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

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

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

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

By Sean O'Shaughnessey

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

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

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

Read the rest of the article…
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 – 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.

Navigating the Sales Maze: Overcoming Missed Steps in Your Sales Process

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. 

Read the rest of the article…
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.

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

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.

Read the rest of the article…
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.