Crazy Stories From My Tech Sales Career Sales Players is brought to you by: ZoomInfo:The go-to-market platform to find, acquire, and grow customers. Free Trial Alright, we're going to have some fun with this week's edition of SP. After over a decade working in startups/scale-ups, I have my fair share of crazy stories and this week I'll be sharing two of those with you... Oh, and if you like this sort of thing, be sure to reply and let me know. I want to make story time an ongoing part of SP's...
9 days ago • 5 min read
20 Questions I Use to Stress-Test My Deals Sales Players is Brought to You By: Surfe: High-quality data that powers high-converting pipeline Get started for free *LAST CALL! Coaching Promo Expires Tonight at 11:59 PT. $99 one-hour coaching sessions (normally $250). Potential focus areas: Land a top role, close the largest deal of your career, build 5x pipeline coverage, launch a side business. 👉 Click here to book your session 20 Questions For Introducing (Good) Friction Into Your...
16 days ago • 3 min read
What I Learned (and Earned) From Getting Acquired 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 for FREE! Have you ever wondered: what really happens when the startup you work for gets acquired? Does everyone get to cash out and eventually retire on a beach? Or does it end up being a huge letdown?I used to wonder the exact same thing earlier in my tech career. I'd hear...
23 days ago • 5 min read
20 High-Growth Startups Hiring Sellers Right Now Sales Players is Brought to You By: 1:1 Coaching Promo for August, 2025! For the month of August, I'm offering $99 career and performance coaching sessions (Normally $250). *Book before 8/31/25, 11:59 PT. Session can be scheduled out beyond the 8/31 deadline. No session limit, but subject to my availability. Book Now! Join The Upcoming Virtual Meetup & MasterClass! 3 Steps to Fast-Tracking Wealth & Financial Independence as a Tech Seller...
about 1 month ago • 3 min read
7 Ways to Use The New GPT-5 to Outsell the Competition Sales Players is Brought to You By: 1:1 Coaching Promo for August, 2025! For the month of August, I'm offering $99 career and performance coaching sessions (Normally $250). *Book before 8/31/25, 11:59 PT. Session can be scheduled out beyond the 8/31 deadline. No session limit, but subject to my availability. Book Now! Unless you've been off the grid for a while, you're probably already well aware of all the buzz around the release of...
about 1 month ago • 3 min read
My Step-by-Step Strategy for Acing Sales Interviews $99 Coaching Promo for August, 2025 🔥 August is One of the Most Critical Months in B2B Selling Now is the time to get locked in on your plan for a strong finish in 2025! Which is why for the month of August, I'm offering $99, coaching sessions (Normally $250). If you've ever been on the fence about booking 1:1 coaching, now is your chance to try it out. Focus areas for your session: Landing a better role in tech sales Improving discovery,...
about 1 month ago • 4 min read
How Sellers Can Build Income Outside of Quota (5 Ideas) Sales Players is Brought to You By: Increase productivity with the #1 rated AI Notetaker Records, transcribes, highlights, and summarizes your meetings so you can focus on the conversation. Free Forever! Free Forever > "When I Grow Up, I Want to Be A Sales Player!" Wait! Before we get into the topic of today’s newsletter, I had to share this… My son brought this home from school the other day and I just about died laughing 😆 (Yes, here...
about 2 months ago • 4 min read
I Lost a 6-Figure Deal This Week, Here's What I Learned Sales Players is Brought to You By: Increase productivity with the #1 rated AI Notetaker Records, transcribes, highlights, and summarizes your meetings so you can focus on the conversation. Free Forever! Free Forever > This past Monday, after six months of hard work, I got hit with a deal-killing email from a major enterprise prospect.Let me set the stage... It's Monday morning and I've just returned from a week-long family vacation, and...
about 2 months ago • 5 min read
Part II: A Guide to Closing Your First (Or Next) $100K+ Annual SaaS Deal Sales Players is Brought to You By: Increase productivity with the #1 rated AI Notetaker Records, transcribes, highlights, and summarizes your meetings so you can focus on the conversation. Free Forever! Free Forever > Last week, I shared the first 3 steps I use to close $100K-plus SaaS deals: Target the right accounts Run a tight discovery process Build an internal deal team that helps you win If you missed that one,...
2 months ago • 4 min read