Welcome to The Compass:
Your Guide to Winning Deal Strategies
Why the Compass Exists
Early in my sales career, I focused on learning how to sell. While I was making my number, I wasn’t achieving the targets I set for myself by just focusing on sales tactics. My territory was always Enterprise accounts—highly competitive, with many moving parts and rapidly changing business conditions. Working harder yielded marginal gains in performance.
As I scaled my coverage to hit my revenue targets, I realized I was getting lost in my deals—not always sure of the right next steps. There was so much to manage, and sales tools made it more difficult. Then it hit me: Sales isn’t just about how to sell. It’s about who, what, when, where, and why to sell. There was a strategy gap in my sales process.
So, I started learning everything I could about strategy—military, business, political—and applying it to my deals. Success came not from following static sales playbooks or methodologies but in learning how to apply strategy to help me navigate through my deals. Enterprise sales is not a math problem to solve but a physics exercise. It is about having the right strategy in place at the right time to improve your position, accelerate deal velocity, and compress time to create the power to maneuver you and your Buyer to a successful outcome.
I started documenting the conditions under which the different deal strategies worked and didn’t work. I mapped thousands of sales processes (over 8,000 actually) across thousands of deals with many of the G2000 and most of the F100 companies I did business with. It only took a couple of decades 😊, but the Compass sales strategy system is the result.
Sales strategy is the discipline of creating the power to achieve your sales objectives in competitive and dynamic markets.
An interesting thing happens when you master sales strategy:
🔹 Your income increases dramatically—2-4x what you’re earning now.
🔹 You are offered better territories and accounts to cover.
🔹 Customers value your strategic approach and trust working with you.
🔹 You get tapped for leadership roles—Sales Management, Executive Leadership, even CEO positions.
Why You’re Here
Enterprise sales is more competitive and dynamic than ever. Deals are harder to win, decision-makers are tougher to reach, and AI is changing the entire Buyer/Seller relationship, rendering existing sales models & methodologies obsolete. Figuring this out is challenging.
The Compass is designed to help sales professionals and business leaders navigate through this evolving landscape to consistently make your number.
If you are:
✅ Operating in B2B or Enterprise sales.
✅ Selling in competitive markets.
✅ Working to close must-win deals that could transform your career or business.
✅ Committed to making your number.
✅ Engaged with multiple decision-makers & influencers.
…then you’re in the right place.
Where to Start
To get the most out of The Compass, start here:
📌 New here? Start with this: What is Strategy
📌 Curious how AI can help? Read this: Own Your AI
📌 Want to win more deals? Check this out: Winning Deal Strategies
Subscribe now and take control of your sales career!
Each of these posts gives you actionable strategies you can apply immediately
What You Will Get
Every week, I share deep-dive insights on competitive deal strategy—based on battle-tested frameworks, AI-powered analysis, and real-world experience.
🔹 Breakdowns of winning deal strategies—what works, what doesn’t, and why.
🔹 Exclusive insights on AI in sales—how to leverage AI to gain an edge.
🔹 Proven strategies for improving your competitive position, increasing your deal velocity, and compressing time—helping you close faster and more effectively.
My goal is to help you make your number and achieve success.
Ready to Engage
What’s the biggest deal strategy challenge you are currently facing? Reply and I’ll share my thoughts—or feature it in an upcoming post.
📩 Subscribe now and get good at strategy. You will take control of your success!
