The Two-Spike Talent Economy
The Future of Customer Success in the AI Era
A few weeks ago, I traded in a MacBook Air that couldn’t keep up with the pace of my life. Between building GPTs, debugging code in Cursor, hopping between Zooms, running Granola in the background, and juggling 140 open tabs, it would tap out by lunchtime. So I walked into the Apple Store, swiped my card, and walked out with a new MacBook Pro.
But what stuck with me wasn’t the machine—it was the person who helped me.
Fast. Friendly. Curious. Confident. They didn’t just sell me a laptop—they became a partner in my productivity. And in that moment, I realized: in this AI-saturated world, that Apple Store hire might be one of the most future-proof roles we have.
Wait, what? Retail talent is the model for tech?
Yes. Because Apple figured something out long ago: hire for human magic.
We’re Entering a Two-Spike Talent Economy
My friend Andrew Chantra, who led recruiting ops at Meta and Apple—but got his start managing the Santa Monica Apple Store—once told me:
“Apple Retail doesn’t hire for what you know. They hire for who you are.”
That’s not a hiring tactic. It’s a strategic moat.
Apple hires people who reflect their customers: curious, design-aware, creative, confident, helpful without being pushy. Walk into a store as a student, founder, or grandparent trying FaceTime for the first time, and you’ll likely meet someone who gets you. That’s not an accident. It’s “vibe hiring.”
Apple looks for connectors. People who read emotional cues. Who bring calm to chaos. That energy is the product. And in the era of AI, it’s exactly what companies need most.
Today’s job market reflects that same split:
Spike on IQ—supercoders, AI-native builders, system thinkers.
Spike on EQ—strategic communicators, de-escalators, trusted advisors.
Everything in between? Getting eaten alive.
AI Is Rewiring Every Corner of the Customer Experience
I’ve yet to see a single “AI-powered CS platform” pitch that truly excites me.
But I’ve made several AI investments that are quietly reshaping Customer Success—one building block at a time. SammyLabs, 1Mind, Gradual and Persona.
Onboarding. Technical Support. Expansion. Renewal. Advocacy. Community. Customer Insights.
Each is being reimagined—or replaced—by tools that are faster, more responsive, and infinitely scalable.
Support is the clearest proof point. LLMs already outperform the bottom 40–80% of reps on speed and accuracy. Meanwhile, GenAI is compressing product cycles. Bugs vanish faster. Features ship sooner. The product improves—constantly.
So CS has to keep up. Which raises the question:
If AI handles the repetition, what’s left for the human?
That’s the question every CS leader should be asking right now.
Consumer-Grade AI Is Setting the Bar—Even in B2B
If you haven’t onboarded into a product like WindSurf, try it. Build a simple app—the experience is so smooth it feels like magic. Then compare it to your average SaaS onboarding flow. Oof.
Consumer-grade tools are defining expectations. Even in the enterprise. If your product claims to be “AI-native” but still requires a 90-minute kickoff call and five people to get started, you’re not AI-native. You’re legacy with a wrapper.
Every touchpoint—onboarding, activation, support—has to feel as modern as your pitch deck says you are. If it doesn’t, your customer will notice.
Slack is proof: it’s essentially social media for the workplace. Facebook came first and rewired how we communicate online. Slack rewired how we work. Now, that same shift is coming for every corner of enterprise software.
If you’re a CS leader, spend your evenings and weekends playing with AI—in your own life.
The CS Role Is Being Unbundled—and Re-Composed
This is where it gets uncomfortable.
The traditional CS motion—onboarding, renewal, expansion—used to live within one department, or even one person. Not anymore. AI is unbundling the role—sometimes into specialized functions, sometimes into entirely different orgs.
That’s not a red flag. That’s evolution.
As AI strips away the repetitive work, what’s left are the high-leverage moments: strategic thinking, complex problem-solving, genuine human connection.
The CSM of the future—if we even call it that—won’t do more. They’ll do less, but go deeper. And they may not sit inside a CS org at all.
In the investor community, I’m known as the Customer Success guy—and you know what? I don’t even care if a company has a CS team. What I care about is whether the founder is relentlessly focused on their customers. If they are—if they love their customers more than anything else—that company will win.
In a world where products can be cloned in a weekend, knowing what to build matters even more than being able to build it. And the most customer-centric founders will always know what to build.
Maybe onboarding moves to Product. Maybe expansion rolls up to the CRO. I don’t really care—both models can work. The best companies won’t optimize around job titles. They’ll design around their customers, their product, and their talent.
Jensen Huang, CEO of Nvidia, famously manages dozens of direct reports, skips private 1:1s, and lets mission clarity—not hierarchy—drive execution. His org chart isn’t built for control. It’s built for velocity.
Great CS orgs will follow suit. The ones that win will look less like fixed departments and more like flexible networks.
When everything changes fast, flexibility is the structure.
“One Partner to Trust” > “One Throat to Choke”
I’ve never liked the phrase “one throat to choke.” It’s always felt too combative, too rooted in blame. A softer—and smarter—version is what my friend Joshua calls “one partner to trust.” That framing is closer to what customers actually want: clarity, confidence, and consistency.
For a long time, though, that idea felt unrealistic. People hit capacity fast—both in terms of skill depth and account volume. Even if someone had the range to handle onboarding and expansion, how would you comp and motivate them fairly? The structure just didn’t seem scalable.
In fact, I used to preach the opposite. After our startup rocketed from $1 million to $60 million in ARR in just six months, I gave a talk at a major CS conference arguing that the key to scale was perfecting the handoff—from Sales to CS, from CS to Support. That felt like the only path forward.
But AI changes everything. It connects systems, fills gaps, and resolves routine issues automatically. The coordination layer we once relied on human teams to manage is now being handled by software.
So maybe the breakthrough isn’t better handoffs—it’s no handoffs at all.
What if one person could own the entire customer relationship? Someone well-trained, well-liked, and supercharged by AI. A single, trusted point of contact who can solve problems, escalate when needed, explain clearly, and follow through—without bouncing the customer between five different teams.
We’ve already seen hints of this shift. Account Executives have long use tools like Salesloft and Outreach to run their own outbound campaigns—marketing in the hands of a seller. Why can’t AI do the same for Customer Success?
This model isn’t just more efficient. It’s what customers actually want. They don’t care how your org chart is structured. They care whether their problem got solved—quickly, clearly, and without friction.
The Future Belongs to the Relatable and the Radical
AI will reshape every tool, role, and team structure we know. But it won’t change the one thing customers remember: how you made them feel.
So yes—build your stack. Train your GPT. Automate like your life depends on it, because it does. But if you’re hiring—especially in Customer Success—take a page from Apple Retail:
Hire the person your customer will want to call again.
Because in the AI era, you might only get one call.