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. 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
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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. 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
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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 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
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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. 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
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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. 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
Acerca de The Revenue Leadership Podcast with Kyle Norton
The Revenue Leadership Podcast with Kyle Norton is a new show from Topline 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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