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.

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…
Validation Events: The Unsung Hero of Sales Process Discipline

Validation Events: The Unsung Hero of Sales Process Discipline

By Sean O'Shaughnessey

In the complex world of B2B selling, trust is built in stages. The challenge in all sales campaigns is ensuring the prospect trusts they are making the best decision for their business.

  1. Do they trust that the salesperson is giving them all of the information?
  2. Do they trust that the company will support them after the sale?
  3. Do they trust that the product will perform as they expect it to perform?

As I have explained in my book, Eliminate Your Competition, as well as the blog for that book and in this blog, the prospect needs to trust all three elements the salesperson is selling:

  1. They need to trust the product.
  2. They need to trust the company behind the product.
  3. They need to trust the salesperson.

Prospects listen to your sales message, review your materials, and hear your claims, but none of that guarantees belief or trust. Trust is validated when your claims are validated. That’s why validation events are crucial to any rigorous sales process.

In The Qualified Sales Leader, John McMahon stresses the importance of customer-driven validation. He cautions sales leaders against relying on internal optimism or anecdotal “good signals” from prospects. Instead, McMahon emphasizes observable proof—real buyer behavior that confirms alignment, commitment, and value. Validation events are when the customer takes action to validate that what you’ve promised is accurate and valuable.

An excellent sample sale process flow looks like this:

  1. Discover
  2. Scoping
  3. Economic Buyer Meeting
  4. Validation Event
  5. Business Case and Final Proposal
  6. Negotiate and Close

As you can see, the Validation Event is the last step before creating the final business case, which will be bundled with your final proposal.

Read the rest of the article…
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 – The Four Buckets of Sales Growth with Steve Wittal

Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

By Sean O'Shaughnessey

In this dynamic episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome Canadian SalesXceleration expert Steve Wittal for an in-depth look into the foundations of effective sales strategies. Steve brings decades of experience in startup advisory, sales management, and business growth, sharing a robust framework that simplifies complex growth challenges into four digestible buckets: desirability, clarity, predictability, and deliverability. If you’re a business leader looking to strengthen your sales processes, sharpen your messaging, or improve revenue generation, this conversation is a goldmine.

Key Topics Discussed

  • The Power of Leadership in Change Management (~01:02)
    Steve opens by explaining why leadership is the starting point for any growth initiative, especially when change is involved.
  • The Four Buckets Framework for Growth (~03:00)
    Steve outlines his method for diagnosing and resolving growth issues by focusing on four pillars: desirability, clarity, predictability, and deliverability.
  • Desirability and Understanding the Customer’s Pain (~04:00)
    Why identifying whether your product is a “must-have” or “nice-to-have” is critical to sales success.
  • The Importance of Clarity and Quantifying the Cost of Inaction (~06:39)
    Sean and Steve unpack how clarity in messaging and value proposition can move buyers from indecision to action.
  • Predictability, Scalability, and Sales Playbooks (~09:20)
    How aligning your sales process with the customer’s buying journey enables scale and drives predictable revenue.
  • Deliverability and the Voice of the Customer (~10:50)
    Steve emphasizes the importance of retention, early wins, and referrals as indicators that your solution truly delivers.

Key Quotes

  • Steve Wittal: “A problem well-defined is a problem half-solved. Before we prescribe, we have to truly understand.” (~02:46)
  • Kevin Lawson: “When you’ve dotted all those i’s, it makes you a market-facing product. That’s how you achieve market fit.” (~13:25)
  • Sean O’Shaughnessey: “When a customer comes to you and says, ‘Can you help me solve this?’ — that’s sales nirvana.” (~08:35)

Additional Resources

  • Connect with Steve Wittal on LinkedIn – https://www.linkedin.com/in/stevewittal/
  • Steve’s email: Steve Wittal <swittal@salesxceleration.com>

A Significant Actionable Item from this Podcast

Audit Your Sales Strategy Through the Four Buckets.
Take a moment to evaluate your organization’s performance across Steve’s four key areas:

  • Desirability: Is your product essential or optional to your buyers?
  • Clarity: Can your team articulate your value proposition in a way that resonates with prospects and highlights the cost of inaction?
  • Predictability: Do you have a repeatable sales process that aligns with how your customers buy?
  • Deliverability: Are you consistently delivering on promises and capturing client feedback to validate success?

This self-assessment will uncover gaps in your current sales approach and point to immediate areas for improvement.

Summary

Whether you’re leading a startup or managing a growing sales team, this episode delivers a concise yet powerful framework for achieving sales success. Steve Wittal’s “Four Buckets” offer practical, business acumen–driven insights that will help you reframe your growth strategy and improve every stage of your sales process. If you’re serious about improving revenue generation and becoming a trusted advisor in your client relationships, don’t miss this episode. Tune in now and transform your approach to value selling.

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

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

By Sean O'Shaughnessey

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

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

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

Ideal Client Profile

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

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

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

What is your message?

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

Read the rest of the article…
Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

By Sean O'Shaughnessey

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

Read the rest of the article…
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.

Read the rest of the article…