Thinking Out Loud
Frameworks, tools, and perspectives on AI-powered sales and revenue leadership.
What I Learned About Resilience From Being Laid Off 3 Times
The best sales leaders I know have all been through the fire. The dangerous ones are the ones who came out building.
I've Used MEDDPICC, SPICED, Sandler, and Challenger. Here's When Each One Wins.
Sales methodology is not a religion. It's a tool. The right one depends on the job - and AI changes which parts of each you actually need humans for.
The Board Is Going to Ask About Your AI Strategy. Here's What to Say.
Most sales leaders don't have an AI strategy. They have AI anxiety. Here's how to turn that into a credible plan before the next board meeting.
From $0 to $415M: The 5 Things I'd Do Differently with AI
If I had today's AI tools during the Groupon scale-up, I could have hit the same numbers in half the time.
Your SDR Team Is Too Big. Here's the Math.
Most companies have 3x more SDRs than they need if they deployed AI correctly. Here's the actual cost math.
The 3 Hires That Define Your Revenue Trajectory (and How AI Changes Who You Hire)
Your first sales leader, first RevOps hire, and first enablement lead define whether your revenue org scales or stalls. AI changes who each of these people needs to be.
How to Run an AI-Assisted Pipeline Review in 20 Minutes (That Used to Take 90)
AI doesn't eliminate the pipeline review. It eliminates 70 minutes of status theater so you can spend 20 minutes on strategy.
I Co-Founded an AI Company in 2013. Here's What This Wave Gets Right - and What It Gets Dangerously Wrong.
The technology is better than 2013. The hype cycle is exactly the same. And the winners will be the ones who figure out workflow integration before the market corrects.
MEDDPICC Is Not Dead. But It's About to Get a Brain.
AI doesn't replace sales methodology - it makes methodology enforceable at scale for the first time in history.
The $20M Forecast That Was Never Right - and How I Finally Fixed It
Forecasting fails because we ask humans to objectively assess the probability of their own deals closing. That was always the problem.
I Replaced 40% of My SDR Workflow with an AI Agent. Here's Exactly What Happened.
40% of what a typical SDR does is research, admin, and coordination. An AI agent eliminates that. Here's the exact architecture and the honest results.
The Sales Leaders Who Survive the AI Transition - and the Ones Who Don't
The AI transition won't be crowned by technologists. It'll be led by operators who learn to build.
By 2028, AI Agents Will Outnumber Human Sellers 10 to 1. Here's What That Actually Means.
Gartner, McKinsey, and Forrester just released data that tells a story most revenue leaders aren't ready to hear. Here's the unfiltered version.
What Changed in AI Sales Tools in 2025 - And What's Coming in 2026
I've been in the trenches watching this space evolve in real time. Here's an honest assessment of what moved the needle, what was hype, and where I'm placing my bets for 2026.
The Fractional CRO Model: Why More Companies Are Choosing Flexible Leadership
The full-time CRO model made sense when companies scaled linearly. AI-era companies don't. Here's why fractional leadership is becoming the default for smart founders.
I Gave My AI Agent a Budget. Here's What Happened.
I gave my autonomous agent $50 and told it to generate pipeline. What it did - and what it couldn't do - taught me more about the future of sales than any conference I've attended.
The 5 AI Tools Every Sales Leader Should Be Using Right Now
Most sales leaders are still treating AI like a novelty. The ones who aren't are pulling away from the pack. Here's what's actually worth your time.
Why Your Forecast Is Wrong - And How AI Fixes It
Every CRO has sat in a board meeting defending a number they knew was fiction. It doesn't have to be this way. AI-native forecasting changes everything.
I Built an Autonomous AI Agent. Here's What It Taught Me About the Future of Work.
I spent a weekend building an agent that runs on a Mac Mini in my home office. It changed how I think about every role on a revenue team.
MEDDPICC in the Age of AI: What Changes and What Doesn't
The methodology isn't dead - it's about to get a significant upgrade. Here's how I think about deal qualification when AI can do half the research.
From $0 to $400M: The Playbook I'd Run Differently Today (With AI)
Looking back at Groupon and what I'd do differently if I had today's AI tools in my hands. The answer might surprise you.