“Sales is an AI-proof job. That might sound like denial given that I’m two decades into a sales career, but it’s one of my most firmly-held beliefs.”

This perhaps seems like a strange bet to make in an era when AI can research any prospect, draft every outreach sequence, summarize each call and update the CRM. But for Emery Rosansky, a 20-year sales veteran and First Round’s VP of GTM, those advances make humans more valuable, not less.

The average seller focuses on the mechanics of sales: following up on open opportunities every week, executing the right number of activities (emails, calls etc.) or offering a discount to get the deal done. But the mechanics were never the hard part of sales. The hard part of sales is the human part — the nuanced judgment, trust creation and emotional intelligence, Rosansky argues.

“It’s tough to envision an AI SDR asking the exact right question at the exact right moment in a call, reading the power dynamics in a room and acting accordingly, training a champion to pitch to their decision committee without condescending them, or turning a prospect into a friend who wants you to win as badly as you do,” she says.

In today’s essay, Rosansky breaks down the craft of sales and how to develop those decidedly human skills in a ton of detail, including:

• Frameworks for picking up on what a prospect isn’t saying, with tips for getting comfortable asking the direct questions most sellers avoid.
• Specific stories from founders selling today, including how a $300K+ proposal died in an inbox and the question that helped a founder hold firm on pricing after a bakeoff.
• The micro-habits that will help you build the discipline it takes to succeed (plus handy little tools like a pipeline math calculator and a prompt for discovery call prep).

If it's of interest, this essay is a preview of the one of the sessions Emery is teaching in Sales Combine, a newly launched, free program to find and train the next generation of sales talent. With hundreds of open sales roles at AI-native startups that are hard to fill with truly excellent sellers, she thinks it’s time to start looking for talent differently.

Participants will join Emery and other experienced sales leaders for two days of training in San Francisco on November 6–7, followed by direct intros to companies like Notion, fal, Together AI, Parallel, Clay, and many others that are hiring early sellers. Apply here by 10/3.