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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!

The Dual Blueprint Requirement: Why Growth Demands Two Plans, Not One

Launching a company or steering one through a merger, turnaround, or major transition requires clarity about how value will be created and, just as importantly, how revenue will actually be generated.

Many leadership teams recognize the need for a Business Plan, but overlook that sustainable growth requires a second, complementary plan. The main breakdown is not the strategy itself, but the assumption that strategy automatically creates revenue. Bridging strategy and revenue requires a distinct plan for that conversion, targeting a different audience.

The Business Plan sets direction from the top down. The Sales Plan is validated by demonstrating how that direction can become actual revenue from the bottom up.

Both are essential. Neither works in isolation.

The Business Plan: Charting the Course (Top-Down)

The Business Plan exists to answer specific questions for a particular audience. Its primary readers are CEOs, CFOs, bankers, private equity partners, and venture investors. These stakeholders are evaluating risk, scale, and return. They want to know where the company is going and why the destination is worth the journey.

At its core, the Business Plan articulates strategic intent. It defines the mission, the long-term objectives, and the differentiated value proposition that the company believes the market will reward. It frames the opportunity in language that aligns leadership, capital, and governance.

Market analysis in this context is necessarily high-level. It focuses on the total addressable market, industry dynamics, competitive positioning, and macro trends. The goal is not to explain how every deal will be won, but to establish that a meaningful opportunity exists and that the company has a credible right to pursue it.

Financial projections follow the same logic. They are built on broad assumptions: projected market share, average selling price, renewal and retention rates, inflation, and multi-year revenue targets. These numbers are directional. They signal ambition and scale rather than operational certainty.

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From Leads to Clients: How Aligning Sales and Marketing Fuels Sustainable Growth

There’s a common sentiment among sales teams this time of year: a sense of urgency. The calendar flips, Q4 starts, and suddenly it feels like you’re already behind. Sound familiar? That mid-Q4 pressure is real. But before you sprint into outreach and activity, step back and assess what’s actually fueling your pipeline? More importantly, is it aligned with long-term growth?

Sales leaders and CEOs often default to lead generation as the focal point. It’s understandable. More leads, more conversations, more deals, right? But that mindset skips a critical first step. You can’t scale what isn’t aligned. If your marketing message doesn’t match your sales conversations, you’re wasting time and budget. If your sales team is chasing poorly qualified leads, you’re burning cycles. And if your customers can’t articulate why they bought from you, you’ve got a positioning problem.

The foundation starts with clarity. What value do you truly deliver? Why do customers choose you over alternatives? If you can’t answer that in a clear, 50-word statement, your team is likely improvising in the field, and that’s costing you revenue. This is where sales and marketing alignment becomes more than just a buzzword. It’s operationally necessary.

Sales enablement isn’t only about tools and training. It’s about empowering sales with the right message at the right time. That starts with defining three core customer states:

  1. leads,
  2. prospects,
  3. clients.

Each phase requires different messaging, timing, and expectations. Most organizations blur those lines. That’s where inefficiency creeps in.

Leads sit at the top of the funnel. They are either unaware or only lightly aware of your offering. At this stage, marketing owns the responsibility. However, marketing without sales feedback is akin to shooting in the dark. Sales needs to inform marketing what makes a lead qualified.

  • What signals intent?
  • What common objections surface early?

Without that feedback loop, marketing tends to optimize for volume rather than quality.

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Differentiating Through Value: Mastering the Art of Consumable Sales

Navigating the competitive landscape of consumable sales calls for a thoughtful and kind-hearted approach. Salespeople, sales managers, and CEOs of small companies should remember that their role is about more than just making transactions. In a market where products often seem very alike in quality and price, what truly sets you apart is your ability to consistently show value. So, how can you create lasting relationships with your customers, even when many options are available?

Consider the analogy of fast-food giants like Burger King and McDonald’s. Both offer similar products, yet they each have a dedicated customer base. The key lies in creating a unique selling proposition that resonates with your target audience. 

As a salesperson, your goal is to become indispensable to your customers. This means transforming from a mere vendor to a trusted advisor who is deeply integrated into the customer’s business operations.

Become Part of Their Team

A critical part of this integration is understanding what a “gatherer” is. A gatherer is more than just an account manager. They build a close, almost inseparable bond with the customer. They become a trusted part of the customer’s team, often turning to them for advice and solving problems together. Building this kind of trust requires a genuine understanding of the customer’s business, enabling you to offer insights and solutions that extend beyond the products you provide.

In the realm of consumable sales, where products are used and replaced regularly, the salesperson’s value lies in their ability to maintain and continually grow the relationship. This involves not just selling a product but also selling yourself and your company. Your expertise, reliability, and ability to anticipate and solve problems become the key differentiators. When customers face challenges, they should instinctively think of you as the go-to person for solutions, regardless of minor price differences or delivery times.

To attain this trusted advisor status, you must focus on three core elements: 

  1. the product, 
  2. the company, 
  3. yourself. 

While the product and the company are essential, the most significant value often comes from you as the salesperson. Your ability to understand the prospect’s needs, guide their purchasing decisions, and challenge them to think differently about their business can set you apart from the competition.

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How to Use AI to Write Personalized Cold Emails at Scale

It’s Sunday night. You’re staring at your CRM and that dreaded task appears: “Prospecting Block: 100 Accounts.” The feeling in your stomach tells you what’s coming. You’ll either blast generic messages and feel like a spammer or spend hours crafting a handful of handcrafted emails that barely move the needle.

This is the central productivity crisis in modern B2B sales. We’re constantly forced to choose between efficiency and relevance. But what if that choice was a false one? What if artificial intelligence could help you achieve both, without sacrificing your authenticity or sanity?

The False Choice: Efficiency vs. Effectiveness

The traditional approaches to sales outreach, templates versus deep personalization, represent the old world of “one-to-many” or “one-to-one.” But the future of sales lies in one-to-one at scale. The key is understanding that AI isn’t replacing salespeople, it’s augmenting them.

Your job is no longer to write every email from scratch. Your job is to be the editor-in-chief of your outreach strategy. The human decides the target, tone, and message. The AI executes your direction at scale.

The Strategic Brief: Your Blueprint for AI-Powered Outreach

To adopt this workflow, replace your 50-email grind with one Strategic Brief containing three sections:

  1. Voice Profile – Teach AI to sound like you. Include examples of your best emails and guidelines for tone, structure, and style.
  2. Prospect Context – Gather simple, factual data on each contact: title, company, recent events, and pain points.
  3. Mission – Define your goal and message direction. What’s the objective of the email: reply, insight, or meeting?
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The Evolution of Sales: Scaling from 10 to 100 Customers

The journey of a business unfolds as a story of growth, change, and ongoing adaptation. As salespeople, sales managers, and CEOs, we all share the ups and downs that come with this path. One of the most exciting moments in sales is the shift from landing your first ten customers to growing your family of clients to 50 or even 100. This milestone is truly a game-changer, shaping the future direction of your business.

When you’re starting, your focus is on acquiring those first ten customers. You’re trying to find your footing in the market, identify your target audience, and refine your product or service offering. You might be customizing your product or service for each customer to ensure it fits their specific needs. However, as you aim for the next level of growth, you need to start thinking about systemizing your sales process. 

To grow successfully, it’s helpful to have a standardized product or service. While customizing can be useful when you’re just starting out, it can become hard to manage and slow you down as your customer base expands. 

Focus on creating a product or service that you can sell over and over again with just small tweaks. This approach simplifies your sales process and makes it easier for others to sell your offerings, too.

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From 10 to 100 Customers: Scaling Your Sales Process for Growth

For founders of companies, the journey of a business is a narrative of evolution, growth, and constant adaptation. As salespeople, sales managers, and CEOs, we are all too familiar with the challenges and triumphs that punctuate this journey. In the world of sales, one of the most critical turning points is the transition from acquiring your first ten customers to expanding your customer base to 50 or even 100. This pivotal moment sets the trajectory of a business and is a key focus of our discussion.

When you’re starting, the founding team is focused on acquiring those first ten customers. They’re trying to find their footing in the market, identify their target audience, and refine their product or service offering. You might be customizing your product or service for each customer to ensure it fits their specific needs. However, as you aim for the next level of growth, it’s crucial to start thinking about systemizing your sales process. This will ensure efficiency and prepare you for the next level of growth. 

To scale effectively, company leaders need to standardize their product or service offering. While customization can be beneficial in the early stages, it becomes impractical and inefficient as your customer base grows. The key here is to create a product or service that can be sold repeatedly with minimal adjustments. This streamlines the sales process, making it easier for others to sell the product or service.

In the early stages of a business, the founders might be the ones doing all the selling. But as the company grows, this becomes less feasible. To reach a larger number of customers, you need to bring others on board to sell for you. This is where standardization comes into play. By standardizing your product or service, you make it easier for others to understand and sell it. 

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Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

Building a successful sales team requires more than just filling open seats with available candidates. Company leadership must strategically align its hiring process with business objectives, market needs, and long-term goals. 

Whether you’re a solopreneur transitioning to a team-based approach or a CEO managing a growing sales force, the principles of intentional recruitment and onboarding remain the same. Hiring the right people is an investment in the future of your business.

One of the most common pitfalls in sales hiring is a lack of intentionality. Too often, small businesses hire out of convenience, choosing candidates from their immediate network or taking the first person who seems interested. While this approach may solve an immediate need, it rarely leads to long-term success. 

Hiring a salesperson means selecting someone who can actively drive growth and represent your brand with competence and integrity. The stakes are even higher when you’re working with a lean team; every hire matters, and mediocrity is not an option.

To avoid these missteps, it’s essential to approach hiring with the same rigor you apply to your sales process. Think of recruiting as a parallel to securing a high-value client. Just as you wouldn’t sell your product without qualifying leads or understanding their needs, you shouldn’t hire without a structured process to evaluate candidates. 

Begin by defining what success looks like for the role. What skills and attributes are non-negotiable? What specific outcomes do you expect this person to achieve within their first 90 days? A clear job description and measurable KPIs set the foundation for finding the right fit.

Cultural alignment is another critical factor. Your salespeople are the face of your business to prospects and customers. Their ability to embody your company’s values and mission can make or break the customer experience. A candidate might have a stellar track record, but if their approach clashes with your team’s culture, the partnership is unlikely to succeed. At the same time, skills and experience must align with the specific demands of the role. For instance, if your goal is aggressive market penetration, you need a hunter mentality, someone skilled in building relationships from scratch and closing deals in uncharted territory.

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Mastering Sales Channels: How to Align Your Strategy for Maximum Impact

Understanding the dynamics of sales channels can transform how businesses approach their markets. Many sales professionals, whether they are salespeople, managers, or CEOs, often miss a critical distinction: the difference between the product they are selling and the value it provides. 

This gap in understanding can lead to suboptimal sales performance, particularly in environments where products are sold through intermediaries, such as distributors, referral partners, or dealer networks. The challenge is not just about knowing your product, but also about understanding how to position it in a way that resonates with every player in the sales chain.

Sales success starts with recognizing who your true customer is. In sales management or channel sales, the end customer is often not the person you interact with directly. Instead, your “customer” might be the intermediary, your distributor, reseller, or even your own sales team. These intermediaries are the ones who ultimately connect your product to its final user. If you don’t understand their challenges, motivations, and context, you risk failing to equip them with the necessary tools to succeed. Are you selling a product’s features, or are you helping them understand how to sell it effectively? This distinction is vital.

When selling through intermediaries, the emphasis should shift from “what the product does” to “how the product can be sold.” Your distributors or referral partners don’t need every technical detail of your product. They need clarity on how it solves problems for their customers, how it fits into their existing offerings, and how they can position it to drive sales. 

The goal is not to overwhelm your partners with information but to provide actionable insights that align with their specific needs. If you’re focusing solely on product features, you’re likely missing the mark.

Salespeople and sales managers must also recognize the game they are playing. Are you selling a commodity, a widely available product, or an exclusive offering? Each scenario demands a different strategy. 

Commodities often compete on price, necessitating bulk sales or value-added services to differentiate themselves. Widely available products often rely on relationships, service quality, or unique add-ons to differentiate themselves. Exclusive products, on the other hand, can often avoid price wars by emphasizing their uniqueness and superior quality. Knowing which game you’re in allows you to tailor your approach and avoid misaligned strategies.

For small businesses and solopreneurs, the challenge lies in effectively managing referral partners. Referral partnerships are a powerful way to generate leads, but they require careful management and oversight. 

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Two Tall Guys Talking Sales – Sales Strategies That Outperform AI Tools: ICP, Value Selling, and Revenue Management – Episode 150

In today’s fast-changing sales landscape, everyone is talking about AI, automation, and digital tools, but are these the keys to sales success? In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey explore why documenting your sales processes, defining your ideal client profile (ICP), and sharpening your value selling approach must come before chasing shiny new technologies. Whether you’re leading a sales team or building revenue generation strategies as a… Two Tall Guys Talking Sales – Sales Strategies That Outperform AI Tools: ICP, Value Selling, and Revenue Management – Episode 150

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.

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