productivity

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

By Sean O'Shaughnessey

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

Hard-to-automate skills
Deployment-related skills
Scarce, high-utility skills
Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

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The Power of Personal Branding in Enhancing Sales Productivity

By Sean O'Shaughnessey

Navigating the world of sales can sometimes feel like traversing a labyrinth. Salespeople, sales managers, and CEOs alike grapple with the challenge of increasing revenue and enhancing productivity in their sales processes. To be successful, you need more than knowledge of products and services; you need to develop trust and a strong personal brand.

Business-to-business (B2B) sales involves transferring trust from ourselves to our prospects. We trust in our products and company, but convincing prospects to share that trust is the real challenge. This trust should encompass the product, the company, and perhaps most crucially, the salesperson. Remember, B2B sales could be defined as helping prospects decide in our favor within the desired timeframe.

The key to B2B sales is developing a personal brand that inspires trust in salespeople. The salesperson’s ability to convey reliability, expertise, and credibility can significantly influence how fast a prospect invests in a product or service.

Developing a strong personal brand begins with creating a presence that signals control and understanding of the business. This can be achieved by showcasing the benefits of your product or service to your customer’s business. A straightforward way to build your brand is by seeking references from your network, former employers, and customers, and showcasing these on professional platforms like LinkedIn.

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Two Tall Guys Talking Sales – AI for Sales Success: Tools, Tactics, and Why You Can’t Ignore It – E124

By Sean O'Shaughnessey

Artificial intelligence (AI) is transforming the sales industry, but does that mean salespeople are becoming obsolete? Absolutely not! In this high-energy episode, Kevin and Sean debunk the myth that AI will replace sales professionals. Instead, they reveal how AI can be a game-changing tool for sales success.

From using AI to refine communication to automating time-consuming tasks, this episode is packed with insights on how AI can help sales leaders and reps work smarter, sell better, and stay ahead of the competition. Tune in to discover practical ways to leverage AI, improve efficiency, and dominate your market.

Key Topics Discussed

🔹 Will AI Replace Salespeople? – The truth about AI’s role in sales and why your job isn’t at risk—but your quota might be. (00:00:45)

🔹 The Evolution of Sales Tools – A nostalgic (and hilarious) look at how tools have always changed work processes—remember manual garage doors and TV dials? (00:02:21)

🔹 AI for Writing & Communication – How tools like Grammarly can make your emails, proposals, and presentations sharper, clearer, and more professional. (00:04:00)

🔹 Boosting Productivity with AI – From auto-generating customized sales presentations to intelligent scheduling, AI can free up time for what matters most: selling. (00:06:01)

🔹 The AI-Powered CRM – If your CRM doesn’t have AI integration or a plan for it, it’s time to rethink your strategy. A modern CRM is essential for competitive sales teams. (00:12:00)

Key Quotes

🗣️ Sean O’Shaughnessey: “You are not going to be replaced by AI. You’re going to be replaced by a salesperson using AI.” (00:01:00)

🗣️ Kevin Lawson: “AI isn’t here to take your job—it’s here to make you a better salesperson. Weaponize your tools and sharpen your axe.” (00:07:33)

🗣️ Sean O’Shaughnessey: “Being afraid of AI is like being afraid of Microsoft Word instead of a typewriter.” (00:10:18)

Additional Resources

🔗 Grammarly – AI-powered writing assistant for better emails, proposals, and reports.

🔗 Canva – AI-enhanced design tool for creating presentations and marketing materials in seconds.

A Significant Actionable Item from this Podcast

🚀 Start Using AI Today! Don’t wait—integrate AI into your daily sales routine now. Whether it’s improving your writing with Grammarly, using AI for scheduling, or leveraging AI-powered CRM features, pick one AI tool and start experimenting. The sooner you adopt AI, the further ahead you’ll be.

Final Thoughts

AI isn’t a threat—it’s an opportunity. The best salespeople will be the ones who embrace AI to work smarter, sell more efficiently, and build stronger customer relationships. Want to future-proof your sales career? It starts here.

👉 Hit play now and learn how AI can be your competitive advantage in sales!

Two Tall Guys Talking Sales – Future-Proofing Your Sales with the Right Tech Stack – E115

By Sean O'Shaughnessey

In this thought-provoking episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive into the transformative power of technology in sales and operations. From the essentials of adopting a CRM to leveraging AI and automation, Kevin and Sean discuss how modern businesses can streamline operations, boost productivity, and prepare for the future. Whether you’re managing a small team or a large enterprise, this episode will provide actionable insights into creating an integrated tech stack that supports growth and resilience.

Key Topics Discussed

The Importance of a CRM System (Approx. 00:01:00)
- Why every organization needs a CRM to centralize and share data across teams, from sales to manufacturing.
- How a CRM can prevent revenue loss during sales team transitions.
Building an Integrated Tech Stack (Approx. 00:03:00)
- Understanding the interconnectedness of CRM, ERP, and project management tools.
- Simplifying operations with modern, cloud-based solutions.
Preparing for the AI Revolution (Approx. 00:04:00)
- How AI and machine learning are redefining operational workflows.
- Why having an AI strategy is essential for staying competitive.
Forecasting and Automation (Approx. 00:09:00)
- Leveraging technology to improve forecasting, pipeline management, and resource allocation.
- Automating routine tasks for efficiency and scalability.
The Role of Sales and Marketing Alignment (Approx. 00:11:00)
- Why sales and marketing collaboration is critical for success.
- How technology bridges the gap between these teams.

Key Quotes

Sean O’Shaughnessey:
“Your journey to 2035 starts right now. By staying on outdated tools, you’re not just behind—you’re making it harder to catch up later.” (Approx. 00:06:06)
Kevin Lawson:
“Technology is now part of the fabric of how we do business. If you want to grow and scale—or even just survive—adopting the right tools is the right battle to fight.” (Approx. 00:02:34)
Sean O’Shaughnessey:
“Revenue solves all problems in companies, but only if your systems are set up to support it.” (Approx. 00:12:23)

Additional Resources

McKinsey Report on AI in Business: September 2024 Edition.
HubSpot Marketplace: Tools to integrate CRM with calling apps and social media management platforms.
Ninety.io: Software for tracking KPIs and achieving quarterly goals.

A Significant Actionable Item from this Podcast

Start with Your CRM:
Evaluate your current CRM system (or lack thereof) and its integration with other business tools. Focus on centralizing data and enabling seamless communication between teams. This single step can drastically improve productivity, forecasting accuracy, and cross-functional collaboration.

Why You Should Listen

This episode of Two Tall Guys Talking Sales is a must-listen for anyone looking to future-proof their business. Kevin and Sean offer practical advice and actionable strategies to help you streamline operations, adopt cutting-edge technologies, and align your team for success. Whether you’re planning for 2025 or 2035, the insights shared in this episode will set you on the path to achieving your goals.

Tune in and discover how to take your sales operations to the next level!

From Micro-Manager to Leader: Fostering Growth in Your Sales Team

By Sean O'Shaughnessey

Are you unknowingly sabotaging your sales team’s success? The answer might surprise you. The actual cost of micromanagement extends far beyond immediate productivity concerns.

Trust forms the bedrock of every high-performing sales organization. Yet many sales leaders unconsciously undermine this foundation through micromanagement. You’ve seen the signs – constant check-ins, questioning every decision, and hovering over your team’s shoulders. The culture you’ve worked so hard to build is slowly eroding.

Your best salespeople are leaving. Team morale is plummeting.

Let’s be clear about what constitutes micromanagement in sales. It’s not about being involved or interested in your team’s work. The real issue emerges when you start dictating every move and creating an atmosphere of constant surveillance.

Consider the cost of replacing top sales talent in today’s market. Beyond the substantial financial investment, you’re losing institutional knowledge and client relationships. Your organization can’t afford this drain on resources, and the impact reverberates throughout your entire sales ecosystem.

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Roadblocks, Detours, and Destinations: The Intricate Art of Sales Strategy

By Sean O'Shaughnessey

There’s an ongoing conversation about the importance of strategy, process, and anticipating potential challenges in B2B sales. There’s an analogy that encapsulates this perfectly – imagine you’re on a road trip. You have a destination in mind but are unfamiliar with the route. This is where tools like Waze, Google Maps, or Apple Maps come into play. They direct you to your destination and alert you about potential roadblocks, construction, traffic, or other unexpected events that might delay your journey.

This is precisely how a sales strategy should work. It’s not just about getting from point A to point B but also about understanding the complexities of the journey and preparing for potential roadblocks. For salespeople, managers, and CEOs, understanding the strategy is critical to increasing revenue and improving productivity.

Understanding that a strategy involves more than just the turns along the way is vital. It also involves how to navigate through different areas, understand the speed limit, and anticipate any warnings that might come up. Many salespeople don’t fully grasp these challenges and tend to take them as they come rather than anticipating them and planning accordingly.

Like Waze uses real-time data to adapt to changes on the road, a sales strategy should adjust to new information and circumstances. For example, if there’s construction up ahead or a detour is required, Waze will adapt and provide a new route. Similarly, salespeople should be able to adjust their strategies based on new information or unexpected challenges.

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From Chaos to Order: Improve Your Sales Productivity with Effective Pipeline Management

By Sean O'Shaughnessey

Sales is a complex and intricate world, a jigsaw puzzle where each piece must fit perfectly to create a successful picture. This is especially true when it comes to managing sales, whether you’re a salesperson, a sales manager hoping to enhance your leadership skills, or a CEO in the trenches of a small company. Understanding the challenges and nuances of the sales process is crucial to increasing revenue and productivity.

Imagine you’re in a room full of sports equipment scattered everywhere, from basketball shoes to cheerleading pom-poms. It’s a total mess, and you can barely see the floor. This is a perfect metaphor for what a disorganized sales pipeline can look like. It’s messy chaotic, and there’s always something that doesn’t quite smell right.

The sales pipeline is vital for tracking and managing sales prospects from the initial contact to the deal’s closing. It visually represents where potential customers are in the sales process. However, if not properly managed, the pipeline can become a mess.

A common issue is when a deal gets pushed from one month to the next. The sales rep simply changes the closing date, making it seem like procrastination has become a part of the process. This can be due to various reasons, such as a lack of commitment from the customer, the sales rep not understanding the customer’s needs, or simply a lack of follow-up. To avoid this, it’s essential to go back to basics. Understand where the customer is in their evaluation and buying process. Are they genuinely interested in buying or just exploring the idea? It’s perfectly fine for a customer to be in the exploratory stage, but that doesn’t mean they’re ready to buy. These customers should be considered early-stage prospects and not be rushed into buying.

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Differentiating in the Sales Process: The Key to Boosting Bottom Line

By Sean O'Shaughnessey

The roles of salespeople, sales managers, and small business CEOs are ever-evolving. A common problem faced is increasing revenue and productivity in sales processes. This goal is common for all, from individual salespeople striving to provide for their families to CEOs seeking to boost their company’s bottom line. The key to achieving this lies in understanding the dynamic nature of the sales environment and leveraging it effectively.

A significant part of the sales process revolves around the buyer’s perception of a product or service as a commodity. This misclassification is usually caused by insufficient differentiation in the early stages of the sales process. Differentiation is crucial in any sales process, regardless of the industry or scenario. Creating enough differentiation can be the difference between closing a deal at a discounted rate or the desired price.

Salespeople are experts in their field, whether selling a unique product specific to their company or a common commodity. They typically have a deeper understanding of what they are selling than their prospects have about what they are buying. This expertise should be leveraged to guide prospects through the buying process, adding value to the relationship and making the salesperson indispensable. This approach can reduce the emphasis on price and increase the potential for higher earnings.

Every business has unique values that differentiate it from its competitors. These unique values could be anything from their mission, vision, and values to their market commitment and guarantee. This is commonly called a Unique Value Proposition (UVP) or a Unique Sales Proposition (USP). While a UVP and a USP are similar, there is a slight difference in that the former is typically created by the Marketing department (or sometimes with the help of a business adviser such as an EOS implementer. The latter is directly targeted at salespeople and what a salesperson should say to their prospects and customers. Salespeople should understand what makes them different and communicate this effectively to their prospects. The ability to create separation and differentiate oneself is why people pay for a product or service.

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Navigating Through Sales Slumps: A Strategic Approach for Sales Leaders

By Sean O'Shaughnessey

Like any other profession, sales is not immune to periods of underperformance or slumps. These periods can be particularly challenging when a top performer in your sales team is slumping. Addressing this issue effectively can significantly improve the productivity of your sales processes, ultimately leading to increased revenue for your company.

Various factors can trigger a sales slump, but it often implies a deviation from the sales process or strategy. Sales is a time-based process, not a transactional one. It involves selling to other businesses, which takes time. Therefore, as a sales leader or CEO, it’s crucial to identify when the sales trend starts to slide. This identification is not just about revenue; it requires a retrospective look at the early stages of a sale. If there aren’t enough leads or active relationships in your pipeline, you can foresee a slump and take proactive measures to change outcomes.

A common mistake is focusing on the revenue loss resulting from the effort expended. A more constructive approach is to evaluate the salesperson’s activities in the sales process. If they do the right things daily, they will quickly work out of the slump. The focus should be on maintaining an effective pipeline and executing all the necessary tasks, such as good scoping and discovery calls.

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Transform Your Sales Strategy with the Three-Legged Stool Approach: Resonate, Differentiate, Substantiate

By Sean O'Shaughnessey

Business-to-business (B2B) sales is more than selling a product or service. It involves a strategic approach that includes understanding the customer’s needs, differentiating your offering, and building trust. This strategic approach is often called the three-legged stool of sales: Resonate, Differentiate, and Substantiate.

Resonating with customers is the first step (leg) in the sales process. It involves answering the questions “Why should the customer act?” and “Why should they act now?” To resonate with customers, you must understand their goals and how your product or service can meet them. This requires careful listening, understanding, and empathy.

The second leg of the stool is differentiation. This answers the question, “Why choose us?” Differentiation is all about highlighting what makes your product or service unique from the competition. This could be anything from superior quality and innovative features to excellent customer service. It’s crucial to communicate this differentiation clearly and effectively to the customer.

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