AI in B2B Sales Isn’t Optional Anymore

AI in B2B Sales Isn’t Optional Anymore

By Sean O'Shaughnessey

Several months ago, I was serving as a fractional VP of Sales for a $50 million manufacturing company. Their top salesperson was a 15-year veteran who knew the industry inside and out. Yet he was consistently being outsold by a competitor’s much newer hire. At first, it didn’t make sense until we discovered the reason.

The competitor’s rep wasn’t just more energetic or aggressive. They were AI-enabled. While my client’s rep was manually scrolling LinkedIn and drafting emails from scratch, the competitor’s rep was using AI tools to research prospects, craft personalized outreach, and prepare for meetings. In other words, the competitor had a partner working 24/7—freeing them to focus on what humans do best: building trust and closing deals.

That was the turning point. I realized we weren’t just competing against other salespeople anymore. We were competing against AI-enhanced sales teams.

The Most Urgent Technology Wave in Sales

Throughout my career, I’ve watched new technology waves disrupt the sales profession. Robotics transformed manufacturing in the 1980s. Solid modeling replaced drafting tables in the 1990s. Cloud computing reshaped IT in the 2000s.

Each time, early adopters gained the edge while laggards struggled to catch up. The AI wave is different for two reasons:

  1. It’s broader: touching every aspect of sales, from prospecting to forecasting.
  2. It’s faster: companies have months, not years, to adapt before the competitive gap becomes overwhelming.

AI in sales isn’t coming. It’s already here.

The Four Pillars of AI Sales Transformation

To make sense of AI’s role in sales, I use a framework I call the Four Pillars of AI Sales Transformation.

1. Efficiency Amplification

Salespeople lose hours each week on research, data entry, and administrative tasks. AI automates these repetitive activities, turning wasted time into revenue-generating capacity. If a rep with a $2 million quota spends 40% of their time on admin work, reclaiming even half of that time can translate into hundreds of thousands of dollars in additional revenue potential.

2. Personalization at Scale

Buyers expect relevance. AI enables sales teams to tailor outreach at a scale that was previously impossible. One client of mine went from producing 10 personalized emails per day to 500, each one referencing company news, industry pain points, or competitive dynamics. The result: higher engagement and faster response times.

3. Predictive Intelligence

AI spots patterns humans miss. It identifies which deals are at risk, when prospects are most likely to respond, and which leads are worth pursuing first. For one client, simply shifting demos to Tuesday afternoons increased conversion rates by 40%. When your competitors are guessing, AI gives you confidence.

4. Continuous Learning & Optimization

Unlike static playbooks, AI evolves. It analyzes win/loss data, tests messaging, and provides real-time coaching insights. One client discovered that pricing discussions were their biggest choke point. AI flagged the pattern, we built automated battlecards, and close rates improved by 18%.

Real-World Results

These aren’t theoretical benefits. In my own client work:

  • An AI-powered prospecting rollout increased appointment-setting rates from 8% to 23% in just six weeks.
  • A lost-deal analysis uncovered patterns that helped recover $2 million in the pipeline.

The reality is clear: companies already experimenting with AI are pulling ahead. Those who delay are watching the gap widen daily.

Three Things You Can Do This Month

If you’re ready to start, here are three immediate steps:

  1. Audit your workflow. Identify one repetitive task you can automate—prospect research, meeting prep, or follow-up emails.
  2. Pilot an AI tool. Start small with an affordable, no-code platform. Many cost less than $200/month.
  3. Learn with others. Don’t navigate this change alone. Surround yourself with peers who are experimenting, learning, and winning with AI.

Join the B2B Sales Lab

The best way to accelerate your adoption is to connect with others on the same journey. That’s why we built the B2B Sales Lab, a private, member-led community for sales professionals who want actionable insights, not theory. It’s where strategy meets execution.

In the Lab, you can:

  • Ask real questions about sales challenges.
  • Share proven best practices.
  • Learn from other sales professionals and veteran leaders.

Your first 90 days are free. Join us today at b2b-sales-lab.com.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Those who adapt now will thrive. Those who wait may not get the chance to catch up.

To learn more, listen to this podcast on the subject.

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 – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

By Sean O'Shaughnessey

Sales isn’t about persuasion but service, resilience, and growth. In this episode of Two Tall Guys Talking Sales, co-hosts Kevin Lawson and Sean O’Shaughnessey welcome sales leader and former professional athlete Jeff Parris to explore the fundamental skills that separate elite salespeople from the rest. Drawing on decades of experience, Jeff shares three often-overlooked yet foundational competencies that drive sales success, and they’re not what you’d expect. Whether you’re a VP of Sales building a high-performance team or a seller looking to level up, this episode delivers sharp insights on value selling, business acumen, and sales management excellence.

Key Topics Discussed

  • Why great salespeople see themselves as servants first (approx. 04:00)
    Jeff outlines why a “motivation to serve” mindset creates stronger client relationships and more consistent revenue generation.
  • Ego Drive vs. Ego Trip: Understanding the will to win without arrogance (approx. 07:30)
    Learn how ego drive, a hunger to persuade for the buyer’s benefit, builds durable sales performance.
  • Curiosity as the gateway to sales mastery (approx. 10:15)
    Jeff and Sean dig into why curiosity fuels continuous improvement and business acumen across every sales process.
  • How to coach the “accidental salesperson” into a top performer (approx. 11:45)
    Kevin asks how people without formal sales backgrounds can thrive by developing the right mindset.
  • Sales leaders as talent architects: Building high-performance teams (approx. 02:00)
    Jeff draws on his athletic past to share what makes a sales team championship-worthy.

Key Quotes

  • “Sales isn’t something we do to people, it’s something we do for people.”
    — Jeff Parris (04:00)
  • “The real goal of a great salesperson is: ‘Mr. Prospect, let me help you solve that problem.”
    — Sean O’Shaughnessey (05:55)
  • “Having the right people, with the right skills, in the right seats makes winning so much easier.”
    — Kevin Lawson (03:36)
  • “Curiosity leads to better solutions. Every interaction is a chance to learn and improve your craft.”
    — Jeff Parris (10:50)

Additional Resources

A Significant Actionable Item from this Podcast

Evaluate your team (and yourself) on the “Service–Drive–Curiosity” Triad.
Start by asking three questions:

  1. Does this salesperson show a genuine desire to serve the customer’s goals?
  2. Do they take pride in persuading with purpose, not just for commission but impact?
  3. Are they consistently seeking to learn more about the customer, the industry, and their performance?

Use these questions in your next 1-on-1 or team coaching session to align your talent strategy with the kind of sales success that sustains revenue generation.

Why You Should Listen to This Episode

If you’re tired of surface-level sales advice, this conversation will challenge your thinking and expand your toolkit. Jeff Parris brings clarity, conviction, and humility to what it means to lead with purpose in today’s complex B2B landscape. From building elite sales teams to refining your individual sales strategy, this episode is packed with practical wisdom for leaders, sellers, and anyone serious about mastering the craft of sales. Tune in now and discover the underestimated traits that drive extraordinary outcomes.

Two Tall Guys Talking Sales – Chris Spanier Explains Marketing Professional Services: Sales Strategies That Actually Work – Episode 142

Two Tall Guys Talking Sales – Chris Spanier Explains Marketing Professional Services: Sales Strategies That Actually Work – Episode 142

By Sean O'Shaughnessey

When marketing professional services, the playbook isn’t the same as product sales, and today’s episode dives into exactly why. Sean O’Shaughnessey and Kevin Lawson are joined by returning guest Chris Spanier, CEO of Carpe Diem Consulting Group and host of the Practical Actionable Marketing podcast. This conversation tackles the nuances of sales strategies for service-based businesses, blending value selling with measurable marketing and aligning both functions for stronger revenue generation. If you’re a business owner, consultant, or fractional executive trying to sharpen your sales processes and improve messaging, this episode is a goldmine of practical advice.

🔑 Key Topics Discussed

  • [02:44] Why traditional product marketing doesn’t work for professional services—and how to adapt
  • [03:46] The importance of measuring marketing effectiveness and integrating KPIs into the sales process
  • [07:36] How to position and market services that don’t have tangible “speeds and feeds”
  • [08:28] Letting go of the fear of “giving away your secret sauce” in thought leadership content
  • [10:30] Systemizing stories and messaging to scale sales efforts across a growing team
  • [12:14] How to use lead nurturing email campaigns to drive engagement and trust over time

🗣️ Key Quotes

  • Sean O’Shaughnessey:
    “Sales is a really expensive marketing arm if you’re not doing really good marketing.”
    — [05:59]
  • Kevin Lawson:
    “Tell how you win, how you help others win, and how they win when working with you—this is as key as anything in professional services.”
    — [10:52]
  • Chris Spanier:
    “If you freely share value, people won’t take advantage of you—they’ll start trusting you. That’s the first step in real sales success.”
    — [08:54]
    “Marketing is half magic and half numbers. But the numbers—that’s where the proof comes in.”
    — [04:14]

📚 Additional Resources

✅ A Significant Actionable Item from this Podcast

Systemize your lead nurturing.
Create a recurring, value-focused email campaign to maintain top-of-mind awareness. Whether your cadence is every three or six weeks, focus 80% on providing helpful insights and only 20% on pitching your services. Tracking measures email open rates and clicks, and then the behavior is aligned with site visits or follow-up outreach. This strategy turns occasional touchpoints into consistent momentum, critical for long-cycle sales in professional services.

🎧 Why You Should Listen Now

This episode is packed with strategic clarity and tactical insight for anyone selling invisible services. Whether you’re a fractional executive, consultant, or marketing-savvy sales leader, you’ll leave with a more innovative approach to messaging, a stronger understanding of sales and marketing alignment, and actionable ways to drive revenue generation with business acumen. Tune in now and rethink how you build trust and momentum in your professional services pipeline.

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

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

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

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.

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.