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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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Navigating the Sales Maze: Overcoming Missed Steps in Your Sales Process

By Sean O'Shaughnessey

The challenges for a salesperson or a sales manager are numerous. One such challenge that often arises during the sales process is the realization that a crucial step has been skipped. This situation is not uncommon and is faced by many salespeople. However, it’s not a moment for reprimanding or pulling out an accountability chart. Instead, it’s a moment of realization and an opportunity to rectify the error to avoid ending up in the ‘no decision lane.’

I have written about the importance of skipping stages of the sales process elsewhere on this site, most recently in “The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process,” where I remind you that, according to the Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth.

When you recognize you’ve missed a step in your sales process, it resembles backing up a train. You’ve got a lot of cars put together, but one is out on its own. Addressing this situation requires a specific style and approach. As a sales leader, your focus should be on the next step in the process. Have you covered this step from a question in the sales meeting? It’s important to ask questions like, “What is next? What is missing? What is now?”

As a salesperson, if you realize you’ve missed a step, address it head-on. This approach allows you to rectify your error and builds trust with your prospect by demonstrating transparency and accountability.

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Validation Events: The Unsung Hero of Sales Process Discipline

By Sean O'Shaughnessey

In the complex world of B2B selling, trust is built in stages. The challenge in all sales campaigns is ensuring the prospect trusts they are making the best decision for their business.

Do they trust that the salesperson is giving them all of the information?
Do they trust that the company will support them after the sale?
Do they trust that the product will perform as they expect it to perform?

As I have explained in my book, Eliminate Your Competition, as well as the blog for that book and in this blog, the prospect needs to trust all three elements the salesperson is selling:

They need to trust the product.
They need to trust the company behind the product.
They need to trust the salesperson.

Prospects listen to your sales message, review your materials, and hear your claims, but none of that guarantees belief or trust. Trust is validated when your claims are validated. That’s why validation events are crucial to any rigorous sales process.

In The Qualified Sales Leader, John McMahon stresses the importance of customer-driven validation. He cautions sales leaders against relying on internal optimism or anecdotal “good signals” from prospects. Instead, McMahon emphasizes observable proof—real buyer behavior that confirms alignment, commitment, and value. Validation events are when the customer takes action to validate that what you’ve promised is accurate and valuable.

An excellent sample sale process flow looks like this:

Discover
Scoping
Economic Buyer Meeting
Validation Event
Business Case and Final Proposal
Negotiate and Close

As you can see, the Validation Event is the last step before creating the final business case, which will be bundled with your final proposal.

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Stop Guessing. Start Assessing: The First Step Toward Sales Growth

By Sean O'Shaughnessey

Are you feeling stuck in your sales organization? You’re not alone. Many founders, CEOs, and sales leaders eventually hit an invisible wall—a growth plateau. Key deals slip away. Your top salesperson, who carries far too much weight, starts to burn out.

In these moments, the instinct is often to push harder. But what’s needed isn’t more hustle. It’s clarity. And clarity starts with a strategic sales assessment.

What a Sales Assessment Means

Too often, leaders see assessments as formalities—checklists that confirm what they already believe. That’s a mistake. An accurate sales assessment is diagnostic. It reveals what’s working, what’s broken, and what’s missing.

Revenue growth doesn’t always mean you’re on the right path. Many companies are growing despite misalignment, not because of strategic execution. Are your sales activities aligned with your market opportunity? Are you pursuing the right prospects with the right message? Or are you just getting lucky?

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Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

By Sean O'Shaughnessey

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

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Two Tall Guys Talking Sales – Know Your Numbers: A Sales Leader’s Guide to Growth Metrics – E132

By Sean O'Shaughnessey

As Q2 kicks into full gear, it’s time to pause and reflect—are you ahead, on pace, or falling behind on your sales targets? In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey unpack one of a sales leader’s most crucial yet often overlooked responsibilities: knowing your numbers. With equal parts practical advice and strategic vision, this conversation walks you through the foundational metrics every sales leader should track—customer acquisition cost, average transaction size, support staffing ratios, and more. Whether you’re forecasting growth, scaling headcount, or simply trying to stay ahead of the competition, this episode is your playbook for building a metrics-driven sales organization that thrives.

Key Topics Discussed

Why “Keeping Score” Matters in Sales Leadership (00:00)
Kevin kicks off the episode with a strong analogy to competitive sports, emphasizing that tracking performance metrics is non-negotiable for sales leaders aiming to grow.
Building a Forward-Looking Sales Metrics Matrix (00:01)
Kevin walks through how to build a simple but powerful matrix using transaction volume, average deal size, and headcount to visualize both current performance and future goals.
Calculating Average Transaction Size and Quota Coverage (00:02)
Learn how to reverse-engineer quota achievement by dividing sales goals by average transaction size to determine activity targets for your team.
Understanding Customer Acquisition Cost (CAC) (00:05)
Sean breaks down the components of CAC and explains why every sales leader must know this figure to scale sustainably and profitably.
Debunking the “Geopolitics Are Killing Sales” Excuse (00:09)
Sean challenges the notion that global events are valid reasons for missed quotas, reinforcing that internal execution and strategic clarity are what really matter.
Aligning Sales Activity with Strategic Growth Goals (00:12)
Kevin closes the episode with a systems-thinking approach to leadership, showing how small adjustments in metrics, team development, and compensation can drive exponential growth.

Key Quotes

Kevin Lawson: “Keeping score is important. Really important. I’m talking like March Madness. Final game. Important.” (00:00)

Sean O’Shaughnessey: “If it takes you more than 20 minutes to figure out this information, then you need a better bookkeeping system.” (00:06)

Sean O’Shaughnessey: “You need to know what your average deal size is. You need to know how long it takes you to get a customer. Your CRM should be solving that.” (00:07)

Kevin Lawson: “We want to gently steer our company towards our goals. So the thinking about this process is all about knowing your numbers.” (00:12)

A Significant Actionable Item from this Podcast

Build Your Sales Metrics Matrix This Week
Start with your annual revenue goal. Break it down by the number of salespeople, average transaction value, and number of transactions needed per rep per month. Then layer in your customer acquisition cost, support staffing ratios, and expected margin. This matrix becomes your roadmap for scaling intelligently—whether you’re doubling headcount, expanding territory, or just trying to hit a consistent quota.

Episode Summary

In a world of uncertainty, Two Tall Guys Talking Sales reminds us that clarity comes from data. Kevin and Sean deliver a compelling, no-nonsense discussion about how to take control of your revenue engine by genuinely understanding the math behind your sales motion. Whether you’re a CEO, VP of Sales, or just starting to lead a team, this episode offers an essential primer on aligning your operations to your goals. Don’t miss this one—it might be the wake-up call your spreadsheet has been waiting for.

👉 Hit play now to future-proof your sales strategy by learning how to know your numbers like a pro.

Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

By Sean O'Shaughnessey

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or a sales executive interested in how sales performance impacts company valuation, this episode delivers invaluable guidance. It’s part education, part strategy session, and all high-value insight.

Key Topics Discussed

The Three Core Approaches to Business Valuation – Asset, income, and comparative market methods explained simply and practically. (04:22)
Preparing a Business for Sale: Lessons from Real Estate – Why “curb appeal” matters for companies and how to improve it over time. (07:36)
What Buyers Want: Sales Growth, Consistency, and Processes – How prospective buyers assess the health of a business beyond profit margins. (09:00)
The Hidden Red Flag: When the Owner Is the Only Salesperson – Risks for buyers and strategies for mitigating dependency on the founder. (13:31)
Leveraging AI to Gain Competitive Market Intelligence – How technology is transforming buyer and seller knowledge in M&A. (11:32)

Key Quotes

Tom Gottlieb: “Every buyer wants the same thing: a business that works without the owner. That means strong processes, steady sales growth, and predictable profitability.” (09:01)
Sean O’Shaughnessey: “So if you don’t want to stick around after the sale, then train your sales team now—and watch the value of your company go up.” (14:16)
Kevin Lawson: “Tom, every time we talk, I walk away with something new. This episode is no exception.” (11:31)
Tom Gottlieb: “Buyers rarely show up with a bag of cash. There’s a timeline. A deal doesn’t close in a weekend—it’s often a year-long journey.” (07:00)

Additional Resources

Connect with Tom Gottlieb on LinkedIn
Tom’s Email: tgottlieb@bhhspro.com
Direct Contact: (562) 225-4567
Berkshire Hathaway HomeServices Professional Realty – Business Brokerage Services

A Significant Actionable Item from this Podcast

Start documenting your sales process today.
If you are a business owner—or advise one—and the majority of revenue hinges on a single salesperson (often the owner themselves), that’s a red flag for any future buyer. Begin formalizing your sales process, distribute responsibilities among team members, and track sales metrics consistently. This improves operational resilience and significantly enhances company value in a potential sale.

Why You Should Listen to This Episode

Selling a business isn’t just about profit, perception, process, and preparedness. In this episode, Kevin and Sean extract wisdom from Tom Gottlieb that applies to any B2B organization considering an exit in the next 3 to 10 years. It’s packed with strategic takeaways, sales insights, and behind-the-scenes truths about what makes a business attractive to buyers. Whether you’re a founder, an investor, or a sales leader, this episode will reshape how you think about long-term value creation. Tune in and learn how to make your business sell-ready—starting now.

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

How to Create an Elevator Pitch That Opens Doors

By Sean O'Shaughnessey

Seize the Moment—Even If It’s Only 30 Seconds

You’re at a networking event. Or in line at the airport. Or maybe, quite literally, in an elevator. Someone turns to you and asks, “So, what do you do?”

That question—simple as it is—can be the beginning of a great opportunity… or a missed one.

As a small company fighting for attention in a crowded market, you don’t have the luxury of wasting that moment. You need a clear, concise, and compelling elevator pitch to earn a second conversation.

The Purpose of an Elevator Pitch

Your elevator pitch—or Unique Selling Proposition (USP)—is your verbal business card. It should quickly communicate what you do in a way that intrigues the listener and invites them to want more.

Your goal isn’t to close a deal on the spot. It’s to spark curiosity. It’s to turn a casual chat into a qualified lead.

The Anatomy of an Effective Elevator Pitch

Let’s break down what makes a pitch effective—and memorable.

1. Start with a Clear, Impactful Statement

Skip the jargon. Skip your job title. Lead with value.

“I help company owners dramatically increase the market value of their company.”

That kind of opener gets attention. It invites the natural question: “How do you do that?”

2. Avoid the “AND” Trap

Trying to cram too much into your pitch dilutes your message. Avoid saying, “We do this AND that AND also this.”
Instead, focus on one powerful value proposition. If you confuse your listener, you’ll lose them.

3. Know Your Audience

Adapt your pitch to fit the moment and the person. You wouldn’t speak to a private equity investor the same way you would to a small business owner. Tailor your language, examples, and tone to resonate with the listener.

Use a Mini Case Study with the PONI Method

If you have 10 more seconds of their attention, use it to share a brief, compelling client success story using the PONI method:

Project: What challenge did your client face or what were they trying to accomplish?
Old: How did they do that before?
New: What did you provide that changed things?
Impact: What was the measurable result?

“One of my clients leveraged increased revenue to grow their company’s market value by 167% in just 10 months.”

That’s the kind of story that gets remembered.

Don’t Forget the Ask

Close by inviting the next step:

“I’d love to share how we did it—can we schedule a follow-up conversation?”

That one line can turn a random encounter into a real opportunity.

Watch the Video

To see these concepts in action and learn how to craft your own elevator pitch, watch this short, practical video:

Want Help Refining Your Elevator Pitch?

If you’re ready to sharpen your messaging and make every introduction count, I’m happy to help.
Email me at Sean at NewSales dot Expert or send me a message here.

Let’s turn your next chance meeting into a business breakthrough.

Becoming a Trusted Advisor: Solve Problems, Not Just Sell Products

By Sean O'Shaughnessey

In B2B sales and sales leadership, problem-solving is an art that goes beyond selling a product or service. The secret to becoming a trusted advisor is addressing business problems, not just selling a product. This concept resonates with salespeople, sales managers, and small business CEOs who sell themselves or manage a team of salespeople.

Sales is not just about pushing a product or closing a deal; it’s about forging relationships, understanding businesses and their unique challenges, and offering solutions to these problems. The role of a trusted advisor is not to sell a product and become a trusted advisor, but rather to become a trusted advisor who can sell a product.

The reward for earning trusted advisor status is immeasurable. It is fantastic to receive a call from a client asking for advice on solving problems they have never discussed with you. Imagine having relationships that stand the test of time and outlast competition and challenges.

So, how does one become a trusted advisor and solve problems for clients rather than just selling them a great product? It starts with building a relationship from scratch. When starting with a prospect list or an ideal client profile, the goal is not to find anyone who will respond but to seek opportunities to build meaningful relationships.

The cornerstone of these relationships is reliability.

Are you always punctual?
Do you cancel at the last minute?
Do you forget to return phone calls?

These behaviors erode trust. On the other hand, showing up when needed, providing solutions even when they are not directly related to your product or service, and connecting clients to others who can help them are behaviors that build trust.

Becoming a trusted advisor also involves understanding and curiosity about the client’s business. Do you ask questions about how the prospective company makes and loses money, how it dealt with past challenges like the pandemic, and how it deals with current challenges like rising inflation or supply chain disruption? The aim is to understand the client’s business, challenges, and competitors and offer insights and parallels to other companies.

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Two Tall Guys Talking Sales – From Regular Season to Postseason: Coaching Your Sales Team to Win – E128

By Sean O'Shaughnessey

As a sales leader, are you coaching your team for the long haul, or are you scrambling in the final weeks of the quarter? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the difference between regular season and postseason play—whether in sports or sales. They explore why last-minute Hail Mary strategies can be damaging, how to manage time, and the importance of effective and consistent coaching. With March Madness and The Masters as the backdrop, this conversation is packed with insights to help you refine your sales approach and ensure your team is always in winning form.

Key Topics Discussed

The Sales Tournament Mentality (00:02:00) – What sales teams can learn from March Madness and The Masters, and why only one team wins while the rest lose.
Building a Winning Sales Team (00:03:30) – How business owners can prepare their sales teams to perform under pressure by ensuring the right people are in the right seats.
The Role of Sales Coaching (00:05:00) – Why sales leaders must incorporate skills development into every sales meeting instead of just reviewing the pipeline.
The Pitfalls of End-of-Quarter Desperation (00:07:50) – How last-minute discounting and rushed deals create long-term problems and train customers to buy at a discount.
Mastering Time Management in Sales (00:10:00) – How prioritization and disciplined execution throughout the quarter prevent last-minute chaos and boost consistent performance.

Key Quotes

Kevin Lawson (00:07:53): “If you’re behind in sales right now, don’t throw Hail Marys. Don’t discount. You’re teaching your prospects to wait until the end of the quarter for a better deal—and that’s a losing game.”
Sean O’Shaughnessey (00:13:00): “You have one thing in sales you can never get back: time. If you wasted today, it’s gone forever. You can’t go back and fix it.”
Kevin Lawson (00:09:00): “Salespeople with commission breath stink. If your only focus is closing the deal before Friday, your prospects will smell it a mile away—and that’s not how you build relationships.”

A Significant Actionable Item from this Podcast

Develop a Five-Week Sales Training Plan – Sales leaders should map out the next five sales meetings, dedicating at least five minutes to skills development in each session. Focus on topics such as pipeline progression, prospect qualification, and closing techniques. Training should not be an afterthought—it should be a fundamental part of your sales strategy.

Why You Should Listen to This Episode

Whether you’re a sales leader or a frontline salesperson, this episode is your playbook for maintaining momentum all year long. Avoid the common traps of end-of-quarter desperation, build a disciplined approach to sales training, and master the art of time management. Just like in sports, sales success isn’t about last-minute heroics—it’s about consistent execution.

Tune in now and take your sales game to the next level!