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Welcome to the “Savvy Seller”
Shadow Seller’s stories that  simplify…

Welcome to Shadow Seller's blog, where we're all about ditching outdated sales methods for cutting-edge excellence. Here, we offer insights and strategies to boost the savvy of sales leaders, pros and CEOs. Dive into innovative sales tactics, bust myths, and discover hidden gems to streamline your workflow and enhance productivity. Our posts are packed with practical tips and real-world examples to shake up your sales approach. Whether you're a sales vet looking for an edge, a sales leader trying to finally overcome some of those repetitive problems or a CEO aiming for growth, you've found your resource. Join us on this journey to sales success and stay tuned for content on making sales simpler and more effective. Welcome aboard Shadow Seller's world

Mainly written by Sam Jacobs of Pavilion — borrowed & curated by me! ✂️📚

Most salespeople suck. Not because they’re bad people. Or lazy. But because sales is really hard. 😓📞


In 2023, across 650,000 opportunities representing ~$50B of pipeline, just 20% of reps delivered 80% of revenue. In 2024, that number fell to 14%. Just 14% of reps delivered 80% of all revenue in B2B tech! 📉

Want to know the funny thing? 😏

Those numbers haven’t changed much in the 25 years I’ve been doing this. ⏳

15 years ago, we used Objective Management Group to assess our sales team. The numbers were the same. The assessment told us to:

  • Hire 2 out of 10 people we thought would be a good fit 🧠

  • Keep 2 out of 10 that already worked for us 💼

  • The rest? ❌ Unsalvageable.


Over and over again, a small percentage of sellers generate almost all the revenue in an organization. 💰

So, the real question is:👉 Are the other 80% redeemable?

A better one might be:🔍 Can we shift the median performance of the 80% enough to warrant investing in development?

📊 Research says: YES.Investing in B players increases their odds of becoming A players by 63%. 🚀

Can you afford to make that investment? 💸

Or better yet...Can you afford not to? 🤔


Let’s break it down:

💪 INVESTING IN DEVELOPMENT

📈 According to Spotio:

  • ROI of training is 3.53:1 → Every $1 you invest returns $4.53 💵

  • Companies that prioritize training are 57% more effective than competitors 🏅

  • High-growth companies are ~2× more likely to provide ongoing sales training 🔄


🧠 HIRING ONLY A PLAYERS

Sounds smart, right? Well… ❌

Two problems:

  1. You’re probably bad at hiring 🙃

  2. Performance isn’t portable 🧳Top 1% at Company A? Could flop at Company B due to different:

    1. Products

    2. Processes

    3. Culture

    4. Team dynamics

Harvard calls this the “portability of performance” problem. Star employees are “imperfectly mobile” resources. 🤷‍♂️


More reasons to pause before chasing stars:

  • 💸 High cost & ROI uncertainty — Big salaries, bonuses, guarantees, recruiter fees. If they slump? You burn cash.

  • 🧯 Expensive mistakes — A failed sales hire can cost $500k+ including lost revenue and morale drag.


🧾 BOTTOM LINE:

Most people are bad at their jobs.Most salespeople cannot sell. 🧍‍♂️📉

You can invest in development — it’ll help.You can try to hire only A players — good luck. 🎯

The best answer?💡 Do both.But route your best leads to proven performers 🔄And build a system that feels unfair — but works. ⚖️📈

Yes, that means 10–20% of your reps will generate nearly all your business.And maybe…That’s OK. 🤷

 
 
 

"The elephant in the room” refers to the big, obvious issue everyone sees but avoids discussing.
"The elephant in the room” refers to the big, obvious issue everyone sees but avoids discussing.

Pride & Prejudice in Generative AI - the Elephant in the Room

AI has arrived, and many are experimenting with tools like ChatGPT. Yet fully embracing AI across sales organizations is slow and often stalls. Emerging scandals at companies like 11X don't help. Leaders rightly cite data security, costs, or unpredictable ROI, but these “first objections” hide a deeper fear, and as any competent seller knows, the objections first raised are rarely the objections most real.


In the context of AI, the elephant all leads back to one thing - Fear. The fear of being replaced, being wrong, or losing relevance. While few openly admit it, this anxiety derails progress.


Listen to the Pod:


Fear & Loathing: Emotional Undercurrents


  1. Fear of Obsolescence - We take pride in our instincts and expertise. The idea that a machine might replicate or surpass these skills can feel like a direct threat to personal value.


  2. Fear of the Unknown - AI can seem like a black box. When sales professionals don’t fully understand how it arrives at insights, distrust grows—and people often fear what they can’t control.


  3. Fear of Losing Purpose - Salespeople thrive on personal connections and problem-solving. If AI handles some of this, many wonder what’s left for them.


  4. Fear of Not Keeping Up - No one wants to be the leader who “doesn’t get” AI. The prospect of falling behind or being seen as out of touch sparks defensiveness.


Like current political scenes across the West, we have become conditioned to not concede any ground (on anything), ever, including the admission of some trepidation around something like AI.  It’s become seen as one extreme or the other - “all” fear or “no” fear. But as Bill Paxton rightly points out in the movie Edge of Tomorrow – “there is courage without fear.”


Pride & Vanity: Fear of Admitting You Need Help

In modern culture—especially sales—confidence is currency. Everyone seems to be the smartest person in the room these days! Accepting that AI could offer a better way means acknowledging gaps in one’s knowledge or strategy.


  1. The Image of Competence - Leaders build careers on having the right answers. Suggesting an algorithm might outperform long-honed techniques can feel like betraying core expertise.

    • High-Ego Cultures: In sink-or-swim environments, uncertainty is taboo. Leaders who don’t immediately see AI’s fit may dismiss it to protect their authority.

    • Performance Pressure: With quarterly targets under scrutiny, endorsing a new, unproven approach can be risky. If AI fails, it’s on them; if it succeeds, it might highlight prior inefficiencies.


  2. Dismissing New Approaches - Calling AI “just hype” preserves the status quo. That way, leaders can avoid pilot programs that might fail—or succeed too well and force change.

    • Avoidance of Change: Implementing AI often reveals inefficiencies. Many prefer to keep the lid on potential disruptions.

    • Cultural Resistance: Top-down environments rarely welcome outside help. Admitting a knowledge gap can feel like weakness.


  3. Downplaying Ineffective Methods - Leaders may blame poor leads, mediocre products or inconsistent team performance rather than admit traditional strategies are faltering. AI could expose those shortcomings.

    • Cognitive Dissonance: It’s painful to discover a championed method is outdated. AI, as a disruptor, threatens to shine a light on blind spots.

    • Ego Protection: Accepting AI means revealing diminishing returns in “tried-and-true” approaches—a tough pill to swallow.

    • Fear of Letting Go: Trusting algorithms over gut instinct is unsettling for leaders used to making calls based on experience.


Conclusion


Company leaders need to be looking through the prism of AI “every” time they consider their business challenges and opportunities. Their team can exhibit all the natural fears and vanities we’ve discussed, but even though it would be unnatural for them not to suffer from the same, they need to recognize this and push through. Every member of a leadership team needs to have, or come in with, ideas and suggestions as to how they can use AI to benefit their people and the business. To end with a fabulous cliché, any other behavior is failing to plan. And we all know that means you’re planning to fail!

 
 
 
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