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 8, 2026 | Agentic, AI, Business Strategy, CEO, Customer Success, Growth, Product Marketing, Sales, Sales Playbook
You’re a Startup CEO looking to get Series B/C funding. However, your sales team just missed its quarterly revenue target. You suspect it could be your playbook. How are you going to pivot from a broken playbook to one that works before your board meeting? The Painful... 
by Carla A. Fleming | Jan 26, 2026 | Agentic, Agents, AI, CEO, Sales, Sales Playbook, Strategy
The Painful Present: Your top sales rep just lost to a competitor with an inferior product. The prospect’s feedback? “They were clearer about how they solve our problem.” You’ve invested in AI tools to scale your messaging, but... 
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,...
