The Revenue Leadership Podcast with Kyle Norton
The Revenue Leadership Podcast with Kyle Norton is a new show from Pavilion that dives deep into how to succeed as a revenue leader. Kyle Norton, CRO of Owner.com, will host real revenue operators and share framework and tactics you can apply today. No fluff, no sales pitches, and no platitudes.
This podcast is built for Founders, CRO’s, Directors and VP’s of Sales (and people who aspire for those roles) who want to level up their craft and grow revenue faster.
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$40M ARR with 50‑Person Team (in less than a year) - Bryan Adams, VP Sales at bolt.new
11/19/2025
$40M ARR with 50‑Person Team (in less than a year) - Bryan Adams, VP Sales at bolt.new
Bolt.new blew past past $40M ARR in just one year with only 50 people. In this episode, Bryan Adams, VP Sales at Bolt.new sits down with host Kyle Norton to break down how go-to-market operates at a hyper-growth AI company. Bryan shares some of their tech stack, and gets real about leadership—hiring “adults,” firing fast, and focusing on what reps actually need to win. If you’re leading a modern GTM org, this one’s worth your next commute. Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 01:30 Meet Brian Adams, VP of Sales at Bolt.new 02:06 What Is Vibe Coding and How Bolt Works 03:54 Building Successfully with Bolt’s “Plan” Feature 06:11 Layering Builds and Iterative Development 08:47 Real Use Cases Built with Bolt 10:24 The Build vs. Buy Decision Framework 12:57 Inside Bolt’s Go-to-Market Tech Stack 13:59 Using Freckle to Unmask and Enrich Leads 15:08 AI-Powered Prospecting and Support Automation 17:41 Shifting GTM Strategy: From PMs to Engineers 19:54 Outbound Strategy, Target Accounts, and LinkedIn Engagement 25:13 How RevOps and SDR Growth Teams Collaborate 29:13 Bolt’s Growth, Scale, and Competitive Landscape 33:03 Competing in a Knife Fight Market 36:56 Contract Structures, Compensation, and Profitability 40:38 Hypergrowth Lessons and Leveraging Automation 44:47 Leadership Philosophy: Empowerment and Accountability 48:08 Building Trust and Team Culture 51:17 Leadership, Firing Fast, and Team Integrity 52:59 Quick Fire: Great vs. Good Sales Leadership 54:32 Hard Lessons, Best Advice, and Book Recommendations 57:13 Closing Remarks and Outro
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E53: Sales Capacity Planning That Doesn’t Suck (Jenny Dingus, SVP Global Sales @ Clio)
11/12/2025
E53: Sales Capacity Planning That Doesn’t Suck (Jenny Dingus, SVP Global Sales @ Clio)
Clio’s SVP of Global Sales, Jenny Dingus, joins Kyle Norton to talk about why the “people × quota” revenue planning model is terrible, and what they’re using instead. Jenny shares how Clio’s $1B acquisition flipped their planning model, how they forecast in high-uncertainty markets, and what “drawing the owl” looks like in real life. If you run revenue and you’re tired of spreadsheet fantasy planning (or just want to know what two senior GTM leaders are thinking about these days), worth a listen! Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 02:15 Jenny’s Career Journey from RingCentral to Clio 04:00 Vertical SaaS and Expanding Market Opportunity 06:10 Disruption, AI, and Modernizing Legal Tech 08:00 Educating a Skeptical Market on AI Adoption 10:15 The Myth of the “People x Quota” Growth Model 12:05 Why Linear Capacity Planning Still Persists 14:45 The Integrated Planning Alternative 17:10 Planning Amid Product Launches and Acquisitions 20:15 Quotas, Motivation, and Momentum in Sales Teams 23:00 Multi-Factor Revenue Planning and Emerging Markets 27:05 Managing Speculative Growth Bets and Reforecasting 31:10 Balancing Capacity and Demand in High-Growth Environments 34:40 Strategic Congruence: Playing the Right Company Game 38:30 Communication, Change Management, and Leadership Alignment 43:45 Inside Clio’s Acquisition and GTM Integration Process 48:40 Leadership Communication Principles and “Feeling” the Message 52:00 Frontline Enablement During Massive Change 56:45 Building Continuous Feedback Loops and AI-Enabled Training 01:00:30 Quickfire: Lessons in Leadership, Humility, and Focus 01:04:00 Favorite Reads and Closing Reflections
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E52: Winning in Crowded Markets - The CRO Playbook (Jonathan Leaf, CRO @ BambooHR)
11/05/2025
E52: Winning in Crowded Markets - The CRO Playbook (Jonathan Leaf, CRO @ BambooHR)
How do you stand out when your feature list looks like everyone else’s? In this episode, Jonathan Leaf, CRO of BambooHR, joins host Kyle Norton (CRO at Owner.com) to break down how he’s built competitive edge in undifferentiated markets—from Softchoice to AWS, RingCentral, and now BambooHR. Jonathan shares how to: - Win when products look the same - Stay maniacally focused on a specific segment and ICP - Use values and leader visibility to drive accountability and performance - Build organizational rhythm that fuels execution Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 00:00 Introducing Jonathan Leaf, CRO of BambooHR 01:06 Career Journey: From SoftChoice to AWS to BambooHR 03:14 Inside BambooHR: Scale, Customers, and Focus Areas 04:35 Defining SoftChoice and Competing Without IP 06:25 Competing in Crowded, Undifferentiated Markets 09:37 Building Differentiation Through Mission, Focus, and People 11:39 How Culture and Customer Experience Win Deals 17:02 Being Prescriptive: Focusing on the Right Market Segment 21:42 Hiring for Mission Alignment and Go-to-Market Evolution 26:38 Testing and Validating Sales Profiles with Data and AI 29:47 Inspecting Strategy and Operating Cadence for New Growth Bets 39:12 Why Execution and Focus Win in Competitive Markets 40:09 Positioning Products Beyond Features and Selling Peace of Mind 43:15 Point-of-View Positioning and Radical Transparency in Sales 47:19 When the Sales Experience Reflects Customer Experience 49:29 Culture as a Revenue Driver and Operationalizing Company Values 57:55 Maintaining Culture During Change and Leading with Visibility 03:52 Building Alignment and Empowerment Across the Executive Team 12:26 Lessons in Career Patience, Growth, and Self-Balance 13:42 Quickfire: Leadership, Learning, and Hard-Earned Lessons
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E51: How Lightspeed Commerce Built a $1B+ Sales Engine - JD Saint-Martin, President @ Lightspeed Commerce
10/30/2025
E51: How Lightspeed Commerce Built a $1B+ Sales Engine - JD Saint-Martin, President @ Lightspeed Commerce
Kyle Norton (CRO at Owner.com) sits down with JD Saint-Martin, President of Lightspeed Commerce, to unpack how he went from startup founder to public-company executive. They discuss scaling Lightspeed from $75M to $1.2B in recurring revenue, and the leadership lessons behind that growth. The conversation covers building high-performance sales cultures, promotion systems, enablement investment, RTO and culture philosophies, and more. Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters 00:01:51 – Startup to Acquisition 00:03:34 – Global Upbringing & VC Start 00:04:03 – Scaling to $1.2B ARR 00:05:25 – Growth Through SaaS & Payments 00:05:44 – Founder to Exec Transition 00:07:21 – Empathy From Doing Every Role 00:09:11 – Leading 3,500 Employees 00:11:07 – “Roll in the Mud” Leadership 00:13:28 – Early Lessons & Advice 00:16:37 – Building High-Performance Culture 00:18:28 – Candid Hiring & Fit 00:21:42 – Transparency in Recruiting 00:22:06 – Obsession With Metrics 00:23:55 – Inputs vs Outputs 00:24:58 – Manager Pyramid Framework 00:27:57 – Promotions & Company Values 00:29:42 – Elite Points System 00:33:29 – Systemized PIPs 00:36:20 – Retaining Top ICs 00:40:31 – Investing in Enablement 00:42:05 – COVID & Lost Osmosis 00:45:06 – Return-to-Office View 00:49:18 – GTM Owns Enablement 00:51:05 – Balancing Autonomy & Consistency 00:53:32 – Payments & Compensation 00:55:35 – No Work-Life Balance 00:59:41 – Energized by the Work 01:18:34 – Favorite Book & Takeaways 01:20:13 – Closing & Outro
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E50: The Secret to High-Trust, High-Performance GTM Teams - CRO @ Houzz, Tara DiCristo-Schmitt
10/23/2025
E50: The Secret to High-Trust, High-Performance GTM Teams - CRO @ Houzz, Tara DiCristo-Schmitt
Tara DiCristo-Schmitt (CRO at Houzz) joins host Kyle Norton (CRO at ), to explore how elite sales leaders build culture, trust, and clarity. Drawing lessons from her time at ADP and HubSpot, Tara explains why vision beats velocity, why recognition is an underrated tool, and why forecasting is more about trust than it is about simple numbers. A candid, tactical conversation about getting the best from your teams. Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters 00:00 – Introduction 01:00 – Tara’s Career Journey 03:15 – ADP Sales Culture 06:20 – Shift Away from Structure 09:00 – Rebuilding Outbound Motion 11:00 – Recognition and Team Motivation 15:00 – Trust as Cultural Foundation 17:30 – Vision Beats Velocity 21:00 – Setting and Communicating Vision 25:30 – Company-Wide Recognition Rituals 32:00 – Execution Model for Hard Times 39:00 – Building Trust and Credibility 47:00 – Hiring for Trust and Self-Awareness 52:00 – Forecasting Through Trust
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E49: All about AI and GTM at Clay - Round Two with Everett Berry
10/15/2025
E49: All about AI and GTM at Clay - Round Two with Everett Berry
Head of GTM Engineering Everett Berry returns to join Kyle Norton (CRO at Owner.com) for a rapid-fire Q&A on how Clay structures its ops, automates everything from QBR decks to redlines, and experiments with the next wave of AI-native sales tools. Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters & Timestamps 00:00 — AI Q&A Format: Everett Berry returns to talk AI and GTM 01:02 — Inside Clay’s GTM Engineering Team: structure, size, and stack 06:08 — Reporting Lines: How GTM engineering fits under Clay’s leadership 06:26 — Matrix Org Design: RevOps, Finance, and cross-functional ops 09:05 — Balancing Self-Serve vs. Sales-Led Growth 10:54 — When to Add a CRO-type role 13:12 — Clay’s Favorite AI Tools: Dust, Crosby, Granola, and Gong 15:39 — How Legal Ops Got Automated with Crosby 18:44 — Top Internal Clay Use Cases: content creation and sequencing 19:41 — Clay’s Sequencer and the Future of Sales Engagement 20:27 — The “Pane of Glass” Future for Reps 24:33 — Custom-Built Sales Stacks and Telephony Gaps 26:30 — The Rise of Text- and DM-Based Selling 28:49 — New Frontiers: WhatsApp, iMessage, and automation in DMs 32:02 — Does AI Replace Sales Reps? Not so fast. 33:47 — Creative, Expert-Level Selling in the AI Era 40:47 — Education, Creativity, and the Future of Work 42:51 — How to Convince Your CEO to Invest in AI 45:48 — When to Hire a GTM Engineer (and why the “Golden List” matters) 48:21 — Closing Thoughts: It’s a great time to build in GTM
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E48: Work Sprawl and the Future of Marketing with Global VP Marketing @ ClickUp, Kyle Coleman
10/08/2025
E48: Work Sprawl and the Future of Marketing with Global VP Marketing @ ClickUp, Kyle Coleman
In this episode, Kyle Coleman (Global VP Marketing @ ClickUp) joins Kyle Norton (CRO @ Owner.com) to unpack the evolving marketing landscape. The double Kyles dig into: The growing problem of “work sprawl.” The rise of AI-powered marketing teams How to get better results with lower headcount Why the best leaders today focus less on empire-building and more on process-building And a whole lot more Thanks for tuning in! Catch new episodes every Wednesday. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Episode Chapters: 1:02 – The Changing Mandate for CMOs 6:00 – From Process Management to “AI-ification” 10:40 – The New Responsibility of Marketing Leaders 13:45 – Managing Campaigns in the AI Era 17:15 – Domain Expertise Before Prompting 19:15 – Positioning ClickUp as an AI-Native Company 24:40 – Aligning Marketing, Product, and AI 27:35 – Leadership Philosophy in the Age of AI 33:00 – Horizontal Leadership and Cross-Functional Alignment 35:25 – Blurring Lines Between Sales, Marketing, and Product 41:00 – Owning Metrics and Healthy Friction 44:35 – Building an Applied AI Center of Excellence 46:57 – Operating in AI-Native vs. Traditional SaaS Environments 48:13 – Helping Traditional Companies Modernize with AI 53:05 – Change Management and the Challenge of Adopting AI 55:32 – Where Marketing Teams Should Start with AI 58:45 – Standing Out Amid Market Noise 1:00:31 – Owning the Language and Evangelizing the Problem
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E47: Kyle Norton’s Bets for GTM Domination (While Building a Generational Tech Company) - CRO @ Owner.com
09/24/2025
E47: Kyle Norton’s Bets for GTM Domination (While Building a Generational Tech Company) - CRO @ Owner.com
In this episode, Kyle Norton, CRO of Owner.com, is interviewed by Sophie Buonassisi from the GTMnow Podcast. He shares the decisions and frameworks that helped take the company from $2M ARR to over $50M and a billion-dollar valuation. Kyle breaks down the bold early moves—like letting go of half the sales team in his first 45 days—alongside the pivotal role of setting a high talent bar, investing in RevOps early, and building scalable infrastructure. He also unpacks lessons on churn reduction, hiring for DNA over case study performance, and why strategic congruence across product, GTM, and fundraising is critical. Finally, Kyle offers his perspective on AI in go-to-market, balancing in-office vs remote work, and the leadership principles that drive long-term growth. Episode Chapters: (01:00) — Intro (02:26) — Scaling to Unicorn (03:21) — Bold Sales Reset (05:33) — Early GTM Decisions (13:22) — Fixing Churn (16:31) — Hiring for DNA (31:08) — Leadership Alignment (33:23) — Data-First AI (48:25) — Remote vs. In-Office (55:26) — Leadership Principles Cool links: to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!
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E46: The RevOps Mind Behind Owner.com’s Billion-Dollar Valuation: Steve Dinner
09/10/2025
E46: The RevOps Mind Behind Owner.com’s Billion-Dollar Valuation: Steve Dinner
In this episode, host Kyle Norton (CRO at Owner.com) sits down with his longtime colleague Steve Dinner, VP of RevOps at Owner.com. Together, they unpack how to build a revenue operations team that drives real business outcomes rather than just managing tools and processes. Steve shares lessons from his journey to becoming a world-class RevOps leader, and highlights why empathy, trust, and business alignment matter more than endless automation. The conversation touches on why ride-alongs are one of Steve’s secret weapons, agile frameworks for RevOps, and what CROs should look for when hiring their first operations leader. Packed with insights from two seasoned operators, this episode is a must-listen for CROs, RevOps leaders, and anyone scaling high-growth revenue teams. Thanks for tuning in! Catch new episodes every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Episode Chapters & Timestamps (00:00) Introduction & Kyle sets the stage (01:25) Steve’s background and path into RevOps (03:50) The importance of blending sales leadership with RevOps thinking (07:20) Empathy, rep experience, and solving business problems beyond tech (11:50) Winning big vs. losing small (19:15) Why trust and collaboration matter in cross-functional partnerships (23:55) Ride-alongs and staying connected to frontline reps (37:10) Transitioning RevOps to agile methodology (51:00) How CROs should think about hiring their first RevOps leader (1:05:10) Building the CRO–RevOps partnership and avoiding “yes/no” traps (1:13:20) Advice for new heads of RevOps (1:17:00) Hardest leadership lessons learned
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E45: The inside scoop on GTM engineering with Clay’s Everett Berry
09/03/2025
E45: The inside scoop on GTM engineering with Clay’s Everett Berry
Clay’s Everett Berry breaks down how elite revenue teams are actually winning with AI today. We cover the GTM Engineer model Clay runs in-house, why prompt iteration and “taste” still matter, and the unsexy but vital work of segmentation, account scoring, and orchestration across the funnel. Plus, where AI SDR efforts go off the rails, and the concrete first steps a CRO should take to get real adoption and lift. Thanks for tuning in! Catch new episodes every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Timestamps: (01:16) — Guest intro: Everett Berry, Head of GTM Engineering at Clay (02:09) — Origin story → growth roles → discovering Clay (04:52) — What is a GTM Engineer? Clay’s embedded (Palantir-style) model & why it works (08:10) — Automating the busywork: pre-call research & more (10:53) — Why many AI GTM pilots miss ROI, plus AI-SDR hype (17:01) — Agent scope and lossiness, checks/evals, and prompt iteration best practices (24:20) — Day-1 win: industry classification; when to use GPT vs. Anthropic for the job (27:54) — CRO AI rollout sequence (33:32) — Data foundations: pipelines, API realities, and org readiness (41:25) — Org design: where GTM Engineering lives (52:10) — Team & stage: roles to hire, GTME + RevOps + agency model; what to insource vs. outsource (1:00:24) — Rapid fire questions
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E44: Psychologist Dr. Michael Gervais on Mastering the Mental Game of Leadership
08/27/2025
E44: Psychologist Dr. Michael Gervais on Mastering the Mental Game of Leadership
Dr. Michael Gervais, renowned high performance psychologist behind the Seattle Seahawks’ Super Bowl win and mental coach to Olympic athletes and NASA jumpers, reveals the often-ignored psychological drivers behind elite sales and leadership performance. This episode challenges revenue leaders to rethink competition—not as a zero-sum game, but as a relentless pursuit to be their very best while elevating teammates. Visit to get Dr. Mike's Morning Mindset Routine. Thanks for tuning in! Catch new episodes every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Key chapters: (00:00) - Introduction to Dr. Michael Gervais and His High-Performance Psychology Impact (02:30) - Finding Mastery: Mental Training for Peak Performance (04:30) - Seahawks Legacy: Building Optimism and Mental Toughness in Teams (08:00) - The Power of Input Focus: Clarity and Culture Over Outcome Obsession (12:00) - Compete to Create: Redefining Healthy Competition in Sales and Sport (18:30) - The Teammate Mindset: Bill Russell’s Blueprint for Winning Together (22:30) - Stress and Survival: Why Leaders Struggle to Foster Collaborative Environments (26:00) - Recovery Practices in Business: The Missing Link for Sustainable High Performance (29:30) - The 92-Second Morning Mindset Routine: Setting Your Signal Amidst the Noise (34:30) - Neuroplasticity in Leadership: Training Optimism and Confidence as Learnable Skills (37:00) - Felix Baumgartner’s Mental Mastery: From Panic to Space Dive Success (42:00) - Shifting from Performance-Driven to Purpose-Driven Leadership Identity (47:00) - Purpose as the North Star: Aligning Thought, Word, and Action Under Pressure (49:30) - Journaling, Conversations, and Meditation: Practical Steps to Discover Your Why (52:00) - Introducing FOPO: Overcoming the Fear of People’s Opinions (56:00) - The Evolutionary Roots and Neuroscience Behind FOPO (59:30) - Navigating the High-Stakes Sales Ecosystem: Combating Insecurity and FOPO (01:03:30) - Balancing Caring and Worry: Constructive Feedback vs. Destructive Noise (01:06:00) - The Framework to Overcoming FOPO: Unmask, Assess, and Redefine (01:09:30) - Leading Teams Through FOPO: Building Trust and Psychological Safety (01:12:30) - From Insight to Action: Applying Gervais’ Mental Strategies in Your Sales Leadership
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E43: Geraldine MacCarthy, CRO of Oyster HR, Demystifies Distributed Sales Teams
08/13/2025
E43: Geraldine MacCarthy, CRO of Oyster HR, Demystifies Distributed Sales Teams
Remote sales leadership is anything but one-size-fits-all. Geraldine MacCarthy, CRO at Oyster and former CRO at Personio, unpacks the complexities of building and scaling distributed sales teams across multiple continents. With deep experience at Google, Dropbox, and leading remote-first businesses, she reveals why the rigid remote vs. office binary misses what’s really happening—and what works. She also challenges common beliefs about onboarding and coaching remote reps, sharing how enabling managers to own “last mile” enablement drives real performance impact. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. . , the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You’re invited! to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key Chapters: (00:00) - Introduction to Geraldine McCarthy and the Challenges of Scaling Distributed Sales Teams (02:00) - Key Skills for Leading International Markets and Remote Teams (05:00) - The False Binary: Debunking Myths About Remote Versus In-Office Work (09:30) - Frameworks for Deciding When and Where to Co-Locate Sales Functions (13:00) - Building Infrastructure and Norms for Successful Distributed Sales Organizations (17:30) - Communication Best Practices for Distributed Revenue Organizations (22:00) - Remote Working Norms: Setting Expectations Around Availability and Response Times (27:30) - Trust Building in Remote Revenue Teams: ‘Work With Me’ Documents and Radical Candor (33:00) - The Power of Written Communication and Documented Processes in Remote Organizations (38:45) - Overcoming Common Remote Enablement Challenges with Intentional Coaching and Structure (44:30) - The Critical Role of Frontline Leaders in Driving Enablement and Accountability (48:30) - Measuring Manager Participation in Coaching and Sales Calls for Remote Success (53:00) - Common Misconceptions About Remote Sales Onboarding and Performance (58:00) - When Remote Sales Teams Thrive Versus When Co-Location Makes a Difference (01:03:00) - Core Principles for Sales Enablement Programs That Move the Needle (01:08:00) - Partnering Enablement With Product Marketing for Streamlined GTM Execution (01:12:30) - Leadership Advice: Prioritize Learning, Radical Candor, and Trust as Foundations (01:16:30) - Final Reflections and The Need for a New Paradigm in Workforce Models (01:18:00) - Outro and Resources
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E42: Cutting the Fat and Building Sales Machines That Scale with Tom Hanrahan
08/07/2025
E42: Cutting the Fat and Building Sales Machines That Scale with Tom Hanrahan
Sales efficiency isn’t just a buzzword—it’s the razor-edge that separates thriving GTM organizations from the rest. Tom Hanrahan, EVP and Global Head of Sales at Square, shares ten years of hard-earned insights on building lean, specialized sales teams that don’t just grow—they grow profitably. Hanrahan breaks down how obsessing over every dollar invested, from quota modeling to lead distribution, shapes a more sustainable and scalable revenue machine. He challenges the common trap of "more reps means more revenue," revealing why oversized teams often hide inefficiencies and create churn risks. Instead, he emphasizes smart specialization, rigorous data-driven segmentation, and maintaining a tight balance between lead volume and rep capacity. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. . , the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You’re invited! to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key Chapters: (00:00) - Introduction of Tom Hanrahan and Today’s Sales Efficiency Focus (02:56) - Defining Sales Efficiency: Balancing Growth and Profitability (04:33) - Why Large Sales Teams Often Breed Inefficiency (06:48) - Early Career Lessons That Shaped Hanrahan’s Sales Philosophy (09:24) - Cultivating Patience to Build Foundations Amid Growth Pressures (12:46) - Core Sales Efficiency Metrics: Quota Modeling, Lead Efficiency, and Specialization (14:06) - How to Approach Quota Modeling to Maximize Capacity and Win Rates (17:00) - Reframing the Mental Model: Opportunity Volume as the Real Bottleneck (18:32) - The Underrated Power of Sales Team Specialization and Segment Focus (22:59) - The Risks of Over-Specialization and Sales Org Brittleness (27:02) - Modeling Sales Team Growth with Churn and Ramp Dynamics (30:42) - Incubation Pods: Experimenting with Sales Motions Under Controlled Conditions (33:56) - Metrics to Evaluate Before Committing to Sales Team Reorganizations (36:43) - Hidden Inefficiency Drivers: Frontline Manager Consistency & Lead Weighting (40:00) - The Value of Weekly Business Reviews to Maintain Rigor and Transparency (44:18) - Deep Data Analysis Culture: Finding Gaps by Embracing Hard Truths (47:01) - Current Team Structure at Square: Vertical Specialization and Channel Diversity (48:58) - Recalibrating Incentives and Focus: Driving New Business Growth vs. Farming (50:50) - Fine-Tuning Inbound vs. Outbound Mix to Enhance Sales Productivity (52:43) - The Concept of “Sweet Spot” Targeting for Optimal ROI on Sales Efforts (55:30) - Full Cost Modeling: Loading All Expenses to Reveal True Unit Economics (56:14) - Building Efficient Revenue Organizations from the Ground Up: Why Entry-Level Talent Matters (58:30) - Identifying Ideal Sales DNA: Coachability, Competitiveness, Hard Work, Motivation (01:02:30) - Assessing Motivation and Hard Work During Hiring to Weed Out Misfits (01:06:40) - Leveraging Data Science in Hiring: Scorecard Retro and Pattern Recognition (01:12:00) - What Makes a Great Revenue Leader: Balancing Operational Mastery and People Skills (01:13:15) - Advice for New Sales Leaders: Get Curious Before Acting on Presumptions (01:14:20) - Navigating Cross-Functional Dependencies: The Enterprise Sales Parallel (01:17:39) - Personal Reflections: The Enduring Lesson from Hanrahan’s Father on Commitment and Grit
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E41: Jessica Chiew of Canva on Building AI-Native GTM Org
08/01/2025
E41: Jessica Chiew of Canva on Building AI-Native GTM Org
AI is transforming go-to-market operations—and at Canva, it's not just a trend, it's a mandate. In this episode, Jessica Chiew, Head of GTM Operations and Strategy at Canva, joins Kyle to break down how her team is leading AI adoption across a 5,000-person organization. She shares how Canva blends centralized support with functional ownership, why they created a dedicated GTM AI Lead role, and how they prioritize use cases that deliver real business impact. Jessica and Kyle also dig into the realities of build vs. buy decisions, how to avoid tool sprawl, and why every GTM leader needs to be hands-on with AI. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. . , the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You’re invited! to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key chapters: (00:00) - Jessica Chu’s GTM AI Transformation Journey at Canva Begins (02:48) - The Most Exciting Time in Ops: Creativity and Existential Dread (04:30) - From Vendor Fatigue to AI Enthusiasm: Renewed Curiosity in Tooling (06:59) - Early Days of AI Momentum at Canva (09:30) - Making AI Transformation Everyone’s Job (11:45) - Defining the Role: GTM AI Lead and Workflow Innovation (14:25) - The Changing Nature of Data Ops in AI-Powered Sales (16:50) - How Canva Organizes AI Transformation: Central Council vs. Functional Innovation (18:29) - Cutting Through the Noise: Where to Start with AI in GTM (21:00) - Why Data Quality Is the Prerequisite for GTM AI Success (24:30) - Vendor Sprints and the Realities of Building vs. Buying AI Solutions (29:00) - Execution as the Only Moat: Staying Ahead in the Commoditization Wave (35:10) - Limiting Surface Areas: The Case Against Point Solutions (38:30) - Balancing Experimentation with Simplicity for Field Teams (41:51) - Organizational Change: Iterative Improvements vs. Big AI Bets (46:45) - Hands-On Leadership and the Decline of Middle Management
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E40: Partnership Lessons from COELEVATE with Author Richard Ezekiel
07/23/2025
E40: Partnership Lessons from COELEVATE with Author Richard Ezekiel
has created partnerships with Fortune 500 companies and helped scale market-defining startups in Silicon Valley. He joins Kyle to share hard-won lessons on building strategic partnerships that deliver real business impact—not just press. They cover how to assess if partnerships are the right growth lever, why most programs fail, and what it takes to build a durable, high-impact strategy. Richard breaks down his “Partnership T” framework and offers practical guidance for CROs and GTM leaders scaling post-product-market fit. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. . , the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You’re invited! to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! , “Coelevate: How to Unlock Business Growth and Consumer Value with Strategic Partnerships.” Key chapters: (00:00) - Introduction to Revenue Leadership and Partnerships (02:43) - Defining Partnerships and Their Importance (05:49) - Core Components of Successful Partnerships (08:42) - Assessing the Right Time for Partnerships (11:31) - Building a Strategic Partnership Plan (14:51) - The Role of Partnerships in Business Growth (17:41) - Identifying Potential Partners (20:32) - The Spark of Partnership Ideas (23:57) - Navigating the Complexity of Partnerships (26:53) - Methodical Approaches to Finding Partnership Opportunities (29:43) - Evaluating Partnership Types and Strategies (41:18) - GTM 2025: Elevating Go-to-Market Strategies (42:42) - Common Failure Modes in Partnerships (44:55) - Operational Rigor: The Key to Partnership Success (51:02) - Defining Strategic Partnerships (52:59) - Assessing Ideal Partner Profiles (59:49) - Testing Partnership Viability (01:04:38) - Knowing When to Walk Away from Partnerships (01:12:22) - The Future of Partnership Management (01:13:17) - Reflections on Successful Partnerships
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E39: CRO James Roth on Resilience, Reinvention, and AI at ZoomInfo
07/09/2025
E39: CRO James Roth on Resilience, Reinvention, and AI at ZoomInfo
What does it take to lead a public go-to-market organization through rapid change without losing focus? In this episode, Kyle Norton sits down with James Roth, CRO of ZoomInfo, to unpack the leadership principles, GTM evolution, and cultural shifts powering ZoomInfo’s next chapter. From rethinking account ownership models to re-centering around core strengths like data and AI enablement, James shares how he's helping rebuild ZoomInfo into a sharper, more focused enterprise. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. . , the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You’re invited! to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key chapters: (00:00) - Introduction to Revenue Leadership Podcast (01:16) - Guest Introduction: James Roth's Journey (03:11) - Building Resilience and Grit in Sales (07:41) - Leading Through Change: Personal Experiences (09:29) - Navigating Market Challenges and Personal Growth (18:34) - The Importance of a Growth Mindset (36:57) - The Rebirth of ZoomInfo: Adapting to Market Changes (45:48) - Go-to-Market Strategy: Shifts and Innovations (59:45) - Segmentation and Account Management Strategies (01:12:22) - The Enablement Journey for Sales Reps
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E38: How Adam Alfano Is Leading Salesforce Into Its AI Era
06/27/2025
E38: How Adam Alfano Is Leading Salesforce Into Its AI Era
, EVP of Global SMB and Emerging Products at Salesforce, joins Kyle Norton to share what it takes to lead through change at scale. Over 17 years at Salesforce, Adam has navigated market cycles, evolving go-to-market models, and now the rise of AI—while building and inspiring high-performing teams. He explains how to stay relevant as a leader, scale culture across thousands, and embrace mindset as a competitive advantage. Kyle and Adam also dig into Salesforce’s AgentForce strategy, how AI is transforming sales execution, and why adaptability is the most underrated leadership skill. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday. Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. . , the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You’re invited! to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key chapters: (00:00) - Introduction to Revenue Leadership Podcast (00:54) - Guest Introduction: Adam Alfano from Salesforce (02:45) - Career Lessons and Leadership Insights (03:43) - Leading Through Change and Reinvention (05:39) - The Importance of a Balanced Mindset (08:05) - Scaling Mindset and Mental Fitness (12:27) - Creating a Positive Team Culture (16:18) - Competitive Stamina in SMB Sales (17:42) - Scaling Corporate Athlete Mindset (19:42) - Engaging with the Field and Team Feedback (23:22) - Building Trust and Psychological Safety (26:43) - Inspiring and Motivating Teams (29:57) - Balancing Company and Team Culture (33:21) - Evolving Company Culture Over Time (40:02) - Reinventing Yourself in a Changing Market (44:38) - Embracing an Evolutionary Mindset (46:48) - The Importance of Experimentation and Learning (48:38) - Shifting Perspectives on Sales Processes (50:53) - Calculated Risks and Career Growth (52:44) - Intentional Career Planning (56:03) - Integrating AI into Sales Strategies (01:00:38) - Driving Engagement with AI Tools (01:04:37) - The Future of Sales with AI (01:08:55) - Navigating Change and Fear in AI Adoption (01:13:57) - The Role of Leadership in Market Adaptation (01:17:39) - Lessons in Leadership and Team Dynamics
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E37: Jason Wolf on Uncovering Hidden Growth Opportunities in Go-To-Market
06/18/2025
E37: Jason Wolf on Uncovering Hidden Growth Opportunities in Go-To-Market
Jason Wolf, President of FullStory and former CRO at Ping Identity and SAP Ariba, joins Kyle Norton to share how companies unlock step-change growth by entering new markets, building new capabilities, and aligning cross-functional teams. Jason has led revenue growth from $200 million to $1.6 billion and brings hard-won lessons from scaling globally.
He explains how to time multi-product and multi-region moves, validate new growth bets, and build strategies driven by customer pull rather
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E36: Why Product Thinking Beats Process Obsession in GTM with Sangeeta Chakraborty
06/11/2025
E36: Why Product Thinking Beats Process Obsession in GTM with Sangeeta Chakraborty
Most GTM teams operate in straight lines. Sangeeta Chakraborty believes they should function more like product organizations, with constant iteration, testing, and learning.
In this episode, the former CRO of Miro shares how applying product management principles helped her design go-to-market systems that reflect the full customer journey. She explains how her team ran structured GTM experiments, embraced cross-functional collaboration, and built systems for long-term customer growth. K
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E35: Building a Multi-Product Platform with Seismic’s CRO, Hayden Stafford
06/04/2025
E35: Building a Multi-Product Platform with Seismic’s CRO, Hayden Stafford
In this episode, Kyle Norton sits down with Hayden Stafford, President and CRO at Seismic, to unpack what it really takes to transform a company from a single-product business into a true multi-product platform. Drawing from his experience leading global teams at Microsoft and now steering Seismic toward half a billion in ARR, Hayden shares the go-to-market, organizational, and cultural changes required t
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E34: Why Enablement Is the Most Overlooked Growth Lever with Luke Arno, CRO of Transcend
05/28/2025
E34: Why Enablement Is the Most Overlooked Growth Lever with Luke Arno, CRO of Transcend
Is enablement the most overlooked growth lever in sales? Luke Arno thinks so—and he’s got the track record to prove it.
In this episode, Kyle Norton talks with Luke Arno, CRO at Transcend and veteran of Salesforce, Box, and Segment, about how great enablement can drive real sales productivity. Luke breaks down his three-part framework—onboarding, ongoing development, and in-the-moment fiel
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E33: What It Takes to Be a Revenue Leader in the AI Era with Mike Donohue, CRO of 11x
05/21/2025
E33: What It Takes to Be a Revenue Leader in the AI Era with Mike Donohue, CRO of 11x
What happens when a company completely replaces its SDR team with AI? In this episode, Kyle Norton sits down with Mike Donahue, CRO at 11X, to unpack how digital workers—AI agents named Alice and Julian—now generate over 90% of the company’s pipeline.
Mike shares how 11X is pioneering an AI-native go-to-market model, where full-cycle reps are supported by centralized agent orchestration, and where growth marketing owns what used to be outbound sales. You’ll hear how AI is reshapi
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E32: Layering SLG Without Breaking the Product with John Eitel
05/08/2025
E32: Layering SLG Without Breaking the Product with John Eitel
Most product-led companies hit a wall when they try to add sales-led growth. Too often, the motions clash, teams misalign, and growth stalls. So, how do you scale revenue without sacrificing your product-led roots?
In this episode of The Revenue Leadership Podcast, Kyle Norton sits down with John Eitel, former Global VP of Sales & Success at Canva and CRO at Demandbase, about how to success
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E31: The Rise of the 10X SDR with Florin Tatulea of Common Room
04/30/2025
E31: The Rise of the 10X SDR with Florin Tatulea of Common Room
In today’s episode, Kyle sits down with Florin Tatulea, Head of Sales Development at Common Room, to discuss the evolution of outbound sales in the context of AI and technology. Florin shares insights on the importance of understanding signals and intent in sales, the changing profile of sales reps, and the role of RevOps in strategizing outbound efforts. The discussion highligh
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E30: Building AI-Powered Sales Teams with Finally's CRO Kevin "KD" Dorsey
04/23/2025
E30: Building AI-Powered Sales Teams with Finally's CRO Kevin "KD" Dorsey
Kevin "KD" Dorsey is the Chief Revenue Officer at Finally, an all-in-one accounting and finance platform that recently raised $200 million in Series B funding. KD joins the show to discuss real-world examples of how he uses AI in his day-to-day: from developing internal AI agents to evaluating his team's calls.
New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday
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E29: Mastering Sales Commission Plans with QuotaPath's Ryan Milligan
04/16/2025
E29: Mastering Sales Commission Plans with QuotaPath's Ryan Milligan
Kyle is joined by Ryan Milligan, VP of Sales, Marketing, and RevOps at QuotaPath, to discuss sales commission planning. They dive into the essentials of creating effective comp plans that align with business goals, the importance of incremental incentives, and how to drive desirable sales behavior. Ryan shares insights from h
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E28: Interns to Enterprise: How Cresta’s CRO Built a Category Leader
04/09/2025
E28: Interns to Enterprise: How Cresta’s CRO Built a Category Leader
What does it take to go from zero to your first enterprise customer? For Cresta, it meant their CEO and CTO becoming interns at Intuit—and their engineering team living in an Airbnb next to the call center they were trying to disrupt.
In this episode, Kyle talks with Alex Cramer, CRO of Cresta, about the unglamorous grind of cold-starting in enterprise, why today’s deals demand more consensus (and skill) than ever, and how to scale a team when every deal feels like
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E27: How Matt Braley Built a Multi-Million Dollar Alliance Ecosystem at InvoiceCloud
04/02/2025
E27: How Matt Braley Built a Multi-Million Dollar Alliance Ecosystem at InvoiceCloud
Matt Braley joined InvoiceCloud as the third AE, rose to CRO, and led the company from early growth through a successful IPO, and ultimately a $4B acquisition by Vista Equity Partners. In this episode, Matt reveals how he grew their alliance ecosystem from 15 to 50 partners—ultimately generating over half of the company's revenue. You'll discover the VECTOR framework he developed for qualifying par
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E26: Signals That Separate Great Companies from Risky Bets with Neal Patel, CRO of Crunchbase
03/26/2025
E26: Signals That Separate Great Companies from Risky Bets with Neal Patel, CRO of Crunchbase
What should CROs really be looking for when evaluating their next move? In this episode, Kyle sits down with Neal Patel, CRO at Crunchbase, to unpack how revenue leaders can vet companies like investors—by looking past vanity metrics and digging into signals that actually matter. They cover how to evaluate long-term viability, the importance of alignment with executive peers, and why being asked to "just run your old playbook" is a red flag.
The conversation also dives deep into how AI
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E25: Transitioning from Product-led to Sales-led Growth with Andrew Johnston of Superhuman
03/19/2025
E25: Transitioning from Product-led to Sales-led Growth with Andrew Johnston of Superhuman
How do you transition from product-led growth to sales-led growth without losing momentum? In this episode, Kyle Norton talks with Andrew Johnston, Head of Sales at Superhuman, about how the company is evolving its go-to-market strategy to win larger B2B deals. They discuss the key challenges of moving upmarket, the differences between PLG and SLG sales motions, and how Superhuman is leveraging data and AI to scale. Andrew also shares insights on building the right sales team, adapting the product for en
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