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 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 | 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,... 
by Carla A. Fleming | Oct 8, 2025 | Alignment, CEO, CMO, Growth, Sales
4 p.m. The CRO just dropped a forecast bomb. Again. As CMO, your temples throb as you process the implications: The Painful Present: Product Management delivered a launch no one wanted. Customers were lukewarm about the last launch. The top Account Executive heard... 
by Carla A. Fleming | Oct 5, 2025 | Business Strategy, Growth, Marketing Strategy, Sales, Software, Strategy
2 PM. Another virtual customer meeting. Another “we’ll think about it cycle,” which you know is a no. Breaking this cycle is critical for CEOs to achieve revenue transformation. The Painful Present: Revenue stalled because your message sounds like noise. Purchasing... 
by Carla A. Fleming | Sep 28, 2025 | Business, CEO, Services, Software, Strategy
3 AM. Again. You’re staring at the ceiling, mind racing. The Painful Present: 🔥 Sales team turns every software pitch into a services conversation 🌋 Best clients “love you” but won’t buy your product 💣 Marketing still writing about... 
by Carla A. Fleming | Aug 24, 2025 | Business Strategy, CEO, CMO, Customer Success, Growth, Leadership, Marketing Strategy, Sales, Strategy
Luxury Experience Principles. What did I learn at the Waldorf Astoria that can impact B2B software? More than you think. According to Marketing Week, 68% of customers feel most brands have very similar communications and marketing messages. I’ve experienced this... 
