In Part 2 of this Selling the Cloud conversation, Stephen Messer, Co-Founder of Collective[i], continues to challenge the status quo of sales technology and leadership—this time focusing on how GTM teams can embrace AI, real-time data, and agile principles to navigate today’s complex buying environments.

Stephen and the hosts explore what’s broken in forecasting, why reactive CRM systems create risk, and how the modern seller’s mindset needs to evolve in a world where speed, adaptability, and intelligence win.

What You’ll Learn:

• The Rise of Agile Selling: Why sales leaders need to build systems that adapt in real time—not ones that just report what already happened.
• AI-Enhanced Forecasting: How predictive intelligence is helping teams eliminate bias and plan more accurately.
• Why CRM Alone Is a Liability: A deep dive into why legacy sales systems fail in fast-moving markets.
• How to Spot Buying Signals Earlier: What modern sales orgs are doing to move faster and respond with precision.
• Changing the Sales Culture: Why the future of sales leadership depends on embracing new data models and tech-forward practices.

Key Topics:

• Limitations of CRM forecasting
• Integrating AI for signal-based selling
• Buyer journey complexity and data latency
• Building an agile, responsive GTM motion
• Real-time revenue intelligence tools
• Leadership shifts for the AI-enabled seller
• 
  

Guest Spotlight: Stephen Messer

Stephen is Co-Founder and Vice Chairman of Collective[i], a revenue intelligence platform leveraging AI to enable agile sales execution. He’s a serial entrepreneur with a passion for reshaping how sales teams operate in dynamic, data-rich environments.

Resources & Mentions:

• Company: Collective[i]
• Topics: Agile revenue strategy, AI forecasting, CRM alternatives
• Suggested Reading: The JOLT Effect, The Qualified Sales Leader, The Sales Acceleration Formula

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