Make It Happen Mondays - B2B Sales Talk with John Barrows

John Barrows

John Barrows helps sales leaders decide whether to replace or rebuild their teams for the AI era, drawing on 25+ years working with Salesforce, LinkedIn, Google, and Amazon. He advises CROs and VPs of Sales on AI readiness, team structure, and go-to-market strategy. He trains sales teams on the fundamentals that drive consistent performance, with or without AI.

  1. 2d ago

    How to Bet on Yourself and Build a Winning Sales Career with Justin Jay Johnson

    Most reps wait for their company to train them. Justin Jay Johnson paid for his own coaching while broke, $100,000 in debt, and living in his brother’s basement, and that choice has driven every career move since. In this episode, John sits down with Justin Jay Johnson, Co-Founder & CRO at Synopsis. They talk about grit, betting on yourself, and making career decisions with a clear view of the worst case scenario. Justin shares his path from a blue collar background and a first year with one deal that got clawed back to Salesforce, becoming a CRO at 33, building a coaching business, and co-founding Synopsis. He also breaks down the hard lesson from a $15 million deal with Benioff involved and why everyone, from SDR to CEO, is winging it. If you’re a rep waiting on someone else to invest in you, a sales leader weighing your next big move, or someone fighting imposter syndrome in rooms that feel too big, this conversation is for you. You’ll hear why owning the deal beats deferring to titles, how to weigh risk against reward, and why AI only amplifies the habits you already have. Want to build a sales team that can hold its own in the AI era? Visit https://www.jbarrows.com and learn how you can Make It Happen. What You’ll Learn Why investing in your own training beats waiting for your company, and what a $20 ChatGPT subscription reveals about a rep’s mindset How to quarterback big deals as the account owner instead of deferring to executives when the room feels too big How to make career and deal decisions with the worst case scenario lens and a realistic risk reward ratio Why everyone from SDR to Fortune 500 CEO is winging it, and how that realization helps you push past imposter syndrome Why AI makes great reps better and bad reps worse, and why clear messaging and a tight ICP still matter more than the tech Justin Jay Johnson is the Co-Founder & CRO at Synopsis. Coming from a blue collar background as the youngest of five boys, he was the first in his extended family to graduate from college and started in sales selling knives in college. After a rough first year in sales, he moved into tech, joined Salesforce, and later helped scale the sales team of a competing CRM before it was acquired. He became a CRO at 33, then built a coaching and consulting business helping reps and sales leaders break through, before co-founding Synopsis. Connect with Justin Jay Johnson: LinkedIn: https://www.linkedin.com/in/justinjayjohnson/ Instagram: https://www.instagram.com/justinjayjohnson/ Facebook: https://www.facebook.com/thesoftwaresalescoach/ Learn More at Synopsis: Website: https://getsynopsis.ai/ John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment. Connect with John Barrows: LinkedIn: https://www.linkedin.com/in/johnbarrows Instagram: https://www.instagram.com/johnmbarrows TikTok: https://www.tiktok.com/@johnmbarrows Check out John’s Membership: https://learn.jbarrows.com/pages/individual-packages Join John’s Newsletter: https://www.jbarrows.com/newsletter

  2. Oct 19

    How to Run Evidence-Based Deal Reviews That Predict Revenue with Mark Siciliano

    Most forecast calls run on what the rep says, not what the customer said. According to Mark Siciliano, that’s exactly where revenue gets lost, and it has a name: the discipline gap. In this episode, John sits down with Mark Siciliano, Global VP of Sales Enablement & Productivity at Prometheus Group and author of Working the Gray: Where Revenue Leadership Actually Happens. They talk about the distance between the strategy announced at kickoff and the standards actually enforced week after week. Mark shares his path from CPA at Pricewaterhouse to helping build the Oracle Sales Academy and scaling revenue teams at Marketo, Demandbase, Drift, and Sprinklr. He also explains why the best CROs he worked with always asked the uncomfortable question before week 12. If you’re a CRO tired of forecast surprises, a first-line manager with no time to coach, or an enablement leader who knows what should happen but can’t make it stick, this conversation is for you. You’ll hear why evidential deal reviews beat story time, how a weekly cadence fills the coaching gap at no cost, and which questions tell you if a deal is real. Want to build a sales team that can hold its own in the AI era? Visit https://www.jbarrows.com and learn how you can Make It Happen. What You’ll Learn What the discipline gap is, and why it shows up in every pipeline review, forecast call, and kickoff that never changes a single behavior two weeks laterWhy coaching isn’t what’s broken, and how a weekly deal review cadence gives first-line managers a standard that costs nothing to runWhy “evidential” separates real deals from story time, and why a defined next step on the calendar now matters more than a summary emailHow the discipline gap differs from MEDDPICC and BANT, and why CRO-level questions need to be asked in week two, not week 12Why AI creates time for judgment, and the questions that tell you if a deal is real, from the business problem you’re solving to John’s three go-live questions Mark Siciliano is the Global Vice President of Sales Enablement & Productivity at Prometheus Group and the author of Working the Gray: Where Revenue Leadership Actually Happens. A former CPA at Pricewaterhouse, he moved into tech as a sales engineer at Oracle and helped build the Oracle Sales Academy. He has since helped scale revenue organizations at Marketo, Demandbase, Drift, and Sprinklr, working alongside CROs to build the operating discipline behind consistent sales execution. Connect with Mark Siciliano: Facebook: https://www.facebook.com/mksiciliano/ LinkedIn: https://www.linkedin.com/in/marksiciliano1 Instagram: https://www.instagram.com/mksiciliano/ Learn More at Prometheus Group: Website: https://www.prometheusgroup.com/ LinkedIn: https://www.linkedin.com/company/prometheusgroup/posts/?feedView=all YouTube: https://www.youtube.com/@PrometheusGroup-EAM John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment. Connect with John Barrows: LinkedIn: https://www.linkedin.com/in/johnbarrows Instagram: https://www.instagram.com/johnmbarrows TikTok: https://www.tiktok.com/@johnmbarrows Check out John’s Membership: https://learn.jbarrows.com/pages/individual-packages Join John’s Newsletter: https://www.jbarrows.com/newsletter

  3. Oct 12

    Why the Sales Rep Matters More Than Ever in the AI Era with Brian Benfer

    Any buyer can now run a prompt five minutes before your call and walk in knowing almost as much as your rep. That should make the rep less relevant. According to Brian Benfer, it makes them more important than ever. In this episode, John sits down with Brian Benfer, CRO at Salesloft, to talk about where the sales rep fits in the AI era, why buyers using AI are ending up in analysis paralysis instead of self qualified, and why AI's real step function gain in sales productivity is opportunity volume, not faster cycles. Brian also shares his path from running a competitive swim program to leading 300 reps through the Citrix acquisition, and what coaching taught him about bringing teams together around one outcome. If you're a sales leader rethinking what to train your reps on, a rep wondering where your value sits now that research is a click of a button, or a CRO leading through mergers and constant AI change, this conversation gives you the three competencies sellers need now, why curious sellers get the truth while scripted sellers lose deals they could have won, and how to build trust in AI recommendations when most leaders don't trust the data underneath them. Want to build a sales team that can hold its own in the AI era? Visit www.jbarrows.com and learn how you can Make It Happen. What You'll Learn Why the sales rep is more important than ever when buyers using AI get lost in analysis paralysis, and why the martini funnel doesn't match what Brian sees in real dealsWhy curious sellers who let the conversation wander earn trust and get the truth, while sellers with blinders on lose deals they could have wonThe three competencies reps need on top of the fundamentals: business acumen for CFO and CIO conversations, technical acumen, and project management across growing buying committeesWhy AI delivers marginal gains on stage velocity and conversion rate, no change to deal size, and a potential doubling of opportunity volumeHow Salesloft crowdsources AI wins through its AI Ops Factory, and how logging and measuring AI recommendations builds trust when 67 percent of revenue leaders don't trust their AI data Brian Benfer is the CRO at Salesloft, where he leads go-to-market for the company's AI revenue orchestration platform. He started his career as a competitive swim coach before moving into sales as an SDR at ShareFile, growing into leading a 300 person sales organization through its acquisition by Citrix. He went on to lead global sales at Dude Solutions, helping transform it into Brightly Software and guiding it through its acquisition by Siemens, before joining Salesloft. Connect with Brian Benfer: LinkedIn: https://www.linkedin.com/in/brian-benfer-79280b15/ Learn More at Salesloft: Website: https://www.salesloft.com/ LinkedIn: https://www.linkedin.com/company/salesloft/ Instagram: https://www.instagram.com/salesloft YouTube: https://www.youtube.com/salesloft John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today's AI-driven sales environment. Connect with John Barrows: LinkedIn: linkedin.com/in/johnbarrows Instagram: instagram.com/johnmbarrows TikTok: tiktok.com/@johnmbarrows Check out John's Membership: https://learn.jbarrows.com/pages/individual-packages Join John's Newsletter: https://www.jbarrows.com/newsletter

  4. Oct 5

    The Psychology of AI Adoption: Why 95% of Pilots Fail with Dr. Gleb Tsipursky

    Only nine percent of people at your company are excited about AI. Fifty two percent are more anxious about it than excited. If your rollout plan only accounts for the nine percent, you already know how this ends. In this episode, John sits down with Dr. Gleb Tsipursky, a behavioral scientist and author of The Psychology of AI Adoption at Work, to talk about why 95 percent of AI pilots fail to scale, the three distinct types of resistance blocking your team from adopting AI, and the leadership policy that lets companies grow revenue and headcount at the same time instead of cutting jobs to pay for efficiency. If you're in sales leadership, building or rebuilding a team for the AI era, or just trying to get your own reps to actually use the tools you already paid for, this conversation gives you a practical playbook for the two different rollouts your company needs, one for the people already excited about AI, and one for everybody else. Want to build a sales team that can hold its own in the AI era? Visit www.jbarrows.com and learn how you can Make It Happen. Get the Book on Amazon: The Psychology of AI Adoption at Work: From Resistance to Results https://www.amazon.com/dp/1647127491?lv=shuf&channelId=510&plpRedirect=mhFallback What You'll Learn Why 95 percent of AI pilots fail to scale, and the three psychographic profiles (AI alarmists, pragmatic resistors, reluctant adopters) blocking adoption long before rolloutWhy AI forward companies grow revenue nine percent faster and headcount six percent faster than AI backward competitors, and the leadership policy that makes both trueWhy only about ten percent of the old apprenticeship grind was ever formative, and what junior employees need to learn now that AI does the researchWhy Gleb tells most people to skip college unless their career requires a licensed degree, and how to use AI as a personalized learning roadmap insteadWhy the debate over AI's existential risk isn't a side conversation from adoption strategy, and what Anthropic's own head of research has said about it Dr. Gleb Tsipursky is a behavioral scientist and consultant who has spent over two decades helping companies navigate major shifts in how work gets done. He holds a PhD in the history of behavioral science from UNC Chapel Hill and has taught at Ohio State University. He is the author of eight books, including the global bestsellers Never Go With Your Gut and The Blindspots Between Us, and his newest book, The Psychology of AI Adoption at Work, is available now from Georgetown University Press. Visit disasteravoidanceexperts.com/aibook for a free sample of the book. Connect with Dr. Gleb Tsipursky: Website: https://disasteravoidanceexperts.com/ LinkedIn: https://www.linkedin.com/in/dr-gleb-tsipursky/ Facebook: https://www.facebook.com/DrGlebTsipursky Instagram: https://www.instagram.com/dr_gleb_tsipursky/ John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today's AI-driven sales environment. Connect with John Barrows: LinkedIn: linkedin.com/in/johnbarrows Instagram: instagram.com/johnmbarrows TikTok: tiktok.com/@johnmbarrows Check out John's Membership: https://learn.jbarrows.com/pages/individual-packages Join John's Newsletter: https://www.jbarrows.com/newsletter

  5. Sep 28

    AI Is Changing Sales How Salespeople Can Stay Valuable in 2026 with Tim Sanders

    Half of your buyers already picked their shortlist before your sales team even knew they existed. The only question left is whether your team knows what they typed in to get there. In this episode, John sits down with Tim Sanders, Chief Innovation Officer at G2 and author of five books including Love Is The Killer App, to talk about why half of all software buyers now start their research inside ChatGPT, how BDRs have quietly become the frontline of business intelligence for companies trying to win AI search, and why the one thing AI still can't replace in a sales rep is domain expertise. If you are in sales, sales leadership, or building a go-to-market team that needs to hold up in the AI era, this conversation gives you a practical way to think about what AI search means for your pipeline, why your BDRs might be sitting on your most valuable data, and how to make sure the human in the deal still has something the algorithm doesn't. Want to build a sales team that can hold its own in the AI era? Visit www.jbarrows.com and learn how you can Make It Happen. What You'll Learn Why half of all software buyers now start their research inside ChatGPT or Gemini, and are eighty percent through their purchase before a sales rep ever talks to themWhy the BDR, not the AE, has become the frontline of business intelligence for companies trying to win inside AI searchWhy Tim says today's best AE is a sommelier, not a closer, and what that metaphor means for a buyer drowning in AI-generated optionsWhy verifier's law explains what AI still can't be trusted to do in sales outreach, and why domain expertise is the one thing that makes a generalist model useful Tim Sanders is Chief Innovation Officer at G2, where he researches how AI is reshaping B2B buying and helps G2's customers adapt their go-to-market strategy. Before G2, he was Chief Innovation Officer at Upwork and spent years as an executive at Yahoo, following his early career with Mark Cuban's audio net, which became broadcast.com. He is the author of five books, including Love Is The Killer App and Today We Are Rich. Visit timsanders.com to learn more about Tim's work and books. Connect with Tim Sanders: Website: https://timsanders.com/ LinkedIn: https://www.linkedin.com/in/sanderssays John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today's AI-driven sales environment. Connect with John Barrows: LinkedIn: linkedin.com/in/johnbarrows Instagram: instagram.com/johnmbarrows TikTok: tiktok.com/@johnmbarrows Check out John's Membership: https://learn.jbarrows.com/pages/individual-packages Join John's Newsletter: https://www.jbarrows.com/newsletter

  6. Sep 21

    How Steve Jobs Built the Apple Store: Big Ideas, Innovation & Leadership with Ron Johnson

    The Apple Store almost didn't happen. Not because the idea was bad, because it was too big for anyone but Steve Jobs to say yes to. In this episode, John sits down with Ron Johnson, the retail executive who built the original Apple Store and Genius Bar alongside Steve Jobs, led Target's design transformation, and later served as CEO of JC Penney, to talk about why he turned down a scaled down test of the Apple Store concept, what actually went wrong with the JC Penney pricing overhaul he's still willing to own, and why he tells people to challenge every answer AI gives them the same way he had to challenge decades of accepted retail wisdom. If you are in sales, sales leadership, retail, or building anything that requires a team to believe in an idea before the proof exists, this conversation gives you a practical way to think about pitching big ideas instead of small tests, building a culture of believers instead of skeptics, and using AI to speed up research without letting it make the decision for you. Want to build a sales team that can think as boldly as Ron Johnson built the Apple Store? Visit www.jbarrows.com and learn how you can Make It Happen. What You'll Learn Why Ron turned down a scaled down test of the Apple Store, and the four billion dollar answer from Steve Jobs that changed his mindWhy doubling Target's kids' clothing business came down to something as simple as how the sizes were labeledWhy the JC Penney pricing overhaul improved customer satisfaction but still failed, and why Ron says the mistake was the pace, not the ideaWhy Steve Jobs wanted believers on his team, not skeptics, and how many skeptics is actually too manyWhy Ron says to challenge every answer AI gives you before you accept it, the same way he had to challenge decades of accepted retail wisdom Ron Johnson is the retail executive who led Apple's retail strategy and built the Apple Store and Genius Bar concept alongside Steve Jobs. Before Apple, he spent years at Target leading the company's design transformation, including its original Michael Graves partnership, and he later served as CEO of JC Penney. He is a graduate of Stanford University and Harvard Business School, and his new book releases September 22nd. Visit RonJohnsonShopsDifferent.com to learn more about Ron's work and his new book. Connect with Ron Johnson: Website: RonJohnsonShopsDifferent.com LinkedIn: linkedin.com/in/shopdifferent John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today's AI-driven sales environment. Connect with John Barrows: LinkedIn: linkedin.com/in/johnbarrows Instagram: instagram.com/johnmbarrows TikTok: tiktok.com/@johnmbarrows Check out John's Membership: https://learn.jbarrows.com/pages/individual-packages Join John's Newsletter: https://www.jbarrows.com/newsletter

  7. Sep 14

    AI Is Changing Sales Leadership: The New Skills Every Sales Rep Needs with Kristie Jones

    AI didn't kill the sales fundamentals. It just made everyone forget what they actually are. In this episode, John sits down with Kristie Jones, Author and Founder of Sales Acceleration Group, to talk about why the buyer now wants to talk to a human 80 to 90 percent of the way through their own research, why the post-mortem meeting needs to be replaced with a pre-call meeting, and why AI is forcing sales leaders to teach objective judgment for the first time in their careers. If you are in sales, sales leadership, RevOps, or GTM, this conversation gives you a practical way to think about writing a role brief for the AI tools on your team, replacing the post-mortem with a pre-call meeting, testing for objective judgment instead of just tactical skill, and why the old playbook is dead even though playbooks aren't. Want to build a sales team that can think critically in the AI era? Visit www.jbarrows.com and learn how you can Make It Happen. What You'll Learn Why the buyer now wants to talk to a human 80 to 90 percent of the way through their own research, and what that means for how a rep opens the callWhy the post-mortem meeting needs to be replaced with a pre-call meeting built around objective judgmentWhy every AI tool on your team needs a role brief, the same way every hire needs a job descriptionWhy Kristie tests candidates by making them argue with an AI generated plan live, not just use oneWhy the four skills sales leaders need now are systems thinking, workflow design, decision leadership, and accountability clarity Kristie Jones is the Author and Founder of Sales Acceleration Group, where she works with sales organizations on hiring, training, and leadership development. She's the author of Selling Your Way In and the upcoming The Sales Leadership Gap, releasing October 2026, which looks at how AI is forcing a fundamental rethink of how sales leaders hire, coach, and make decisions. Visit kristiekjones.com to learn more about Kristie's work and get updates on The Sales Leadership Gap. Connect with Kristie Jones: LinkedIn: linkedin.com/in/kristiekjones Website: kristiekjones.com Instagram: instagram.com/kristiejones.sales YouTube: youtube.com/@kristiekjones John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today's AI-driven sales environment. Connect with John Barrows: LinkedIn: linkedin.com/in/johnbarrows Instagram: instagram.com/johnmbarrows TikTok: tiktok.com/@johnmbarrows Check out John's Membership: https://learn.jbarrows.com/pages/individual-packages Join John's Newsletter: https://www.jbarrows.com/newsletter

  8. Sep 7

    How Customer Success Drives Retention, Revenue & Growth with Elizabeth Salmoun

    AI is not replacing customer success. It's turning it into the most important revenue function in the business. In this episode, John sits down with Elizabeth Salmoun, Head of Customer Success at Otter.ai, to talk about why products and tooling have become table stakes in the AI era, why the sales to CS handoff decides whether a client renews inside the first 90 days, and why AI is turning CSMs into AI advisors and workflow consultants instead of relationship managers. If you are in sales, customer success, RevOps, or GTM leadership, this conversation gives you a practical way to think about handoff timing between AE and CSM, segmenting a book of business by tier instead of treating every renewal the same, the three W's framework for discovery, and why AI generated work should never go out the door without a human reviewing it first. Want to build a customer success team that turns renewals into your biggest growth lever? Visit www.jbarrows.com and learn how you can Make It Happen. What You'll Learn Why products and tooling became table stakes, and why the relationship is what actually differentiates you nowWhy the first 90 days after a deal closes decide whether a client renews or churnsWhy Elizabeth starts every renewal conversation 120 days out instead of waiting for the discount fightWhy AI is turning CSMs into AI advisors and workflow consultants instead of relationship managersWhy a sales rep who's just running the process is already irrelevant, and what still makes the role critical Elizabeth Salmoun is the Head of Customer Success at Otter.ai, where she leads retention and expansion strategy in one of the most competitive corners of the AI tooling market. She built her career in retail before moving into tech sales and account management, and she has spent the last several years turning customer success into a revenue generating function built on discovery, relationship building, and clear rules of engagement with sales. Visit otter.ai to learn more about Otter.ai's AI meeting assistant and how its customer success team helps teams capture, act on, and get real value from every conversation. Connect with Elizabeth Salmoun: LinkedIn: linkedin.com/in/esalmoun Connect with Otter.ai: Website: otter.ai LinkedIn: linkedin.com/company/otter-ai YouTube: youtube.com/@Otterai Instagram: instagram.com/otter.ai John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution, helping reps fill pipeline, close deals, and build trust with buyers in today's AI-driven sales environment. Connect with John Barrows: LinkedIn: linkedin.com/in/johnbarrows Instagram: instagram.com/johnmbarrows TikTok: tiktok.com/@johnmbarrows Check out John's Membership: https://learn.jbarrows.com/pages/individual-packages Join John's Newsletter: https://www.jbarrows.com/newsletter

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4.6
out of 5
201 Ratings

About

John Barrows helps sales leaders decide whether to replace or rebuild their teams for the AI era, drawing on 25+ years working with Salesforce, LinkedIn, Google, and Amazon. He advises CROs and VPs of Sales on AI readiness, team structure, and go-to-market strategy. He trains sales teams on the fundamentals that drive consistent performance, with or without AI.

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