CRO Shares The Two Skills That Separate $1M Sales Reps from Everyone Else

Matt Green has sat in on thousands of sales calls. As CEO & Founder of Sales Assembly, he's trained over 10,000 sales professionals at companies like Snowflake, Stripe, and MongoDB.

And he sees the same pattern destroying 20-30% of pipeline across every sales org.

"It sounds really basic and remedial," Matt admits, "but it's listening skills."

In an era where AI can generate perfect email sequences and analyze 10-Ks in seconds, reps are getting lazier about the one thing that actually matters: genuine human connection through discovery.

The Efficiency Trap Killing Your Pipeline

"Reps are trying to find ways to cut corners," Matt explains. "In the service of efficiency, they're missing the really valuable intelligence you only get from human-to-human conversation."

The result? Surface-level discovery that misses the real pain points. Deals that die mysteriously in stage 3. Champions who ghost after seeming engaged.

Matt's solution starts before you even hire: "Test for curiosity during interviews. Ask candidates what they've learned recently. You'd be surprised how many tenured enterprise reps say they haven't learned anything new."

The Two Skills That Matter Most

When asked which two skills deliver the highest revenue impact per dollar spent on training, Matt doesn't hesitate:

1. Discovery: "Deals are won and lost during the initial call, usually due to the effectiveness or ineffectiveness of discovery."

2. Storytelling: "Once you find out what you need through discovery, how do you weave that into a narrative? Not just verbally - writing too. Being able to craft a narrative that appeals to a CFO just as much as a CIO."

The 18-Month Unemployment Clock

Matt's prediction for what will make reps unemployable within 18 months? Lack of storytelling ability.

"Every rep has access to the same AI tools, the same research. What separates you is your ability to synthesize all this information into a story - both verbally and written."

While everyone else is racing to implement the latest AI tool, the winners are doubling down on the fundamentally human skills: curiosity in discovery and compelling storytelling.

The Frontline Manager Crisis

Perhaps most concerning is what Matt calls the "overextension" of frontline sales managers.

"Your average frontline manager has 8-10 direct reports they're supposed to be coaching weekly, they have their own quota to hit, they're doing product training, enablement... It's almost an impossible job."

The solution? Either reduce their span of control (expensive) or bring in external support to fill the gaps.

Key Takeaways:

• AI is making reps lazy about discovery

• Curiosity can't be trained

• Storytelling (verbal and written) will be the #1 differentiator in an AI-saturated market

• Frontline managers are set up to fail with current expectations

• The companies winning are testing for curiosity in interviews, not just experience