The Revenue Leadership Podcast with Kyle Norton

Allison Metcalfe's path to CRO was built on systems thinking, multiplier leadership, and a journalist's instinct for "why." In this episode, Kyle and Allison talk through what separates good revenue leaders from great ones, and how to actually lead peers and execs, not just manage them. And maybe we shouldn't tell you this, but… Allison even reveals her hardcore alter-ego that helps her better ride the highs and lows in the CRO role. Thanks for tuning in! Catch new episodes every Wednesday.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!   Chapters:   01:47 Allison Metcalfe's Career Journey   03:41 Non-Traditional Path to CRO   05:16 Architecture Thinking and the AI Era   07:25 Systems Thinking and Curiosity in Revenue Leadership   09:01 Managing Executive Relationships   10:56 Discovering Multiplier Leadership   18:44 Decision-Making Without Consensus Paralysis   24:30 Building Healthy Executive Relationships   30:11 Authenticity and Connection in Remote Work   33:09 Using Enneagram for Team Understanding   38:00 Radical Empathy Across Departments   46:27 Collaborating Effectively with Finance   53:21 Navigating 2026 Planning Conflicts   58:26 Data-Driven Decision Making and Change Management   01:03:32 Quick Fire: Career Lessons, Alter Egos, and Book Recommendations  

Peter Grant helped take Siebel from $39M to $2B in revenue and was employee #9 for Salesforce in Europe. He knows exactly what a platform shift looks like. Now, as the CRO of You.com, Peter argues that the AI wave is moving 30x faster than the internet era—and your current sales playbook is already obsolete. In this episode, Peter strips away the hype to focus on the operational reality of running an AI-first GTM organization. He explains the skill stack today's sellers need, why your team needs to understand APIs, and the specific benchmarks you need to hit to survive the next two years. Plus a whole lot more!   Thanks for tuning in. Catch new episodes every Wednesday.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!   Chapters:  00:00 Peter Grant's Career and Revenue History  07:32 Choosing You.com and Pivoting to Enterprise  11:46 How AI Search Transforms Sales Discovery  16:12 The Speed and Scale of AI Sales  20:55 Embedding AI Agents into Existing Workflows  27:11 Benchmarking Enterprise AI Spend and Adoption  33:14 Solving the Employee AI Literacy Gap  38:59 The Evolution of the Sales Rep Profile  43:06 Implementing and Prioritizing AI Transformation  52:05 The Hard Reality for Sales Laggards  59:30 Investing Upfront Time to Master Prompting  01:03:10 Why Revenue Leaders Must Be Context Setters  01:10:12 How Tactics Dictate Strategy in Enterprise Deals  01:12:49 Rapid Fire: Leadership Advice and Lessons  

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.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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  

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.    Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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  

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.    Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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  

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.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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    

Tara DiCristo-Schmitt (CRO at Houzz) joins host Kyle Norton (CRO at Owner.com), 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.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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  

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.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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  

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.  Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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

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: Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast!  

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. Use code TOPLINE for 10% off your GA ticket. Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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

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. Use code TOPLINE for 10% off your GA ticket. Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel 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  

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 revenueleadership.findingmastery.com 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. Use code TOPLINE for 10% off your GA ticket.   Subscribe to Topline Newsletter.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech.   Join the free Topline Slack channel 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

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. Use code TOPLINE for 10% off your GA ticket.   Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman.   You're invited! Join the free Topline Slack channel 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

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. Use code TOPLINE for 10% off your GA ticket.   Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman.   You're invited! Join the free Topline Slack channel 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

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. Use code TOPLINE for 10% off your GA ticket.   Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman.   You're invited! Join the free Topline Slack channel 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  

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. Use code TOPLINE for 10% off your GA ticket. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You're invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Buy Richard's book, "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  

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. Use code TOPLINE for 10% off your GA ticket. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You're invited! Join the free Topline Slack channel 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  

Adam Alfano, 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. Use code TOPLINE for 10% off your GA ticket. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You're invited! Join the free Topline Slack channel 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  

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 than competitor pressure. Jason also covers the role of go-to-market in product innovation, how to focus teams around renewals, and what it takes to scale with speed and precision. 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. Use code TOPLINE for 10% off your GA ticket. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman. You're invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key chapters: (00:00) - Jason Wolf's Impressive Journey (02:00) - Defining New Growth Horizons (03:25) - Building Character Through Change (04:10) - Mental Map for Growth Opportunities (05:00) - What Growth Truly Means (06:30) - Finding and Serving New Buyers (07:53) - Stated vs. Observed Truths (10:00) - Deciding Where to Grow Next (14:38) - Lessons from Expanding Globally (18:30) - Staging Product and Geographic Expansion (25:23) - The Pioneer's Mindset in New Markets (35:52) - Go-to-Market's Role in Product Innovation (44:50) - The Rise of the Specialist (57:57) - The New Revenue Algorithm (1:12:00) - Driving World-Class Alignment