Sales 101: The B2B Sales Classroom

Stop Teaching AI Tools...Do This Instead! | Cherilynn Castleman - 26

How do you teach students to actually use AI effectively instead of just relying on random tools and prompts? We invited Cherilynn Castleman, a sales consultant and professor at Harvard University, to discuss how AI is reshaping sales education. She explains why professors should focus less on specific platforms and more on helping students develop true AI fluency. Meet Cherilynn Castleman * Cherilynn Castleman is a sales consultant, AI strategist, and professor at Harvard University, where she teaches courses focused on AI adoption and AI fluency in sales. * She helps sales professionals and organizations understand how to integrate AI into modern sales workflows while still building authentic human connection. * Through her teaching, consulting, and content, Cherilynn focuses on helping people move beyond simply using AI tools and instead develop the confidence and clarity needed to succeed in an AI-driven sales environment. Why AI Fluency Matters More Than Learning Tools * One of the biggest points Cherilynn shares is how quickly AI tools are changing. She explains that between 50 to 100 new AI sales tools are entering the market every single week. That means professors cannot realistically keep up by teaching tools alone. * Instead, students need to understand how to think with AI, communicate with it effectively, and integrate it into their sales workflow. * Cherilynn compares AI fluency to learning a second language. At first, it feels uncomfortable, but over time students develop confidence and clarity in how to use it naturally. Why Companies Are Struggling With AI * Even though companies are heavily investing in AI, many are still not seeing results. * Cherilynn shares that global AI spending is projected to reach $2.5 trillion in 2026, growing 44% year over year. Yet according to MIT research [https://www.forbes.com/sites/andreahill/2025/08/21/why-95-of-ai-pilots-fail-and-what-business-leaders-should-do-instead/?utm], 95% of organizations report seeing little to no ROI from their AI implementation. * The reason? Most companies are focused on tools instead of teaching people how to actually use AI strategically. How AI Can Make Students Better Sellers * One of the most interesting parts of the conversation focused on how AI can help students become stronger communicators and better sales professionals. * Cherilynn explains how students can use AI to: * personalize outreach faster * improve discovery questions * research prospects and industries * create stronger points of view * identify weaknesses in their sales process * Instead of replacing sellers, AI helps elevate them. Teaching Students to Build Better Buyer Relationships * Cherilynn also shares how AI can help students create stronger emotional connections with buyers by improving the quality of their discovery questions. * She explains that 87% of B2B buyers want sales professionals to show up as trusted advisors. * AI can help students prepare better questions, understand customer challenges, and communicate more strategically during conversations. “AI can help you build trust by improving the questions you ask and strengthening your connection with buyers. Develop a POV because your point of view is how you show up.” — Cherilynn Castleman Resources Want to learn more about AI fluency and the future of sales education? Connect with Cherilynn Castleman on LinkedIn [https://www.linkedin.com/in/cherilynn-castleman/] and follow her insights on how AI is reshaping the way sales professionals learn, sell, and build stronger customer relationships. Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom.

The Best Way To Utilize AI In Your Sales Class | Donald C. Kelly & Dr. BJ Allen - 25

Over the last few years, AI has made its way into everything. So how do you actually bring it into your sales classroom in a way that prepares students for the real world? We partnered with Stukent to show you how to use it for roleplay in the classroom. Why AI Is Changing Sales Education * AI is not just a trend. It is already shaping how sales professionals work every day. The challenge for professors is figuring out how to bring that into the classroom in a way that feels practical and relevant. * This is where AI roleplay comes in. Instead of relying only on student to student practice, professors can now create more realistic selling environments. Making Roleplay Feel Real * One of the biggest challenges in teaching sales is making roleplay feel authentic. Students know when it is just practice. * With AI, that changes. The buyer responds in real time, asks questions, and even pushes back like a real prospect would. * That means students are not just memorizing scripts. They are learning how to think, adapt, and respond in the moment. Better Experience for Students and Professors * AI roleplay does not just help students. It also makes things easier for professors. * Instead of reviewing every interaction, AI can handle feedback and evaluation, reducing workload while still giving students a high quality experience. * It also removes bias and creates a more consistent learning environment. Preparing Students for the Real World * The goal is simple. Help students feel what real selling is like before they step into their first role. * With AI, you can adjust difficulty levels, simulate different buyer personalities, and create scenarios that reflect real sales conversations. “One of the best things about AI roleplay is you can adjust the difficulty. For beginners, it can be simple, but at advanced levels, it feels real. I’ve seen it hang up on students within 20 seconds, just like real life.” — Dr. BJ Allen Resources Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom. Learn how you can bring AI into your classroom and more about Stukent here [https://www.stukent.com/].

The Secret to Winning Deals Before Your Competitors Know There’s a Need | Donald C. Kelly & Dr. BJ Allen - 24

Buyers are making decisions before they ever talk to a seller. If your students are not part of that process, they are already out of the running. How do you teach them to become the go-to seller in today’s buyer journey? We’re breaking down three strategies to help them stand out and stay top of mind. The Modern Sales Problem * Thanks to technology, buyers now have a world of information at their fingertips. They are researching solutions, comparing options, and forming opinions long before they ever speak to a seller. * By the time a conversation happens, many have already made internal decisions or narrowed their shortlist. If your students are not part of that early research phase, they are already at a disadvantage. * It gets even tougher with Requests for Proposals (RFPs). Many are built around the features of a preferred solution or based on templates from past vendors, which quietly limits opportunities for new sellers to compete. Classroom Implementation Strategies * So how do you actually prepare students for this shift? It starts with helping them show up earlier in the buyer’s journey. * Build Subject Matter Expertise: Encourage students to use LinkedIn as more than a place for cold outreach. When they consistently share insights and engage with industry content, they start to build a presence. Over time, they become someone buyers recognize and trust before a conversation even happens. * Bring the Buyer Into the Classroom: Let students hear directly from buyers. Invite guest speakers who can walk through how decisions are really made, who is involved, and what their research process looks like. It gives students a clearer picture of what is happening behind the scenes. * Strengthen Discovery Skills: Teach students how to ask better questions during discovery. The goal is to understand what the buyer actually values and whether they have already been influenced by another solution. When students can uncover that early, they can position themselves more effectively without putting down the competition. “In this era, it’s no longer about being the best. It’s about being the best known in your space.” — Donald C. Kelly “It’s great for buyers to have context around what’s happening before they engage.” — Dr. BJ Allen Resources Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to continue the conversation or share how you're applying these strategies in your classroom.

Everything You Need To Know About B2C vs B2B Sales | Patrick Carter - 23

What’s the real difference between B2C and B2B sales? Do students need to go into B2B to build a successful career? And are we teaching the right principles for both? These are the kinds of questions sales professors face in the classroom, especially when many students start their careers in B2C roles. We invited Patrick Carter, a retail sales leader, to break it down. He shares how he’s building and leading successful B2C sales teams and what professors should be preparing students for in today’s sales environment. Meet Patrick Carter * Patrick Carter is a sales leader and enablement strategist with over 20 years of experience building high-performing retail sales teams and driving revenue growth. He focuses on creating the systems, playbooks, and coaching structures that help sales organizations scale. * He’s known for a coaching-first leadership style that builds trust, improves individual performance, and creates a culture where accountability and growth go hand in hand. * Patrick operates at both the strategic and day-to-day level, developing the vision while staying close enough to execution to know when to step in and when to let his team take the lead. B2B vs B2C: What’s the Real Difference? * At its core, retail is business to consumers. You’re selling directly to the end user. Sounds simple, but it’s not. * The biggest difference comes down to speed. In B2B, you might have weeks or months to build relationships. In retail, you may have minutes. Customers often walk in knowing exactly what they want, which means the real skill is how you respond in that moment. You’re Not Just an Order Taker * Patrick makes one thing clear. The website already has the information. Your role is to bring knowledge. * That means asking better questions, understanding what the customer actually needs, and guiding them beyond what they came in for. * Anyone can process a transaction. A real salesperson builds trust fast and adds value early. Where the Real Money Happens * Retail sales can be more lucrative than most people think. With the right skillset and experience, income can grow significantly over time. * But it’s not just about the first sale. It’s about relationships. When customers trust you, they come back. They bring others. And that’s where long-term success is built. * If you’re teaching sales, this episode may challenge how you think about preparing students for the real world. “Your job isn’t to sell products. Your job is to bring knowledge. The website already has the information.” — Patrick Carter Resources Want to learn more about B2C sales and how to apply it in your classroom or career? Connect with Patrick Carter on LinkedIn [https://www.linkedin.com/in/patrickgcarter?utm_source=share_via&utm_content=profile&utm_medium=member_ios] and follow his insights. Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to chat about this episode or ask any questions.

How My College Sales Program Prepared Me To Work At Gong.io! | Joseph Wood - 22

What does it take to turn classroom learning into real sales results? Joseph Wood shares how the BYU sales program helped launch his career at Gong.io, where he quickly moved from BDR to Account Executive. He shows how the right mix of education and experience can help you scale in B2B sales. Meet Joseph Wood * Joseph is a former Sales Society collegiate competition winner and President, now a full-time Account Executive at Gong.io and part-time founder. * He enjoys training in Jiu Jitsu so he can continue defeating his five younger brothers in wrestling matches. * Happily married and always ready to nerd out about business and entrepreneurship. How Sales Education Builds Real Skills * Joseph didn’t initially plan on a sales career. But once he was exposed to it, everything changed. * Through role plays, practical exercises, and learning how to think persuasively, he developed skills that translated directly into the real world. * Sales education gave him a strong foundation, but applying those skills in the workforce made the difference. Why Sales Clubs and Competitions Matter * The classroom introduced sales, but hands-on experience built confidence. Sales competitions and networking opportunities helped Joseph sharpen his skills and connect with companies. * Winning early gave him proof that he could succeed, while consistent exposure helped him understand what a career in sales actually looks like. Lessons Learned in the Real World * Transitioning into a full-cycle sales role came with new challenges. Managing deals, identifying decision-makers, and controlling the sales process were skills developed on the job. * Joseph talks about the importance of strong discovery and understanding every stakeholder involved in a deal. The Mindset That Drives Long-Term Success * Sales is a long-term game. Early in his career, fear of failure held him back. * Now, he sees failure as part of growth. With the right skill set and persistence, opportunities will always follow. “Realizing that sales is a marathon and not a sprint helped me see that it’s okay to fail and mess up because there will always be another opportunity. I used to be afraid of failure, but now I understand that with a strong skill set, you will always find a way to provide value.” - Joseph Wood Resources * Find Joseph Wood on LinkedIn [https://www.linkedin.com/in/joseph-wood-contact/] to learn more about his journey into B2B sales. Connect with Dr. BJ Allen [https://www.linkedin.com/in/bjallen3/] and Donald C. Kelly [https://www.linkedin.com/in/donaldckelly/] on LinkedIn to chat about this episode or ask any questions.