top of page

Welcome to the “Savvy Seller” - Shadow Seller’s stories that spell out & 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Welcome to Shadow Seller's blog, where we're all about ditching outdated sales methods for cutting-edge excellence.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

As a Brit, there's some irony to penning something on American Independence. But the universal quest for freedom transcends borders, much like the transformative powers of Generative AI in the realm of sales. That sounds terribly grand, doesn’t it and might be a bit of a stretch, but here goes!

In the sweltering summer of 1776, America's Founding Fathers deliberated intensely in Philadelphia, drafting a document that would boldly declare their independence and reshape the future. There was lots of weeping, wailing, gnashing of teeth and sweating bullets (so to speak.) Today, in a similar spirit of revolutionary change (and summer heat), modern sales teams can declare freedom from outdated practices and constraints. With the advent of Generative AI (such as the innovative solutions provided by Shadow Seller AI - shameless plug), salespeople and sales leaders can liberate themselves from ineffective training, overbearing management, and the unpredictability that has long plagued the profession. So cast off those shackles, shout “no taxation without representation”, and read how GenAI ushers in a new era of independence and empowerment for sales professionals, leaders, and company executives alike.

  • The Revolutionary Promise of GenAI in Sales In the storied past of American Independence, the colonists sought freedom from oppressive governance and the limitations imposed by distant rulers (although I didn’t think they were that bad!) Similarly modern sales teams face their own set of challenges—outmoded training methods, constant pressure, unrealistic expectations, unnecessary and intrusive scrutiny, with sales leaders usually having to rely on a few top performers. Generative AI solutions (like Shadow Seller) represent a modern 'Declaration of Independence' for the sales world, offering freedom through technology (and domain know-how)  that revolutionizes sales readiness.

  • Emancipating Sales Teams For sales professionals feeling stifled by traditional training and management, GenAI provides a liberating alternative. By leveraging GenAI, sellers are equipped with tailored insights and real-time coaching & guidance, allowing them to manage & improve their performance independently. This shift reduces the reliance on sporadic training sessions and unproductive oversight, enabling salespeople to take control of their outcomes with confidence and autonomy.

  • Liberating Sales Leaders Sales leaders often find themselves tied down by the need to closely supervise deals and manage the uneven performance across their teams. GenAI offers an escape from these burdens by democratizing the skills and tactics typically reserved for top-tier sales performers. With the application of the right solutions & tools, leaders can elevate their entire team's performance, reducing the disparity between 'A players' and the rest. This not only alleviates the pressure on leaders to micromanage but also spreads opportunities more evenly across the team.

  • Freeing Company Leadership At the highest levels, company leaders grapple with the unpredictability of sales outcomes and the intense scrutiny from investors and board members that comes with it. GenAI can significantly mitigate these issues by providing more consistent and predictable performance. With a clearer understanding of sales dynamics and enhanced performance predictability, leaders can make more informed decisions, reducing the stress of unforeseen sales fluctuations.

Just as the signing of the Declaration of Independence marked a new beginning for America, the integration of GenAI in sales marks a pivotal shift towards independence and empowerment in the business world. Shadow Seller AI and similar technologies are not just tools; they are the bearers of a new sales revolution. By embracing these advancements, sales teams, leaders, and company executives can liberate themselves from the chains of traditional constraints, ushering in a new era of freedom, performance, efficiency, and success. Declare your independence today and lead your sales team into a new era of possibilities. Now you can go get a beer and a hot dog and enjoy America as we celebrate our independence.

15 views0 comments

A play on the phrase from olde England. When one monarch passed, and the heir to the throne took their place, it was an announcement that the (current) Queen (or King) is dead followed by a wish that the (new) Queen (or King) lived a long time.

Now that's cleared up...moving on...The first time I heard of a sales playbook I was introduced to it by someone I competed with and later collaborated with. They made a grand claim that they'd written a playbook that a much larger company hijacked and propelled them to success. Massive overstatement, but whatevs. At the time I was too dumb to ask the obvious question which was and remains “what is a sales playbook?” When I eventually did ask the question and got to see one, I was disappointed to say the least. All it was, and what most sales playbooks were, is pages of overcomplicated hard to read, word salad, mumbo jumbo. The word playbook was used loosely in the extreme.

It wasn't until a few years later that I'd actually saw a real football playbook and realized how the two couldn't be more different. Which explains the lack of success of sales playbooks despite their fashionable and popular status. But fortunately, we can see the end of the playbook era. Let's explain that.

Origins and Evolution

The idea of a sales playbook (as mentioned) is inspired by the concept of a playbook in sports, where coaches develop a series of predefined plays or strategies that players can execute during a game, given an intent and set of circumstances. Similarly, sales leaders create playbooks to equip their teams with predefined sales strategies, tactics, and actions given an intent and set of circumstances. According to TechCXO: “this approach has evolved over time with advancements in technology and data analytics, allowing for more dynamic and adaptive sales playbooks that can be updated in real-time to reflect changing market conditions and customer needs​.”

What is (or was) the sales playbook?

A sales playbook is a strategic document or toolkit designed to guide sales teams through various aspects of the sales process. It includes a compilation of best practices, strategies, messaging, and tools that sellers can use to effectively guide their engagement with prospects. It was designed to help answer the question “what do I do next?” The playbook typically outlines the following components:

  1. Sales Processes: Detailed descriptions of each step in the sales process, from prospecting to closing and beyond.

  2. Sales Strategies: Specific strategies tailored to different customer personas and sales scenarios.

  3. Messaging: Key messages, value propositions, and objection-handling techniques.

  4. Tools and Resources: Templates, scripts, and other resources that sales reps can use during their interactions with prospects.

  5. Metrics and Benchmarks: Performance indicators and goals to track progress and effectiveness.

  6. Training Materials: Content designed to help salespeople improve their skills and stay updated with the latest techniques.

It's getting complicated - right?

What was the Idea Behind Sales Playbooks?

The concept of sales playbooks is rooted in the idea of providing a standardized approach to sales that can be replicated and scaled across an organization. The primary goals of a sales playbook are to:

  • Ensure Consistency: By standardizing the sales approach, companies tried to ensure that all sales representatives behave similarly in given sales stages. They are supposed to deliver a consistent message and follow a process. Literally an attempt to get everyone on the same page!

  • Increase Efficiency: With a structured guide, sales reps could quickly access the information they need, reducing the time spent on planning and increasing the time spent on selling (not).

  • Improve Performance: By incorporating best practices and successful strategies, playbooks aim to improve the overall performance of the sales team.

  • Facilitate Training and Onboarding: Playbooks serve as a valuable training tool for new hires, helping them to get up to speed quicker with the company’s sales processes and methodologies.

Why sales playbook’s fail(ed)

Despite their benefits, traditional sales didn't help much:

  • Static Nature: Many sales playbooks are static documents that do not evolve with market changes, making them less effective over time. They get “developed once – used seldom.” The only place they “evolve” to is from being a printed doc, sitting on a desk, lonely and ignored, to a printed doc sitting on a bookshelf, feeling equally lonely and ignored.

  • Time-Consuming: to create and maintain. And too complicated to use. A comprehensive sales playbook takes time and people. Time we don't have and people who are generally unwilling or unable to do maintain them or use them.

  • Low Adoption: Sales teams never consistently use playbooks. They find them generic, rigid, over complicated or irrelevant to their daily activities. They’re un-engaging and boring. They can’t talk back!


So what does “long live playbooks” actually mean. Remember the definition. A playbook is a “document or toolkit designed to guide sales teams through various aspects of the sales process.” The next incarnation (just like the new Monarch) is the latest version. In this case sellers still need guidance and mentoring, there are simply far better ways of doing it these days. Ways that don’t suffer the shortcomings of the “olde” sales playbook idea. Ways that are dynamic, fast, and interactive. Ways that are agile and can adapt to the thrills and spills, ups and downs and ebbs and flows of the sales pursuit. So we salute the olde sales playbook, say thanks and God’s speed, and usher in the age of a new solution that really answers the question “what do I do next?”



0 views0 comments

We posted a few weeks ago about the idea that Gen AI is the great equalizer and used the idea of the old TV show and more recent movies starring Denzel Washington. In his book “Co Intelligence: Living and Working with AI,” Ethan Mollick talks about how AI has the biggest impact on the poorest or average performers. "In study after study the people who get the biggest boost from AI are those with the lowest initial ability - it turns poor performers into good performers."

Well, that sounds plausible and great and all that – but where’s the use case in B2B sales & marketing. Well, there’s a few, and one example is the dreaded account planning mission. That’s when you all get together and identify, discuss and plan several target accounts that, for whatever reason, you feel like you should be doing business with. This is a great use case for a specialized GenAI (like Shadow). How so, I hear you ask.

Lets quickly run through the shortcomings of the generally used current process, accepting that even using the various information tools available, it remains a real drag.

1. Inefficient Use of Time and Resources

  • Excessive Time Spent on Research: While understanding your target account is important, spending too much time gathering information is a huge time suck…and it’s BORING. It slows down the sales cycle and ultimately reduces the number of prospects you can engage with.

  • High Cost of Customization: Crafting highly tailored messages for each target account is also resource-intensive and highly debated. This can be particularly costly for small to mid-sized companies with a limited marketing and sales bandwidth.

  • It’s a task that is too often assigned to opposite ends of the capability and cost spectrum – e.g. junior reps and junior marketing people on the one hand (but they’re cheap!), people sitting offshore with nothing else to do (and they’re cheaper!) and senior sellers at the other end of the spectrum.

2. Assumptions and Misalignment

  • Assuming Needs and Priorities: Even with thorough research, there is a risk of misinterpreting or overestimating the importance of certain needs and priorities of the target account. We’re all victims of bias, being overly influenced by mistaken assumptions - e.g. “Company X buys Sitecore services from us, so now we offer Salesforce services they should buy those from us as well!”

  • Only we know our customers – the misplaced confidence that only you know best.

  • We’ve got our ICP: (a personal favorite.) You’ve analyzed your customers and think you’ve identified the reason they did business with you. Notwithstanding the obvious, (like “we only sell blue cars, so we only want to sell to people who want blue cars!”), the assumptions are too broad. ICP’s are slanted towards you (often subconsciously) – that’s the antithesis of being customer centric and obsessed with personalization.

 3. Scalability Issues

  • Difficulty Scaling Personalization: As your target list grows, maintaining a high level of personalization becomes increasingly difficult. This can lead to inconsistent messaging quality and effectiveness. What happens is that the closer you get to the end of the list the more you’ll see repetition in the messaging.

  • Resource Strain: Over-reliance on personalized messaging for each account strains your sales and marketing teams, potentially leading to burnout and reduced overall performance. Once more boredom rears its ugly head.

4. Delayed Engagement

  • Slow to Market: The time taken to gather information and craft personalized messages delays your engagement with potential customers. In fast-moving markets, this can result in missed opportunities.

5. Overcomplication and Lack of Focus

  • Complex Messaging: Crafting overly detailed and complex messages can dilute your core value proposition. Clear, concise, and compelling messaging often resonates more effectively. But you have to find the balance – we live in the era of increasing personalization and doing it at “scale” is something of an oxy-moron.

Alternative Approach: Finding the Balance

Most of these intentions and ideas of what target account planning is about and how it's done are valid - they just take too long, cost too much and are fraught with assumptions and biases. Why wouldn’t you use AI tools to gather insights, automate parts of the research, help craft the messaging, and combine it all together? This helps streamline efforts and ensure more timely, relevant engagement with prospects. Go back to the original thesis – GenAI is an equalizer. Used properly, it gives small and mid-sized companies the intellectual horsepower and time bandwidth of larger companies. How so?

  • Time – (is money). Its hard to get a statistically valid estimate of the amount of time companies spend doing this, and as we all know anyway, there are three types of a lies – “lies, damn lies and statistics.” Anecdotally, and based on my own experience, we spend hours on this across multiple people (per account). Even with resources sitting offshore, using GenAI will still save you time, money and produce better, unbiased results.

  • Boredom – most of this type of work is a real drag. The uncomfortable truth is people don’t like it, and as the time goes by the quality of their work declines. The explosion in internet information has actually made it worse, ‘cos there’s so much information out there, and God forbid we miss something.

  • Bias - Teams will sit around and identify their USP's (biased), then make superficial connections between those and the target companies. A well tuned, specialist AI is incapable of those types of biases. It'll tell you where the synergies really exist between your two organizations, and they're probably not where you think they are!

And now the hanging pitch:

  • Can’t I just use Chat GPT? – Chat GPT can neither get to the detail of the target company nor can it match those details up to your most contextually relevant USP’s. A specialized Gen AI (which is correctly tuned) can.  

A specialized Gen AI (which is correctly tuned) is also totally objective. It might not tell you what you want to hear, but as Denzel Washington says in another one of his movies (Man on Fire), in this context GenAI is like a bullet “and a bullet always tells the truth.”

15 views0 comments
bottom of page