Sales in the Age of AI and Unruliness

Don't just create a "burning platform" - figure out how to keep it burning until your client buys from you.

I’ve run sales teams for the last decade and the best advice I ever received on sales was:

Salespeople are usually right about who will buy from them. They are usually right about how much that buyer will spend. But they are almost always completely wrong about timing.

For anyone who has managed sales teams in the professional services world, this no doubt rings true. Deals that seem within reach stretch on perpetually. Deals that were verbally confirmed are suddenly upended by a firing or a new hire. Even deals that are signed can become unsigned at the plea of a client for whom external conditions have changed.

Salespeople often bear the brunt of these outcomes, being fired for not meeting goals, only for an executive or a new hire to claim victory by capturing the same deal a year later. In reality, the original sales person was right about the client, they were right about the amount, but they could not control timing.

In an unruly world, this is becomes an even bigger challenge.

Sales in an Unruly World

There are two key factors to appreciate when thinking about selling things in the new world - particularly if you sell knowledge goods.

First, your customers are dealing with far tougher “external conditions” than in recent decades absent acute crisis moments. Some of this is geopolitical. Clients are typically not in buying mode when the cost of energy spikes, their supply chains get reorganized, and their goods are facing an uncertain soup of tariff codes.

As humans, they are still genuinely interested in your service. And when things calm down, they may still buy from you. But will things calm down? If you’re familiar with my view of the unruly world, I think you’ll be waiting a long time for peace.

Second, every single day that your client is not cementing a deal with you, they are facing a raft of substitutes for what it is you do. This is is very different than before. If you are trying to sell a research suite to a client who asks you to re-engage in three months, are they more or less likely to see AI-powered versions of research that render your old-school approach obsolete? Are they more or less likely to experiment with their own tooling? Are they more or less likely to be hit by AI-powered sales techniques of all your competitors touting their superior offers?

Law firms and strategic consultancies have long relied on soft selling approaches, wining and dining clients for months or years hoping that when a bet the company issue arises they get the first phone call. Higher-end advisory firms often rely on hosting banner client events to build brand and regularly following up with clients to try to discover a hook for work they can do together

In today’s world, if you’re unable to close the deal quickly, then you aren’t just wrong about timing - you’re more likely to be wrong about the deal overall.

Keep the platform burning

If you’re not proactive, you’re dead. But proactivity does not mean frantically calling clients to pressure them to do a deal.

An AI-native accounting firm was trying to sell me their solution recently, and I made clear I wanted it but I didn’t think their pricing was reasonable. Instead of addressing the pricing issue or adding further value to my business, they offered me a $250 Lululemon gift card if I signed up within 48 hours. Now, corrupting consumer psychological techniques (like offering the buyer a benefit that accrues to them personally to take a bad deal for the company) can be effective - though, for me, that would be something like coffee rather than yoga pants.

But the bigger issue is once I went back into the market, I found there are a dozen other companies doing exactly the same thing, all willing to undercut the first. That’s because instead of there being one AI-native accounting firm there are now dozens - and the same goes for whatever it is you are trying to sell. If the first company had a lower reservation price than they articulated, they won’t get the chance to articulate it in the future because I quickly discovered I had a lot of choices and I’m out of the market.

Proactivity would have been issue spotting rather than pressure sales. If that first company had told me that the issues I wanted to solve were only part of my challenge and by looking at public information about my company, there were three things I wasn’t thinking about that they could help me with, I probably have been disarmed about pricing. I probably would have felt like I needed to get to work on the balance of issues quickly. But most importantly, I would have felt like the company understood me. Instead, the company treated me like an undifferentiated opportunity.

In the new world of sales, it’s not enough to develop a pre-meeting briefing about a client before you walk in the door to try to wow them. You need to be 24/7 on in monitoring what’s important to these clients and you need to be able to add value to those clients over the course of their consideration cycle at every turn. It is literally costless to know as much as you can about your client - and it will cost you a lot if you don’t.

At Unruly, we are building software to increase client awareness for law firms and consulting firms. We track all of a firm’s top clients and help them see every concrete issue that their client is dealing with in the external world today. This helps the firm see scenarios that will affect that client tomorrow and to be the first one to reach out to their client every day with an understanding of what that client needs.

Sales people are often taught to create a “burning platform” so that a client feels like they have no choice to jump off into the safe waters of whatever is being sold to them.

The goal now is to figure out how to keep the platform burning by throwing on the accelerant of real-time evidence of all of the issues that will imperil the client’s business if they don’t make the decision to work with you now.

Every day, there are more and more companies in the AI-powered lifeboat business. In an unruly world, if the client doesn’t jump soon, someone else will now rescue them before they catch fire.

-SW