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...
11 days ago • 5 min read
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...
18 days ago • 3 min read
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...
about 1 month ago • 2 min read
My 7 Rules for Working With Technical Buyers Tech acumen has become something of a lost art in software sales. Somewhere along the way, sales orgs decided reps should stop worrying about the technical parts of their product and focus only on value and business outcomes. That shift made sense in many ways, but it created a gap. A lot of sellers can speak to ROI and pain points, but they freeze the second a technical, IT buyer persona joins the call. And here is the truth. You will deal with...
about 2 months ago • 2 min read
Lessons Learned From Being a Founding AE If you have hung around the Sales Players community for a while, you already know I have a soft spot for early stage companies. I like messy environments. I like figuring things out on the fly. I like being close enough to the founders to see what is happening behind the curtain. But I get asked all the time about whether it's a good idea to take the plunge and become the first sales hire at a brand new startup. Instead of giving you a list of pros and...
about 2 months ago • 5 min read
A Guide To Implementing Executive Peering Into Your Deals A while back, I wrote wrote a thread about how to use executive peering in enterprise deals to beat your competition, improve your close rate, and increase your deal size. The thread got some decent traction, so I figured I'd re-share it here in case you missed it. Exec peering is a skillset I'm SUPER passionate about since it was a major part of how I've won the larger deals of my career, but it's something that rarely gets talked...
2 months ago • 3 min read
You Might Be Just One Deal Away... After over a decade in tech sales, I've learned a simple, but very important truth about success: It's not linear. As much as we all want have a consistent "up and to the right," trajectory in our results, growth and careers, the cold hard truth is it seldomly happens that way. There's always going to be a lot of ups and downs on the road to professional and financial success and in our profession this is as constant as death and taxes. On the bright side...
2 months ago • 2 min read
The Skills You Need to Consistently Hit a $200K+ W2 Be honest, you didn't get into tech sales to make an average income.If you're anything like me, you heard stories of elite reps making hundreds of thousands per year and you thought, why not me?If you're getting this email, I'm going to assume you've already achieved the coveted six-figure W2 (no worries if you haven't yet; the skills needed to get to $100K+ aren't all that different than the ones it takes to get to $200K+ so keep...
3 months ago • 5 min read
All The Small Things (That Will Help Your Sales Career) Sales Players is brought to you by: Chat AE: AI without organization is just noise ChatAE provides 24/7 account intel, stakeholder mapping, and value messaging—all organized in an AI account planning workspace. Try It for Free From Blink-182's "All The Small Things" Music Video (1999) If you've spent more than a few minutes with me, then you already know I'm a huge fan of rock music, more specifically punk and pop punk. In fact, long...
3 months ago • 4 min read