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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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Admin Drag Is Killing Your Sales Capacity: How to Reclaim Selling Time With AI

Episode 23 of “AI Tools for Sales Pros” is built around a reality most leadership teams have started to feel in their gut. Buying AI does not increase revenue. It might increase activity, content volume, and dashboard noise, but revenue generation improves only when you reclaim selling time and redeploy it into the actions that move deals forward.

The executive version of the problem is simple. Your tech stack cost keeps rising. Your board wants proof that those investments translate into pipeline quality, cycle-time reduction, win-rate improvement, and improved margins. “Are we getting value?” is the polite question. “Where is the revenue?” is what they ask when patience runs out. This is a revenue management problem, not a software problem.

Most B2B companies are operating with a hidden productivity ceiling. Salespeople spend roughly a third of their time on revenue-producing work. The rest disappears into administrative drag: CRM updates, transcript cleanup, internal coordination, re-entering data across tools, searching for collateral, chasing security documentation, fixing records, and managing handoffs. None of that is value selling. Most of it is friction disguised as “process.”

A useful way to see it is the Tollbooth Effect. One approval feels reasonable. One form feels harmless. One handoff feels like good governance. Together, they turn selling into paperwork. The rep has a strong discovery call and a clear hypothesis. Momentum is real. Then they hit the toll plaza: systems require updates, internal teams need briefings, fields need to be filled, and the same information gets retyped because two systems disagree on the truth. By the time the rep finishes paying the tolls, urgency has cooled, follow-up becomes generic, and the deal loses its edge.

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Building a Zero-Cost AI Sales Stack: How to Validate Value Before You Spend a Dollar

Most sales leaders today feel the tension between innovation and fiscal responsibility. You know artificial intelligence can accelerate productivity, clarify messaging, and drive revenue generation. You also know your competitors are implementing AI-driven sales processes and reaping the benefits. Yet you are expected to somehow produce results without the budget to experiment, test, or validate new technology.

This pressure creates the classic chicken-and-egg dilemma. You cannot get budget approval without demonstrating value, but you cannot demonstrate value without access to capable tools. That tension often leaves sales leaders paralyzed, observing advancements but unable to participate. It is an exhausting cycle that erodes confidence and slows down organizational progress.

The good news is that modern software economics have shifted. You no longer need an enterprise-level budget to run meaningful AI pilots. Instead, today’s freemium models allow teams to build real workflows, automate real processes, and create real sales success with no financial risk. These free tiers exist because vendors want you to become reliant on the workflow, meaning you can use that dynamic to your advantage as you design early-stage pilots.

A practical approach for sales management is to treat free AI tools as validation engines rather than long-term solutions. You begin with lightweight experimentation, focusing on a single friction point that slows your team. Whether the issue involves pre-call research, drafting follow-up emails, or scoring inbound leads, AI can automate repetitive tasks, freeing your sellers to focus on value selling. The goal is not perfection; it is measurement.

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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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Stop Betting on Superstars: How Operating Standards Turn Sellers into Predictable Producers

Many teams grow, but few truly scale revenue beyond individual hero efforts. That difference changes everything for leaders today and in the future. Growth relies on hustle; scaling depends on repeatability across segments and individuals. Your strategy must reflect that hard truth in practice.

Are you relying on one standout to win deals month after month? That looks strong until risk turns visible and costly. One resignation can cripple momentum and expose brittle systems that you had previously ignored.

Scalable sales replaces heroics with defined, teachable operating rhythms that everyone follows. It turns chaos into predictable pipeline progress and results. It clarifies markets, messages, motions, and measurable expectations for every seller on a weekly basis. It builds leverage into onboarding and coaching for consistency. It protects margins while systematically accelerating win rates and velocity across territories.

The foundation begins with a clear picture of your ideal customer, including any disqualifying factors. Having an accurate Ideal Client Profile (ICP) helps minimize waste and reduce uncertainty in your efforts. Take time to define firmographics, pain points, triggers, and buying behaviors using consistent language based on shared evidence. Understand who cares about these issues and why it matters to them now. Also, identify negative personas to sharpen your focus and qualification processes in marketing and sales. A well-defined ICP can significantly boost your conversion rates and shorten the sales cycle.

Next, turn your ICP into straightforward messaging and discovery frameworks tailored for each stage. Consider what unique problems you solve for your customers. What outcomes are most important to them, and who are the key stakeholders by role and priority?

Build talk tracks that lead buyers, not chase buyers with purpose always. Anchor questions to the business metrics and risks they feel. Teach a qualification that tests mutual commitment and outlines next steps with attached dates. Avoid fluffy demos; design relevant proofs using their data. Process specificity turns B players into consistent producers without copying another personality.

I suggest you establish a practical, stage-based operating rhythm that everyone can easily understand and follow. By sharing clear definitions and expectations, managing the pipeline becomes a consistent and smooth process each week. Define each stage with specific exit criteria—avoiding vague intentions or subjective feelings. For example, discovery is considered complete when stakeholders confirm the consequences and impact, and solution fit is achieved when success criteria and ownership are clearly aligned. The commit stage should be backed by a shared plan with clear dates and assigned owners. During weekly reviews, focus on assessing quality rather than just quantity or activity counts. Ask yourself:

  • Does evidence from buyers’ backstage moves have a direct impact on their purchasing decisions?
  • Are the next steps specific, mutually agreed upon, and already scheduled on both calendars?
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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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Reclaiming Hours of Selling Time with AI – Lessons from MAICON 2025

You just checked your team’s dashboard. Activity looks fine. But deep down, you know that the numbers don’t tell the whole story.

Every salesperson loses time to the same unseen burden: administrative drag. After each successful discovery call, there’s a 20-minute grind with CRM updates, email summaries, and internal handoffs. This “sales tax” cuts into selling time, hurts momentum, and costs your company thousands weekly in lost productivity.

I just returned from MAICON 2025, and I was so inspired that I wanted to share some of the biggest lessons. At the MAICON 2025 conference in Cleveland, the message was clear: artificial intelligence is changing sales management, not by replacing people, but by empowering them. The winning teams are using AI to eliminate “digital grunt work” through orchestration, not standardization.

Orchestration, Not Standardization

MAICON’s main message was that sales leaders should stop searching for the “one magical platform.” Instead, the most successful organizations coordinate several top-tier tools. Their AI ecosystems are modular, flexible, and collaborative.

It starts with three pieces:

  1. a transcription tool like Fireflies,
  2. an automation hub like Make.com or Zapier,
  3. your existing CRM and communication systems.
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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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