Episodios

  • Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2

    Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2
    Feb 10 2026

    In Part 2 of this Selling the Cloud conversation, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership.

    Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor expectations.

    The conversation also explores what executive vetting really looks like at the senior level, how boards assess integrity and credibility over time, and why understanding context behind results matters more than headline numbers. This episode is essential listening for CROs, CEOs, and revenue leaders aspiring to board seats or the CEO role.

    What You’ll Learn:

    • Board Governance for CROs: Why sales leaders must understand how boards think and operate
    • Investor Empathy: How understanding investor pressure builds trust and credibility
    • Learning Over Bravado: Why boards care more about why results happened than confidence alone
    • Risk Awareness: How governance thinking changes how CROs evaluate decisions and tradeoffs
    • Succession Planning: Why boards expect leaders to plan for a future beyond themselves
    • Board Readiness: What boards actually look for when recruiting sales leaders as directors
    • Executive Vetting Reality: What senior leadership evaluation really includes
    • Integrity Signals: Why honesty about misses builds long-term executive trust

    Key Topics:

    • Board governance through a sales leadership lens
    • Operator mindset vs investor mindset
    • Risk management and risk of inaction
    • Stakeholder alignment beyond compensation plans
    • Succession planning and leadership maturity
    • Board selection criteria for sales leaders
    • Executive search and forensic referencing
    • Ethics, credibility, and long-term reputation
    • Contextualizing revenue performance and growth
    • Preparing for CEO and board-level roles

    Guest Spotlight: Jason Baumgarten

    Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he advises boards, investors, and executive teams on leadership selection, succession planning, and governance. He has led more than 250 CEO and board transitions and brings deep expertise in evaluating executive readiness, integrity, and long-term leadership impact.

    Resources & Mentions:

    • Spencer Stuart
    • Harvard Business Review: How CEOs Build Confidence in Their Leadership
    • Board governance and executive succession best practices

    🎧 Listen now and follow Selling the Cloud for deeper conversations on executive leadership, governance, and what it truly takes to move from CRO to CEO.



    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    22 m
  • Ep. 112 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 1

    Ep. 112 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 1
    Feb 3 2026
    In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level.Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as they move from execution to enterprise leadership. The conversation explores founder-led transitions, boardroom presence, customer lifecycle thinking, and why sales excellence alone does not guarantee executive readiness.This episode is essential listening for CROs, founders, and revenue leaders who want to move beyond quota and operate at the highest levels of leadership.What You’ll Learn:From CRO to CEO: The mindset shifts sales leaders must make to be considered for top executive and board rolesBoardroom Credibility: How sales leaders can show up as strategic business operators, not just revenue ownersFounder Transitions: When founder-led selling breaks and what must change to scale the organizationSystems Thinking: Why understanding the full revenue and customer lifecycle matters more than pipeline aloneExecutive Readiness Signals: What boards look for when evaluating senior sales leadersHiring at the Right Time: Common board mistakes when transitioning away from founder-led salesKey Topics:Evolving from sales operator to strategic executive CRO presence and influence in the boardroomFounder-led sales versus scalable go-to-market systemsRetention, lifecycle metrics, and long-term growth signalsBoard governance and leadership transitionsWhy sales is not always the answerGuest Spotlight: Jason BaumgartenJason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he leads executive search and board advisory engagements for companies ranging from early-stage ventures to multi-billion-dollar enterprises. He has advised on more than 250 CEO and board transitions, with deep expertise in founder-led technology companies, succession planning, and board effectiveness.Before joining Spencer Stuart, Jason was an Associate Principal at McKinsey and a Program Manager at Microsoft. He holds an MBA from Stanford Graduate School of Business, serves as Chairman of the Board for IslandWood, and is a frequent contributor to Harvard Business Review, including his article How CEOs Build Confidence in Their Leadership.Resources & Mentions:• Spencer Stuart• Harvard Business Review: How CEOs Build Confidence in Their Leadership• Mark Roberge: The Science of Scaling🎧 Listen now and follow Selling the Cloud for conversations with leaders shaping the future of go-to-market, executive leadership, and board-level decision making.Mark Petruzzi (00:37)Welcome to today's episode of Selling the Cloud Podcast. I'm thrilled to welcome Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stewart. Jason leads Executive Search and Board Advisory for one of the world's premier leadership consulting firms. He's completed over 250 CEO and Board Transitions.across companies ranging from early stage ventures to multi-billion dollar enterprises. His expertise spans CEO succession planning, board effectiveness, and leadership transitions, particularly for founder led technology companies. Before Spencer Stewart, Jason was an associate principal at McKinsey and a program manager at Microsoft.He holds an MBA from Stanford's Graduate School of Business and serves as chairman of the board for Island Wood. His thought leadership appears regularly in the Harvard Business Review, including a recent article, How CEOs Build Confidence in Their Leadership. What makes Jason's perspective uniquely valuable is his vantage point. He's interviewed thousands of sales leaders and observes whatseparates those who successfully transitioned to CEO and board roles from those who just can't get there. Today we'll explore four critical themes. The sales leaders evolution from operator to strategic executive. Founder transitions building a leadership capacity beyond the go-to-market motion. Board governance for sales leaders. Why thinking like an investor makes you better at your job.and landing your next role, what really matters at the senior executive level. So I guess a couple of things there. You really don't work hard enough or really haven't accomplished most in your life Mano man, Jason, what an amazing career you've had already.And I'm sure you're not going to be slowing down anytime soon. So thank you. Thank you for joining us and joining us here on Selling the Cloud podcast.Jason Baumgarten (02:40)Well, thanks for having me. And I felt a little tired listening to it, but it was all fun in the moment and delighted to try and share some learnings from the many, many, interviews and board discussions and CEO ...
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    25 m
  • Ep. 111 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman - Part 2

    Ep. 111 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman - Part 2
    Jan 27 2026
    In Part 2 of this Selling the Cloud conversation, Cherilynn Castleman joins Mark and KK Anderson to unpack what strong CRO leadership looks like in a time of rapid AI adoption and constant go-to-market change. As every team claims to be AI-first and tech stacks continue to converge, Cherilynn explains what truly differentiates leaders who drive real results.This episode dives into how curiosity with AI, disciplined daily usage, and protecting selling time translate into cleaner pipelines, shorter sales cycles, and fewer end-of-quarter surprises. Cherilynn also shares practical guidance on modern operating rhythms, how to run meetings that actually matter, and which metrics prove that change is working now, not quarters from now.What You’ll Learn:Building AI Fluency as a Leader: Why modeling curiosity, transparency, and experimentation matters more than mastering toolsAI as a Daily Discipline: How consistent usage creates confidence, clarity, and better decision-makingProtecting Selling Time: How CROs can reduce meetings and increase seller productivity from 10 hours to 15 to 20 hours per weekHumanized Outbound at Scale: Using AI for micro-segmentation while keeping messaging personal and relevantRunning Meetings That Matter: How 30-minute meetings, no slides, and clear ownership tighten pipeline executionProving Change with Metrics: The three numbers boards and CFOs care about to fund and support transformationKey Topics:CRO leadership in an AI-saturated GTM landscapeModeling AI curiosity and transparency across revenue teamsStop chasing tools and start building the right mindsetExact meetings, executive engagement, and decision-maker accessMicro-segmentation by persona, industry, region, and generationModern revenue operating rhythms and pipeline hygieneMeasuring cycle time, executive involvement, and multi-threaded win ratesGuest Spotlight: Cherilynn CastlemanCherilynn Castleman is a sales and leadership advisor who helps revenue teams adapt to modern buying behavior and post-pandemic selling realities. She is the author of Post-Pandemic Selling, a top Amazon bestseller that has been recognized by Salesforce as one of the top sales books for modern leaders. Cherilynn is also an active LinkedIn voice, hosting frequent LinkedIn Lives where she shares practical insights on sales leadership, AI fluency, and authentic connection.Resources & Mentions:Book: Post-Pandemic Selling by Cherilynn CastlemanWebsite: postpandemicselling.comRecommended Book: The Untethered Soul by Michael A. SingerLeadership Voice to Follow: Bill Green, former CEO of Accenture🎧 Listen now and follow Selling the Cloud for more insights on AI-driven leadership, modern sales execution, and building trust across today’s go-to-market teams.Mark (00:30)All right. Let's move to topic three. Leading as a CRO in a time of intensechange. So every team nowadays says they are AI enabled, they're AI first, and everyone's sales and marketing stack just looks very similar. So from the seat of the CRO, what actually differentiates leadership right now in your opinion? Could you give us two or three weekly behaviors you expect to seein the numbers of a CRO that is leading well.Cherilynn Castleman (01:04)Yeah, so a couple things. I think that if a CRO is demonstrating curiosity with AI, they are using AI, they are sharing with their team, this is what I did. I was working with the CFO for a huge company recently and they do a pricing exercise. And they normally would sit down for a couple weeks and work on this pricing exercise. And I challenged them to open AI and pull their data into their proprietary system.And in 30 minutes, they had done the entire exercise. And so it was like, wow, everybody's going to be impressed. I said, no, it's transparency. Tell them you used AI to do it. Demonstrate, model that you're curious. If you fail, talk about that. So number one, they're modeling curiosity. Two, it's a discipline. They're using it on a daily basis. They're talking about it on a daily basis.There are somewhere between 50 and 200 new AI tools every day. There are, when you look at go-to-market tools, there are somewhere between seven and 10 new tools every day. There's no way you can master the tools. Stop chasing the tools. It's a mindset. It's about confidence and clarity. The next thing that I would say is that ⁓ protect the selling time.Look at your meetings and make them very efficient. Get them down to 30 minutes. The goals is most sellers sell about 10 hours a week. You want to get your sellers to 15 to 20 hours a week. And so where you're going to see this, are you going to see a cleaner pipeline, you're going to see higher exact meetings. And so those are things you want to measure is not just meetings, but exact meetings, decision-maker meters. It will shorten the sales cycles and you'll have fewer surprises at the end of the quarter.KK Anderson (02:43)So good. was just on a coaching call just before this podcast episode actually...
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    13 m
  • Ep. 110 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman – Part 1

    Ep. 110 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman – Part 1
    Jan 20 2026
    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 toolsetDaily AI routines for sellers and managersPOV creation using LinkedIn profiles, 10Ks, and industry analysisRelationship selling and the science of trustDiscovery questions that increase buyer confidenceAvoiding buyer defensiveness and ethical AI useExecutive conversations and CFO expectationsFinancial storytelling with insight, context, and impactGuest Spotlight: Cherilynn CastlemanCherilynn 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 AIBook: Post-Pandemic SellingResearch Reference: Dr. Jane Dutton on High Quality ConnectionsConcepts: 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.Mark (00:31)to Selling the Cloud. Our guest today is Cheryl Lynn Castleman, an enterprise sales leader turned strategic coach and Harvard instructor as well. She helps teams become trusted advisors with practical AI fluency and relationship skills. She also builds accessible learning at scale as a new to me creator. Her course, Smart Tips, Sales,Master Relationships Driven Selling Via AI is super highly rated and available versus a via Udemy business. Her programs focus on outcomes you can see on Monday morning. Better discovery, cleaner deal strategy, clear next steps. She has coached thousands of sellers and leaders, lifted promotion rates through hands-on coaching.and built a large learning community through weekly live sessions and workshops. She teaches simple operating rhythms that free time for customer conversations rather than adding more dashboards. And she's on a mission to equip 1 million women in sales and leadership with the fluency, confidence and playbooks to thrive. Here are three topics we'll cover today. AI fluency as a daily mindset.How to use AI to amplify strengths and turn prep into a repeatable routine that shows up every day in results. Relationship selling and the science of trust, the questions and behaviors that build credibility fast with modern buying groups, and leading as a CRO in a time of extremely rapid change. How to focus to team, communicate change, improve impact without adding any additional noise.Sherlyn, we're so happy and proud to have you here. Welcome to Selling the Cloud.Cherilynn Castleman (02:13)Thank you, Mark. Thanks, KK. I'm thrilled to be here today.Mark (02:16)All right, we're gonna take you right ...
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    26 m
  • Ep. 109 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 2

    Ep. 109 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 2
    Jan 13 2026

    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.


    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    18 m
  • Ep. 108 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 1

    Ep. 108 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 1
    Jan 6 2026

    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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    20 m
  • Ep. 107 - Building Revenue Teams That Thrive in the Age of AI with Amy Weber - Part 2

    Ep. 107 - Building Revenue Teams That Thrive in the Age of AI with Amy Weber - Part 2
    Dec 28 2025

    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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    14 m
  • Ep. 106 - Building Revenue Teams That Thrive in the Age of AI with Amy Weber - Part 1

    Ep. 106 - Building Revenue Teams That Thrive in the Age of AI with Amy Weber - Part 1
    Dec 16 2025

    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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    22 m