sales evolution

Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

By Sean O'Shaughnessey

Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it’s a wake-up call, a roadmap, and a motivational boost for anyone in the world of revenue generation, sales processes, and messaging strategy.

Whether you’re a frontline salesperson or a VP of sales leading a team, this conversation will inspire you to rethink how you work, what skills future-proof your career, and how AI can become your competitive advantage instead of your competitor.

Key Topics Discussed

The 4 Irreplaceable Skills That Safeguard Sales Careers (01:00)
Sean breaks down a framework for evaluating whether your job is AI-proof, hint: if you’re in B2B sales and good at it, you’re likely already building a durable edge.
How AI Mirrors the Arrival of the Internet in Sales Evolution (04:10)
Kevin draws a compelling parallel between today’s AI landscape and the early days of the internet, showing why this shift is just as transformative.
Sales Management and Strategic Value in an AI World (02:46 & 07:31)
From leadership and team building to messaging and workflow design, the episode highlights why sales managers need to think beyond quotas and towards long-term enablement.
A Personal Story of Old-School Sales and the Power of Adapting Tools (08:00)
Sean shares a nostalgic (and relevant) story about his father’s sales career before personal computers, offering perspective on how sales adapts across generations.
Weaponizing Your Time: Using AI to Amplify Human Strengths (13:00)
Kevin delivers a call to action on how to audit your own sales day and offload low-value tasks through automation, freeing up more time for high-impact strategy and consultation.

Key Quotes

“You won’t lose your job to AI, you’ll lose your job to a better salesperson who uses AI.”
– Sean O’Shaughnessey (01:02)
“If you’re not using AI, or any sales technology, you’re not doing your job. You’re underperforming.”
– Kevin Lawson (06:11)
“Sales worked before computers, and it will work after AI. What changes is how well you adapt the tools available.”
– Sean O’Shaughnessey (10:04)
“Your time is your greatest asset, and your biggest liability, when you’re not using it to its highest utility.”
– Kevin Lawson (14:00)

Additional Resources

Sean’s original blog post on this topic (available in the B2B Sales Lab and LinkedIn) https://newsales.expert/2025/06/b2b-sales-in-the-age-of-ai-why-top-salespeople-will-thrive-while-the-repetitive-roles-disappear/
B2B Sales Lab community discussion on sales evolution and AI https://b2b-sales-lab.com/
Tools mentioned: ChatGPT, Perplexity, Gemini (as starting points for AI integration)

A Significant Actionable Item from this Podcast

Audit your sales day for repeatable, low-value tasks that can be automated.
Pick one of them, like researching prospects, summarizing meeting notes, or drafting follow-ups, and replace it with an AI tool like ChatGPT or Perplexity. You’ll recover time, increase productivity, and move closer to building a modern, AI-augmented sales practice.

Final Summary

This episode of Two Tall Guys Talking Sales isn’t about fear, it’s about focus. Sales success today requires a sharp blend of strategic thinking, tool adoption, and human skills that are nearly impossible to replicate. Kevin and Sean lay out a blueprint that every sales leader, rep, and business owner should follow to thrive in this new era. If you’re serious about sales management, value selling, messaging clarity, and staying ahead of disruption, this episode will give you the mindset and tactical clarity to act now. Don’t just listen, level up.

Driving Sales Performance with Strategic Competitive Analysis

By Sean O'Shaughnessey

Ever wonder why some sales teams consistently outperform their competitors while others struggle to close deals? The answer often lies in how well they understand and leverage competitive analysis in their sales process.

Let’s talk about competitive analysis in sales. It’s not just about knowing your competition – it’s about understanding how to use that knowledge to drive results. You need to grasp why prospects choose specific solutions over others and, more importantly, why they sometimes choose to do nothing at all.

Have you considered how many deals you’ve lost not to competitors but to indecision? These “no decision” outcomes often stem from a fundamental gap in prospect qualification. Intelligent sales professionals dig deeper, asking targeted questions about organizational priorities, resource allocation, and strategic initiatives. They understand that timing can be just as crucial as the solution itself.

The modern sales landscape demands a sophisticated approach to competitive analysis. Your success hinges on aligning your organization’s strengths with your prospect’s needs. But here’s the real question: Do you truly understand what your ideal client values most?

Many sales professionals miss the mark by focusing solely on feature comparisons. While product capabilities matter, they’re just one piece of the puzzle. The real power lies in understanding how your solution addresses your prospect’s challenges. This requires a comprehensive view of your competitive landscape, including direct and indirect competitors.

Think about your last few lost deals. What patterns emerge when you analyze the feedback? Every objection and hesitation after presenting pricing are valuable data points that should shape your competitive strategy. Your sales conversations must reflect a deep understanding of your prospect’s value metrics.

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Mastering Sales in the Digital Age: A Case Study on Megan O’Hara

By Sean O'Shaughnessey

The sales landscape constantly evolves, and the tools and techniques used to reach potential clients are continually refined and reimagined. One such innovative approach to sales and marketing is pioneered by salespeople and sales managers leveraging technology to add value to their client relationships and boost their sales figures.

Megan O’Hara, an executive solution specialist in Columbus, Ohio, is at the forefront of this movement. She has developed a unique method of reaching out to clients that adds value to their lives, increases her customer access, and builds her credibility. This method is simple yet impactful: Megan sends a weekly tech tip in a short video format every Monday.

This approach is designed to keep her name at the top of her clients’ minds. In a world where attention spans are increasingly limited and competition for customer attention is fierce, being the first person a client thinks of when they need a product or service is vital. By sending out these tech tips, Megan is providing a valuable service to her clients and ensuring that she remains at the forefront of their minds.

The success of this approach is evident in the response Megan has received from her clients. Many have contacted her after receiving her tech tips, expressing appreciation for her added value to their lives and initiating further business conversations. This is a clear testament to the power of this approach in building strong client relationships and driving sales.

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