In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams.

Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy.

This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise.

What You’ll Learn:

• AI as a Daily Sales Discipline: How a simple 15 minute daily AI prep routine helps sellers develop POVs, anticipate change, and continuously improve.
• POV Development at Scale: A repeatable framework for triangulating industry, company, and persona insights using AI.
• Making AI Revenue Relevant: Why leaders should evaluate AI through insights, context, and business impact instead of activity metrics.
• Trust in the Age of AI Noise: How better questions and deeper listening create credibility when buyers are overwhelmed with automation.
• High Connection Discovery Questions: How to use AI to reframe discovery questions that trigger trust, openness, and buyer engagement.
• Prospecting Without Pitching: Why offering value through insights, case studies, and tools beats asking for meetings.
• Navigating Modern Buying Groups: How to adapt when new stakeholders like CFOs enter late-stage conversations.
• Financial Fluency for Sellers: Why precise numbers, not rounded estimates, matter when speaking with executive buyers.

Key Topics:

• AI fluency as a mindset, not a toolset
• Daily AI routines for sellers and managers
• POV creation using LinkedIn profiles, 10Ks, and industry analysis
• Relationship selling and the science of trust
• Discovery questions that increase buyer confidence
• Avoiding buyer defensiveness and ethical AI use
• Executive conversations and CFO expectations
• Financial storytelling with insight, context, and impact

Guest Spotlight: Cherilynn Castleman

Cherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops.

Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles.

Resources & Mentions:

• Course: Smart Tips Sales – Master Relationship Driven Selling via AI
• Book: Post-Pandemic Selling
• Research Reference: Dr. Jane Dutton on High Quality Connections
• Concepts: AI fluency, POV selling, high connection discovery, financial storytelling

🎧 Listen now and follow Selling the Cloud for more insights on modern sales leadership, AI-driven GTM strategy, and building trust at scale.

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In Part 2 of this Selling the Cloud conversation, Mark Roberge joins KK Anderson and Mark Petruzzi to go deeper into what happens after product market fit is achieved and why going too fast too early can quietly break a business.

Mark breaks down the transition from product market fit to go to market fit, explaining why these stages must be earned in sequence, not pursued in parallel. He outlines what real go to market readiness looks like, how to design a buyer centric sales system, and why retention and unit economics are the true signals of readiness to scale.

The discussion also tackles sales process design, hiring profiles by stage, and the common mistakes founders make when front loading headcount after a fundraise. Mark closes by sharing a disciplined pacing model for growth and why predictable scaling beats vanity growth every time.

What You’ll Learn:

• Why product market fit must be proven before optimizing go to market execution

• How retention serves as the strongest signal of long term product market fit

• What defines go to market fit beyond revenue growth alone

• The core components of a buyer centric go to market system

• How to build a sales process that mirrors the buyer journey

• The difference between discovery driven selling and pitch driven selling

• How sales hiring profiles should change across product market fit, go to market fit, and growth stages

• Why aggressive headcount expansion often leads to future layoffs

• How pacing hiring and spend creates predictable and durable growth

Key Topics:

• Product market fit versus go to market fit

• Retention as a leading indicator of success

• Founder selling and unscalable early motions

• Go to market system design

• Ideal customer profile and buyer journey alignment

• Discovery, qualification, and modern selling principles

• Sales hiring by company stage

• Scaling headcount responsibly

• Unit economics and growth pacing models

Guest Spotlight: Mark Roberge

Mark Roberge is the founding CRO of HubSpot, where he helped scale the company from zero to IPO. He is a Senior Lecturer at Harvard Business School, co-founder and managing partner at Stage 2 Capital, and author of the bestselling book The Sales Acceleration Formula. His latest book, The Science of Scaling, distills decades of research into a practical, stage specific roadmap for sustainable growth.

Resources & Mentions:

• Book: The Science of Scaling by Mark Roberge

• Book: The Sales Acceleration Formula

• Organization supported: McLean Hospital

• Opportunity to download the first chapter via Mark’s website

• Pre order The Science of Scaling with proceeds supporting mental health research

🎧 Listen now and follow Selling the Cloud for more insights on building durable go to market engines and scaling the right way.

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In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Mark Roberge, founding CRO at HubSpot and author of The Sales Acceleration Formula, to unpack why most companies scale at the wrong time and with the wrong signals. Mark introduces a stage-specific, data-driven framework for moving from product market fit to go to market fit, and explains why managing to readiness and retention beats chasing top-line revenue alone.

Mark breaks down how founders and boards get trapped copying outdated playbooks, why product market fit is often misunderstood, and how to define it through value realization, not just revenue. He also shares a practical approach for finding a leading indicator of retention, then translating unit economics into clear operating KPIs that make scaling repeatable, profitable, and measurable.

What You’ll Learn:

• Why scaling “scientifically” requires managing to readiness and retention, not just revenue growth.
• The difference between market-message fit and true product market fit.
• How to define product market fit using retention and value realization.
• How to build a leading indicator of retention using a simple “P percent do event every T time” framework.
• Why startups should delay scalable processes until product market fit is proven.
• What go to market fit actually means and how unit economics define it.
• How to translate LTV:CAC targets into practical KPIs like quota, close rates, and meeting volume.
• How to diagnose pipeline problems as readiness issues vs volume issues using conversion patterns across reps.

Key Topics:

• The danger of copying borrowed playbooks from past unicorns
• Readiness pacing vs hiring based on fundraising timelines
• Product market fit as value creation, not revenue milestones
• Leading indicators of retention and early customer success signals
• Go to market fit and unit economics as the profitability test
• Turning unit economics into a repeatable go to market formula
• Quick tests for pipeline issues: lead quality vs sales execution
• Why small funnel improvements compound faster than single big swings

Guest Spotlight: Mark Roberge

Mark Roberge is the founding CRO at HubSpot, where he helped scale the company from zero to IPO. He is co-founder and managing partner at Stage 2 Capital, a Harvard Business School senior lecturer focused on sales and go-to-market strategy, and the best-selling author of The Sales Acceleration Formula. His newest book, The Science of Scaling, distills decades of research into a stage-specific roadmap for scaling with measurable readiness.

Resources & Mentions:

• Book: The Science of Scaling (pre-order available)
• Book: The Sales Acceleration Formula
• Concept: Product Market Fit vs Go to Market Fit vs Growth and Moat
• Framework: “P percent of customers do event every T time”
• Example: Slack’s activation benchmark (high-volume team messaging)
• SaaS Metrics: Retention, Leading Indicator of Retention, LTV:CAC, Payback Period
• Reference: Winning by Design and compounding funnel improvement

🎧 Follow Selling the Cloud for more episodes on building durable GTM systems, improving sales execution, and scaling revenue with confidence.

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