Make It Happen Mondays - B2B Sales Talk with John Barrows

Before your buyer takes your call, their AI has already researched you, evaluated your solution, and started forming an opinion. The question isn't whether AI is changing sales. It's whether you're going to catch up to what's already happening on the other side of the table.
In this episode, John sits down with Kris Lawson, the sales leader, founder of Ruby, and Snowflake alumnus, to unpack the most important shift in B2B sales that most people are completely ignoring. Kris was the first Oracle rep ever to lose a deal to Salesforce, went on to build and scale sales teams across some of the most iconic tech companies of the last 25 years, and is now building the AI-powered sales assistant he always wished he had.
From how buyers are already using AI to screen vendors, to why generic AI tools will never replace purpose-built sales intelligence, to how to pick a rocket ship company before anyone else knows it's one, this conversation covers the ground that matters most right now.
If you're in sales, leading a sales team, or building a company and trying to figure out how to win in an AI-saturated market, this episode will change how you think about what's coming. Visit www.jbarrows.com and learn how you can Make It Happen.
What You’ll Learn
Why your buyer's AI is already evaluating you
How OpenAI and Anthropic told one company to "just send the documentation" and let their LLMs decide
The framework Kris uses to evaluate whether a company is worth joining
Why the first Oracle rep to lose a deal to Salesforce ended up joining Salesforce
Why the chat interface will never work for the average sales rep
The build-vs-buy fallacy in the AI era and the real risks nobody is talking about
How AI will reshape sales methodologies
The rubber duck exercise and how to use AI to learn, not just execute
Why choosing the right life partner is the most important career decision a salesperson will ever make

Kris Lawson is a sales leader, entrepreneur, and co-founder of Ruby (heyruby.ai) — an AI-powered sales assistant purpose-built to help sales reps be excellent in every customer interaction. Kris has spent 25 years scaling go-to-market organizations at Oracle, Salesforce, Microsoft, and Snowflake. He was the first Oracle rep ever to lose a deal to Salesforce, went on to become a key early sales leader in Canada for Salesforce, and has since built and exited multiple sales organizations in the tech sector. He is also co-founder of Snow Angels, a Snowflake alumni investor syndicate focused on data and AI startups.
Connect with Kris Lawson:
Website: https://www.heyruby.ai/
LinkedIn: https://www.linkedin.com/in/krislawsonland/
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://go.jbarrows.com/
Join John's Newsletter: https://www.jbarrows.com/newsletter

Every founder who has ever handed sales off too early has paid for it. Every single one.
In this episode, John sits down with Lou Shipley, a Harvard Business School lecturer, board member, investor, and author of Unlikely Entrepreneurs, to dig into why sales is still the most misunderstood function in business, and why founders who treat it as a second-class citizen almost always fail. Lou draws from decades of experience running companies, building sales cultures from scratch, and teaching MBAs how to sell before they ever launch a product.
From cold-calling encyclopedia buyers to opening Asia for Avid Technology to building the sales curriculum at HBS, Lou has lived every stage of the sales journey, and he's done it at the highest level.
If you're a founder, a sales professional, or anyone trying to understand what it actually takes to build a company in the age of AI, this conversation will challenge everything you think you know about selling. Visit www.jbarrows.com and learn how you can Make It Happen.
What You’ll Learn
Why founders who delegate sales too early almost always fail
How Lou built one of Harvard's most in-demand courses
The cultural disdain of sales
Why sales is not about convincing anyone of anything
How to use AI as a learning tool instead of an answer machine
What the Guy Kawasaki GPT experiment revealed
Why curiosity is the most important professional skill in the AI era
What SaaS companies should be doing right now
How to build a farm system for sales talent
17 stories that prove anyone can build something worth buying

Lou Shipley is a multi-time tech CEO, entrepreneur, and enterprise software leader with over 25 years of experience driving growth and innovation. He has led several successful startups through rapid expansion and acquisition, including Black Duck, WebLine (acquired by Cisco), Reflectent (acquired by Citrix), and VMTurbo. In addition to his executive leadership, Lou serves on multiple boards, teaches technology sales at Harvard Business School, and is a respected mentor, speaker, and commentator in the tech industry.
Connect with Lou Shipley:
Website: https://www.loushipley.com/
LinkedIn: https://www.linkedin.com/in/loushipley/
Grab a copy of Lou Shipley’s book, “Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons on Building Great Companies,“ on Amazon: https://www.amazon.com/Unlikely-Entrepreneurs-Lou-Shipley/dp/1394345895/
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://go.jbarrows.com/
Join John's Newsletter: https://www.jbarrows.com/newsletter

If your prospect thinks they can already get what you're selling for free, you don't have a product problem — you have a positioning problem.
In this episode, John sits down with Eric Appel, CRO of Island, the company that turned a free commodity — the browser — into one of the fastest-growing enterprise security platforms in the world. Eric pulls back the curtain on how Island landed eight of the top ten US financial institutions as early customers, why the advisor network beats outbound at scale, and what today's sales reps are getting catastrophically wrong before they even open their mouths.
If you're navigating a market where AI is commoditizing everything around you and buyers think they don't need what you're selling, this conversation will change how you think about value, positioning, and the future of selling. Visit www.jbarrows.com and learn how you can Make It Happen.
What You’ll Learn
How Island sold a "free" product to the world's biggest enterprises — and won
The advisor network strategy that replaced traditional outbound prospecting
Why the first 15 sales hires at Island were all known killers — and why that matters
How to build a real feedback loop between sales and engineering
The three questions you should never ask a prospect (and what to do instead)
Why hypothesis selling is replacing discovery in today's AI-driven sales environment
What separates leaders from followers in the AI era — and why followers will get left behind

Eric Appel is the Chief Revenue Officer at Island, the enterprise browser company redefining how organizations think about security, productivity, and AI enablement. With a career that spans Arthur Anderson, Yahoo, McAfee, and some of the most pivotal chapters in information security, Eric has spent over two decades building go-to-market engines for category-defining companies. At Island, he helped architect the sales strategy that brought the world's largest financial institutions, pharma companies, and global enterprises onto the platform — proving that even a "free" product can command a premium price when the value proposition is airtight.
Connect with Eric Appel:
Website: https://island.io
LinkedIn: https://www.linkedin.com/in/eric-appel-605310/
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://go.jbarrows.com/
Join John's Newsletter: https://www.jbarrows.com/newsletter

Sales is about solving problems. It’s about helping people achieve their goals—and that’s exactly what innovation is at its core.
In this episode, John sits down with Jason Wild, author of Genius at Scale: How Great Leaders Drive Innovation, to talk about his journey from Chicago to becoming a high-level entrepreneur. Drawing from his experience working with companies like IBM and Salesforce, he breaks down the ABC structure that helps business owners think differently and drive meaningful innovation.
If you’re ready to elevate how you approach growth, this conversation will challenge your perspective on leadership, strategy, and the results you’re capable of creating. Visit www.jbarrows.com and learn how you can Make It Happen.
What You’ll Learn
What it’s like to work with IBM and Salesforce
The ABC structure for innovation
Laying out the framework for innovation
Aligning People In One Vision
Approaching innovation in the era of AI

From a child actor in Hollywood to tech executive in Silicon Valley, Jason Wild has collaborated with some of the most talented and creative people in the world. He is an adviser and author on growth, innovation, strategy, and leadership, having led projects in 40 countries from Disney and AT&T to NATO and the City of Paris. He is the co-founder of Wild Innovation Consulting and helps leaders and organizations unlock their genius at scale, with significant experience in AI, business, and operating models, and digital transformation. He worked for over 20 years in executive roles at Microsoft, IBM, and Salesforce. He is dedicated to ensuring that AI and emerging tech benefit all of humanity.
Connect with Jason Wild:
Website: https://geniusatscale.com/
LinkedIn: https://www.linkedin.com/in/jasonwild/
Get a copy of “Genius at Scale: How Great Leaders Drive Innovation” on Amazon: https://www.amazon.com/Genius-Scale-Great-Leaders-Innovation/dp/1647827507
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://go.jbarrows.com/
Join John's Newsletter: https://www.jbarrows.com/newsletter

Start by asking yourself: What am I good at? What do I love doing? And ultimately, what will I get paid for?
In this episode, John is joined by Roderick Jefferson to have a real conversation about ambition, ego, and the true cost of success across our lives, relationships, and leadership. Together, they unpack the importance of slowing down, why constant hustle can come at a price, and the powerful lessons Roderick learned after experiencing a stroke.
If you’re at the stage where you’re focused on building a legacy and discovering your deeper “why,” this episode will challenge and expand your perspective on what it really means to be successful.
Want to equip yourself for success before it’s too late? Visit www.jbarrows.com and learn how you can Make It Happen.
What You’ll Learn
Why work-life balance is a lie
The impact of taking a break
How to use AI to your advantage
Understanding ambition vs ego
Building your own legacy

Roderick Jefferson is an internationally recognized speaker, author, and thought leader who lives and breathes enablement. With more than 25 years of experience, he has held senior executive positions at companies such as Siebel, NetApp, Salesforce, Oracle, and others. He had delivered keynotes, guest lectures, webinars, and podcasts in fourteen countries at prominent events and conferences, sharing his vibrant and engaging insights with a worldwide audience. Roderick is an acknowledged thought leader in the enablement space and the author of Sales Enablement 3.0: The Blueprint to Sales Enablement Excellence™, an Amazon #1 New Release and best-selling book, and the Sales Enablement 3.0 Companion Workbook™, which guides organizations aiming to enhance their sales strategies through effective enablement practices.
Connect with Roderick Jefferson:
Website: https://www.roderickjefferson.com/
LinkedIn: https://www.linkedin.com/in/roderickjefferson/
Facebook: https://www.facebook.com/ThevoiceofRod/
Instagram: https://www.instagram.com/roderick_j_associates/?hl=en
YouTube: https://www.youtube.com/channel/UCShK1i36e1AY1yVHHPh93wQ
X: https://x.com/thevoiceofrod?lang=en
Grab a copy of “Sales Enablement 3.0: The Blueprint to Sales Enablement Excellence” on Amazon: https://www.amazon.com/Sales-Enablement-3-0-Blueprint-Excellence/dp/1736190903
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://go.jbarrows.com/
Join John's Newsletter: https://www.jbarrows.com/newsletter