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

🎧 Listen now and follow Selling the Cloud for more episodes on modern GTM, enterprise sales, and AI-led transformation. Subscribe wherever you get your podcasts.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Stephen Messer, Co-Founder of Collective[i], joins Mark Petruzzi and KK Anderson to challenge outdated sales systems and thinking—starting with the traditional CRM mindset.

Stephen shares why CRM is no longer enough to keep up with how modern B2B buyers actually buy, and how AI, agile selling, and real-time intelligence are enabling sales organizations to operate with precision, speed, and adaptability. If your team is still relying on lagging indicators to drive revenue, this conversation is a must-listen.

What You’ll Learn:

• Why CRMs Fall Short: How today’s buying environments outpace static, backward-looking CRM data.
• AI’s Role in Sales Agility: How machine learning and predictive intelligence change how reps prepare, forecast, and engage.
• Modern Buyer Behavior: Why linear sales cycles are dead and what sellers need to do to stay relevant.
• Real-Time Revenue Intelligence: How agile systems give sellers an edge by tracking live signals, not just past activities.
• Breaking Old Habits: What it really takes to shift from CRM dependence to a future-forward, AI-enhanced GTM approach.

Key Topics:

• CRM limitations in today’s sales environment
• How AI enhances human selling, not replaces it
• The evolution of sales ops and forecasting
• Agile frameworks in B2B sales
• The speed and complexity of modern buying journeys
• Building a responsive, data-informed sales organization

Guest Spotlight: Stephen Messer

Stephen is Co-Founder and Vice Chairman of Collective[i], a platform that delivers AI-powered insights for enterprise sales organizations. A serial entrepreneur and digital innovator, Stephen brings deep insight into how technology and data can transform sales performance.

Resources & Mentions:

• Company: Collective[i]
• Topics: AI in sales, agile revenue systems, sales enablement tech
• Recommended Reading: The JOLT Effect, The Challenger Sale, Predictable Revenue

🎧 Listen now and follow Selling the Cloud for weekly expert conversations on the future of enterprise selling, GTM strategy, and revenue innovation. Subscribe wherever you get your podcasts.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.