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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Welcome to Shadow Seller's blog, where we're all about ditching outdated sales methods for cutting-edge excellence.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



I don’t usually write multiple blogs in the space of a few days but Andy Kessler’s article in the WSJ this morning has compelled me. Kessler is discussing concern, on the one hand, around ai, and the excitement on the other. Kessler uses a Silicon Valley investment metaphor (that of painkillers and vitamins) to help us in our categorization. Anyone who knows me, knows that I’m always warning against using these kinds of extreme positions and how humans gravitate toward them They make our lives easier (or we think they do). The question here is using Kessler’s advice, how does Shadow stack up? Vitamin or painkiller? Net contributor, or net destroyer? I think its both, and here’s why.


AI's Rollercoaster Ride in 11 Months

In a mere 11 months since OpenAI's ChatGPT was introduced, the AI landscape has expanded exponentially. New players and capabilities have emerged, extending beyond text into uncharted territories. The question that lingers: Will generative AI steal our jobs, lead to human extinction, or create unprecedented wealth? The answer, as always, is complex.


Some perspective:

  • Sam Altman's Vision: UBI and Existential Risks - Sam Altman, the mind behind OpenAI, envisions a future where AI shoulders an increasing share of human work. He predicts that by 2031, AI's profits could fund a universal basic income (UBI) of $13,500 per year for every American, even without them lifting a finger. Yet, Altman remains acutely aware of the grave existential risks AI brings to the table.

  • Venture Capitalist Vinod Khosla's Bold Prediction - Vinod Khosla joins the conversation, boldly declaring that within a decade, AI could handle 80% of 80% of today's jobs. However, he overlooks the fact that AI has the potential to create 80% more and better jobs, not just displace existing ones. And to quote Leslie Neilson in Naked Gun, "there's only a 50% chance of that."

Shadow as the Perfect Balance

Shadow embodies the duality of AI as both a painkiller and a vitamin in the realm of B2B sales. Here's how:

  • Painkiller Aspect: Streamlining Sales Operations

Shadow acts as a painkiller by automating some mundane sales tasks, allowing sales professionals to reclaim their time and focus on higher-value activities. It enhances efficiency, and effectiveness. It's the tool that eases the burdens and time constraints sellers confront. As we say; it helps sellers be better prepared, faster and with less effort. It a poster child for the idea of “working smarter, not harder.”

  • Vitamin Aspect: Fueling Revenue Growth

Shadow AI, in its vitamin role, empowers B2B sales teams to basically “be better.” You’d think if that’s true, sellers using Shadow will win more, therefore boosting revenue. Shadow provides personalized insights and recommendations that lead to higher conversion rates. And it’s not that Shadow is always sharing something you didn’t know (so all you cleverest people in the room can relax) they’re sharing subtleties and nuances. They’re reminding us, in this world of cognitive overload, about fundamental thoughts and ideas that are often forgotten or ignored.


Roy Bahat's Perspective: Looms, Slide Rules, and Cranes

Venture capitalist Roy Bahat offers a refined perspective, categorizing AI projects as looms (replacing workers), slide rules (assisting humans), or cranes (extending human abilities). Again, it’s hard to pick one category, it often depends on how you use such tools and how good you are at using them. Shadow is a slide rule AND a crane, assisting and extending the capabilities of sellers, not replacing them.


Shining a light - Shadow AI's Dual Role in B2B Sales

In the evolving realm of AI, Shadow embodies a delicate equilibrium. We are both a painkiller, streamlining sales for efficiency, and a vitamin, fueling effectiveness and success that leads to revenue growth. Our multifaceted nature extends beyond categorization, acting as both a slide rule, aiding daily tasks, and a crane, elevating capabilities.


We mentioned duality earlier, so not to wrap things up too dramatically, but maybe ai is even more similar to us, in that it possesses its own duality. You know, like Matthew Modine, as Pvt Joker, pointed out in Full Metal Jacket when being asked about having "born to kill" on his helmet and a peace symbol on his uniform - "you know the Jungian thing."

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Imagine a salesperson we'll call Jack. Jack just sat through a week-long sales boot camp (in person or otherwise). By Friday, his brain is like a sponge that's been left under a running faucet—dripping with excess information and incapable of soaking up another drop. Jack, like so many in his field, is a victim not just of bad timing in training, but also the corporate belief that when it comes to training, more is always better. Spoiler alert: It's not.


When Just-in-Time Beats Just-in-Case

Traditional sales training operates on a "just-in-case" model. It's the equivalent of learning how to fix a tire before you even know how to drive—sure, it might come in handy someday, but by the time you need it, you'll probably have forgotten which tool does what. Contrast this with the "just-in-time" model, which is like having a mechanic show you the ropes when you're roadside with a flat. This method ensures that learning is immediately relevant and applicable, and is becoming more available with AI-powered sales coaching tools.


The benefits of just-in-time learning aren't just anecdotal. The Forgetting Curve—a concept first introduced by psychologist Hermann Ebbinghaus—demonstrates that without reinforcement, we start losing the memory of learned knowledge in a matter of days. In fact, research suggests that within one hour, people will have forgotten an average of 50 percent of the information presented. Within 24 hours, this number rises to 70 percent, and if a week passes without that knowledge being applied, up to 90 percent could be lost. That’s not just a curve; it’s a cliff.


Imagine we plot Jack's training retention on a graph. It wouldn't be a slow, gentle slope but a steep dive, like a rollercoaster when you've just reached the peak and are bracing for the drop. Now, that’s the type of adrenaline rush you want your sales team to avoid - right?


Cognitive Overload: When More is Less

Then there’s the information overload. It’s the age of big data, but bigger isn't always better, especially when it comes to learning. Cognitive load theory tells us that our working memory has limits. Bombard it with too much information, and you'll jam the gears. Sales training is full with too much information, and crammed with complexity.

In our age of multitasking myths, cognitive overload is the supervillain. It swoops in when we pile up the sales techniques, sales methods, strategies & tactics, industry insights, pollical know-how, psychology, neuroscience, expecting sellers (young & old) to switch gears at lightning speed. But here's the kicker: A study published in the journal 'Computers in Human Behavior' found that participants who multitasked during cognitive tasks experienced significant performance drops. In terms of sales training, this means that the more we dump on our trainees at once, the less they’re actually learning. It's like expecting Jack to learn to juggle while riding a unicycle. Entertaining, yes. Effective? Not so much. And as our window of opportunity to spend time with prospects continue to close – we have to be at our best when these opportunities present.


It's complicated…and expensive

There's a peculiar badge of honor that traditional sales training seems to pursue—complexity. Somewhere along the line, we started to measure the effectiveness of a training program by how intricate it could become. Instead of sticking to the core principles of sales—connection, understanding, solution, and closure—we've entangled the process with a labyrinth of techniques, acronyms, and processes that would make even Da Vinci's head spin. This convoluted approach may have succeeded in making sales training seem like an arcane art only accessible to the few with a Rosetta Stone, but in reality, it has done a disservice to many sales professionals. They're often left with a toolbox so overstocked and disorganized it's nearly impossible to find the right tool when the moment of truth arrives in front of a potential client. Simplicity is the soul of efficiency, especially in AI sales coaching tools, but traditional sales training has forgotten this, opting instead for a complex system where less could truly be more.


Shining the light

So, what’s the takeaway? The old approach to sales training needs to be put out to pasture. Instead, it's time to water the garden gently—with targeted, timely readiness thinking, ideas and tools that get sellers better prepared, faster and with less effort. Let's give Jack and his colleagues what they need when they need it, so that information is a tool they use, not a flood they feel will drown them.


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Updated: Sep 17



Ever been alone on an empty train station platform? It's an eerie feeling. Train stations are usually bustling places, so when they're not, and you're the only one there, they feel particularly alien. Sales & revenue leadership are starting to feel like deserted train stations. "I'm waiting for my train to come in. I'm betting everything on this one." Often it doesn't come at all - if it does, it's always late! If I look down the track will I see the light at the end...of my own tunnel of doom.


In sales & revenue leadership, familiar challenges persist, demanding resolute action and innovative solutions. Conversations with industry insiders reveal a disconcerting status quo. Sales leaders, burdened with shockingly short tenures, are often held hostage by a ceaseless pursuit of elusive mega-deals, while a yawning chasm divides executive strategies from frontline realities.


Low conversion and win rates, pipeline pandemonium, recruitment quagmires, strategy whiplash, and the uphill battle of managing sky-high expectations form the battleground.


However, let's dive headfirst into the five relentless challenges and seize them by the horns:


1. Overreliance on a Subset of the Team

Sales leaders habitually bank on a tiny cadre of top performers, a perilous bet that risks burnout and skews team dynamics.


2. Ensuring Team Consistency

Consistency in sales approaches and customer interactions isn't a luxury; it's the lifeblood of success. Deviations sow confusion and stifle growth.


3. Setting Expectations for Sales Cycle Stages

Effectively navigating the intricacies of each sales cycle stage is a Herculean task. Inconsistent behaviors jeopardize win rates and pipeline integrity.


4. Managing Onboarding Amid Turnover

Skyrocketing turnover rates in sales roles necessitate perpetual onboarding and training, or risk operational paralysis.


5. Leveraging Technology Effectively

The sales tech landscape is a jungle, and navigating it overwhelms sellers already drowning in information.


Shining the light


It's time to shatter the shackles of antiquated practices and demand a revolution. Sales training (for example) is an age-old relic that hasn't changed in years, and hasn't delivered in decades. It's time to consign it to the scrap heap of modern commerce.


We require dynamic, real-time knowledge, and know-how, delivered precisely when it matters, at the point of engagement. The time for change is now. In this tumultuous landscape, embracing innovation isn't an option; it's a survival imperative. Let's shed the old skin, demand transparency, and arm ourselves with strategies attuned to the modern sales battlefield. Only then can we empower sales leaders and their teams to not just survive but thrive in this ever-evolving marketplace.

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