This special episode kicks off our Mastering Sales with AI series with a candid, high-impact discussion on how revenue leaders can move beyond AI buzzwords and actually apply intelligent selling strategies—especially in volatile markets.

Stephen Messer and Paul Melchiorre join Mark Petruzzi to break down the hard truths about what makes AI work in real sales orgs: leadership alignment, data readiness, and daily execution. This is your first step toward modern, adaptive selling—driven by signal, not guesswork.

What You’ll Learn:

• Execution Beats Ambition: Why success with AI doesn’t start with big vision decks—but with specific, high-impact use cases.
• Your CRM Can’t Keep Up: Why traditional tools break in volatile markets, and how neural net AI models adjust in real time.
• Forecasting Needs a Reboot: How daily deal signals—red, yellow, green—are replacing “gut feel” and weekly sales meetings.
• Buyer-Centric Strategy: Why studying sellers won’t help you predict revenue—but studying buyers will.
• Leading with Insight: How top CROs gain board trust through data, not opinions.

Key Topics:

• Moving from AI theory to operational reality
• Fixing broken forecasting processes
• Leveraging volatility as a growth advantage
• Redefining enablement with signal-based coaching
• Why AI is a co-pilot, not a replacement
• How to scale insights across sellers, teams, and time zones
• 
  

Event Recap – Top Takeaways:

• Start small, win big: Tie AI to real revenue use cases.
• Clean data wins: No insights without data discipline.
• AI empowers, not replaces: Give time back to sellers, and sharpen execution.
• Execution > tools: Adoption follows alignment.

🎧 Listen now and follow Selling the Cloud for more episodes in our Mastering Sales with AI series. New sessions coming soon.

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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.

In this episode of Selling the Cloud, Kristina Jaramillo, President of Personal ABM, joins KK Anderson to unpack why most ABM programs fall short; and what it really takes to win and expand six- to seven-figure enterprise accounts.

Kristina shares how B2B teams can go beyond persona-based playbooks to deliver personalized, strategic account experiences. She explains how to redefine your ICP, align marketing and sales with shared revenue accountability, and build campaigns that influence real pipeline movement; especially when targeting enterprise buyers.

What You’ll Learn:

• ABM Foundations that Win: How true account insights—beyond intent data or personas—unlock six- and seven-figure deals.
• Strategic ICP Redefinition: Mapping accounts by strategic readiness and revenue potential, not just firmographics.
• Full-Funnel Alignment: Tactics that unite sales, marketing, and CS around shared expansion and retention goals.
• Personalization at Scale: Frameworks for moving from one-to-one to one-to-few without losing relevance.
• Revenue-Centric Metrics: Using stage progression, influenced pipeline, and NRR to prove ABM impact.

Key Topics:

• Strategic account-based marketing for mid-market & enterprise growth
• Differentiating ABM from demand gen
• Intent data traps and tech misuse
• Metrics that go beyond MQLs: NRR, stage progression, deal influence
• Aligning CS, sales, and marketing around buyer relevance
• Orchestrating account experiences, not just sourcing leads

Guest Spotlight: Kristina Jaramillo

Kristina is President of Personal ABM and host of the ABM Done Right podcast. With a deep focus on revenue-driven marketing, she helps B2B tech and SaaS companies build customized go-to-market motions that win and expand high-value enterprise accounts.

Resources & Mentions:

• Podcast: ABM Done Right
• Go-to-market strategist to follow: Sangram Vajre
• Recommended Books:
• The Challenger Sale
• The Challenger Customer
• The JOLT Effect

🎧 Listen now and follow Selling the Cloud for more GTM insights from leading voices in enterprise growth. 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 Part 2 episode, co-host Mark Petruzzi continues the conversation with Jack Zimnavoda, Head of Customer Success at Insightful. This time, they explore how Jack’s team is scaling Customer Success by embedding AI, aligning post-sale marketing, and applying smart segmentation strategies.

Jack shares how predictive tools, data-informed health scores, and hybrid touch models enable CS teams to identify churn risks, streamline workflows, and drive expansion; all while maintaining a personal touch.

What You’ll Learn

• Predictive CS in Action: Jack explains how his team uses AI within their CS platform to surface risk, recommend proactive next steps, and highlight expansion-ready accounts.
• Marketing + CS = Growth: How Insightful brings CS and marketing together to educate customers, promote feature adoption, and scale communication—without losing personalization.
• Segmentation for Scale: Why Insightful uses a hybrid touch model to support over 5,000 customers across different industries and sizes—without compromising value delivery.
• Retention Forecasting: Discover how qualitative inputs, usage data, and AI models combine to anticipate churn and improve long-term customer outcomes.

Key Topics

• Building a predictive, AI-supported CS platform
• Aligning CS, product, and marketing post-sale
• Hybrid-touch models for scale
• Customer health scoring and churn prediction
• Operationalizing expansion strategy
• Creating scalable CS motions with a human touch

Guest Spotlight: Jack Zimnavoda

Jack is Head of Customer Success at Insightful, where he leads global efforts in retention, adoption, and expansion. With over 10 years of experience in B2B SaaS, Jack has developed practical, scalable strategies that connect Customer Success with revenue growth.

Resources & Mentions

• Book: The Seven Pillars of Customer Success by Wayne McCulloch
• Podcast Mention: This is Growth by Daphne Costa Lopes
• Tool: Vitally – CS platform used by Insightful

🎧 Listen now and follow Selling the Cloud for more expert insights on scaling GTM teams. 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, co-host Mark Petruzzi welcomes Jack Zimnavoda, Head of Customer Success at Insightful. Jack shares how modern B2B SaaS organizations can turn customer success from a support function into a true driver of revenue and retention.

Together, they explore what it takes to align CS with sales, marketing, and product—without creating channel conflict. Jack reveals how predictive AI, smart segmentation, and aligned incentives can turn expansion into a scalable and proactive motion.

What You’ll Learn

• Customer Success as a Revenue Driver: Jack explains how to reframe CS from a cost center to a growth engine—through structure, ownership, and incentives.
• Avoiding Channel Conflict: Learn how clearly defined swim lanes, compensation clarity, and collaboration between CS and Sales create harmony and momentum.
• Building a Scalable CS Model: From white-glove enterprise accounts to hybrid-touch models, Jack outlines how to maintain personalized value delivery at scale.
• Metrics That Matter: Understand the importance of net retention, lifetime value, and how CS teams can build pipelines and forecast revenue just like Sales.
• AI + Customer Health: Hear how Jack uses predictive AI to monitor product usage, signal risk, and surface expansion opportunities at scale.

Key Topics

• Structuring CS to own post-sale revenue
• Aligning CS, Sales, Marketing, and Product
• Channel conflict: where it happens and how to prevent it
• Using AI in CS forecasting and health scoring
• Segmenting your customer base to drive upsell plays
• Scaling without losing the human touch
• How to hire for commercial CSMs (hint: curiosity and creativity)

Guest Spotlight: Jack Zimnavoda

Jack is Head of Customer Success at Insightful, where he leads a global team focused on retention, adoption, and expansion. With over a decade of experience in B2B SaaS, Jack has helped transform CS into a proactive, commercial function that partners across the go-to-market org to drive real business outcomes.

Resources & Mentions:

• Book: The Seven Pillars of Customer Success by Wayne McCulloch
• Podcast Mention: This is Growth by Daphne Costa Lopes
• Tool: Vitally – CS platform used by Insightful

🎧 Listen now and follow Selling the Cloud for more expert insights on scaling GTM teams. 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, co-hosts Mark Petruzzi and KK Anderson welcome back their friend and former Selling the Cloud host, Cathy Minter, now CEO of Wisdom.io. Cathy brings her deep go-to-market expertise to a timely conversation on what it really takes to scale in today’s fast-changing SaaS environment.

Together, they explore why the traditional, siloed approach to sales, marketing, and customer success no longer works—and why a unified CRO model is becoming essential for growth-minded organizations.

What You’ll Learn

• Why a Unified CRO Model Works
• Discover the strategic advantages of aligning sales, marketing, and customer success under one revenue leader and when it doesn’t make sense.
• The Death of Departmental Silos
• Learn how shifting buyer behavior, faster sales cycles, and AI-driven insights demand end-to-end alignment across the customer journey.
• Data Fluency as a CRO Superpower
• Cathy shares why today’s CROs must think like data scientists and psychologists and how that’s changing the role forever.
• From Chaos to Clarity: Leading Through Change
• Practical advice for CROs navigating organizational chaos, short tenures, and constant pivots. Hint: Start with what you can change tomorrow.
• AI as Your New Intern
• Hear how Cathy leverages AI to supercharge research, prep, and forecasting—freeing up time to do what matters most: build trust and close deals.

Key Topics

• The evolution of the modern CRO
• Aligning KPIs across sales, marketing, and success
• Why boards have resisted the unified model and how to change their minds
• The impact of AI on seller productivity and buyer behavior
• Building trust in a late-stage, digitally empowered buying process
• Practical tips for early wins in your first 90 days as a CRO

Guest Spotlight: Cathy Minter

Cathy is the CEO of Wisdom.io and a proven go-to-market executive with a track record of scaling high-growth SaaS businesses. She has led world-class sales, marketing, and customer success teams and now shares her playbook for building modern, aligned revenue organizations.

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