messaging

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 Three Pillars of Sales Success: Ideal Client Profiles, Effective Messaging, and Aspirational Offers

By Sean O'Shaughnessey

Let’s start this article with a rhetorical question to the sales professionals, sales managers, or CEOs: Have you ever found yourself guilty of sending messages to prospects without fully considering their specific needs or how your offer aligns with them?

If so, you’re not alone—this is a common pitfall in sales. The good news is, it’s entirely fixable by developing a straightforward, strategic approach.

An effective sales strategy hinges on three core components: defining your ideal client profile (ICP), crafting a resonant message, and presenting a compelling offer. These elements are interconnected. Mastering their alignment will significantly enhance your sales effectiveness.

Ideal Client Profile

Let’s start with the ideal client profile. How well do you know the companies you’re targeting? Identifying your ideal customer is foundational to your entire sales approach. It’s not enough to say that your market is “small businesses” or “tech companies.” Instead, think about your best clients—the ones you genuinely enjoy working with, who value your product, and who generate profitable, sustainable business. Think about companies that rarely devalue your product or service by asking for a discount. What do these clients have in common?

Now that you have your favorite customers from above, reflect on your top five or ten accounts. Are they in the same industry? Do they share similar challenges or company structures? Perhaps they all have common goals that your product consistently solves. Pinpoint these commonalities. This process will help you create a precise and actionable ideal client profile.

But don’t stop at company-level characteristics. Remember, even in B2B sales, you’re ultimately selling to individuals. Identify the specific roles or buyers within these organizations that are responsible for making buying decisions. Who are these decision-makers? What motivates them personally and professionally? Do they all have the same kind of college education? Do they all have similar career paths? Understanding the people behind the logo makes your outreach more personal, targeted, and effective.

What is your message?

Once you’ve developed a clear picture of your ideal client and the people within those companies, the next step is crafting a message that reflects your value-selling message. This message is how you communicate your value proposition—it’s the bridge between your product and your prospect’s needs. Too often, sales messaging falls flat because it focuses heavily on the seller rather than the buyer. Statements that emphasize “we,” “I,” or “our product” rarely resonate deeply. Instead, effective messaging highlights the customer’s perspective, clearly communicating the benefits they will experience.

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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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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.

Two Tall Guys Talking Sales – Prepping for Q2 – Getting Ahead, Catching Up, and Staying on Track – E129

By Sean O'Shaughnessey

As the first quarter comes to a close, sales leaders and professionals must assess their performance and gear up for the challenges and opportunities ahead in Q2. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the essential strategies for those ahead of the plan and those struggling to catch up. From refining your sales process to maximizing customer relationships, this discussion has insights to help you dominate your numbers in the coming months.

Key Topics Discussed:

The Reality of Q1 Performance and the Need for Urgency (00:00:31)
- Why waiting until Q2 to fix Q1 is too late, and how to position yourself for success early in the year.
Strategies for Those Ahead of Plan (00:01:00)
- How to maintain momentum, close key deals, and ensure a strong Q4 while staying ahead of quota.
Critical Steps for Those Behind on Quota (00:04:01)
- Conducting a win-loss analysis, diagnosing deal flow issues, and fine-tuning lead generation strategies.
The Importance of CRM Usage and Sales Efficiency (00:06:35)
- How sales leaders and reps can maximize their CRM to drive efficiency and uncover missed opportunities.
Pricing Strategies and Customer Engagement (00:09:13)
- Why now is the time to strengthen relationships with your top customers and confidently raise prices to improve margins?

Key Quotes:

Sean O’Shaughnessey (00:01:32): “You have a chance at greatness if you are even or ahead at the end of Q1. Now’s the time to double down and make sure you close deals that will set you up for an incredible year.”
Kevin Lawson (00:05:00): “Everyone has a leads problem. Either you don’t have enough, they’re not the right fit, or you’re not communicating your value effectively. That’s where the real focus should be.”
Sean O’Shaughnessey (00:11:00): “Your best customers likely don’t know you as well as you think. Strengthening those relationships can open up new revenue streams and prevent you from falling behind.”

A Significant Actionable Item from this Podcast:

Perform a rapid win-loss analysis on your Q1 deals. If you’re ahead, identify the behaviors and strategies that got you there and double down. If you’re behind, determine whether the issue is a lack of quality leads, poor messaging, or weak follow-through. Adjust your sales approach immediately so you can enter Q2 with a clear plan to recover lost ground.

Summary:

Whether you’re ahead of plan, right on track, or scrambling to catch up, the strategies discussed in this episode will help you refine your sales process and make Q2 a success. Sean and Kevin share actionable insights on deal flow, CRM optimization, pricing strategies, and customer engagement that will set you up for a strong year. Don’t let another quarter slip away—tune in now to get ahead, stay ahead, and finish the year on top!

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/

Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the art of sales prospecting using an unusual but powerful analogy—chasing butterflies versus building a garden. Are you tirelessly running after leads or cultivating an environment where ideal prospects naturally come to you? Learn how to create a long-term strategy for consistent revenue growth by positioning your business as the go-to solution for your ideal customers.

Key Topics Discussed:

The Butterfly Effect in Sales (00:01:00) – The difference between chasing every lead and strategically attracting the right ones.
Building a Sales Garden (00:02:49) – Developing a long-term strategy that consistently nurtures and attracts the best-fit prospects.
Marketing & Content Strategy Alignment (00:04:22) – Collaborating with marketing to ensure the right messaging.
The Value of Inbound Leads (00:06:11) – Why leads that come through your marketing efforts are often easier to close and more profitable.
Tactical Steps for Sales Leaders (00:08:00) – Actionable insights for sales managers to help their teams attract, engage, and convert better.
Crafting a Strong Value Proposition (00:10:18) – The foundation of effective lead generation and how to align it with your ideal customer profile.

Key Quotes:

Sean O’Shaughnessey (00:01:52): “If you’re hungry for revenue, you’re probably running around chasing butterflies. But if you want sustainable growth, you need to create an environment where prospects naturally come to you.”
Kevin Lawson (00:03:55): “Sales leaders, think about your team—have you equipped them with butterfly nets, or have you taught them how to build a garden?”
Sean O’Shaughnessey (00:06:44): “The best prospects aren’t the ones you chase—they’re the ones who find their way to your garden because you’ve built something valuable for them.”

Additional Resources:

Previous episodes featuring Amy Connor on inbound marketing and lead generation.
https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159
https://podcasts.apple.com/us/podcast/measuring-marketing-success-with-amy-connor-of-cmo-onloan/id1668686029?i=1000696058066
Join Sean for a Value Proposition Workshop and learn how to refine your messaging to attract the right clients. Contact Sean to schedule a session.

A Significant Actionable Item from this Podcast:

If you rely solely on outbound prospecting, evaluate your value proposition and content strategy today. Align your marketing and sales teams to ensure your messaging is clear, consistent, and tailored to your ideal buyer. Identify gaps in your digital presence and take the first step toward creating a sales garden that nurtures and attracts the right leads.

Final Thoughts:

Sales is more than just chasing down deals—it’s creating an ecosystem where prospects feel drawn to your expertise, insights, and solutions. In this episode, Sean and Kevin explain shifting from frantic outbound prospecting to a methodical approach that fosters sustainable revenue growth. Whether you’re a sales leader or an individual contributor, you’ll walk away with practical steps to build your high-converting sales garden.

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

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/

Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

By Sean O'Shaughnessey

Welcome back to another episode of Two Tall Guys Talking Sales with Kevin Lawson and Sean O’Shaughnessey! This week, we’re diving deep into measuring marketing effectiveness with special guest Amy Connor, founder of CMO OnLoan. If you’ve ever struggled to connect marketing strategies to real business results, this episode is for you. Grab your marketing colleague and tune in—understanding what’s working (and what’s not) in your marketing is the key to driving sales growth.

Key Topics Discussed:

The Importance of Measuring Marketing Performance (01:08)
Many companies don’t effectively track their marketing impact. Amy shares how focusing on key metrics—without overwhelming dashboards—can create a direct path to success.
Sales and Marketing Must Be Aligned (02:09)
Customers don’t see marketing and sales as separate—they see one company. Amy explains why integrating both functions is crucial for a seamless customer journey.
Why Vanity Metrics Don’t Matter (02:55)
Impressions, clicks, and leads may look impressive, but if they don’t translate to business results, they don’t matter. Learn how to focus on meaningful data that connects to revenue.
The Billboard Advertising Myth (03:12)
Can a billboard drive B2B sales? Amy and Sean discuss the realities of traditional advertising and why small businesses should think critically about marketing spend.
Aligning Sales Messaging with Marketing Content (05:57)
Sales teams shouldn’t be the only ones communicating key messages. Amy shares why marketing content must reinforce what salespeople say to build trust and shorten sales cycles.
Tactical vs. Strategic Marketing – What’s the Right Balance? (08:29)
Should your marketing focus on brand awareness or immediate sales action? Amy explains the difference and how to measure each effectively.

Key Quotes:

Amy Connor: “Marketing and sales are part of the customer’s journey in a united way. The customer doesn’t see ‘marketing did this and sales did that’—they see the company as a whole.” (01:45)

Sean O’Shaughnessey: “Salespeople start at a disadvantage because buyers inherently don’t trust them. That’s why marketing must reinforce their message to build credibility.” (05:40)

Kevin Lawson: “Up to 70% of the buyer’s journey happens before they talk to sales. If marketing isn’t working ahead of time, you’re already losing.” (07:52)

Additional Resources:

Visit CMO OnLoan for free marketing resources: www.cmo-onloan.com
Connect with Amy Connor on LinkedIn: Amy Connor LinkedIn
Listen to the first episode featuring Amy: Last Week’s Podcast: https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159

A Significant Actionable Item from this Podcast:

Audit Your Marketing Metrics
Take 30 minutes this week to assess what marketing data your company is tracking. Are you focusing on impressions and clicks or lead conversion and revenue impact? Identify one metric that directly connects marketing activity to business growth and make it your priority.

Why You Should Listen to This Episode

Marketing is more than just branding—it’s a revenue-driving function. In this conversation, Amy Connor unpacks how B2B companies can measure what truly matters, align sales and marketing, and ensure every dollar spent on marketing contributes to the bottom line. If you want your marketing efforts to drive real sales results, don’t miss this insightful discussion. Tune in now!

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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Unlocking Sales Success: The Power of KPIs in Sales Processes

By Sean O'Shaughnessey

Are your sales KPIs helping your team succeed? Many sales leaders focus solely on closed deals. This narrow view misses crucial elements of sustainable sales growth.

The journey matters more than the destination. Sales excellence follows a similar path. Your team’s daily actions and behaviors create the foundation for lasting success.

Effective sales measurement requires a comprehensive view of your team’s activities. Top performers consistently execute vital behaviors that drive results. They prospect strategically, nurture relationships, and expand their presence within existing accounts. These leading indicators paint a clearer picture of future performance than lagging metrics alone.

Your KPI framework must evolve beyond historical analysis. Forward-looking metrics help you spot opportunities and challenges before they impact revenue. What’s happening in your pipeline right now? How are your teams finding new prospects? Which accounts show growth potential?

Experience levels significantly impact appropriate performance measures. New salespeople face different challenges than seasoned veterans. A rookie might need help with fundamental sales behaviors while learning your company’s approach. They need clear operational guidance and structured metrics that reinforce proper execution.

Veteran salespeople bring established skills and proven track records. Their KPIs should emphasize continuous improvement and cultural alignment. How are they advancing their capabilities? What value do they add to the broader sales organization?

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