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

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:

  1. Hard-to-automate skills
  2. Deployment-related skills
  3. Scarce, high-utility skills
  4. Skills hard for others to learn or replicate

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

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

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

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

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.

Level Up Your Sales Prospecting with Advanced Research Techniques

Level Up Your Sales Prospecting with Advanced Research Techniques

By Sean O'Shaughnessey

A shoutout to Chris Spanier and Episode #85 of the Practical, Actionable Marketing Podcast

Sales prospecting has always been a grind. What if you could cut your research time in half and dramatically improve your outreach results?

In Episode #85 of the Practical, Actionable Marketing podcast, host Chris Spanier delivers a masterclass on how to do just that. Titled “Advanced Prospecting Research Tools,” the episode is packed with time-saving techniques and tools that help sales professionals build sharper prospect profiles faster.

As someone with over four decades in sales and sales management, I believe this kind of tactical insight makes a difference. If you haven’t already, listen to the episode. Then, come back here for a quick breakdown of what Chris covered—plus a few of my thoughts.

Why Prospect Research Matters More Than Ever

In a market saturated with sales messages, relevance is your only competitive advantage. The days of blasting generic emails to massive lists are over. Today, the winners are the ones who personalize their outreach with precision—and that begins with better research.

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

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

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/

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

By Sean O'Shaughnessey

Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.

In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.

Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.

Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.

Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.

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Two Tall Guys Talking Sales – Fixing the Funnel – Building a Sales Pipeline That Actually Works – E130

Two Tall Guys Talking Sales – Fixing the Funnel – Building a Sales Pipeline That Actually Works – E130

By Sean O'Shaughnessey

Welcome back to Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey. In this episode, the tall guys dive deep into one of the most critical yet commonly broken elements in any sales organization: the sales funnel. Whether you’re stuck with a clunky three-stage process that tells you nothing or overwhelmed with 35 micro-stages that only confuse your reps, Sean and Kevin offer a practical guide to rethinking and rebuilding your pipeline strategy. Packed with metaphors (yes, even superhero ones) and sharp analysis, this episode will leave you inspired to take a hard look at your funnel—and finally fix it.


Key Topics Discussed

  • Why Most Sales Funnels Are Broken (00:00:45)
    Sean unpacks the common pitfalls in how companies define and manage their sales stages, including oversimplified or overly complex CRM setups.
  • Defining Sales Stages Based on the Buyer Journey (00:04:30)
    Kevin emphasizes the need to align your sales stages with how buyers actually buy—not how your company wants to sell.
  • How Many Sales Stages Are Too Many? (00:05:00)
    The guys explore the delicate balance between not enough insight and too much complexity in stage design.
  • The Case for Multiple Pipelines (00:08:00)
    When does it make sense to separate budgetary planning pipelines from active sales discussions? Kevin and Sean explain.
  • What a Healthy Funnel Actually Looks Like (00:10:45)
    Sean introduces a visual and mathematical approach to evaluating whether your funnel is properly shaped—and what to do if it’s not.


Key Quotes

“The Avengers became a team, not just Iron Man. You need to have a team. Even superhero salespeople like to have support.”
— Sean O’Shaughnessey (00:02:50)

“Fixing the funnel starts visually. Does it fit well on one sheet of paper? If not, you’ve already lost the battle for clarity.”
— Kevin Lawson (00:04:45)

“Stages should be built to qualify someone into the next step—not just to log an activity. Every transition should represent progress, not busyness.”
— Kevin Lawson (00:06:15)

“If your pipeline doesn’t look like a funnel, then you’re either wasting time or losing deals. Probably both.”
— Sean O’Shaughnessey (00:12:20)

Additional Resources Referenced

A Significant Actionable Item from this Podcast

Audit Your Sales Funnel for Shape and Stage Effectiveness
Pull a report from your CRM and visualize your current pipeline by number of deals and total revenue per stage. Does it actually look like a funnel? If it doesn’t, dig deeper. Are your stages aligned with your buyer’s journey? Are reps stuck in certain stages too long? This snapshot identifies gaps and opportunities for stage redefinition or activity refinement.

Summary

Whether managing a sales team or closing deals yourself, this episode of Two Tall Guys Talking Sales gives you the blueprint to diagnose and repair a misaligned funnel. Sean and Kevin combine humor, hard truths, and highly actionable insights to help you bring structure and sanity back to your sales process. If you’re ready to create a pipeline that reflects how buyers buy—and helps your team win more deals—this episode is a must-listen.

🎧 Listen now and take the first step in fixing your funnel for good.

How to Create an Elevator Pitch That Opens Doors

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

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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