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Your Playbook is Teaching You Something

Your Playbook is Teaching You Something

by Carla A. Fleming | Mar 15, 2026 | CEO, Growth, Sales, Sales Playbook

Watch the video below. https://www.pivotingstrategies.com/wp-content/uploads/2026/03/playbook_taught_carousel-4.mp4-031526-4.mp4 What did your playbook teach you about your business? What new behaviors are you observing? Ready to build a playbook your sales team uses?...
Sales Playbooks: Intelligence and Business Feedback

Sales Playbooks: Intelligence and Business Feedback

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...
Your Playbooks: What’s Broken?

Your Playbooks: What’s Broken?

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...
Your Sales Playbook is Stuck in Your Head?

Your Sales Playbook is Stuck in Your Head?

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...
Your Misalignment Can Cost You A Market

Your Misalignment Can Cost You A Market

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...
Why Do Your Best Customers See Three Different Companies?

Why Do Your Best Customers See Three Different Companies?

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...
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Recent Posts

  • The Translation Layer: What Your CFO and CMO Are Both Missing
  • What Has Expired? The CFO or CMO Strategy?
  • The Revenue Gap
  • The Revenue Gap Midmarket CFOs See, But Can’t Explain
  • Your Playbook is Teaching You Something
  • Pivot Newsletter Survey
  • Playbook Intelligence: What’s Broken in Your Business?
  • Growth Strategy Stuck in Your Head
  • Sales Playbooks: Intelligence and Business Feedback
  • Your Playbooks: What’s Broken?

Recent Blog Posts

  • The Translation Layer: What Your CFO and CMO Are Both Missing
  • What Has Expired? The CFO or CMO Strategy?
  • The Revenue Gap
  • The Revenue Gap Midmarket CFOs See, But Can’t Explain
  • Your Playbook is Teaching You Something

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