Context wins deals. Sales enablement ignores it.

Soon after I started my first job in pre-sales, I went to a customer meeting at one of the top three online retailers in the US. I went there with my boss, let’s call him Ralph. We were there to save the account. We were on the brink of losing their business because our CDN performance was lagging our competitors.

Ralph was a funny guy. Likeable, always smiling. We met some folks from the company outside the building. There were many jokes and laughs as we made our way to the conference room. Sat across the table was a man, let’s call him Albert. Ralph wasn’t expecting Albert at all. His face changed in an instant. He told me quietly: “Albert hates me. We’re dead”. 

Instinctively, I took control of the meeting. But here is the important part. I changed the context. I abandoned our original plan of repairing the relationship. Instead, taking advantage of my role as the “new technical guy”, I shifted attention to the problem right away. It worked wonders. What could have been a potentially frosty meeting, turned out to be a very productive one.

I learned two sales lessons that day. I was aware of the first one, that relationships matter. But the second lesson was subtle and yet equally powerful. The person who reads the situation and adjusts on the fly wins. It was true in that conference room. It has been true in nearly every deal situation I've seen since.   

Context matters. A lot.

For sellers, saying the right thing, at the right time, to the right people is so important that a couple of decades ago, a whole new function called sales enablement was formalized. Since then, that industry has grown dramatically. In 2024, the global market for sales enablement platforms was $5 billion, projected to grow at roughly 16-18% annually through the rest of the decade. Technological innovations such as microlearning, gamification, AI-driven content recommendations, and role-play simulations, among others, have fueled this growth. 

But has that translated into the sales performance that leaders had hoped? The data seems to indicate otherwise. In 2011, the average quota attainment rate was 63%. By 2017, it had dropped to 53%. By 2024, the average B2B sales rep achieved only 43% of quota. A survey of over 450 revenue, finance, and sales leaders found that 91% reported failing to hit quota expectations. Meanwhile the top 20% is still generating 80% of the revenue and new hires are taking longer to ramp up. 

So what’s missing? It’s not knowledge. It’s not learning. All of those are necessary and sales enablement does a great job of that. What’s missing is situational knowledge. In other words, the ability to take everything you know and have learned from training and previous engagements, and contextualize it for the current situation. Unfortunately these learning platforms don’t prepare you for that. It only comes from years of experience.

Imagine you are a new hire who has been handed a deck of SLED accounts. But you don’t have any experience in B2G sales. How do you come up with a plan of attack? How do you take the generic battle cards and use cases and customize them for the different accounts? Do you know if there are other vendor requirements (not product) that you need to check to determine if you can even pursue these accounts? Stuck between lack of experience and lack of relevant knowledge, you stress about your job while your manager stresses out about the team’s long ramp leading to revenue slippage. 

To be clear, knowledge is only part of the equation. In a real life situation, a human seller still needs to make the right judgement. That is an inherent human trait. For that, a revenue leader still needs to hire and train the right talent. But those resources will be ineffective without up-to-date, situational knowledge. As such, it’s crucial that companies make that contextual knowledge available to sellers, just when they need it, so that they can make the best decision in the moment.

Because context matters.