about AI productivity 04:16 Jay's origin story: from intimidated to obsessed 07:23 Sarah's start: from fantasy football to health reports 10:14 The danger of betting everything on one tool 13:27 How to think about privacy risk 16:25 Match the LLM to your personality 19:33 Using multiple LLMs against each other 25:32 Jay's three personal AI wins ABOUT THE HOSTS Jay Feitlinger is the CEO of StringCan Interactive and co-host of Revenue Rewired.  Connect with Jay on LinkedIn: https://www.linkedin.com/in/jayfeitlinger/ Sarah Shepard is the COO of StringCan Interactive and co-host of Revenue Rewired.  Connect with Sarah on LinkedIn: https://www.linkedin.com/in/sarahshepardcoo/ ABOUT REVENUE REWIRED Revenue Rewired is a podcast for B2B marketers, sales leaders, and business owners navigating the intersection of sales and marketing. Every episode delivers actionable insights for mid-market companies that are serious about growing revenue strategically. Email: podcast@stringcaninteractive.com Website: www.stringcaninteractive.com  Get the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ  Newsletter: https://www.linkedin.com/newsletters/revenue-rewired-7423414515779936256/  KEYWORDS:2026 AI in B2B sales, B2B leadership podcast, business growth podcast, CEO leadership podcast, B2B go-to-market 2026, revenue efficiency, B2B business podcast, custom GPT strategy, AI tools for business owners, ChatGPT vs Claude, personal AI use cases, LLM comparison 2026

    32 min
  3. APR 16

    Ep 56: The One Thing Your Team Knows About You That No One's Saying Out Loud

    Honest feedback doesn't fail because people don't have it. It fails because leaders haven't made it safe enough to give. Jay Feitlinger and Sarah Shepard pull back the curtain on the "One Thing" exercise they've run inside StringCan's quarterly planning for years, and why it took nearly two dozen iterations before it clicked. Jay walks through the format live, using Sarah as the example. They talk openly about what it takes to build a team where this kind of conversation not only survives but also becomes something people genuinely look forward to. If your review process leaves the room feeling unchanged, this episode is for you. KEY TAKEAWAYS: Why the feedback you're dreading to hear is almost never what your team actually brings up, and what that gap is really telling youHow one structured exercise can reveal the true trust level of your leadership team before you launch anything newWhat it looks like when a leader receives hard feedback in front of their team, and why it's one of the most powerful signals your culture is sending right nowWhy annual reviews are structurally broken and what a quarterly alternative actually looks like in practiceHow applying this exercise between sales and marketing could quietly dissolve the cross-department friction that's costing you revenue alignmentEPISODE CHAPTERS: 00:00 - When You Actually Look Forward to Hard Feedback 01:15 - Why Sarah's Buying Walking Shoes for France and What It Has to Do With Boredom on Purpose  03:47 - The One Thing Exercise: Where It Came From and Why It Works 06:13 - Trust Isn't a Value You Post on the Wall, It's How You Respond in the Room  08:51 - Jay Puts Sarah in the Hot Seat Live: Watch the Process in Real Time 13:19 - What Jay Actually Said to Sarah and Why It Mattered More Than a Performance Review  15:58 - Why High Performers Are Usually Hardest on Themselves and How This Exercise Resets That  20:30 - The Moment a Team Member Said This Was the Part of Planning He Dreaded Most  24:36 - How to Introduce This If Your Team Has Never Done Anything Like It 26:13 - Why Writing Feedback Down Instead of Saying It Out Loud Is a Red Flag 27:30 - What Happens When Sales and Marketing Do This Together ABOUT YOUR HOSTS Jay Feitlinger is the CEO of StringCan Interactive and co-host of Revenue Rewired. Connect with Jay on LinkedIn: https://www.linkedin.com/in/jayfeitlinger/ Sarah Shepard is the COO of StringCan Interactive and co-host of Revenue Rewired. Connect with Sarah on LinkedIn: https://www.linkedin.com/in/sarahshepardcoo/ ABOUT THE REVENUE REWIRED Revenue Rewired is a podcast for B2B marketers, sales leaders, and business owners navigating the intersection of sales and marketing. Every episode delivers actionable insights for mid-market companies that are serious about growing revenue strategically. Email: podcast@stringcaninteractive.com  Website: www.stringcaninteractive.com  Get the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ  Newsletter: https://www.linkedin.com/pulse/crm-swamp-you-built-jay-feitlinger-v4pee KEYWORDS: leadership feedback culture, B2B revenue alignment, sales and marketing alignment, quarterly planning process, EOS integrator visionary, leadership trust building, one thing exercise, radical candor leadership, mid-market growth strategy, revenue operations podcast, B2B leadership podcast, team feedback framework, executive team trust, performance feedback alternatives, Revenue Rewired podcas

    29 min
  4. APR 9

    Ep 55: Are You an AI Driver or Just a Passenger Princess?

    Most business leaders think they are using AI. They aren't. They're passengers. In this episode, Jay and Sarah break down the growing divide between AI drivers and AI passengers, and why that gap is closing faster than most leaders realize. From the myth of "saving time" to the hidden cost of AI procrastination, this conversation cuts through the noise and gets uncomfortably specific. If you have been waiting for the right moment to get serious about AI in your organization, that moment already passed. Here is how to catch up before your competitors make it impossible. Copy-pasting AI output makes you a passenger. Drivers push back, probe deeper, and use Socratic prompting to get results worth acting on.AI does not save time. It raises the ceiling on what you can accomplish. Leaders who miss that distinction end up with burned-out teams and bloated AI bills.Your CMO is not your AI person. AI is a business-wide operating shift, not a marketing function. Someone needs to own it at the organizational level.Doing nothing is still a decision, and it has a price. AI is already inside the tools you are paying for. There is no budget excuse and no good reason to keep waiting.Run the same prompt through multiple LLMs. ChatGPT, Claude, and Perplexity each have different strengths. Testing across platforms surfaces better answers and blind spots you would have otherwise missed.0:00 Jay is back from Sicily with jet lag, Sarah is two weeks from a two-month trip, and somehow the podcast is still happening 2:05 The driver versus passenger framework and why it is starting to matter in how organizations evaluate AI maturity 4:59 Why generic prompts produce generic results and what it actually looks like to push back on an AI system until it gives you something useful 7:59 The saving time myth and why the hours you free up just fill with more work, which is actually the point, but also kind of the problem 10:34 How Jay and Sarah use AI across operations, SOPs, and leadership planning, and why none of it works if it does not start at the top 15:13 Jay's personal story about building custom GPTs for his college-aged daughters and why fear of the future was the thing that finally got him moving 18:48 The mental residue that builds up when leaders keep pushing AI decisions off, and why the first move does not need to be expensive or complicated 20:21 A real breakfast conversation with a mid-market business owner who assumed AI was a young person's tool, and what that assumption is quietly costing him 23:31 Why handing AI ownership to your CMO is a mistake, and what a more honest org structure around this actually looks like 26:56 Ryan from their ops team shares a simple habit: run the same prompt through multiple platforms and see what comes back differently 29:43 Sarah's somewhat controversial answer to the question every overwhelmed business owner eventually asks Jay Feitlinger https://www.linkedin.com/in/jayfeitlinger/ Sarah Shepard https://www.linkedin.com/in/sarahshepardcoo/ StringCan Interactive is a B2B marketing agency that helps mid-market companies build revenue strategies that stick. Website: www.stringcaninteractive.com   Email: podcast@stringcaninteractive.com  Buy the Revenue Rewired Book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ  AI driver vs AI passenger, AI adoption for business leaders, AI strategy for mid-market companies, AI productivity myth, AI maturity framework, B2B AI strategy, leadership and artificial intelligence, ChatGPT for business, AI tools for executives, AI policy vs compliance, LLM comparison for business, Revenue Rewired podcast, StringCan Interactive, AI ROI per employee, time to failure AI metric, Socratic prompting AI, AI for SMBs, AI competency evaluation, AI passenger princess, business AI mindset Key TakeawaysEpisode ChaptersAbout the HostsAbout Revenue Rewired and StringCan InteractiveSEO Keywords

    34 min
5
out of 5
19 Ratings

About

Reimagine how you approach marketing, sales, and revenue growth with the Revenue Rewired podcast. Hosted by StringCan Interactive’s CEO Jay Feitlinger and COO Sarah Shepard, this podcast dives into the biggest challenges mid-market B2B companies face. Weekly this dynamic duo breaks down complex strategies into actionable insights to help you align your business, maximize ROI, and drive measurable growth. No jargon (ok maybe a lil), but mainly just straight talk to fuel your revenue engine. Tune in and take your business to the next level.