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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!

Sales Management in the Age of AI: Aligning Marketing, Messaging & Revenue Generation

When it comes to modern B2B revenue generation, the conversation is shifting: it’s no longer just about cycle time or activity metrics, it’s about intent, predictive insights, and sharpening your approach to lead engagement. In this post, we unpack how artificial intelligence (AI) can reinforce your sales management discipline, refine your sales processes, and elevate your team’s business acumen.

Many sales organizations still rely on traditional lead-scoring models: “five points for a white-paper download, ten points for visiting the pricing page.” These rules-based frameworks sit at the heart of countless debates over marketing-qualified lead (MQL) vs. sales-qualified lead (SQL). Yet research shows that such arbitrary scoring systems often perform little better than chance.

By contrast, predictive lead scoring powered by AI changes the game: algorithms ingest data from your CRM, marketing automation, website activity, firmographics and behavior patterns. They then compute each lead’s statistical probability of converting, turning your outreach efforts from scatter-shot to precision-targeted.

In value selling, the objective is to engage high-potential buyers with meaningful differentiation—messaging that resonates with their specific business challenges. When your team is handed leads that reflect a 90 %+ probability of conversion, the conversation changes: it becomes strategic, not just transactional. Your reps spend less time chasing noise and more time facilitating high-impact dialogues.

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Beyond Spell Check: How Grammarly’s AI Can Transform Sales Communication

Clear, professional communication is the foundation of sales success. Yet, in 2025, much of our selling occurs not face-to-face, but through written words, emails, proposals, CRM notes, and social media messages. This shift means your writing is no longer just a form of communication; it’s your personal brand, your first impression, and often the deciding factor in whether a conversation continues or comes to a halt.

Grammarly has evolved far beyond its original purpose as a grammar checker. Today, it’s an artificial intelligence–powered platform that helps sales teams increase efficiency, refine their messaging, and accelerate revenue growth. It works directly within the tools you already use, such as Gmail, LinkedIn, Salesforce, and HubSpot, helping sales professionals write with greater confidence and clarity.

Sales organizations using Grammarly have seen measurable improvements: Databricks saved $1.4 million annually; Smartsheet cut thousands of hours from proposal creation; and Zoom reported higher customer satisfaction thanks to improved written communication. These results aren’t luck; they’re the product of refined sales processes, consistent messaging, and clear communication supported by AI.

For individual salespeople, Grammarly helps improve value selling by ensuring that every message is professional, engaging, and on-brand. Its AI engine not only corrects errors but also suggests stronger phrasing, predicts reader reactions, and even aligns your tone with your business acumen and brand voice. For sales leaders, it standardizes team communication and reinforces a culture of professionalism across departments.

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Sales Management with AI: Chat Interfaces vs. Automation Workflows

Sales organizations today face a critical decision: should they rely on interactive chat interfaces like ChatGPT, Claude, or Gemini, or should they focus on automation workflows? The answer isn’t either/or. Each approach has unique strengths, and choosing the right one directly impacts sales processes, productivity, and revenue generation.

The problem many sales teams encounter is “random implementation.” They hear about a new AI tool, adopt it quickly, and use it for the wrong purpose. The result? Chat interfaces get bogged down with repetitive work, and automation gets tasked with jobs that require creativity and nuance. Misuse not only reduces efficiency but also frustrates teams and erodes trust in artificial intelligence altogether.

So how do you know when chat is the right fit? The decision comes down to task complexity and uniqueness. Chat excels in situations that require creativity, flexibility, and human judgment. Four categories consistently stand out:

  • Creative and strategic tasks: proposals, executive messaging, strategic planning, and competitive positioning.
  • Complex problem-solving: sales opportunity strategy sessions, unique customer needs, and crisis management.
  • Learning and development: role-playing objection handling, skill coaching, and competitive intelligence training.
  • Research and analysis: prospect research, market analysis, and strategic planning.
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Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

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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.
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Two Tall Guys Talking Sales – From Comp Plans to Territory Alignment: Sales Strategies Every Leader Needs for Revenue Generation – Episode 153

As the year draws to a close, sales leaders and business owners face a critical challenge: preparing for growth in the year ahead. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into sales management strategies that set the stage for long-term sales success. From refining compensation plans and aligning territories to planning product lifecycles and avoiding the dreaded “hockey stick” growth trap, this conversation is packed with insights on business acumen, value selling, and revenue generation strategies that every sales leader should master.

Key Topics Discussed

  • 01:00 – Planning Beyond This Year: Why sales leaders need to start preparing now for next year’s revenue generation and sales processes.
  • 02:11 – Building Smarter Compensation Plans: Evaluating and refining comp structures to drive sales success and attract top talent.
  • 03:13 – Product Lifecycle & AI Readiness: How shifts in markets and technology demand updates to your offerings and messaging.
  • 05:00 – Departmental Alignment for Growth: Understanding how revenue management and sales growth affect every department in your business.
  • 07:12 – Right People, Right Roles: Assessing whether your sales team is positioned for success in the next stage of your growth plan.
  • 11:20 – Avoiding the “Hockey Stick” Trap: Why spreading growth evenly across years is a better long-term sales strategy.

Key Quotes

  • Sean O’Shaughnessey (01:07): “If I asked you to write out your three-year plan, next year already knocks off the first year. Are you one-third of the way there, or do you need to rethink your path?”
  • Kevin Lawson (02:33): “Be planning ahead. Compensation plans aren’t a set-and-forget item—you need to revisit them every year to make sure they’re delivering the right results.”
  • Sean O’Shaughnessey (07:59): “Do I have the right people in the right place in my sales organization for next year? Not every salesperson has to leave, but maybe their role needs to evolve.”
  • Kevin Lawson (11:38): “You don’t want that third year of your plan to be a hockey stick. Don’t put yourself in a position where you suddenly need 40% growth in one year to hit your goals.”

Additional Resources

  • B2B Sales Lab: A peer community for sales leaders and professionals to sharpen strategies, exchange best practices, and get actionable feedback.
  • EOS Framework: For leaders who want to align messaging, sales strategies, and revenue management with long-term goals.

A Significant Actionable Item from this Podcast

Review and finalize your sales compensation plans by December 1st. This gives your team enough time to digest changes, ask questions, and align their sales strategies before the new year begins. Waiting until January leaves your salespeople unprepared, which can delay revenue generation and momentum.

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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

Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive deep into one of the most misunderstood dynamics in business: the relationship between sales and marketing. Pulled directly from a thought-provoking question inside the B2B Sales Lab community, this conversation explores how sales teams can contribute meaningfully to marketing efforts and why that collaboration drives better revenue generation. Whether you lead a sales team, run marketing campaigns, or wear both… Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

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