Skip to content

artificial intelligence

What An MBA Didn’t Teach You About Sales

The sales profession is challenging. You need to work hard at it to succeed. You need to learn from the best. You need to improve your skills continuously. If you think you can sell since you are a hit at parties and have a lot of friends, you may soon find that you are a failure as a salesperson. Blunt truth:

because the sales profession is so hard, you have to focus on doing everything in sales very well, or you will be considered a failure.

I call this blog, Skinned Knees because I try to relate all of the learning that I have done over the past 4+ decades (while skinning my knees in the learning process).

I hope that you learn from my mistakes so that your business will grow!

Choosing the Right AI Stack for Your Sales Organization

A VP of Sales recently confided in me: “We have six different AI tools, but our reps are still doing manual work. What went wrong?”

This is the AI tool proliferation problem. Sales leaders often collect tools without a strategy, mistaking a pile of features for a cohesive system. It’s like buying a hammer, screwdriver, saw, and drill without realizing you’re actually trying to build a house. An effective AI stack means integration. When tools work together, they amplify each other’s value. When they don’t, they add complexity, confusion, and wasted money.

Why Strategy Beats Random Adoption

Random tool adoption is rampant across sales organizations. Teams chase shiny new software, often ending up with overlapping features, siloed data, and productivity lost to tool-switching. Instead of solving problems, the stack itself becomes the problem.

But when built strategically, the benefits are profound. Integrated systems reduce manual data entry, accelerate response times, and deliver actionable insights for reps. Three well-chosen, well-connected tools can outperform six isolated ones. Integrated stacks also improve adoption rates by providing consistent interfaces and reducing training overhead.

The Five-Layer AI Stack Framework

To avoid the chaos of random adoption, I use a five-layer framework for structuring sales AI tools:

  1. Data Foundation – Your CRM and data management system, enriched and maintained for accuracy.
  2. Intelligence & Analytics – AI-driven insights, lead scoring, forecasting, and market intelligence.
  3. Automation & Workflow – Sequences, task automation, and cross-platform orchestration.
  4. Content & Communication – AI writing, proposal generation, and customer-facing tools.
  5. Optimization & Learning – Conversation analysis, performance tracking, and continuous improvement.
Read the rest of the article…

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

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

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

Time is a salesperson’s most valuable asset. 

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

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

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

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

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

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

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

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

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

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

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

Read the rest of the article…

APIs Explained for Sales Leaders: Drive Growth Without Extra Headcount

A sales manager recently told me, “I have to copy the same prospect data into five different tools. There has to be a better way.” That frustration is more common than most sales leaders realize, and fortunately, there is a better way. The reality is that sales teams are hemorrhaging productivity due to disconnected systems. Top performers spend hours manually entering data, bouncing between platforms, and correcting inevitable errors. This administrative overhead steals time from… APIs Explained for Sales Leaders: Drive Growth Without Extra Headcount

ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

A few days ago, a sales manager asked me which AI platform to use for writing cold emails. I told him it depends on what kind of emails he’s writing, and he looked confused. That confusion is common and costly. ChatGPT, Claude, Gemini, and Copilot all look similar at first glance, but in reality, they serve very different purposes depending on your sales workflow. Choosing the right platform matters because the wrong choice drains time,… ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

Cut Through the AI Hype: Practical Definitions for Sales Professionals

Artificial intelligence is transforming sales, but too many leaders are investing in tools they don’t fully understand. The result? Costly mistakes, poor adoption, and missed opportunities. This episode of AI Tools for Sales Pros breaks down the three core technologies behind AI: and explains them in plain language that every sales professional can use. The episode compares the current AI confusion to the database revolution of the 1990s. Just as sales leaders once needed to… Cut Through the AI Hype: Practical Definitions for Sales Professionals

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

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

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

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

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

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

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… 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 – AI for Sales Success: Tools, Tactics, and Why You Can’t Ignore It – E124

Artificial intelligence (AI) is transforming the sales industry, but does that mean salespeople are becoming obsolete? Absolutely not! In this high-energy episode, Kevin and Sean debunk the myth that AI will replace sales professionals. Instead, they reveal how AI can be a game-changing tool for sales success. From using AI to refine communication to automating time-consuming tasks, this episode is packed with insights on how AI can help sales leaders and reps work smarter, sell… Two Tall Guys Talking Sales – AI for Sales Success: Tools, Tactics, and Why You Can’t Ignore It – E124