AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

By Sean O'Shaughnessey

AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t. 

It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.

Time is a salesperson’s most valuable asset. 

Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.

Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood. 

If your message isn’t clear, it won’t convert.

Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.

CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships. 

If your CRM doesn’t have AI capabilities, it’s time to upgrade.

AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it. 

Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.

Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.

Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward. 

A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.

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Two Tall Guys Talking Sales – Workflows, Automation, and AI: Building a Smarter Sales Organization – Episode 145

Two Tall Guys Talking Sales – Workflows, Automation, and AI: Building a Smarter Sales Organization – Episode 145

By Sean O'Shaughnessey

In this compelling episode, co-hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial distinctions between workflows, automations, and artificial intelligence (AI), and why understanding these differences isn’t just technical trivia, but foundational to improving sales processes, enhancing sales management, and accelerating revenue generation. If you’re a sales leader, business owner, or B2B rep striving to improve how you use technology to boost sales success, this episode is a must-listen. Packed with real-world examples and expert commentary, you’ll walk away with a clearer understanding of how to integrate automation and AI into your selling environment without losing the human touch that drives value selling.

Key Topics Discussed

  • The Distinction Between Workflow and Automation (approx. 01:00)
    Kevin and Sean explain that workflows are rule-based sequences (what should happen), while automations are system-triggered actions (when they happen).
  • Applying Workflow and Automation to Common Sales Scenarios (approx. 03:00)
    Sean walks through onboarding, fulfillment, and follow-up processes that can be automated to save time and reduce human error.
  • The Role of AI in Enhancing Sales Tasks (approx. 05:00)
    Discover how AI moves beyond automation by adding intelligence and insight, like writing customized thank-you messages or enriching CRM data.
  • What Sales Leaders Should Expect from Modern CRM Systems (approx. 12:00)
    Sean lays out a vision of AI-enabled CRMs that proactively suggest key contacts and actions for deeper account penetration.
  • Creating Sales Infrastructure That Supports Scale (approx. 09:00)
    Kevin emphasizes how business logic, automation, and AI build a more agile, informed sales team that’s prepared for disruption.

Key Quotes

  • Kevin Lawson (approx. 00:46):
    “Workflows are trigger-based events that tell business logic what to do next… but automation is what makes things happen automatically, without human intervention.”
  • Sean O’Shaughnessey (approx. 05:43):
    “We used to personalize thank-you letters with a person. Now we can automate that process and use AI to generate something that’s still meaningful but takes no time.”
  • Kevin Lawson (approx. 10:00):
    “AI plus workflows plus automation creates the bedrock for a better sales organization… a more nimble organization that can adapt to changes in the environment.”
  • Sean O’Shaughnessey (approx. 13:08):
    “Does your CRM say, ‘Did you know there are three directors of manufacturing at that company?’ That’s where workflows, automation, and AI converge to fuel revenue growth.”

Additional Resources

  • Join the B2B Sales Lab Community – A peer-driven space where sales professionals, managers, and leaders exchange insights, share best practices, and build smarter revenue systems.

A Significant Actionable Item from this Podcast

Audit your CRM and lead-handling processes.
Ask yourself: Is my CRM working for me, or am I working for it? Review whether incoming leads are routed automatically, if emails are logged without manual entry, and whether sales leaders receive alerts on stalled opportunities. Implement at least one automation or AI-powered enhancement, such as auto-logging emails or enriching lead data, to eliminate repetitive tasks and enable your team to focus on strategic selling.

Why You Should Listen Now

This episode isn’t just a primer on sales tech buzzwords; it’s a blueprint for operational excellence in B2B sales. Kevin and Sean break down complex topics with clarity and offer practical advice that can immediately improve your sales team’s responsiveness, accountability, and business acumen. If you’re serious about building a scalable sales infrastructure, aligning your team with cutting-edge sales strategies, and using AI as a force multiplier for your messaging and revenue management, then queue up this episode today. You’ll walk away with new ideas, sharper thinking, and a to-do list worth acting on.

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

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.

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

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.

Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

By Sean O'Shaughnessey

In this week’s episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined by the “Elder Statesman” of fractional sales management: John Lee. With nearly four decades of experience and a deep track record of helping companies hire top-performing sales professionals, John shares a masterclass in sales hiring strategy. Whether you’re scaling from a two-person team to ten or trying to avoid costly hiring mistakes, this episode delivers practical, field-tested advice on building elite sales teams, strengthening your sales processes, and aligning talent with company culture.

Don’t miss this conversation if you’re committed to improving your sales success through smarter hiring, better business acumen, and scalable revenue generation.

Key Topics Discussed:

  • The Hiring Mindset for Growth Companies (00:01:45)
    Why hiring rock stars—not warm bodies—matters and how John filters for high performers.
  • From First Hire to Scaling a Team (00:04:44)
    CEOs and sales leaders must ask the evolving questions when hiring their 3rd, 5th, or 10th rep.
  • Psychographics, Not Just Resumes (00:05:24)
    How John builds candidate profiles that match top performers using behavior and motivation, not just skills.
  • Parallel Sales and Hiring Processes (00:08:00)
    Why a successful sales hiring process mirrors your value selling strategy—with defined steps, assessments, and clear messaging.
  • Avoiding Common Hiring Mistakes (00:11:43)
    The critical danger of hiring salespeople who are better at selling themselves than your solution.
  • Top 3 Rules for Hiring Sales Talent (00:13:33)
    John’s unfiltered checklist for hiring decisions that fuel revenue growth and protect your sales culture.

Key Quotes:

  • John Lee: “Don’t hire someone who can’t show they’ve been successful—and don’t hire someone who doesn’t fit your culture.” (00:13:57)
  • Sean O’Shaughnessey: “A salesperson might not be able to sell your product to save their life—but they’re often great at selling themselves. That’s a trap for business owners.” (00:11:55)
  • Kevin Lawson: “You talk about hiring the way you talk about sales infrastructure—it’s all about process, fit, and purpose.” (00:07:42)

Additional Resources Mentioned:

A Significant Actionable Item from this Podcast:

Design a Hiring Process Like a Sales Process
Treat your hiring efforts with the same rigor as your sales process. Start by defining a psychographic profile based on your top performers. Use structured assessments to evaluate “sales DNA” and focus interviews on demonstrated success, not just confidence. Then, make cultural fit a deal-breaker. Great hires aren’t just competent—they’re aligned with your mission, methods, and team dynamics.

Summary Paragraph:

This episode is essential listening for sales leaders and business owners looking to scale their teams without sacrificing culture, performance, or momentum. John Lee brings a rare mix of seasoned sales management expertise and real-world hiring acumen to the table. If you want to improve revenue generation through smarter hiring and better sales strategies, you’ll find actionable insights packed into every minute. Don’t settle for average; build a sales team that drives success. Tune in now.

Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

By Sean O'Shaughnessey

In this powerful episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined once again by Steve Caton, CEO of Altezza Solutions, for a thought-provoking conversation that zeroes in on one of the toughest decisions in sales leadership: when to sell, when to coach, and when to hire. Whether you’re a business owner, VP of Sales, or a player-coach juggling a quota and a team, this episode brings clarity to the strategic inflection point where growth hinges on letting go. With frank discussion, lived experience, and tactical advice, Kevin, Sean, and Steve guide you through the complex terrain of sales management, revenue generation, and scaling your team without sacrificing results.

Key Topics Discussed:

  • [00:01:58] The pros and cons of player-coach sales roles, and why this model often fails without intentional strategy
  • [00:05:34] How to create a psychologically safe sales environment where learning from failure drives sales success
  • [00:07:11] Steve Caton’s personal transition from sales operator to CEO—and how it triggered exponential business growth
  • [00:09:20] The difference between hiring to “swim faster” and hiring to scale—how business acumen guides the decision
  • [00:13:00] Real-world use cases for fractional sales roles to test new markets or offerings without disrupting core revenue streams

Key Quotes:

  • Kevin Lawson [00:04:57]: “Sometimes you have to let people fail. You can’t push them into failure, but you do have to give them the room to learn. The challenge is, as a leader, you’re still accountable for that failure.”
  • Sean O’Shaughnessey [00:04:01]: “It’s much easier to do one thing well. Let great salespeople sell and great managers manage—don’t dilute either role.”
  • Steve Caton [00:08:30]: “I made the decision to stop selling before I could afford it. Why? Because I knew the payoff would be big. Sometimes, you just have to invest in your business to grow.”
  • Kevin Lawson [00:11:34]: “A sales process with control metrics, plus intentional feedback loops, informs exactly how and where your business should grow.”

Additional Resources:

A Significant Actionable Item from this Podcast:

Reevaluate your team structure and decide: are you scaling or surviving?
If you’re a business owner or sales leader wearing multiple hats, it’s time to assess whether you’re enabling growth or capping it. Consider where your time is most valuable—rainmaking, coaching, or closing—and invest in building the right team around you. Start with fractional or part-time hires to test new roles or markets, then double down when the data supports it.

Closing Summary:

This episode cuts through the noise around sales team building with a refreshing mix of vulnerability, experience, and strategic depth. Whether you’re weighing your first sales hire or deciding to step out of the player-coach role, Two Tall Guys Talking Sales delivers real-world sales strategies that help you align your messaging, sales processes, and revenue management decisions with long-term growth. Don’t miss this one—it’s 15 minutes of business-building insight that could change the trajectory of your sales organization. Hit play now and discover how letting go might be the smartest way to grow.

Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

By Sean O'Shaughnessey

What does it take to scale a sales organization in today’s unpredictable business environment? In this dynamic episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson welcome back Steve Caton, CEO of Altezza Solutions, to unpack the nuances of scaling sales teams, especially through the power of fractional sales professionals. Together, they explore the critical role that sales processes, sales management, and business acumen play in enabling organizations to grow without overspending or compromising performance. Whether you’re navigating the “zero to one” phase or planning your expansion from one rep to five, this episode offers a roadmap for smart, sustainable revenue generation.

Key Topics Discussed

  • Zero to One vs. One to One Hundred: Two Models for Scaling Sales Teams (00:01:14)
    Kevin and Steve outline the difference between launching your first rep and accelerating team expansion, with a focus on structured growth.
  • Fractional Salespeople as a Low-Risk Growth Strategy (00:02:45)
    Steve explains how the fractional model supports learning, experimentation, and ROI without overcommitting resources too early.
  • Determining the Right Time to Expand Territories or Add Headcount (00:04:10)
    The team discusses key signals—like activity level, lead flow, and deal volume—that indicate when it’s time to grow.
  • Using Leading Indicators vs. Lagging Indicators in Sales Management (00:06:16)
    Steve shares the importance of measuring inputs (calls, meetings, proposals) over outputs (closed deals) to ensure predictable scale.
  • The Power of Process-Driven Selling for Sales Success (00:13:08)
    Sean and Steve emphasize why experienced sales pros rely on systems, not improvisation, and why process must precede people.

Key Quotes

  • Kevin Lawson (00:01:34):
    “Think hockey stick versus gradual—zero to one is about getting that first good hire. That’s when you unlock real scale potential.”
  • Steve Caton (00:02:45):
    “Start small, see what works, then expand. That’s the foundation of scalable revenue—and the fractional model makes that possible without spending a crazy amount of money.”
  • Sean O’Shaughnessey (00:08:00):
    “Sales is about finding the customer that is going to buy—that’s not just a marketing thing, that’s a sales thing.”
  • Steve Caton (00:13:08):
    “Process comes before people. If there’s no process, your reps will build one—and that distracts them from actually selling.”

Additional Resources

A Significant Actionable Item from this Podcast

Use leading indicators—not just closed deals—to decide when it’s time to grow your sales team. Many companies scale reactively, hiring after success arrives. But Steve Caton challenges leaders to evaluate the activity level of their reps—calls made, meetings scheduled, deals created—to make data-driven decisions before hitting a bottleneck. If your top performer is maxing out their productive hours, it’s time to split territories, not overload. Review your leading indicators this week and see where your next growth step should begin.

Why You Should Listen

This episode is a must-listen for founders, CEOs, and sales leaders trying to build smarter, not just bigger. With deep insight into the value of fractional sales professionals, the importance of sales strategies, and how to use data for effective revenue management, Steve Caton offers a practical, grounded view of what scalable sales success looks like. If you’re serious about growing your team without growing your headaches, hit play and take notes.

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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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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