Late 2024, your LinkedIn feed turned into an obituary page. Enablement leaders you'd worked with for years — people who built programs from scratch, who had the receipts on pipeline impact and rep productivity — all posting the same message with minor variations.

"Excited to announce I'm exploring new opportunities."

You know what that means.

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It hit SaaS first. Then fintech. Then across B2B. It wasn't one company making a bad call. It was hundreds of companies making the same bad call at the same time.

And if you're reading this newsletter, you either lived it, watched it, or you're wondering when your number comes up.

Nearly one in four enablement teams shrank over the past twelve months. Average compensation dropped $5,619 year over year — from $137,032 to $131,413. And only 23% of enablement professionals believe their salaries reflect the value the function delivers.

Let that sink in.

Here's the part that should keep you up at night: at the exact same time those numbers were dropping, 87% of Cloud 100 companies had enablement teams on staff. "Sales Enablement Specialist" was the 6th fastest-growing job title on LinkedIn.

The function is growing. The people inside it are getting squeezed.

That's not a contradiction. It's a pattern. And if you don't understand the pattern, it will happen to you again.

The story most executives told their boards was clean. AI is here. We can do more with less. Enablement is a cost center we can optimize.

It wasn't true.

Not because AI can't transform enablement — it absolutely can — but because the people making the cuts had no plan for how. They saw what AI could demo. They assumed it could operate. They confused a purchasing decision with a strategy.

I've been in these rooms. I've seen the contractions up close. I've been on the other end of the Zoom call where leadership can't even bear to show their face while they "downsize" — read: fire — their teams. And then in the next breath, deploy a huge chunk of cash into an AI tool they don't even understand.

No conversation about what the organization stops doing. No conversation about what AI could actually do right now. Hell, even in 2024 the technology was considered flimsy compared to today's functionality — and they were betting the org chart on it.

Just a budget line and an assumption the tools would figure themselves out.

They didn't.

Forrester's Predictions 2026 report found 55% of employers regret laying off workers because of AI. More than half. Not because the layoffs were morally wrong — though many were — but because the AI didn't do what the executives thought it would do.

Companies cut people for the future promise of AI. They were betting on capabilities that didn't exist yet.

Klarna is the case study everyone should study. They replaced 700 customer service employees with AI. Quality collapsed. Customers revolted. They rehired humans. The AI wasn't ready. The executives didn't know because they never asked the design question — what does the workflow actually look like after AI is embedded?

They asked the budget question instead.

And the budget question always has the same answer.

Here's the thing. Forrester predicts half of AI-attributed layoffs will be reversed — but "offshore or at lower salary, under the guise of AI." The roles come back. The compensation doesn't.

This wasn't a conspiracy. Nobody coordinated the enablement purge in a boardroom somewhere. What happened was simpler and harder to fix.

Hundreds of executives, independently, made the same bad bet. They cut the humans who would have designed the integration. When the AI didn't deliver, they reopened the roles into a market flooded with displaced talent willing to take less.

Incompetence with a windfall. That's the mechanism.

Zoom out far enough and the enablement function has been on an upward trajectory for a decade. More companies investing. Bigger teams. Broader scope. Strategic importance climbing year over year.

But that's not what it feels like when you're inside it.

Inside it, it feels like a cycle. Get hired. Build something. Get cut. Watch it break. Get hired back — at a discount — to fix what broke.

Both things are true at the same time. The function trends upward. You experience repeated compression cycles within that trend. Each recovery doesn't fully restore what the previous contraction took.

That's the sawtooth. And it has five stages.

The company is growing. Leadership hires enablement at market rates — sometimes above — because they need people to support a scaling sales org. Scope is broad. Budgets are available. Job descriptions say things like "build the enablement function from the ground up."

It feels like momentum. It is momentum. But it's also the peak of the tooth.

Growth slows, or a new mandate arrives. "Efficiency." "Do more with less." "AI-first." Enablement gets cut. Not because it failed, but because it can't prove it didn't.

That distinction matters. Only 43.8% of enablement professionals are aligned with their leadership on what metrics the function should even be measured on. Less than half.

When the CFO asks "what does enablement actually produce?" and the answer takes more than one sentence, the budget is already gone.

Three to six months where the remaining team absorbs the work. Some things break. Most things don't — at least not visibly. Not immediately.

This is the most dangerous stage, because it creates the illusion the org can survive without dedicated enablement. Rep ramp times creep up. Content gets stale. Win rates erode. But it happens slowly enough that nobody connects it back to the cuts.

By the time the damage shows up in the numbers, six months have passed and the narrative has moved on.

Leadership starts noticing something is wrong. The AI didn't design itself into the workflow. New hires are ramping slower. The content library is a graveyard.

So the roles reopen. But not the same roles.

The Director position comes back as a Manager. The Manager comes back as a Specialist. The scope is broader: "enablement AND ops AND content strategy." And the comp is lower, because the market is flooded with experienced practitioners who've been job hunting for four months and will take the offer.

The function is back. Headcount is restored, sometimes even expanded. But the new baseline is lower. The salary benchmarks reset. The broader scope becomes the expectation, not the exception.

And the next time a contraction comes — and it will — the starting point for cuts is already lower than it was last time.

The function wins. You absorb the cost.

The sawtooth isn't random. It repeats because of three dynamics that reinforce each other.

1. Enablement can't prove its value in one sentence.

When the CFO makes cuts, they cut what they can't quantify. Sales has quota attainment. Marketing has pipeline. Enablement has "we improved rep confidence scores" and "content utilization is up 12%."

Those aren't wrong metrics. They're just not metrics that survive a budget review.

The data showing less than half of enablement pros are aligned with leadership on metrics isn't a communication problem. It's an existential vulnerability.

2. AI is the perfect cover story.

Not because executives are cynical — most genuinely believe AI will transform their go-to-market. But belief without a plan is just a budget cut with better PR.

When "we're investing in AI" means "we bought licenses and cut headcount," the integration never happens. And when it doesn't happen, the failure gets blamed on the technology, not on the decision to eliminate the people who would have made it work.

3. The talent flood resets the market.

When nearly a quarter of enablement teams shrink simultaneously, the job market gets flooded with experienced practitioners all at once. Supply spikes. Comp drops. Companies that reopen roles 3-6 months later aren't offering lower salaries out of malice. They're offering what the market will bear.

And the market bears less when thousands of qualified people are competing for hundreds of open roles.

The pattern I keep seeing: these three dynamics feed each other. Can't prove value → gets cut when AI provides cover → talent floods the market → roles reopen cheaper → lower comp becomes the benchmark → and the next cycle starts from a weaker position.

The upward trend is real. The demand for enablement keeps growing. The strategic importance keeps climbing. Each trough in the sawtooth sits slightly higher than the last, because more companies recognize they need the function — even when they periodically forget they need the people.

This is not a downward spiral. It's a compression cycle within an upward trend. The function is winning a long war while individual practitioners keep losing short battles.

Which means the question isn't whether enablement survives. It will.

The question is whether you survive with it — or get caught in the teeth.

The practitioners who get cut in Stage 2 and re-enter at a discount in Stage 4 tend to share a pattern. They defined their value at the task level. I run onboarding. I manage the content library. I coordinate SKOs.

Those are real contributions.
But they're also job descriptions easy to replicate, easy to automate, and easy to justify cutting when the mandate comes down.

The practitioners who survive Stage 2 — or who re-enter in Stage 4 at premium comp instead of a discount — defined their value differently.

They're not running programs. They're designing how humans adopt change and measuring whether it worked.

When AI entered the picture, they didn't wait to be told what to do with it. They audited the current workflow. They identified where AI changed the design. They brought a before-and-after to leadership before anyone asked for one.

That's not a different job. It's the same job, described in the language that survives budget cuts.

Within eighteen months, the enablement function will split into two tiers. And the comp gap between them will be wider than anything this profession has seen.

Think about what that actually means day to day. These are the people who look at a workflow — onboarding, content delivery, coaching, deal support — and ask the design question: what does this look like if AI is a native component, not a bolt-on?

They map the current state. They identify where steps disappear, where new steps emerge, where the human role fundamentally changes. Then they measure whether the humans actually moved.

That's not a new skill set. That's the enablement skill set applied to the biggest change management challenge most organizations have ever faced.

The difference is these practitioners can walk into a room with leadership and show the before-and-after in dollars. Not "we improved adoption." Not "reps are using the tool." Here's what we were spending. Here's what we redesigned. Here's the result.

That fluency — the ability to connect workflow design to financial outcomes — is what makes these roles resilient. They sit at the intersection of what AI promises and what GTM teams actually need.

That intersection is where the budget lives. And budget proximity is career insurance.

These roles will command $150K and above. Not because the market suddenly got generous, but because the people who can do this work are genuinely scarce. Every company that cut enablement and discovered AI didn't fill the gap is now looking for exactly this person.

The demand is structural, not cyclical.

They run onboarding. They manage content. They coordinate training events. Important work — work that needs to get done. But it's work that is increasingly automatable, and more critically, it's work easy to cut when the next efficiency mandate arrives.

Leadership looks at Tier 2 work and sees a line item. They look at Tier 1 work and sees a capability they can't afford to lose.

Tier 2 roles will compress toward $90-100K, and they'll be the first cut in every future contraction. Not because the people are less talented, but because the work is defined at a level that doesn't survive the CFO's one-sentence test.

Here's the thing. The split isn't about AI skills specifically. It's about whether you define your value as executing programs or designing systems.

The sawtooth has always punished executors and protected designers. AI just made the gap wider and the cycles faster.

The next sawtooth contraction is coming. I don't know if it's twelve months away or twenty-four. But the dynamics that drive it — executive overconfidence in AI, enablement's chronic inability to prove value in financial language, and the cyclical nature of SaaS spending — haven't changed.

They've intensified.

When it comes, the Tier 1 practitioners will be fine. They'll have the proof points, the financial language, and the strategic positioning that makes them expensive to lose.

The Tier 2 practitioners will post on LinkedIn.

That's not cynicism. It's the pattern, exposed. And the only thing that changes it is what you do between now and when the next Stage 2 arrives.

So what do you do?

Start here. This week. Ask your leadership what metric they'd use to justify your role in a budget review. Not what you think your value is. What they would say if someone asked them to defend your headcount.

If you don't like the answer — or worse, if they don't have one — that's your gap. And closing it is the single most important thing you can do before the next contraction.

So my question to you is this...

Which stage of the sawtooth are you in right now? And are you building toward Tier 1 work — or are you still defined by Tier 2 tasks?

Be honest with yourself. That's where it starts.

Hit reply and tell me. I read every one.

Until next time my friends... ❤️, Enablement

Data sources: Sales Enablement Collective 2025 Landscape & Salary Report, Forrester Predictions 2026: The Future of Work, Crunchbase/Layoffs.fyi tech layoff tracking, Highspot State of Sales Enablement 2024