Want to Hit Multiple Six Figures? Nail This First


Improving Your Discovery Game

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If you want a shot at a multiple six-figure year in tech sales, it’s not about working harder. It’s about working smarter — and more intentionally — especially when it comes to the fine art of discovery.

Too many reps treat discovery like a checklist: ask a bunch of questions, find out about their tech stack, and then hope for next steps. And that’s why deals get closed-lost and pipeline evaporates.

Discovery isn’t just a call, it’s a process. A mindset. One that starts with a simple question: Why won’t this deal close?

True Sales Players always challenge the premise. They ask things like, Why not stay with your current solution? or Why us? Why now? These are the moments where trust is built and the real facts come to the surface, not just high-level pain points, but the stuff that actually drives urgency and action.

Also, please don’t turn a discovery call into a game of 20 questions you’ll quickly annoy your buyers, and you likely won’t get next steps. Keep your discovery conversational. Use BANT-C (Budget, Authority, Needs, Timeline, Competition) as a basic framework to define

the scope of the project and uncover details, but remember it's a conversation, not a pop quiz for your prospect.

A great opener I like to use that will immediately change the tone (and outcome) of the entire meeting right from the beginning is What’s one thing you’d like to get from today’s meeting? Boom. Instant buy-in.

Oh, and when it’s your turn to deliver your pitch. Don't torture the prospect with a 30-slide deck. Use 5-7 slides with strong visuals to tell your story — the why, how, and what. Draw a line in the sand that separates your solution from everything else in the market.

The highest earners in tech sales win more deals because they lead smarter discovery conversations, full stop.

Improve your discovery game, and the big commission checks will follow.

BTW, if you're interested in learning my framework for better discovery and crafting a stand-out pitch narrative that wins more deals, hit reply to this email or book a 1:1 coaching intro (use the link down below).

Until next week!
-Jesse


Featured Episode: Want Bigger Deals? Learn the Product

Jesse reminds sellers why understanding the product matters a lot (especially when selling to Enterprise IT buyers).


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Sales Players is on a mission to reach 1,000 reps, founders, and operators in tech with FREE weekly content that explores the mindset, skills, trends, and tools used by the industry's top players to win at the game of tech sales.

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