Why Sales Performance Keeps Falling Even as Enablement Spend Soars: A Conversation with Jim Keenan

Revenue performance is a phrase we’ve been using at Ambition for years, so I was excited to talk with Jim Keenan (Keenan), CEO of A Sales Growth Company and author of Gap Selling, about his new book, Gap Revenue Performance. I asked him what inspired it, and he warned me up front that it doesn’t make him a popular guy.

His simple (but uncomfortable) argument is that spending on enablement, training, and sales tools has grown 6 to 7x over the last 12 to 14 years, while performance has simultaneously gone in the opposite direction. Keenan cited data showing that about 63% of reps hit quota around 2012, compared to only about 16% today. Sales cycles have grown longer while win rates have dropped. His conclusion is that investing more and getting less means something somewhere is broken.

Here's a quick recap of our conversation, or you can watch the full episode on Youtube.

Why sales performance is falling while enablement spend keeps rising

Keenan isn't letting anyone off the hook. Enablement, sellers, managers, and executive leaders all play a part in this broken system. Cutting enablement spend isn't the answer either, because you still have the problem of getting teams to perform.

The cultural piece he highlights is that sales orgs are reactive and "heroic," rewarding those who sprint to get deals over the line at the end of every quarter. He used an example that really stuck with me: Do you buy groceries at the end of every month or quarter? What about your rent or car payment? No, because nobody buys that way. Buyers end up there because sellers force them into it to hit monthly, quarterly, or yearly numbers. (And to be fair, they've been trained to do this.) Sellers think it works, but Keenan says it's been extremely expensive for businesses.

Why the end-of-period scramble keeps happening

Keenan describes it as a circular trap. When deals that shouldn't close until Q4 get pulled into Q3 (probably at a discount to get it done sooner), you enter Q4 already behind. If your sales cycle is longer than three months, you're likely then pulling Q1 deals forward, and likely at a discount to incentivize a quick close.

He offered a practical solution for CEOs, PE firms, or investors who want to break the cycle: Require the organization to capture every discount and report it as a line item for the CFO to see. At the end of the year, you look at what you sold and what percent of that was off retail. That number is the real cost of closing those deals in that quarter, and it's never captured in CAC. Keenan expects CROs wouldn't like this number to be made public, but says it gets attention quickly.

What sales teams can learn from pro sports

The heart of our conversation around Jim's new book opens with a sports story. He proposes that any business where human behavior drives the outcome should look more like a sports team. If a football team were run like a sales team, it would be a disaster: 

• Recruit for the style of play. A team running a run-pass-option offense needs the right personnel. Keenan joked that in sales, we'd hire Tom Brady to run it and it would fail, because he lacks the skills for that type of offense.
• Don't just teach the game plan. If sports ran like sales, everyone would show up Monday, learn the plan, take a test, and then go practice alone with no one watching.
• Coach consistently. The offensive line coach, quarterback coach, and running backs coach would each coach differently because no one told then exactly what to coach to.
• Avoid the Hail Mary on game day. In sales, this is the "we need a touchdown right now" call that Keenan describes as chaotic.

He also pointed to the performing arts as a way to illustrate this point: they’re built around consistent, predictable output. Companies that scramble with discounts and extra marketing to fill the theater after a few bad shows miss the point, because consistent performance means you don’t need to discount to get people in the door.

This hit home for me because of the “black box” conversations we have with enterprise companies. Leaders say they care about performance and that managers are the key. Then you ask what managers actually do, and the answer is that they each do their own thing. In an org with thousands of sellers and hundreds of managers, that’s hundreds of different coaching approaches that nobody tracks. Keenans athletes-and-coaches framing is an extremely apt analogy for why that matters.

The problem-centric operating system

How do we reset the hamster wheel of end-of-quarter scrambling? Keenan says that with commitment, you can change the engine on the plane while you're flying it. He outlined a framework he calls the Problem-Centric Operating System with three layers: 

1. The skills layer, where people are taught
2. The opportunity layer, where you watch them perform, like game time
3. The forecast layer, the output, connected by data and feedback loops

The starting point is accepting that every problem you're facing today is a people execution and behavioral problem. If your team closes late or scrambles, it's likely because deals weren't structured in a way that let them hit the number without discounts or forcing clients to in.

Why cold calling is harder than ever

I asked Keenan what a 25-year old seller should do. He was candid about the fact that outbound has become more complex and difficult. (We are all feeling this, I'm sure.) He added that Gap Prospecting was the hardest of his books to write because so many factors are in play now.

When he first started in sales, he could expect roughly half of cold calls to be picked up (sometimes more), which gave him enough volume to learn through trial and error and get better with every connect. That's not the world today, so Keenan says sellers need to be persistent, build a real outbound engine, block their time, and hone their message. They get fewer shots on goal, so each one has to count.

He also thinks the last 12 to 15 years of tools (like LinkedIn, Gong, Outreach, etc.) created "execution at scale," which allowed reps to start demoing without ever learning to sell. His blunt take is that a lot of reps don't research their customers the way he used to, and that building that discovery skills is the company's job.

Can AI and call transcripts replace CRM stages?

Keenan recently posted that we don’t need stages anymore, and the comments got heated. He’s not against a system of record. His point is that the data should come from the buyer’s voice.

His proposal: record every customer call, push every transcript into a repository where it can be reported on, and define what a good opportunity looks like (problem, impact, root cause, cost of inaction, desired future state, buying process, decision criteria). Then let AI or your system score every transcript and email against that criteria, not the rep or the manager. Your job as a leader is to evaluate whether it’s working. He also noted you’ll see how well your team gets information out of customers “in a heartbeat.”

I added that we see leaders wanting the same thing for managers: every forecast call and performance review captured and analyzed so they aren’t relying on a rep saying “I’m having a great quarter.”

What I’m taking away

My main takeaway is that “knowing” and “performing” are different things, and most of our measurement is built around the first. Completion rates and certifications are easy to count. Whether a manager’s coaching is consistent, whether deals are structured around the buyer’s problem, and whether discounts are the hidden cost of your quarter are harder to see, but they’re what decide the number.

To hear the whole conversation, watch the full episode on the Sales Operator Series. You can find Jim at salesgrowth.com and on LinkedIn, and pick up his books on Amazon.