Stop Automating Bad Sales: Use AI to Win More B2B Deals
Kevin Lawson and Sean O'Shaughnessy discuss how B2B salespeople should use AI as a research and analysis assistant to personalize customer interactions and uncover hidden opportunities, rather than automating outreach activities. They argue that AI enables salespeople to recreate the personalized service model of early general stores by analyzing customer data, financial reports, and sales history to deliver highly targeted value.
Summary
In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessy explore how artificial intelligence is transforming B2B sales when used strategically rather than for automation. They emphasize that AI should function as a sales enablement tool—an assistant, critical thinker, analyst, and researcher—rather than a replacement for human interaction or a method to automate mass outreach.
The hosts draw an analogy to early 20th-century general store owners who remembered individual customers' names, preferences, previous interests, and personal details, then used that knowledge to offer personalized deals and recommendations. They argue that modern AI enables salespeople to recreate this hyper-personalized approach at scale by maintaining detailed customer knowledge and analyzing patterns across entire sales pipelines.
Key applications of AI in the sales journey include territory management, customer engagement, customer research, CRM analysis to identify qualification gaps, and using AI to comb through sales conversations and customer data for new insights. The hosts stress this should be applied across all stages of the customer journey—from awareness and marketing through discovery, proposal, close, and follow-up—but explicitly caution against using AI to run entire marketing campaigns or close deals without human involvement, calling this "doing traditional things that annoy people faster."
They provide practical applications for both enterprise and small business sales: For public companies, salespeople can upload 10-K annual reports and 8-K quarterly filings into AI chatbots to identify five industry-relevant challenges within minutes, then use that research to customize presentations and proposals. For private companies without public filings, salespeople can analyze internal sales data, product reports, and sales history through private LLMs to identify market share gains, at-risk products, pricing pressures, and other insights to bring to quarterly business reviews.
The hosts also discuss how AI can help salespeople understand which 30% of their time spent with customers should be most high-impact by analyzing CRM data to reveal patterns: which industries close most frequently, where deals most often stall, common qualification gaps across the pipeline, and which customer titles or industries represent blind spots. This data-driven approach allows salespeople to focus on effectiveness over efficiency.
About this episode
<p dir="ltr">Artificial intelligence is changing B2B sales, but using AI to send more automated emails or accelerate ineffective sales processes misses the real opportunity. What if AI could help you understand your customers more deeply, identify hidden opportunities in your pipeline, and deliver the kind of personalized attention that once defined great customer relationships? In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore how AI is transforming sales research, account planning, and customer engagement. From analyzing CRM data to creating customer-specific presentations and uncovering revenue opportunities, Kevin and Sean share practical sales strategies that help salespeople work smarter, strengthen relationships, and win more business without sacrificing the human connection that drives sales success.</p> <h2 dir="ltr">Key Topics Discussed</h2> <ul> <li dir="ltr"> <p dir="ltr">00:00 – AI as a Sales Assistant, Not an Automated Salesperson: Kevin explains why the greatest value of artificial intelligence comes from helping salespeople research, analyze, and make better decisions. Discover why automating ineffective outreach with AI just creates more noise, while human-in-the-loop automation can improve customer engagement and sales effectiveness.</p> </li> <li dir="ltr"> <p dir="ltr">01:43 – Bringing Back Personalized Selling with AI: Sean draws a fascinating parallel between the neighborhood general stores of the early 1900s and today's AI-enabled sales environment. Learn how generative AI lets you recreate highly personalized customer relationships at scale, tailoring messaging, presentations, and conversations to each buyer's specific needs and business challenges.</p> </li> <li dir="ltr"> <p dir="ltr">05:46 – Using AI and CRM Data to Find Hidden Sales Opportunities: Kevin shares real-world examples from HubSpot, Zoho, and Pipedrive that demonstrate how AI can identify qualification gaps, analyze historical wins and losses, and reveal overlooked opportunities. These insights improve sales management, sharpen pipeline prioritization, and help salespeople spend their limited customer-facing time on activities that actually produce revenue.</p> </li> <li dir="ltr"> <p dir="ltr">08:36 – Turning Annual Reports into Powerful Sales Intelligence: Sean demonstrates how B2B sales professionals can use AI tools such as ChatGPT, Claude, and Gemini to analyze corporate 10-K reports and SEC filings. Discover how to identify a prospect's business priorities, uncover challenges relevant to your solution, and develop compelling, customer-specific presentations that emphasize value selling rather than generic product pitches.</p> </li> <li dir="ltr"> <p dir="ltr">11:46 – AI-Powered Account Planning for Smaller Businesses: You don't need Fortune 500 customers to benefit from AI-driven sales strategies. Kevin explains how analyzing 24 months of internal sales data can uncover product trends, pricing pressures, growth opportunities, and customer risks. Learn how to turn ordinary quarterly business reviews into strategic conversations that strengthen relationships, boost revenue, and differentiate your company from competitors.</p> </li> </ul> <h2 dir="ltr">Key Quotes</h2> <p dir="ltr">Kevin Lawson (01:35):</p> <p dir="ltr">"This is you getting more out of your selling day by using AI as a tool, not as a silver bullet."</p> <p dir="ltr">Sean O'Shaughnessey (04:12):</p> <p dir="ltr">"Because you have this amazing sidekick sitting beside you all the time, keeping track of all the details, keeping track of all the wisdom, researching every single thing that's going on in the company."</p> <p dir="ltr">Kevin Lawson (07:38):</p> <p dir="ltr">"This is effectiveness over efficiency."</p> <p dir="ltr">Sean O'Shaughnessey (11:26):</p> <p dir="ltr">"It's gonna be about how you are going to help your customer solve their problems."</p> <p dir="ltr">Kevin Lawson (13:29):</p> <p dir="ltr">"So when you're thinking about using AI, think about the story you're gonna tell about the insight that you've derived with your AI-assisted sales enablement."</p> <h2 dir="ltr">Additional Resources</h2> <p dir="ltr">The following tools and information sources are discussed in the episode:</p> <ul> <li dir="ltr"> <p dir="ltr">ChatGPT, Claude, and Google Gemini: Generative AI platforms that can assist with customer research, document analysis, account planning, and personalized sales presentations.</p> </li> <li dir="ltr"> <p dir="ltr">HubSpot, Zoho, and Pipedrive: CRM platforms discussed as examples of how AI can help salespeople analyze opportunities, identify qualification gaps, and improve sales processes.</p> </li> <li dir="ltr"> <p dir="ltr">SEC Form 10-K and Form 8-K: Public company filings that provide information about business performance, strategic priorities, financial risks, and significant corporate developments.</p> </li> </ul> <h2 dir="ltr">A Significant Actionable Item from this Podcast</h2> <p dir="ltr">Use AI to uncover five actionable insights about one important customer before your next sales conversation.</p> <p dir="ltr">Choose an active customer or prospect with an upcoming meeting. If the company is publicly traded, obtain its latest 10-K and relevant recent SEC filings. If you're working with a smaller, privately held customer, consider your company's internal sales history for that account, including purchasing patterns, product mix, and pricing trends.</p> <p dir="ltr">Use an appropriate AI tool to analyze the information and identify five insights that could influence the customer's business decisions. Look for growth opportunities, emerging risks, changes in purchasing behavior, or problems your company might help solve. Keep confidential information within approved systems, and verify the AI's findings against the source data.</p> <p dir="ltr">Select the most compelling insight and incorporate it into your next customer conversation. Instead of delivering your usual product presentation, lead with a relevant business observation and a thoughtful question that encourages discussion.</p> <p dir="ltr">The objective is to demonstrate that you understand the customer's business, not simply that you know how to use AI. One well-researched observation can open a more valuable conversation than another generic sales presentation.</p> <h2 dir="ltr">Summary</h2> <p dir="ltr">AI is creating an extraordinary opportunity for B2B salespeople to combine the personal attention of traditional relationship selling with the analytical capabilities of modern technology. But the competitive advantage won't come from generating more emails, creating more presentations, or automating every stage of the sales process. It will come from using better information to make smarter decisions, deliver more relevant messaging, and create meaningful customer value. In this episode, Kevin Lawson and Sean O'Shaughnessey move beyond the AI hype to share practical techniques you can implement immediately, whether you're managing complex enterprise deals or growing accounts with smaller businesses. If you want to improve sales productivity, uncover opportunities your competitors are missing, and turn AI-assisted research into stronger customer relationships and measurable revenue growth, this episode of Two Tall Guys Talking Sales deserves a place on your playlist.</p> <p><strong id="docs-internal-guid-5d0c65f4-7fff-519f-7fa7-28826b813b3f"><br /> <br /></strong><!-- obsidian --></p> <p><strong>B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory.</strong> It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com</p> <p>You can reach out to Sean at New Sales Expert, LLC - <a class="external-link" href="mailto:[email protected]" rel="noopener" target="_blank"><u>[email protected]</u></a> - <a class="external-link" href="https://www.linkedin.com/in/soshaughnessey/" rel="noopener" target="_blank"><u>https://www.linkedin.com/in/soshaughnessey/</u></a></p> <p>You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - <a class="external-link" href="mailto:[email protected]" rel="noopener" target="_blank"><u>[email protected]</u></a> - <a class="external-link" href="https://www.linkedin.com/in/kwlawson/" rel="noopener" target="_blank"><u>https://www.linkedin.com/in/kwlawson/</u></a></p> <p>You can book time on Kevin's calendar at <a class="external-link" href="https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin" rel="noopener" target="_blank"><u>https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin</u></a></p> <p>You can book time on Sean's calendar at <a class="external-link" href="http://newsales.expert/sean-oshaughnessey-calendar/" rel="noopener nofollow" target="_blank">http://newsales.expert/sean-oshaughnessey-calendar/</a></p>
Key Insights
- The hosts argue that AI enables salespeople to recreate the hyper-personalized service model of early 20th-century general stores—where owners remembered customer names, preferences, and personal details—by analyzing customer data and company information at scale.
- Kevin asserts that salespeople who are not leveraging AI for territory management, customer research, CRM analysis, and sales leader insights across the customer journey are falling behind and should be held accountable.
- The hosts claim that using AI to automate mass marketing campaigns or close deals without human involvement represents doing traditional cold outreach faster and more annoyingly, which is explicitly counter to their recommended AI strategy.
- Sean argues that modern buyers now conduct 90% of their research independently before engaging with sellers (up from 70% before AI), meaning sellers only participate in the final 10% of the decision, making AI-powered research critical to staying relevant.
- The hosts contend that analyzing public 10-K and 8-K filings through AI can extract five industry-specific insights within minutes that directly relate to a customer's business challenges, enabling salespeople to customize presentations around customer problems rather than company solutions.
Topics
Transcript
Artificial intelligence is transforming B2B sales. But are you using it to uncover new opportunities or simply automate the same old activities? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessy reveal how AI can help you identify hidden opportunities in your CRM, understand your customers' business challenges, and deliver highly personalized sales conversations. Discover practical ways to turn customer data, annual reports, and sales history into actionable intelligence that strengthens relationships and helps you win more deals. Whether you're selling to Fortune 500 companies or small businesses, you'll learn how to make AI your competitive advantage without losing the human connection that drives sales success. there and not using AI for territory management, customer…
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