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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!

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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Stop Researching, Start Connecting: An AI-Powered System for Warm Introductions

Most sales teams begin the week by opening a dozen browser tabs and grinding through scattered research, LinkedIn, Google News, company websites, and databases. Hours later, they emerge with a few generic talking points and a cold list that still feels cold. The deeper issue isn’t inefficiency; it’s invisibility. Warm introductions already exist across your company’s network, in email histories, calendars, and executives’ LinkedIn connections, but you can’t see them on Monday morning.

The Relationship-First approach changes that default. Before a single cold call or email, you perform a deliberate “Warm Path Check.” You ask, “Who do we know who knows them?” This question transforms prospecting from random outreach into a repeatable, data-driven process that prioritizes relationships. When you start as a referred conversation rather than an interruption, skepticism drops, credibility rises, and the sales cycle compresses dramatically.

The Hidden Network You’re Not Using

Every organization has an untapped network, a web of past colleagues, vendors, and clients who could open doors to your dream accounts. The problem is that this network is hidden in plain sight. It lives in the collective memory of your company’s communication patterns, but there’s no easy way to access it manually. That’s where KnowledgeNet comes in.

KnowledgeNet serves as your organization’s “relationship intelligence” layer. It analyzes communication data (emails, meetings, messages) to reveal who knows whom, and how strong those connections really are. Instead of guessing, you can instantly see that a colleague in engineering once worked closely with the CFO of a target account. That’s a warm path waiting to be used.

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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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Automating Sales Workflows: When to Use Automation Over Chat

In sales management, there’s often some confusion about when to use artificial intelligence chat interfaces versus automation workflows. Chat interfaces are ideal for creative problem-solving, learning, and strategic research, while automation excels in repetitive, high-volume, data-driven sales tasks. The trick is to recognize when consistency and scalability are more important than customization.

Automation delivers consistent execution, eliminates human error, and operates 24/7. Sales leaders can rely on it for triggered communications, data synchronization across systems, CRM updates, and compliance tasks that require accuracy and complete audit trails. By moving these routine tasks into automated workflows, sales teams free up valuable time for relationship building, revenue generation, and refining sales strategies.

Real-world examples highlight the impact: a team once spent three hours daily crafting manual follow-up emails. Shifting to automated sequences not only saved time but also improved messaging consistency and pipeline response rates. Similarly, another team utilized automation to synchronize sales data across six systems, thereby eliminating bottlenecks and enabling sellers to focus fully on sales.

Hybrid approaches really take things to the next level! By merging human creativity in chat interactions with the quick and precise power of automation, businesses can craft workflows that beautifully balance personalized service with the ability to grow. This type of teamwork enhances value-driven selling, sharpens business skills, and accelerates revenue management throughout the sales journey.

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Energize and Motivate: Essential Tips for an Effective Sales Kickoff Meeting

Before the year comes to a close, it’s time for sales teams and their leaders to prepare for the annual kickoff meeting. Don’t wait until December to start this process. If you have 50 or more people to invite, you may have to plan 6-9 months in advance. If your group is smaller (under 50), you should start planning by late September or early October.

This crucial event sets the stage for the upcoming year, establishing goals, strategies, and the motivation necessary to hit the ground running. Whether you are a salesperson, a sales manager, or the CEO of a small company, organizing an effective kickoff meeting is imperative to ensure a successful year ahead.

The first step in planning your annual sales meeting is to choose an appropriate venue. While it may be tempting to hold the meeting in your usual office space, it’s beneficial to opt for a location outside of your daily work environment. This helps to minimize distractions and fosters a creative atmosphere. 

A nearby hotel or a conference center can serve as an excellent venue. The key is to find a place where your team can focus entirely on the meeting without the usual interruptions from their day-to-day responsibilities.

Once the venue is secured, it’s time to think about who should be in attendance. While the primary focus will be on your sales team, consider including key personnel from other departments such as marketing, IT, and customer service. These individuals play a crucial role in supporting the sales process and can provide valuable insights and updates that will help your sales team achieve success. Additionally, involving them in the kickoff meeting promotes a sense of unity and collaboration across the company.

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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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The AI Sales Process Map: The Ten-Stage Sales Process Framework

Sales leaders today often fall into the trap of using artificial intelligence tools randomly rather than systematically. This sporadic usage is like owning a Swiss Army knife but only using the bottle opener; you miss out on ninety percent of the available value. AI’s real power comes not from isolated tools but from integrating capabilities across every stage of your sales processes. When mapped correctly, AI accelerates every interaction, shortens sales cycles, and makes revenue generation more predictable.

Random AI adoption leads to inconsistent results. Some reps use it effectively, while others revert to manual methods under pressure, resulting in uneven performance. Systematic AI integration, however, compounds improvements across the entire sales cycle. Data captured at one stage strengthens the next, creating a virtuous cycle of sales success that is scalable, measurable, and sustainable. The outcome is not just faster deals, but stronger business acumen and more consistent revenue management.

The ten-stage AI sales process framework provides a structured way to apply AI:

  1. Prospecting,
  2. Outreach,
  3. Qualification,
  4. Scoping,
  5. Presentation,
  6. Economic Buyer meetings,
  7. Validation Events,
  8. Proposals,
  9. Closing,
  10. Onboarding/expansion.
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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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