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Two Tall Guys Talking Sales

Two Tall Guys Talking Sales

Di: Kevin Lawson and Sean O'Shaughnessey
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"Two Tall Guys Talking Sales," where Sean O'Shaughnessey and Kevin Lawson discuss a single sales topic. Kevin and Sean together have about 60 years of experience in professional selling. This podcast helps people in sales, sales leadership, and business leadership or company owners realize the maximum value of their company by improving their revenue generation capability. This podcast is designed to help those people enhance their companies' sales management practices, methodologies, processes, teams, and messaging. Sean O'Shaughnessey and Kevin Lawson are Fractional Vice Presidents of Sales. They operate their own companies separately but have partnered for this podcast to advise salespeople and SMB companies on successful strategies and methodologies. Kevin is the CEO of Lighthouse Sales Advisors. Lighthouse Sales Advisors is a sales leadership solution provider for small businesses. Lighthouse helps business owners navigate the potential pitfalls around sales growth, sales turnaround, or scaling up by leveraging sales acumen and decades of experience to build effective sales teams. https://www.lighthousesalesadvisors.com/ Sean is the CEO of New Sales Expert. He helps company owners realize the maximum value of their company by improving their revenue generation capability. He helps owners enhance their sales management, methodologies, processes, teams, and messaging.2024 Economia Gestione e leadership Management
Episodi
  • Stop Automating Bad Sales: Use AI to Win More B2B Deals

    Stop Automating Bad Sales: Use AI to Win More B2B Deals
    Oct 13 2026
    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. Key Topics Discussed 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. 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. 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. 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. 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. Key Quotes Kevin Lawson (01:35): "This is you getting more out of your selling day by using AI as a tool, not as a silver bullet." Sean O'Shaughnessey (04:12): "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." Kevin Lawson (07:38): "This is effectiveness over efficiency." Sean O'Shaughnessey (11:26): "It's gonna be about how you are going to help your customer solve their problems." Kevin Lawson (13:29): "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." Additional Resources The following tools and information sources are discussed in the episode: ChatGPT, Claude, and Google Gemini: Generative AI platforms that can assist with customer research, document analysis, account planning, and personalized sales presentations. HubSpot, Zoho, and Pipedrive: CRM platforms discussed as examples of how AI can help salespeople analyze opportunities, identify qualification gaps, and improve sales processes. 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. A Significant Actionable Item from this Podcast Use AI to uncover five actionable insights about one important customer before your next sales conversation. 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. Use an appropriate AI tool to analyze the information and identify five insights that could influence the customer's ...
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    17 min
  • Your Sales Comp Plan May Be Killing Revenue Growth

    Your Sales Comp Plan May Be Killing Revenue Growth
    Oct 6 2026
    What happens when your best salesperson hits quota in October? A poorly designed compensation plan may quietly tell them to slow down. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey examine why sales compensation accelerators can be one of the most profitable tools available to a sales leader. They break down the economics behind above-quota sales, explain why fixed costs make incremental revenue especially valuable, and challenge the common fear that high-performing salespeople can somehow be "paid too much." For CEOs, CFOs, sales managers, and any VP of Sales preparing next year's compensation plan, this conversation connects sales management, revenue management, sales motivation, and business valuation in a very practical way. Key Topics Discussed Why Sales Compensation Plans Need Accelerators — 00:49 Sean opens the discussion with a simple problem: once a salesperson reaches quota, what reason have you given them to keep selling? A flat commission structure can unintentionally create a ceiling. Properly designed accelerators reverse that incentive, giving salespeople a financial reason to keep pushing beyond 100% rather than protecting deals for the next compensation period. Incentivize the Outcomes the Business Actually Needs — 03:08 Kevin argues that compensation should do more than reward revenue. It should reinforce the sales strategies that matter to the business. If existing customers will continue buying with relatively little selling effort, paying disproportionately for those transactions may not produce the growth the company needs. Sales processes and compensation design can deliberately incorporate net-new logos, incremental growth, renewals, or other strategic outcomes. Why Above-Quota Revenue Can Be Exceptionally Profitable — 05:24 Sean explains the financial logic behind accelerators. By the time the company reaches its planned revenue target, much of its fixed-cost structure—base salaries, benefits, rent, and other operating expenses—has already been covered. In businesses with low incremental delivery costs, additional revenue can therefore carry significantly higher margins. Paying a salesperson a higher commission rate on that additional business can still generate substantially more profit for the company. Using Compensation Tiers to Drive Sales Success — 07:08 Salespeople tend to be competitive and goal-oriented. Sean describes how graduated accelerators at levels such as 80%, 100%, 120%, and even 140% of quota give sellers another target to pursue. Instead of compensation becoming static once quota has been achieved, the plan creates another scoreboard. That makes the compensation plan part of the company's broader Sales Enablement system, not merely an accounting mechanism. Stop Worrying That Top Salespeople Are Making "Too Much" — 08:27 Kevin challenges one of the most persistent assumptions in sales management: that a high commission check means the company is overpaying the salesperson. If the compensation structure is properly modeled, exceptional variable compensation should indicate exceptional company performance. The more important questions are whether the seller is generating profitable revenue, whether the plan rewards the right behaviors, and whether the economics work for the business. Better Sales Systems Can Increase Enterprise Value — 10:14 Compensation design does not exist in isolation. Kevin connects the comp plan to the sales playbook, marketing, company objectives, customer acquisition costs, customer lifetime value, and the larger operating model. A more intentional and predictable selling system can create a more efficient company—and potentially a more valuable one. Key Quotes Kevin Lawson — 03:08 "Incentivize the outcomes you want." That may be the episode's central principle. Compensation is not simply how a company divides up the money after a sale. It is a management system that tells sellers which results matter most. Sean O'Shaughnessey — 07:08 "You can actually afford to pay more money on your variable compensation…because it's going straight to your bottom line." Sean's point reframes accelerators as an investment in profitable incremental revenue rather than simply an additional sales expense. Kevin Lawson — 04:43 "If there's no additional trophy case winnings for going over quota, they'll stop." The language is colorful, but the management lesson is serious: once the economic incentive disappears, leaders should not be surprised when discretionary selling effort disappears with it. Sean O'Shaughnessey — 07:30 "They want to achieve the next goal. They want to make the next score." An effective compensation plan gives high performers somewhere else to go after they reach quota. Additional Resources Sean references several pieces of research supporting the use of sales accelerators and the risks associated with flat commission structures: Do Bonuses Enhance Sales Productivity? A ...
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    16 min
  • Find Hidden Revenue in Existing Accounts: White-Space Analysis for B2B Sales

    Find Hidden Revenue in Existing Accounts: White-Space Analysis for B2B Sales
    Sep 29 2026
    Most sales organizations are surrounded by useful customer data, but too often, they only examine it after something goes wrong. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey explore a more proactive approach to B2B sales management: using white-space analysis, customer segmentation, executive relationships, and disciplined account reviews to uncover untapped revenue generation opportunities. From identifying products an existing customer should buy to building stronger connections across the buying committee, Kevin and Sean show how better business acumen and smarter sales processes can turn ordinary account management into a repeatable sales success strategy. They also discuss how AI and workflow automation can capture customer conversations, distribute action items, and help the entire company contribute to value selling. Key Topics Discussed Why Sales Leaders Need Data to Find Them — 00:00 A VP of Sales cannot possibly know every detail about every active account, customer, and opportunity. Kevin explains why effective sales management requires systems that surface meaningful insights rather than forcing leaders to continually hunt through spreadsheets, CRM records, and individual deals to discover what has changed. Using White-Space Analysis to Increase Wallet Share — 01:59 Kevin walks through a practical method for comparing the purchasing behavior of an ideal client against similar customers. If strong customers consistently allocate a predictable percentage of their purchases across several product lines, those patterns can expose missing revenue opportunities. The zeroes—and unusually small percentages—are often where the opportunity begins. Finding Revenue Beyond Your Core Offering — 04:06 White space does not have to mean simply selling more of the existing catalog. Kevin shares an example in which becoming proficient at sourcing difficult-to-find products helped a supplier become a vendor of choice. The customer reduced the complexity of managing multiple vendors, while the seller created additional revenue and potentially higher-margin business. Segmenting Customers and Creating an Executive QBR Strategy — 05:20 Sean recommends categorizing customers into A, B, and C groups based on their available revenue potential—not merely what they currently purchase. The largest and most strategic accounts should have relationships extending beyond the AE or account owner. CEOs and other executives should engage top-tier customers, while the VP of Sales and salespeople systematically build relationships with the next tiers. Turn Customer Reviews Into a Program, Then Use AI to Capture the Learning — 09:23 A customer review should not be an occasional sales tactic. Sean argues that it should become an institutional sales process, reviewed by executive leadership and supported across the company. Record the meetings, use AI to produce transcripts, extract action items, and route those insights to sales, marketing, supply chain, operations, or anyone else who can improve the customer relationship. This is workflow automation applied directly to sales enablement and customer retention. Map the Relationship White Space Inside Complex Accounts — 11:54 Product white space is only one dimension of account growth. Kevin recommends analyzing relationship white space as well: Who is above your current contact? Who reports to them? Who could be promoted, transferred, or become part of the future buying committee? In enterprise sales and other complex deals, understanding those relationships creates augmented sales intelligence that can protect an account and uncover additional opportunities. Key Quotes Kevin Lawson — 03:36 "Insights is what we're after here." That sentence captures the larger point of the episode. Data alone has limited value. Sales success comes from turning customer information into insight that changes the next conversation, next question, or next sales strategy. Sean O'Shaughnessey — 09:23 "This needs to be a program, not a project, not a one-off." Sean's distinction matters because customer intimacy cannot depend on individual initiative. QBRs, account development, relationship building, and follow-through need to become part of the operating rhythm of the company. Kevin Lawson — 11:54 "Do the white space analysis on what they're not buying." The most useful sales opportunities may already exist inside your customer base. Instead of immediately searching for another prospect, examine where existing customers are underpenetrated—and determine whether there is a legitimate value-based reason to expand the relationship. Additional Resources Ideal Client Profile Analysis — Use your strongest representative customer as a benchmark for understanding expected purchasing patterns across products, services, locations, units, or other meaningful customer dimensions. White-Space Analysis — Compare what customers currently ...
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    17 min
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