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... 
by Carla A. Fleming | Aug 17, 2025 | AI, Business Strategy, CMO, Growth, Personalization, Sales
Did you know that almost 40% of B2B deals don’t close, as noted in the Challenger’s B2B Buyer Study? According to Gartner, 60% of deals lost are due to non-decisions. I believe forward-leaning CMOs must have a data insights strategy that separates... 
by Carla A. Fleming | Aug 11, 2025 | AI, Business Strategy, CEO, CMO, Growth, Personalization, Sales
B2B software firms are grappling with slower sales. Customers worry about making the wrong decision. I believe CMOs must build a data strategy to decode the B2B buying journey, creating a competitive advantage in the AI era. McKinsey notes gradual data collection can... 
