AI is Redrawing the Sales Playbook But Not How You Might Expect

29 Jul 2025

Dan McLennan, Vice President of Sales at AppFolio, featured alongside the headline “AI Is Redrawing the Sales Playbook — But Not How You Might Expect” on a branded Spiky.ai graphic with a dark background and Spiky logo.

Jason M. Lemkin recently shared 10 bold insights from AI-native CROs, and it’s one of the sharpest snapshots of how revenue orgs are evolving.

As someone advising Spiky.ai and having built and led GTM teams at LinkedIn, Superhuman, Handshake, and AppFolio, I see this firsthand every day — and here’s where I strongly align, plus where I’d add nuance:

1️⃣ The Great Bifurcation is real.

The gap between top and average reps is widening fas,t and AI amplifies this. Tools don’t level the field; they magnify whatever is (or isn’t) working.

2️⃣ AI-native hiring is now table stakes.

If a candidate isn’t actively curious about AI for their workflow, they won’t move the company forward. AI fluency ≠ prompt engineering — it’s a mindset of working smarter.

3️⃣ Speed is the new moat.

I’ve never seen sales cycles compress this fast. Teams that wield AI well get to insight, urgency, and value faster — and it compounds.

4️⃣ Technical sellers pull ahead.

This has always mattered in SaaS. But today’s “product whisperers” turn every discovery into a working session — they don’t just sell software, they co-design solutions.

5️⃣ The ‘people person’ is being redefined.

Charm isn’t what closes anymore. What closes? Clarity. Confidence. Teaching. The best reps aren’t entertainers — they’re guides.

6️⃣ AI doesn’t work out of the box.

Some teams stumble here: You can’t plug in tools and expect transformation. Structure, experimentation, and judgment still matter.

7️⃣ Human + machine orchestration is the new GTM.

This is what excites me most. AI doesn’t kill the funnel; it reroutes it — enabling more seamless, intelligent buyer journeys.

8️⃣ The modern VP of Sales & CRO is a hybrid leader.

Not just head of sales or revenue. They manage humans, data, models, and workflow orchestration. They need to understand how humans and AI cooperate.

9️⃣ Attribution will break — and that’s good.

In AI-assisted selling, the question of “who sourced the deal” becomes fuzzier. What matters now: did the whole system create value? Did every touchpoint add something?

🔟 Meeting prep is just the beginning.

The real unlock is AI shaping live interactions: coaching, nudging, and assisting — all in real-time.

Gong pioneered post-call insights. Companies like Spiky.ai (where I advise) are pushing the next frontier: enabling real-time self-awareness so sellers maximize the exact moment they need to perform at their peak.

We’re still at mile 1.

AI isn’t replacing sellers now — it’s reshaping them.

The teams that embrace this first aren’t just getting more efficient. They’re becoming impossible to catch.

👉 Want to see how real-time sales coaching works?

Check out how Spiky helps sales teams show up sharper — live, in the moment.

https://spiky.ai/en/contact-us

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