by Carla A. Fleming | Feb 16, 2026 | Alignment, CEO, CMO, Growth, Product Marketing, Sales, Sales Playbook
Over the past few weeks, I’ve been writing about what sales playbooks reveal when they stop working. The myths we believe about touchpoints, engagement scores, personas, and scaling. But Here’s What I Really Want to Know From You: When you built your sales... 
by Carla A. Fleming | Feb 1, 2026 | Agentic, Agents, AI, Business Strategy, CMO, Growth, Sales Playbook, Software
The Painful Present: Your product roadmap is on track. Customer satisfaction scores are solid. Your existing clients love what you have built, and your sales team is doing everything right, but the close rate keeps dropping. But new deals have slowed down to a crawl,... 
by Carla A. Fleming | Jan 4, 2026 | Business, Business Strategy, CEO, CMO, Growth, Leadership
Lou Gerstner. I’m sorry to hear of the December passing of IBM’s former CEO. I was lucky to join IBM as a graduate school co-op a couple of months after he did. What none of us knew was how the transformation he engineered still has people talking long after he... 
by Carla A. Fleming | Nov 9, 2025 | Alignment, CEO, CMO, Product Management, Sales, Software
You know the moment of misalignment. As the VP of Marketing, you’ve shared customer insights multiple times with the Chief Product Officer (CPO) as part of roadmap discussions. A curt “Thanks for the input, we’ll consider it.” The Painful Present Economic buyer... 
by Carla A. Fleming | Oct 26, 2025 | Alignment, Business Strategy, CEO, CMO, Leadership, Sales, Software
An 11 am meeting ends at 11:05 am. The CEO just torched your second-half launch plan. No warning. As the VP of Marketing, your ears are ringing with the words, “Just get it done.” The Painful Present • CEO wants to leapfrog the competition with the new AI product and... 
by Carla A. Fleming | Oct 12, 2025 | Alignment, Business Strategy, CEO, CMO, Growth, Sales, Software
You’ve been in this meeting before. The Painful Present: When Consensus Feels Like Quicksand The topic? “Customer Strategy Alignment.” For two hours, everyone nods in agreement. Yes, we need more focus. Yes, our messaging should be consistent. Yes,...
