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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In Part 2 of this Selling the Cloud conversation, Amy Weber joins KK Anderson and Mark Petruzzi to go deeper into how modern revenue leaders should think about AI, outreach, hiring, and coaching. Amy challenges traditional sales motions like cold outreach and rigid playbooks, and explains how AI should be used to personalize engagement, free up seller time, and enable more meaningful one on one conversations.

The discussion also dives into assessment driven hiring and coaching, unpacking why resumes are a poor predictor of success, how to identify true talent signals, and how leaders can reduce friction by understanding identity, motivation, and communication styles across their teams. This episode is a practical guide for CROs who want to build revenue teams that perform, scale, and adapt in a more human centered, AI enabled world.

What You’ll Learn:

• Why cold outreach is losing effectiveness and what CROs should prioritize instead
• How AI can personalize messaging without removing the seller’s individual voice
• The right way to define ICPs based on engagement and impact, not volume
• Why playbooks should act as flexible frameworks, not rigid rules
• How assessment driven hiring reveals true talent signals beyond resumes
• Key differences between hunter, farmer, and CSM profiles and why misalignment hurts performance
• How leaders can reduce friction between managers and sellers through better coaching and communication
• Why understanding identity, emotional resonance, and motivation matters more than process alone

Key Topics:

• AI powered personalization in sales outreach
• ICP refinement and engaged account strategies
• Freeing up seller time for high value conversations
• Assessment driven hiring and role fit
• Coaching frameworks for sales managers and leaders
• Managing conflict between sales leaders and individual contributors
• Identity based leadership and communication styles
• Positive intelligence and managing saboteurs in high performing teams

Guest Spotlight: Amy Weber

Amy Weber is a strategic advisor to growth stage and enterprise revenue teams and the founder of VEDA Sales Consulting. She specializes in aligning people, process, and purpose to drive measurable revenue outcomes. Amy works closely with CROs and executive teams to improve hiring, coaching, and leadership effectiveness using assessment driven insights and practical operating frameworks.

🎧 Listen now and follow Selling the Cloud for more conversations on building modern, revenue focused GTM teams in the age of AI.

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In this episode of Selling the Cloud, Mark and KK sit down with Amy Weber, founder of Vetta Sales Consulting and strategic advisor to GrowthStage and Enterprise revenue teams. Amy specializes in aligning people, process, and purpose so strategy translates into real performance. She shares why many revenue organizations stall not because of tools or plans, but because of role confusion, misaligned talent, and leadership gaps.

Amy breaks down how to design roles that reflect reality, how to hire and coach based on true behavioral identity, and why companies must stop promoting top reps into leadership without assessing desire and capability. She also explains how AI can power a stronger customer experience by removing low value tasks and freeing sellers to focus on discovery, executive access, and relationship building.

This conversation hits the core of modern revenue growth: the right people in the right roles, operating in a healthy, human selling system.

What You’ll Learn:

• The three fastest tells that your people or role design are broken
• How to distinguish hunters, farmers, and CSMs without relying on personality stereotypes
• Why top performers burn out in “Frankenstein” job descriptions
• How to test for core sales behaviors using identity based assessment
• Why leadership is not a reward and should not be given based on quota attainment
• How AI can support human selling by automating research, follow up, and content prep
• How to create operating rhythms that ensure AI actually frees time, not adds more dashboards

Key Topics:

• Role design and talent fit for revenue teams
• Behavioral identity vs personality in hiring
• Misaligned promotions and the manager IC divide
• Why customer success is undervalued and misunderstood
• Modern client experience and relationship driven selling
• Practical, tool agnostic ways to use AI for research and personalization
• Operating cadence changes that make AI adoption real
• Avoiding analysis paralysis when implementing new technologies

Guest Spotlight: Amy Weber

Amy Weber is the founder of Vetta Sales Consulting and an advisor to high growth revenue organizations. She helps CROs and CEOs fix the people's side of revenue through role clarity, talent fit, and leadership development. Her work replaces outdated activity goals with clear rhythms and systems that actually change behavior, increase productivity, and create healthier teams. Amy also advises organizations building AI for talent decisions.

Resources and Mentions:

• Cisco sales story on customer experience
• Medium content repurposing with LLMs
• Talent identity and psychometric assessments
• Operating rhythms for revenue teams
• Relationship led selling frameworks

🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders driving the future of revenue. Subscribe wherever you get your podcasts.

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In this episode of Selling the Cloud, Drew Sechrist, CEO and co-founder of Connect the Dots and longtime Salesforce veteran, joins Mark Petruzzi and KK Anderson to unpack what it really means to build a relationship intelligence layer that changes how your team goes to market.

Drew shares why his own career win stories at Salesforce led him to build Connect the Dots, and how mapping real relationship strength can turn stalled enterprise deals into closed revenue. He breaks down the nuance of activating networks at scale, aligning incentives around introductions, and embedding relationship data directly into the existing workflow so new processes do not die on the vine. From Monday pipeline reviews to executive access and stuck late stage opportunities, Drew explains how the best revenue teams treat relationship intelligence like the air they breathe.

What You’ll Learn:

• Relationship Intelligence Fundamentals: What it really means to build a relationship intelligence layer and why it is a different go to market motion than cold outbound.
• Incentives and Activation: Why simply seeing who knows whom is only half the game and how incentive alignment, compensation, and context determine whether relationships actually get activated.
• Workflow, Not Side Quest: Practical ways to embed relationship data in tools like Salesforce, Slack, and email so managers naturally coach around it in pipeline reviews.
• From Story to Playbook: How one trusted introduction at Salesforce unlocked a seven figure deal and how that kind of magic can be turned into a repeatable team playbook.
• Modern Deal Strategy: How to use relationship maps and heat maps to unblock late stage deals stuck with finance, legal, or executive signoff instead of just hoping the contract gets approved.

Key Topics:

• Building a relationship intelligence layer for GTM and revenue teams
• The nuance of relationship activation and incentive alignment
• Where relationship intelligence should live in the RevOps and sales tech stack
• Using Salesforce embedded views, alerts, and APIs instead of forcing new UI and heavy change management
• Designing Monday pipeline reviews that start with “who do we know” and “have we connected the dots”
• Why LinkedIn connections alone are noisy and how signal based relationship scoring changes the game
• Moving from manual “who knows who” exercises to scalable, AI powered relationship mapping

Guest Spotlight: Drew Sechrist

Drew Sechrist is the CEO and co founder of Connect the Dots and a former Salesforce executive who rose through the ranks during the company’s hyper growth era. His experience closing large, relationship driven enterprise deals at Salesforce inspired him to build a platform that operationalizes the power of real networks for modern revenue teams. Today, Drew helps companies turn hidden relationship capital into measurable improvements in win rates, cycle times, and deal size.

Resources and Mentions:

• Company: Connect the Dots
• Concept: Relationship intelligence and relationship heat maps for GTM
• Book: The Tipping Point by Malcolm Gladwell
• Platform Ecosystem: Salesforce, Slack, email, and RevOps systems as primary surfaces for relationship data

🎧 Listen now and follow Selling the Cloud for more GTM, sales leadership, and AI driven revenue insights from leading voices in enterprise growth. Subscribe wherever you get your podcasts.

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In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Drew Sechrist, CEO and co founder of Connect The Dots and longtime Salesforce veteran, to unpack why traditional ABM motions and high volume outbound are running out of gas and what comes next. Drew shares how relationship intelligence, warm introductions, and network aware playbooks are giving revenue teams a durable performance edge over cold, volume driven tactics.

Drawing from his experience leading enterprise teams at Salesforce and now building Connect The Dots, Drew explains how to operationalize real relationships at scale, how to reimagine the role of the account executive as CEO of the territory, and why senior sellers should lead the shift from spray and pray to relationship driven go to market.

What You’ll Learn:

• Why ABM has reached peak utility and where it still fits in a modern go to market motion

• How relationship intelligence and warm paths consistently outperform cold outbound and one to many ABM

• Why the best enterprise sellers behave like CEOs of their territories and how that model broke during the growth at all costs era

• How to design KPIs that expose when your current motion is tapped out and ready for a relationship first rethink

• A practical 90 day approach to shifting from volume based SDR motions to relationship driven plays led by senior sellers

Key Topics:

• The limits of high volume ABM and cold outbound as primary growth levers

• Mapping networks, scoring relationship strength, and surfacing warm paths into target accounts

• Dreamforce era relationship building and how those habits still drive enterprise deals

• The return of the account executive as CEO of the territory, not just a cog in the sales tech machine

• Using AI and systems like Connect The Dots to make relationship based selling scalable and measurable

• Reweighting your go to market mix across ABM, intent, and relationships instead of relying on mass spray and pray

• How SDRs evolve into behind the scenes orchestrators of introductions, routing requests through executives and board members without breaking trust

Guest Spotlight: Drew Sechrist

Drew Sechrist is the CEO and co founder of Connect The Dots, a relationship intelligence platform that helps go to market teams tap into the power of real relationships at scale. Before founding Connect The Dots, Drew spent more than a decade at Salesforce during its hyper growth era, rising from one of the first account executives to leading enterprise sales teams. His career has been built on leveraging networks, warm introductions, and trusted relationships to win complex, high value deals.

Resources and Mentions:

• Company: Connect The Dots

• Event: Dreamforce

• Topics discussed: account executives as CEOs of their territories, relationship driven GTM, shifting off pure volume motions

🎧 Listen now and follow Selling the Cloud for more conversations on modern go to market, revenue leadership, and the future of relationship driven selling in an AI enabled world. Subscribe wherever you get your podcasts.

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In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrain, joins KK Anderson and Mark Petruzzi for a compelling conversation on how modern sales leaders can use AI to coach more effectively, eliminate wasteful pipeline rituals, and build real self-leadership within their teams.

Paul outlines how high-performing sales managers are shifting from performative metrics to meaningful enablement; using AI to flag risk, generate insights, and equip reps to close complex deals. He also shares how sales leaders can establish operating rhythms, drive accountability, and lead with trust; all while reporting to the board with metrics that prove the business value of relationships.

What You’ll Learn:

• AI-Enhanced Coaching: How to pair red/yellow flag systems with AI insights to pinpoint stalled deals and coach with precisio
• Cadence of Accountability: How to replace unproductive pipeline calls with actionable, written commitments that build trust and execution
• Manager Enablement: Why coaching the coach is the next evolution in sales performance systems
• Board-Ready Metrics: Which numbers matter most to prove relationships and strategic selling actually move the needle
• Practical AI Use Cases: Where AI drives effectiveness now (e.g., summarization, follow-up, personalization), and where it still falls short

Key Topics:

• Operationalizing AI in pipeline reviews and deal strategy
• Moving from activity tracking to outcome coaching
• Systems for continuous manager development
• Real intelligence vs. performative sales theater
• CRO priorities in the AI era: focus, trust, proof
• Enabling full-cycle reps with better content, follow-up, and insights
• Measuring relationship impact: customer engagement, strategic touches, lifetime value

Guest Spotlight: Paul Fuller

Paul Fuller is Chief Revenue Officer at Membrain, where he brings structure, strategy, and coaching to complex B2B sales organizations. A strong advocate for elevating leadership and execution within sales teams, Paul focuses on embedding process, insights, and AI into daily workflows to help reps and managers improve continuously.

Resources & Mentions:

• Company: Membrain

• Book Recommendations:

– The Greatest Sales Question Ever Asked by Brent Long

– A Mind for Sales by Mark Hunter

– The Speed of Trust by Stephen M.R. Covey

– Mere Christianity by C.S. Lewis

• Sales leader to follow: Matt Green (Sales Assembly)

🎧 Listen now and follow Selling the Cloud for more real conversations with revenue leaders building tomorrow’s go-to-market playbooks.

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