👋 Welcome to another issue of The Enablement Edge newsletter!
It’s been a few weeks since I last dropped into your inbox. August was a little quieter on my side, but things are picking up again – and I’ve got plenty to share.
Sit back, relax, and get ready for:
- 🎯 Key Concept – The missing decision between training and live work
- ✅ Key Best Practice – Which sales effectiveness metrics to track?
- 🎬 This Week’s Video – Why your sales onboarding isn’t creating productive reps
- 🤖 Key Piece of Tech – Making approved content easy to find
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🎯 Key Concept
I’ve spent a lot of time writing about how organisations can design, deliver, and reinforce sales training.
Yet every training programme eventually reaches a decision moment that receives far less attention:
“When do we have enough evidence to let a rep handle live customer conversations?”
Completing the assigned learning is rarely enough. A knowledge check can show what someone remembers, while a roleplay can reveal how they perform in one simulated situation.
The organisation still needs to decide whether that evidence supports releasing the rep into the field.
That question led me to explore sales readiness certification in more depth.
The result is a new guide created in partnership with PitchMonster, an AI sales roleplay platform that helps teams build buyer scenarios, score recorded attempts against their own scorecards, and walk each rep through a post-session AI Coach debrief before revealing the evaluation.
The central idea I kept coming back to was that certification should operate as a controlled release decision.
Instead of asking whether a rep is broadly “ready”, define the specific work they can begin performing after they pass:
- Which conversation can they handle?
- With which buyer, segment, and offer?
- What support or job aids can they use?
- Which situations still require a manager?
- What evidence must they produce before gaining greater independence?
A new business development representative, for example, might be cleared to run standard outbound conversations with mid-market buyers using approved messaging.
However, that specific certification would not automatically clear them to lead discovery, make commercial commitments, or handle conversations involving greater risk.
The evidence should also become more direct as the rep moves towards live work.
Knowledge checks can show whether they understand the product, buyer, and process. Case exercises can reveal whether they can choose an appropriate response.
Structured roleplays show whether they can produce the required behaviours, while varied scenarios test whether they can adapt when the conversation changes.
Passing the pre-live certification remains provisional.
Early customer calls provide the next layer of evidence by showing whether the behaviours demonstrated in simulation transfer into normal working conditions. Continued observation then tells you whether those behaviours remain stable over time.
This approach changes how you build the certification. You need a behavioural scorecard, realistic scenarios, clear must-pass criteria, and a defined process for reviewing live performance after release.
In the evidence stack above, AI roleplay can strengthen the Perform it and Adapt it stages by expanding the amount and variety of practice available. The organisation still owns the standard and the final decision.
The full guide explains how to define the release decision, build the scorecard and scenario bank, use AI roleplay appropriately, calibrate assessors, and validate readiness once reps enter the field.
✅ Key Best Practice
Which sales effectiveness metrics do you actually need to track?
I recently put together a guide covering 17 of them.
So, naturally, the answer is...17.
Just kidding. Please, don’t build that dashboard. 😅
Before choosing the metrics, it helps to clarify what we mean by sales effectiveness.
I use the term to describe how well a sales organisation produces its intended commercial outcomes. This includes whether it achieves its targets, converts qualified opportunities, closes deals at the intended value, and wins the customers the commercial strategy has prioritised.
It sits alongside two related ideas:
- Sales efficiency considers the cost, time, effort, and concessions required to produce them.
- Sales productivity considers how much output the organisation generates from its available sales capacity.
These perspectives are closely connected, but they answer different questions. A team may convert opportunities successfully and win valuable deals while requiring excessive time, support, or discounting. Another may operate quickly and economically while producing weak commercial outcomes.
Keeping the concepts separate gives you a better chance of identifying what needs attention.
The useful set of sales effectiveness metrics will depend heavily on what your team is trying to understand, how you sell, and which outcomes different roles actually influence.
Start with the commercial question.
If you’re trying to understand whether opportunities are converting successfully, win rate is an obvious place to look.
If the concern is whether sellers are consistently delivering against expectations, quota attainment becomes more relevant.
If you want to understand the value of the deals you are winning, average deal size deserves attention.
For teams responsible for existing customers, expansion revenue or customer lifetime value might play a bigger role.
The sales motion is another important factor.
A high-volume SMB team, an enterprise new-business organisation, and an account management team should not automatically be staring at the same effectiveness dashboard.
Their sales cycles, opportunity volumes, deal values, responsibilities, and definitions of a successful outcome are different.
I’d also ask a very practical question about every metric, “What are we going to do differently after seeing it?”
A metric may be interesting to leadership without being especially useful for coaching or day-to-day decision-making.
Another important thing to consider is that many of the effectiveness metrics are influenced by plenty of factors outside seller execution: product-market fit, pricing, market conditions, territory design, lead quality, headcount changes, and more.
So, read them as signals within a wider commercial system, rather than perfectly isolated measures of how “good” your sales team is.
The goal is to build a small set that gives you enough visibility to answer the questions your organisation actually has.
In practice, I’d choose based on:
- The commercial outcomes you are trying to understand
- The part of the customer journey the team owns
- Your sales motion, segment, and business model
- Whether the metric can be segmented and investigated further
- Whether someone can realistically act on what it tells you
You can always add or remove metrics as the questions change.
Your dashboard needs to help you understand whether your sales organisation is producing the outcomes you expect, where those outcomes differ, and where closer attention may be warranted.
In close collaboration with revenue acceleration partner revlogic, I’ve broken down 17 sales effectiveness metrics in the full guide, including how each one works, what it can tell you, and the nuances to keep in mind when using it.
Think of it as a menu for building the measurement set that fits your own sales organisation, and not a checklist you need to complete.
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🎥 This Week's Video
Why your sales onboarding isn’t creating productive reps (and how to fix it)
Have you ever seen a new rep finish onboarding, join their first customer call, and realise they still weren’t really ready?
I’ve seen that happen a lot.
In this video, I share a practical way to rethink sales onboarding so the focus moves away from simply completing training and towards preparing reps for the next important part of the job.
🤖 Key Piece of Tech
Picture this.
A rep has a customer call in ten minutes and needs the latest security deck.
There is an approved version somewhere in the content library.
The problem is that finding it means opening another system, navigating a folder structure, applying the right filters, and working out which of three similarly named files is actually current.
Meanwhile, there is a PDF sitting on their desktop from six months ago.
Which one do you think gets used?
This is one of the main tensions that kept popping up while I was doing research for my new guide to sales content management software.
The teams responsible for content have perfectly legitimate priorities.
Marketing wants messaging to stay consistent. Product wants the latest information represented accurately. Legal and compliance may need tight control over what can be shared. Enablement wants sellers using the right assets, in the right situations.
Version control, permissions, approvals, expiry dates, and regional variations all exist for good reasons, there’s no doubt about that.
Sellers, however, have a much simpler priority: I need the right thing quickly.
Whenever those two realities collide, friction appears.
Make the approved route cumbersome enough, and people start creating their own shortcuts.
They download decks locally. Or reuse old email attachments. They keep personal folders. Or they hit up a colleague on Slack to send whatever they used last time.
This is why I like one simple principle when thinking about sales content management:
Make the approved path the easiest path.
A seller should not have to choose between speed and compliance.
The latest approved asset should be easier to find than the outdated copy sitting on their desktop.
In practice, this could involve making search genuinely useful, surfacing content inside the CRM or other existing workflows, clearly identifying the current version, automatically retiring outdated material, applying permissions in the background, and recommending relevant assets based on the seller’s context.
Good governance should reduce risk without inadvertently creating an incentive to bypass the system.
I explored this tension between control and usability in much more detail in my sales content management software buyer guide, alongside content discovery, buyer sharing, analytics, integrations, implementation effort, and how the leading platforms approach the category differently.
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