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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.
The Story of Turning a $10K Pilot Into a 7-Figure Enterprise Deal Last year, I resurfaced an interview I did on the How the Deal Was Done podcast where I broke down the biggest annual contract I’ve ever closed. A seven-figure agreement with a massive, publicly traded consumer brand. And the funniest part? It started with an inbound lead from a UX manager. Not a VP. Not procurement. Not the CFO. A UX manager. So if you’re sitting on a deal that feels “too small” or “too low in the org,” keep...
10 Unconventional Moves I’m Making to Win in 2026 If you have been around Sales Players for any length of time, you know that December is my reset window. It is when I look at what worked, what fell flat, and what I need to change if I want next year to look meaningfully better than the last. The last couple of years have been a grind. Layoffs, budget freezes, deals slipping, and pipelines that felt shakier than they used to. A lot of momentum across tech sales has felt fragile. That is...
10 Ways Enterprise Deals Die Right now, like always, every shot counts when you're running an enterprise deal cycle. I've been at this for over a decade, and if I am being honest, I've lost more enterprise deals than I have won. That's just the math of long sales cycles, complex buying committees, and competitive landscapes. But enterprise sales has a funny way of making the wins matter a lot more than the losses. One good deal can change everything. Your bank account. Your confidence. Your...