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Sales Players

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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Why Sellers Stay Broke and Stuck (Even With Big Commissions)

A Guide to Building Financial Security as a Tech Seller Sales Players is Brought to You By: Scale your professional workforce with freelancers Freelance services for Sales Players right at your fingertips. Join for FREE! Join Fiverr for Free > Let’s talk about something that doesn’t get nearly enough press coverage: money: moolah, dinero, coin, capital, scratch (you get the idea). And no, I'm not talking about company money either. Not revenue, pipeline, deal size, quarterly forecasts, or...

My Storytelling Framework For Winning Deals Sales Players is Brought to You By: Surfe: LinkedIn Prospecting Streamlined! Add prospects to your CRM and access their info directly from LinkedIn. No more tab switching! *Try it out for free. Try It For Free > The best sellers don’t just pitch. They tell a story. 'But, but, Jesse... they didn't cover storytelling in my sales enablement training!!! Besides, Marketing owns our brand narrative, so I'm all set...' Right. In my experience, it's 100%...

How I Re-Engage Closed-Lost Opportunities (Copy My Exact Email Template) Sales Players is Brought to You By: ZoomInfo: The Go-To-Market Intelligence Platform Get the best AI-powered B2B data and software you need to connect with and close your most valuable buyers – all in one operating system. Extended Free Trial for Sales Players Only > Alright Sales Players: If you're trying to get traction on the pipeline generation front, then you're going to want to keep reading. I'm about to share an...

The Truth About Job Hopping in Tech Sales Sales Players is Brought to You By: folk: Like the sales assistant your team never had. folk CRM does the busy work for you, so you can focus on growing your service business. Try for Free Job hopping is one of the most misunderstood and misjudged aspects of working in tech sales. After over a decade in the space, I've come to realize that it's a feature, not a bug. I've been wanting to cover it for quite a while now... I probably have 3 or 4...

Improving Your Discovery Game Sales Players is Brought to You By: folk: Like the sales assistant your team never had. folk CRM does the busy work for you, so you can focus on growing your service business. Try for Free 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,...

Why Urgency Should Be Your Default Setting Sales Players is Brought to You By: folk: Like the sales assistant your team never had. folk CRM does the busy work for you, so you can focus on growing your service business. Try for Free Something that doesn't get talked about nearly enough is the importance of urgency—moving quickly, velocity, bias toward action, striking while the iron is hot (you get the idea...) In the highly competitive world of Tech Sales, urgency must be your default...

10 Traits of Top Tech Sellers Sales Players is Brought to You By: Cognism: Up-to-date, quality data for the companies and decision-makers who matter most! Request a Demo About a week ago, I was scrolling on Reddit and came across a post on r/techsales by u/salesguy0321 titled: What makes a great AE at Upper Mid-Market/Enterprise Level? The post went on to ask the question: What separates a good AE from a great one? By default, I'm a lurker on Reddit and don't typically take time to comment,...

Should You Sell for a Startup? Sales Players is Brought to You By: Commission Impossible! Get your copy of my complete framework to evaluating startup sales opportunities. Get paid, not played! *Available on 5/1/25. Pre-order now and save 50% Pre-Order Now! From the HBO (Max?) series "Silicon Valley," which does a fantastic job of portraying life in a tech startup. Joining a startup can offer life-changing career growth opportunities and earning potential for ambitious Sales Players. I would...

20 High Leverage Sales Activities Sales Players is Brought to You By: Commission Impossible! Get your copy of my no-nonsense guide to evaluating startup sales opportunities. Get paid, not played! *Available on 5/1/25. Pre-order now and save 50%. 100% Money-back guarantee Pre-Order Now! In today's edition of Sales Players, I'll be sharing some of my favorite high-leverage activities to execute as an Enterprise seller in an early-stage startup. I think of high-leverage activities as similar to...

How to Nail the Trial Close Sales Players is Brought to You By: Surfe: LinkedIn Prospecting, Streamlined! Add prospects to your CRM and access their info directly from LinkedIn. No more tab switching! *Try it out for free. Start for Free! Alright, this one's an oldie but a goodie. The Trial Close I still remember learning about this from my very first Sales Manager, and it blew my mind! Over the years I've found different ways to execute it since it tends to look different for Enterprise...