The Revenue Leadership Podcast with Kyle Norton

• $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.  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  

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• 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.    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  

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• 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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