sales manager – Page 2

Two Tall Guys Talking Sales – Managing the Maverick: How to Lead Top Sales Performers Without Breaking Team Culture – Episode 146

By Sean O'Shaughnessey

When a top-performing salesperson refuses to follow the rules, tensions flare, and your culture might suffer. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey tackle a question straight from their B2B Sales Lab community: What do you do with a sales rockstar who drives the rest of the team nuts? If you’ve ever struggled with managing high-output, low-alignment team members, this conversation is packed with valuable insights, practical strategies, and real-world advice to help you strike a balance between performance and healthy team dynamics. Tune in for battle-tested tips on sales management, building a high-integrity sales culture, and protecting your company’s long-term revenue generation strategy.

Key Topics Discussed

Establishing Clear Norms in Sales Teams – Why your “top dog” needs to play by the same rules as everyone else, and how undefined expectations damage sales processes (Approx. 02:00)
The Power of Documented Standards and Culture Alignment – How lack of structure in small businesses creates room for chaos—and what to do about it (Approx. 03:30)
Tactical Solutions for Managing Lone Wolves – Real examples of how to realign high performers through mentorship and responsibility (Approx. 09:00)
Creating a Unified Sales Culture Without Crushing Performance – Why culture eats strategy for breakfast, especially in sales teams (Approx. 04:30)
Using Silence, Expectations, and Consistency to Set Boundaries – Kevin shares how saying “no” and standing firm protects team cohesion and customer relationships (Approx. 12:00)

Key Quotes

“Culture is probably the most important thing you possibly can have—and it starts with setting clear expectations.”
— Sean O’Shaughnessey (Approx. 06:05)
“Sales culture will eat strategy for breakfast. Culture always wins in the long run.”
— Kevin Lawson (Approx. 04:39)
“Sometimes you have to accept a little current pain to create future gain for your entire organization.”
— Kevin Lawson (Approx. 13:00)
“If you’re the person who colors outside the lines and won’t adjust… maybe you just don’t belong here.”
— Sean O’Shaughnessey (Approx. 08:30)

Additional Resources

Learn more about the B2B Sales Lab community: https://b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Assign a High-Performer as a Mentor to Drive Culture Alignment
If you’re dealing with a rule-breaking top performer, try this: assign them as a mentor to a junior rep. This strategic move puts them in a leadership position where they must model the very behavior they’ve been resisting, updating the CRM, following your sales strategies, and representing your company messaging. This peer responsibility often encourages cultural realignment without confrontation.

Why You Should Listen to This Episode

This episode is a must-listen for sales managers, business owners, and team leaders wrestling with the dilemma of performance vs. process. Sean and Kevin don’t just talk theory—they give real, implementable strategies that can help you protect your sales culture, enforce consistent sales management practices, and drive long-term revenue success. If you’re aiming for scalable growth without sacrificing team cohesion, this episode delivers practical wisdom and a few gut-check moments. Hit play and discover how to bring even the most independent salespeople back into the fold—without losing their fire.

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

By Sean O'Shaughnessey

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

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

Key Topics Discussed

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

Key Quotes

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

Additional Resources

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

A Significant Actionable Item from this Podcast

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

Final Summary

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

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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Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

By Sean O'Shaughnessey

When sales professionals hit a roadblock, where do they turn? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey unveil an exciting new initiative: B2B Sales Lab, a private peer networking community designed to support salespeople, sales managers, and business owners in their journey toward revenue generation excellence. This isn’t just a conversation; rather, we are offering an invitation to join something powerful. If you’ve ever felt alone in a tough sales challenge or wished for experienced advice on your messaging, sales processes, or strategy, this episode is for you.

Key Topics Discussed

(00:00) Why selling isn’t easy and how sales professionals can benefit from a support network
(00:39) The creation and mission of the B2B Sales Lab community
(01:42) How the platform fosters peer-to-peer learning without judgment or pressure
(02:58) The importance of community in developing strong sales strategies and business acumen
(03:54) Guardrails that make this space safer and more effective than LinkedIn or Facebook groups
(05:00) Why there’s a membership fee—and why the first three months are free

Key Quotes

Sean O’Shaughnessey (00:01:00): “We’re creating a community where people can get together, bounce ideas off each other without fear—just designed to help.”
Kevin Lawson (00:02:58): “It’s unreasonable to think your small sales team has all the answers. But it’s completely reasonable to find a community that does.”
Sean O’Shaughnessey (00:04:16): “If you’re not a salesperson or sales leader, you’re not getting in. This isn’t about selling to each other. It’s about growing together.”

Additional Resources

B2B Sales Lab Information & Registration: https://newsales.expert/b2b-sales-lab
(Free for the first three months with no obligation.)

A Significant Actionable Item from this Podcast

Join the B2B Sales Lab.
If you’ve ever wished you had a sounding board for a tough sales call, a creative partner to work through messaging, or a peer to validate your sales strategy, this is your moment. Visit the link in the show notes and apply to join the B2B Sales Lab. The first three months are free, giving you access to experienced sales minds, curated content on value selling and revenue management, and a judgment-free environment to grow your sales acumen. Don’t wait for your next deal to fall through; build your support system today.

Why You Should Listen

This episode is a call to action for sales professionals serious about growth. If you’re navigating complex sales cycles, seeking stronger messaging, or simply want a community that understands your world, the B2B Sales Lab might be the resource you’ve been missing. Kevin and Sean, both seasoned in sales leadership and sales management, offer not just insights but an entire framework to elevate your career. Listen now to learn how to take the next step toward sustainable sales success—and connect with others on the same journey.

Two Tall Guys Talking Sales – John McLeod Explains How to Avoid the AI Trap: Using New Tools Without Losing Your Sales Message – Episode 140

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey are joined by veteran fractional VP of Sales, John McLeod. Together, they dive into a critical topic for today’s sales leaders: embracing artificial intelligence tools without compromising your value proposition, messaging, or sales processes. John brings deep expertise in sales management, business acumen, and revenue generation strategies, offering a measured approach to evaluating sales tech, especially AI solutions, through a risk-and-reward lens. Whether you’re a business owner, sales manager, or BDR excited about AI, this conversation grounds you in practical wisdom.

Key Topics Discussed

The Real Risk of AI in Sales (00:01:22): How overreliance on untrained AI tools can misrepresent your brand and do more harm than good.
Sales Productivity vs. Organizational Efficiency (00:02:01): Why the focus shouldn’t just be on doing more faster, but also on syncing with your company’s value selling model
Three Essential AI Use Cases in Sales (00:03:25): Research, qualification, and outreach—and why each comes with its own operational risk.
The Ethical Use of AI and Messaging Integrity (00:07:43): Why maintaining consistent messaging across AI-enabled tools is essential to preserving brand integrity and revenue management.
Training AI for Sales Value (00:10:00): How smart prompt engineering and structured inputs drive better outcomes from generative AI tools.

Key Quotes

John McLeod (00:05:27):
“AI tools are meant to be trained. The biggest risk is: are they in fact supporting your unique and distinctive value proposition and holding true to that?”
Sean O’Shaughnessey (00:11:38):
“You won’t lose your job to AI—but you might lose it to another salesperson who knows how to use AI more effectively.”
Kevin Lawson (00:09:40):
“When you introduce AI and efficiency, that naturally raises the bar of expectation for performance. What is the new normal when you get there?”

Additional Resources

John McLeod’s LinkedIn Profile – https://www.linkedin.com/in/johnmcleod1/

A Significant Actionable Item from this Podcast

Train Your AI with Purpose: Don’t just “plug and play” AI tools. Take the time to structure your inputs and refine your prompts so that the tool reflects your value, not just generic sales content. Spend time A/B testing different approaches to ensure messaging aligns with your company’s strategic sales positioning. Start today by reviewing your most recent outreach generated by AI and ask: “Does this truly represent our value?” If not, retrain your prompts before using them again.

Why You Should Listen Now

If you’ve ever been tempted by the next great sales tool or AI platform promising instant leads and effortless sales success, this episode will recalibrate your thinking. John McLeod delivers candid insights on balancing tech adoption with strategic discipline. With Sean and Kevin steering the conversation, this discussion is rich with real-world experience in sales management, messaging, and revenue generation. Tune in now to stay ahead without losing what makes your company valuable.

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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Two Tall Guys Talking Sales – Patrick O’Donnell Explains How to Hire and Onboard Sales Talent That Actually Performs – Episode 139

By Sean O'Shaughnessey

In this high-impact episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome sales acceleration expert Patrick O’Donnell to tackle one of the toughest challenges facing small business CEOs: hiring and onboarding top-performing sales talent. Together, they dive deep into proven sales strategies that help CEOs find strong candidates and keep them engaged, successful, and driving revenue. If you’ve ever hired a salesperson who didn’t work out, or you’re planning to hire your first, this conversation is your roadmap to sales success. From creating a robust onboarding plan to integrating soft skills training and cultural alignment, this episode is packed with value-selling insights you can apply immediately.

Key Topics Discussed:

[00:01:00] Why small business CEOs struggle to attract and retain top salespeople
[00:03:00] Patrick’s proven hiring and onboarding process for sales roles
[00:05:10] The importance of structured 30-60-90 day plans and Sean’s GUTS framework
[00:07:00] Kevin’s NASA Plan for onboarding: A granular, hourly approach to early success
[00:10:00] The role of soft skills and professional development in retaining talent
[00:11:50] A lighthearted look at entrepreneurship: Why Patrick bought a historic Indianapolis tavern

Key Quotes:

“They’re in such a hurry to take the sales hat off their head that they hire the first person who looks okay on the surface. That rushed approach almost always ends poorly.”
– Patrick O’Donnell [00:02:06]
“I hand every new rep a GUTS document—Getting Up To Speed. It’s a 30-60-90 plan that clearly spells out what they need to accomplish. They can be ahead, but they can’t fall behind.”
– Sean O’Shaughnessey [00:05:10]
“Most small business owners think they have a plan because it’s in their head. But if it’s not written down, it doesn’t exist.”
– Kevin Lawson [00:07:29]
“We want every new hire to be the most professional person in the company, because it’s their job to make everyone around them better.”
– Sean O’Shaughnessey [00:10:35]

Additional Resources:

LinkedIn profile for Patrick O’Donnell https://www.linkedin.com/in/patrickwodonnell/
Soft skills training programs referenced by Sean for onboarding enrichment
GUTS (Getting Up To Speed) framework and NASA Plan discussed during onboarding best practices

A Significant Actionable Item from this Podcast:

Implement a Written 30-60-90 Onboarding Plan with a Two-Week NASA Schedule.
Salespeople need clarity to succeed. Whether you’re a first-time sales manager or a seasoned executive, stop relying on verbal plans or “tribal knowledge.” Create a written 30-60-90 onboarding plan that details expectations, milestones, and key outcomes. For the first two weeks, apply the NASA method: a daily, hour-by-hour schedule that aligns the new hire with every department, cultural cue, and technical requirement. Doing so sets a strong foundation for success and dramatically reduces early turnover.

Summary Paragraph:

If you’re serious about improving your sales management, elevating your sales processes, and building a team that drives real revenue generation, this episode of Two Tall Guys Talking Sales is essential listening. Kevin, Sean, and Patrick break down what too many business owners get wrong—and how you can get it right. Whether you’re scaling a team or hiring your first rep, these insights around onboarding, messaging, and business acumen will accelerate your journey toward consistent sales success. Press play now and walk away with tools you can use today.

The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process

By Sean O'Shaughnessey

Many salespeople, sales managers, and CEOs face a unique problem. This issue concerns the sales process, particularly when specific steps are skipped. The challenge is common among sales teams across various industries, and there are different perspectives on its causes and solutions.

This issue is concerning since, according to Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth. (https://hbr.org/2015/01/companies-with-a-formal-sales-process-generate-more-revenue). That same study states that companies that had trained their sales managers to manage their pipelines saw their revenue grow 9% faster than those that didn’t. But not just any training will do. Sales managers need targeted training to address specific pipeline management challenges.

Sometimes, the sales process might seem tedious, and salespeople may skip steps out of impatience or eagerness to close a deal. However, skipping these steps can lead to further complications down the line. When a sales team is not following the process that has been identified, it can disrupt the team’s rhythm and efficiency. Some might argue that this is a sign that the process needs to change or that more training is required.

This issue extends beyond the sales team. When a company hires a fractional VP of sales, it brings an outside perspective to evaluate its sales process. The fractional VP will often encounter resistance from the existing team, who may feel their industry is unique. While every business has its distinctive elements, the fundamentals of a sales process are universal.

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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 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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