The Revenue Leadership Podcast with Kyle Norton

Ghazi Masood, CRO at Replit, joins Kyle Norton to break down how Replit went from $2 million to over $150 million in revenue in less than a year, is tracking to a billion-dollar run rate by the end of 2026, and is hiring 200+ people over the next 12 months while rebuilding GTM from scratch in the AI era. Topics include the AI-native GTM tech stack (Salesforce as system of record, internally vibe-coded apps for revenue copilot, customer health, CPQ, and forecasting), why Replit is hiring non-traditional sellers like a former Marine and a schoolteacher into AE roles, the 80% hiring bar and 15-minute screen, why automated SDRs didn't work but inbound triage will be fully agentic by Q2, scrapping traditional CSMs in favor of customer advocates, the build vs buy heuristics for enterprise pipeline generation and system of record decisions, and why Salesforce hygiene as a sales motion is dead. Key Takeaways: - Replit's GTM playbook is being written for the first time at hypergrowth scale, which forces a different bar on every hire. As Ghazi Masood, CRO at Replit, put it: "everything we're doing for the very first time, you know, rolling out territories, very first time, rolling out comp plans, very first time, rolling out forecasting cadence, very first time, rolling out, you know, the post-sales motion. So there's a lot of firsts happening in this business because the business has grown so fast, so quickly." - Non-traditional sellers can outperform pedigreed Oracle and Salesforce reps when the product is technical and mission-pull is strong. Ghazi Masood, CRO at Replit, on the team he's building: "when I got here, our number one seller in the company, and the person was already here, was, came from the military, was in the US Marine Corps, never sold a day in his life. Absolutely killed it… one of our top commercial sellers for our downmarket business, Kyle, who's still here in that role, was a schoolteacher, never sold, doing exceptionally well." - Hiring at hypergrowth speed requires explicitly lowering the bar from 100% to 80% and trusting enablement to close the gap. Ghazi Masood, CRO at Replit, on the calibration: "given how fast I have to go hire, I make this call right in the beginning, is we want an 80% bar. So we're we are not striving for 100%… if it's 80% and we think somebody can kind of meet that 80% bar and we know that with the right level of enablement, we can kind of get them that last 20%, get them to 100%, we're actually optimizing and pulling the trigger on that person." - Salesforce-hygiene-as-a-sales-motion is over. Ghazi Masood, CRO at Replit, on the shift: "the salesperson's job is changing, right? Like the amount of research and information gathering. I mean, that's all automated. So I think they can now spend their time in front of customers where they should be. Versus doing the back office crap. You know, the teams we've managed in our previous lives, like Salesforce hygiene and people spending more than half their week updating Salesforce. And I mean, those days are, those days are gone."   Connect with the Hosts & Guests: Host: Kyle Norton, CRO at Owner.com - https://www.linkedin.com/in/kylecnorton/ Guest: Ghazi Masood, CRO at Replit - https://www.linkedin.com/in/ghazi-masood-09195a2/   The Revenue Leadership Podcast is more than a Podcast: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Subscribe to the YouTube channel: https://www.youtube.com/@kyle-norton   Chapters: 00:00 Introducing Ghazi Masood 03:20 Low-Code Is Dead, AI Is the Pivot 05:57 Vibe Coding Your Own CRO Decks 07:58 Replit's AI GTM Stack 12:59 Replit Agent and Personal Apps 16:55 Life as a Hypergrowth CRO 19:52 Hiring Beyond the Top 1% Pedigree 22:24 Marines and Schoolteachers Selling 25:33 No CSMs, Just Customer Advocates 30:20 Sponsor: Momentum 31:00 What Breaks at Hypergrowth 32:51 Build vs Buy in the AI Era 41:05 Hiring System and the 80% Bar 52:16 Future of GTM and AI GTM Engineer 59:38 Quickfire: Scale Down or Get Cut  

Cassie Young, General Partner at Primary Venture Partners, joins Kyle Norton to break down exactly how CROs must master P&L management to survive the new AI-driven go-to-market reality. As the era of software bloat ends, revenue leaders must adapt their GTM strategy to maintain investor trust and drive capital-efficient growth. This episode details the financial metrics, board expectations, and AI workflow integrations required to build a high-performing enterprise sales motion. Key takeaways: -The GTM bloat era is over... companies have to invest in inference and compute so we don't have the luxury of traditional software margins. -Use the PRIME framework to justify any new go-to-market tool... Productivity, Retention, Investment efficiency, Momentum, and Expense reduction. -You cannot sell interoperability effectively if you do not fundamentally understand how AI tools and models work natively. Other Cool Stuff: 🎧 Tune into Topline Podcast (our other show!), the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast 📩 Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ 🤝 Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack   Chapters: 00:00 Episode Overview 01:05 Cassie Young Career Background 03:20 The GTM Bloat Era Ends 08:32 The Rise of the Orchestrator 12:16 Jevons Paradox in Revenue Teams 15:52 Evaluating Early Burn Multiples 18:08 Point Solution Market Risks 25:28 New Rules for Software Pricing 29:59 The PRIME Investment Framework 34:56 Why AI Initiatives Fail 43:09 Aligning Strategy With Your CFO 44:54 Executives Must Use AI Daily 50:08 How Boards Measure CROs Now 1:00:02 Core Four Executive Attributes 1:11:01 Career Advice for New Leaders  

Adrian Rosenkranz, CRO at Webflow, joins Kyle Norton to break down exactly how to rebuild your GTM motion for AI bot traffic and scale internal AI agents. As AI bots reshape enterprise pipeline generation, revenue teams must master AEO (Agentic Engine Optimization) and GEO (Generative Engine Optimization) to capture high-intent search traffic. Adrian shares how to optimize your technical SEO for agent crawls, collapse legacy RevOps silos, and build custom internal AI workflows that drive real sales outcomes. A lil' sneak peek into some key topics we discuss: Optimize for AEO and GEO: AI bot crawls now make up nearly 20% of Webflow's site traffic. Companies must provide markdown-friendly metadata to control their brand narrative inside LLMs and secure citations over standard referrals. Pioneer Go-To-Market Engineering: Fragmented operations teams create workflow bottlenecks. Merging Sales, Marketing, and Post-Sales Ops into a single go-to-market engineering (GTME) unit is required to deploy effective cross-functional AI systems. Deploy Agents with Claude Code: Stop using AI just to write faster emails. Centralize your AI development to build autonomous workflows—like using Claude Code and MCP to draft hyper-personalized customer emails based on live Slack and Salesforce context. Build Dynamic Knowledge Bases: Static documentation is dead. Feed call data into AI to automate your Ideal Customer Profile (ICP) and "...run this every week... and you can see the drift from the previous one" to continuously fuel outbound scripts. 🎧 Tune into Topline Podcast (our other show!), the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast 📩 Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ 🤝 Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Intro and AI bot traffic surge 05:12 AI citations vs website referrals 08:28 Optimizing websites for AEO & GEO 13:14 Controlling brand narratives in LLMs 15:05 Enable sales for rapid product updates 23:22 Escaping the AI efficiency trap 29:01 Why you must collapse your RevOps team 35:43 Building custom AI email agents 48:35 Automating dynamic ICP documentation 54:06 Generating outbound scripts with AI 57:58 Framework for build versus buy in AI 1:02:16 Avoid locking AI in black boxes 1:07:28 What separates elite CROs  

Kevin Bailey, CEO of Dreamfuel, joins Kyle Norton to break down exactly how to manage executive physiology and eliminate inconsistent performance. Mastering your mental state is the ultimate go-to-market tool for navigating high-stakes sales motions and enterprise pipeline generation without burning out. This episode breaks down the applied neuroscience of executive performance, giving GTM leaders the exact tools to regulate their nervous systems and execute flawlessly under pressure. Kevin mentioned a few resources during the show, linked here: Tech Leader Mental Performance Report & Field Guide - A deep dive into tech leader mental performance challenges, frameworks, and tools. Created in partnership with Indiana University and Elevate Ventures: http://dreamfuel.com/report Weekly Tech Leader Breathwork Session - Weekly group breathwork session hosted on Thursdays at 9 PT / Noon ET: https://www.dreamfuel.com/breathwork Complimentary 1:1 Mental Performance Coaching Session - Apply for an individual session with a Dreamfuel mental performance coach: https://www.dreamfuel.com/schedule-your-demo  Other helpful links: 🎧 Tune into Topline Podcast (our other show!), the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast 📩 Subscribe to Topline Newsletter: https://www.joinpavilion.com/topline-newsletter 🤝 Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack   Books mentioned in the episode: Search Inside Yourself by Chade-Meng Tan The Comfort Crisis by Michael Easter The Greatest Secret by Rhonda Byrne Effortless Being by David Bingham Atomic Habits by James Clear Chop Wood Carry Water by Joshua Medcalf The Untethered Soul by Michael A. Singer The Secret by Rhonda Byrne   Key Takeaways: Consistency defines elite performance: Top executives don't just rely on good days. They train their nervous systems to maintain a tight baseline of peak output regardless of external stress or market conditions. Results are downstream of biology: You cannot out-think a biological threat response. Shifting your physical state through breathwork or cold exposure is the absolute prerequisite for changing your emotions, cognition, and ultimate business results. Prime your subconscious with imagery: Treat high-stakes meetings like an athletic event. Using rehearsal visualization to run through potential objections primes your brain to respond calmly and constructively in the moment. Cut cheap dopamine: Endless scrolling and easy distractions drain the motivation required for deep work. Eliminating dopamine wasters reallocates that drive directly into your professional execution and resilience. Chapters:  00:00 Intro & The Cost of Startup Growth  06:17 Defining Elite Executive Performance  09:30 The Neuroscience Performance Chain  13:47 Taming Stress (feat. Default Mode Network) 16:23 Four States of the Nervous System  20:50 Practicing Somatic Awareness  28:00 Building Resilience With Cold Plunges  33:57 Finding Equanimity in Leadership  40:46 Warmups for High-Stakes Meetings  44:35 Rehearsal and Creative Visualization  57:51 Holding Form Under Intense Pressure  67:20 Cooling Down With Anger Journaling  75:00 Understanding Non-Duality at Work  84:00 Modeling Behavior for Your Team  89:52 Eliminating Dopamine Wasters  

Kyle Norton, CRO at Owner.com, is interviewed by Everett Berry to break down exactly how to scale pipeline generation using applied AI and GTM engineering. Scaling an SMB sales motion requires ruthless efficiency and a modern outbound automation stack. This episode covers how to integrate applied AI into your GTM strategy to dramatically increase decision-maker connect rates, streamline pipeline generation, and execute high-volume cold calling campaigns. 🎧 Tune into Topline Podcast (our other show!), the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast 📩 Subscribe to Topline Newsletter: https://www.joinpavilion.com/topline-newsletter 🤝 Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Key Takeaways: Automate pre-call research to maximize SDR output. By injecting AI-generated local name drops and personalized pain points directly into Salesloft, Kyle's reps can make 150 to 200 dials and connect with 20 to 30 decision makers daily - a 5x improvement from where they started. Run GTM engineering pilots in small batches. Seat your applied AI specialists directly next to frontline reps so they can accurately assess impact. Test specific interventions—like shifting call blocks to 5:00 PM—so you're only handing proven workflows for broader application across the team. Leverage executive personal branding for inbound recruiting. Publishing consistent, AI-assisted content on LinkedIn generates massive inbound applicant volume. In Kyle's case, this has completely eliminated the need for expensive external recruiting agencies. Keep sales managers focused on core competencies. Let your applied AI team build the tech while managers focus on hiring and coaching.    Chapters: 00:00 Episode Intro  01:37 Scaling AI-Driven SMB Sales 03:43 The PICRIOS Cold Call Structure 06:25 Running GTM Engineering Experiments 08:38 Structuring an Applied AI Team 10:06 Automating Transactional SMB Sales 13:17 Future Go-to-Market Team Roles 15:39 Personal Branding for GTM Recruiting 18:52 AI Workflows for Content Creation 23:19 Finding Time to Learn AI Tools 26:38 Buying vs Building Data Stacks 28:33 Using Claude to Learn Tech Skills  

Aviv Canaani, CRO at DataRails, joins Kyle Norton to break down exactly how to build a highly predictable, inbound-led revenue machine. This episode details the transition from a purely outbound sales motion to a scalable inbound engine driven by demand generation and organic brand building. You will discover how to align marketing and sales, engineer an efficient B2B SaaS GTM strategy, and leverage AI tools to drastically increase pipeline generation and AE productivity. Key Takeaways: Account Executives should focus entirely on closing deals, not prospecting, to maximize per-rep efficiency and win rates. Revenue leaders must treat GTM as a math equation, balancing pipeline volume, conversion rates, and AE capacity to forecast accurately. Marketing must be held accountable for closed-won revenue because "...you don't count assists if the shooting guard didn't make the shot." AI tools like Momentum and Clay can fully automate CRM updates and lead qualification, freeing reps to focus on active selling. 🎧 Tune into Topline Podcast (our other show!), the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast 📩 Subscribe to Topline Newsletter: https://www.joinpavilion.com/topline-newsletter 🤝 Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 01:23 Path to the CRO Seat 05:13 Outbound to 90% Inbound 08:20 Investing in Organic Brand 12:33 Marketer Running Sales 16:39 AEs Should Never Prospect 21:13 Real Math Behind Quotas 27:31 Building Predictable Revenue 33:38 Using AI for CRM Data 43:47 AI Use Cases in GTM 51:58 Future of the CRO Role 55:05 Books for GTM Leaders

Most revenue leaders see a missed number and immediately jump to a solution: more training, new SPIFFs, or pricing changes. Product leaders isolate variables and solve for root causes. Usha Iyer (Chief Customer & Growth Officer, President - US @ Hivebright) brings a developer's rigor, and a product leader's clarity to GTM. She explains why you should treat your GTM strategy like a product roadmap: test small, validate with data, and only scale what's proven to work. Highlights include: Input vs. Output: Why chasing results without fixing process inputs increases failure ratesThe SWAT Team Model: The safer way to scale processes Churn Forensics: How to use control groups to diagnose retention issues (hint: it's rarely just pricing). Friction Hunting: Stop selling the "happy path" and how to get at the truth. Plus a lot more. And 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: Usha Iyer's journey from engineering to revenue 03:52 Transitioning from product management to go-to-market leadership 07:34 The difference between winning in product versus sales 08:17 Identifying hidden customer friction points that data misses 12:19 How revenue leaders should communicate with product teams 13:36 Applying a product mindset to the sales process 15:56 Input-driven product development versus output-driven sales 21:48 Using data patterns and control sets to diagnose churn 34:46 Running hypothesis-driven experiments in GTM teams 37:39 Building data structures to track the customer journey 43:08 Experimenting with pricing and packaging strategies 46:02 Integrating onboarding directly into the product experience 52:00 Using SWAT teams to pilot new initiatives 56:16 Creating a culture of psychological safety for experimentation 01:01:05 Rapid fire questions and career advice  

Crescendo went from zero to $100M ARR in under two years. And today's guest, CRO Michelle Donnelly, is leading the revenue team. In a market where every AI competitor claims the exact same capabilities, Michelle argues that "trust me" sales tactics don't work anymore, and what her team is doing instead. She explains why she banned traditional sales demos in favor of building functional prototypes using prospect data (sometimes within 24 hours). Michelle also breaks down the transition to outcome-based pricing and how she she's working to compress new rep ramp time. All this, and a ton 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: 01:39 Introduction to Michelle Donnelly and Crescendo 04:54 Leaving Salesforce for a risky hardware startup 11:25 Leveraging your network to spot market trends 16:18 Navigating pivots and finding product-market fit 19:44 Selling amidst the noise of the AI market 25:50 The challenge of simplifying complex messaging 30:45 Strategic priorities for scaling revenue teams 33:18 Replacing standard demos with "show me" solutions 35:50 Building trust by becoming your customer's customer 40:21 Balancing high-level strategy with frontline realities 43:02 Maintaining focus with the rule of three 45:09 Using internal AI to accelerate rep onboarding 48:23 Rapid fire: Traits of great revenue leade  

As EVP of Sales and CS at Insight Partners, Jeremey advises over 500 B2B SaaS companies. In this episode, he reveals why the top 10% of performers are actually expanding their outbound teams, not cutting them. And we cover a ton, including: The Outbound Paradox: Why winning companies are doubling down on SDRs while everyone else pulls back. Build vs. Buy: Why purchasing point solutions right now is a "risky business" (and the case for building your own). The Great Consolidation: How AEs are absorbing the SDR function and what it means for your org chart. The CRO Differentiator: The one trait that separates good revenue leaders from the truly great. 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 and Jeremey Donovan's Career Journey 03:59 AI Adoption: Disillusionment vs. Reality 06:28 Shifting From Bottom-Up to Top-Down AI Innovation 08:29 Navigating Governance and the "AI Czar" Role 13:58 Why Disciplined Execution Trumps AI Tactics 16:11 AI for Performance Reviews and Real-Time Feedback 21:45 The Rise of "Build" and Agentic Coding 27:33 Augmentation, Outbound Sales, and Human Effort 41:40 The Build vs. Buy Debate in RevTech 52:13 Realistic Expectations for AI Productivity Gains 59:13 The Future of SDR and Solutions Engineer Roles 01:03:12 Redesigning Processes and Unbundling Roles for AI 01:13:06 Preserving Critical Thinking in an AI World 01:19:05 Quick Fire: Leadership, Hiring, and Hard Lessons  

Jordan Crawford (Founder @ Blueprint GTM) returns with a reality check for GTM leaders: The ChatGPT era is over. We're entering the season of Claude Code. That means you can move past static prompts and brittle workflows. We are now in a world where autonomous agents write code, execute complex goals, and learn recursively. Jordan breaks down how to set up local environments where context compounds over time, allowing you to deploy "infinite interns" against your most manual processes.   A few of the topics we cover: The 3 Eras of GTM AI: Why we've graduated from ChatGPT (text) and Clay (linear workflows) to Claude Code (autonomous engineering). Adapt or Die: Jordan shares some benchmarks of the absurd growth that's possible in specific areas Atomic Leverage: How to identify the tasks in your sales org that agents can execute at scale. COUPON CODES: Get 10% off AutoClaygent.com with code NortonKnows. No limit on redemptions, but the code expires Feb 28th, 2026.   Get 50% off your own GTM Playbook with code KyleKnows (limited to the first 50 customers only) available at https://playbooks.blueprintgtm.com    Contact Jordan at https://linkedin.com/in/jordancrawford if you have any issues.   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 to Jordan Crawford and Claude Code 02:46 Defining Claude Code and Agentic Capabilities 04:47 Real-World Example: Automating Manual Enrichment 08:17 How Claude Code Differs from ChatGPT and Gemini 11:12 Building Compounding Context in Local Folders 15:23 The Three Eras: ChatGPT, Clay, and Claude Code 19:09 Recursive Improvements and Autonomous Agents 26:08 Claude for Work vs. Terminal-Based Claude Code 28:06 Understanding Plan Mode and Sub-Agent Workflows 37:05 The CRO's Role in Identifying Automatable Tasks 40:06 Scaling Atomic Tasks for Massive Productivity Gains 46:54 Developing Technical Taste and AI Intuition 51:49 The Critical Role of Context and Integration 58:44 Building an AI Chief of Staff for Decision Making 75:40 How to Install and Start Using Claude Code  

Tyler Will (VP RevOps, Intercom) breaks down how Intercom overhauled its go-to-market engine after shifting to AI-first products. What we cover: - Why too many revenue leaders obsess over success metrics but ignore the inputs that actually drive them - The specific comp plan changes Intercom made when moving from seats to usage-based pricing... including giving reps MRR credit for overages without forcing awkward contract conversations - How post-sales motions fundamentally change when you're monetizing resolutions instead of seats - Tyler's four principles for comp plans that actually work Also discussed: When to do a real comp overhaul vs. minor tweaks, why RevOps teams are getting bigger before they get smaller, and using Claude Code to query Snowflake directly.   Chapters: 00:00 Introduction and Guest Background 01:59 Shifting Focus From Success Metrics to Input Metrics 06:06 AI Literacy Required for Modern Revenue Leaders 09:24 Selecting Metrics Without Micromanaging Behavior 17:01 Intercom's Internal and GTM AI Transformation 20:01 Shifting to Resolution-Based Pricing Models 25:46 Evolving the CSM Role for Consumption 28:53 Adapting Compensation Plans for Usage-Based Revenue 33:52 Core Principles for Variable Compensation Design 44:37 Aligning Compensation Strategy With Product Roadmaps 52:00 Restructuring RevOps and Hiring GTM Engineers 56:44 Automating RevOps Tasks With Cloud Code 01:05:58 Impact of AI on SDR and Success Teams 01:09:10 Specific Internal AI Use Cases at Intercom 01:15:20 Quick Fire: Good vs. Great CROs and Advice  

Jason Lemkin (Founder & CEO @ SaaStr) returns to talk about replacing his sales team with 20+ AI agents. What you'll learn in this episode: - Why Jason stopped paying six-figure SDRs who ghost—and what he built instead - The 70,000 AI-sent emails that drove 15% of SaaStr London revenue - How to pick your first AI tool (hint: do a 2-vendor bakeoff, not 10) - Why Salesforce is suddenly the hub every agent needs - The "incognito test" every GTM leader should run on their own website (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!   Chapters: 00:49 Introduction and Jason's Investment Philosophy 04:07 Evaluating Founders and the "Why Now" Question 09:32 The Step Function Change in GTM AI 14:15 Managing Conflict Between Multiple AI Agents 17:43 Replacing Human Sales Teams with AI Agents 21:50 The Importance of Forward Deployed Engineers 24:57 The Terminal Decline of Mid-Pack Sales Roles 30:09 Finding the Internal GTM Nerd to Lead AI 34:15 Executives Must Roll Up Sleeves and Implement 46:22 Fixing Inbound and Support with Instant Answers 53:15 Why You're Failing To Source The Right Tools 57:27 Evaluating Incumbents vs. AI-Native Startups 01:02:41 The Salesforce Renaissance and Agentforce 01:09:45 Triple, Triple, Double, Double in the AI Era 01:15:28 Choosing Between High Intensity and Lifestyle Roles  

Hiring a VP or CRO has never been tougher (or more important). Asad Zaman, CEO of Sales Talent Agency - and one of the most trusted voices in GTM recruiting - joins host Kyle Norton to talk about how GTM leadership hiring is changing fast.   They dig into:   - Why AI broke the traditional interview process, and what they do now instead  - How to build a robust hiring scorecard that performs miles better than a fluffy job description - The trade‑offs that actually kill VP hiring processes - How top CROs should evaluate future leaders (and spot "pre‑peak" talent) - The biggest blind spot CROs have when hiring VPs I mean... who isn't curious about the tested frameworks from the guy behind 1,000+ GTM placements a year?     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:   00:34 Guest Introduction: Asad from STA (Sales Talent Agency) 02:30 Today's Topic: The Challenge of Leadership Hiring   04:14 How AI Has Changed Executive Hiring   07:53 The Rise of the AI-Native Leader   10:26 Market Polarization: Talent Demand and Layoffs   19:03 The New Definition of a Great Leader   24:22 Building an Effective Leadership Hiring Scorecard   29:15 Defining Problems, Jobs to Be Done, and Constraints   35:11 Compensation Psychology and Negotiation Pitfalls   40:34 Mapping the Market and Operationalizing the Scorecard   49:27 Modern Interview Design for Senior Roles   53:12 Teaching as a Core Leadership Skill   56:27 Live Whiteboarding: Replacing Case Studies   01:01:54 Evaluating Candidates for Peak Performance and Potential   02:03:31 CROs' Biggest Blind Spot in Hiring VPs of Sales  

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

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. Kyle and Sangita also discuss why she believes the term "post-sales" is outdated, the mindset shift required to move from functional leadership to company leadership, what CROs need to understand about financial modeling, how to evaluate talent beyond the pitch, and more. 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!

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 to make the shift. From overhauling sales motions and enablement to building a value consulting function and rethinking partnerships, Hayden offers a candid look at the challenges and breakthroughs behind Seismic's platform evolution.  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 Moments: (00:00) Introduction (03:06) Understanding the Transition from Product to Platform (05:47) Seismic's Evolution: From Content Automation to Comprehensive Platform (09:03) The Role of Enablement in Sales Success (11:55) Strategic Decisions: Joining Seismic and Transforming the Company (14:53) Navigating the Go-to-Market Strategy for Multi-Product Companies (17:55) Building a Strong Ecosystem for Platform Success (20:59) Partner Selection and Metrics for Success (23:56) Final Thoughts on Platform Strategy and Future Directions (40:20) Navigating Pricing and Business Value (45:04) The Importance of Value Continuum (47:55) Transitioning to Platform Positioning (55:01) Engaging with CROs and Sales Leaders (01:00:57) Common Pitfalls in Platform Transformation (01:08:47) Lessons from Past Experiences

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 field strategy—and shares how to build programs that actually move the needle. They also dive into how to hire for enablement, measure its impact, and create a high-skill, high-will sales culture rooted in coaching, clarity, and accountability. Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday.  Join the revenue leaders redefining growth at Pavilion's CRO Summit 2025, which will be held on June 3rd at the Denver Art Museum. Register today. 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!

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 reshaping sales roles, why traditional BDR hiring may soon be obsolete, and what CROs must learn today to stay relevant tomorrow. StackOptimise AI Course here New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. 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 Moments: (00:00) Introduction (01:56) Current State of AI Adoption in GTM Teams (04:55) The Importance of AI for CROs (10:16) The Future of AI in Sales and Marketing (14:30) Understanding Digital Workers and Their Impact (18:57) Managing Digital Workers for Sales Efficiency (22:25) The Role of AI in Outreach (25:35) Determining AI's Fit for Different Markets (30:49) Best Practices for AI Adoption in Organizations (45:54) Learning and Adapting in AI (48:59) First Principles Thinking in Sales (01:02:42) The Future of Sales in an AI Era (01:07:54) Key Traits of Successful Revenue Leaders (01:11:49) Lessons Learned in Leadership

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 successfully layer a sales-led motion on top of a product-led foundation. Drawing from his experience at WP Engine and Canva, John shares how to identify the right signals to introduce sales, validate demand through customer conversations, and build a commercially viable offering without cannibalizing PLG momentum. He also reflects on how the CRO role is evolving in today's market—and why adaptability, experimentation, and cross-functional alignment are more important than ever. New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. 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 Moments: (00:00) Introduction (08:51)Commercialization Strategies for SLG (12:13) Customer Success and Support in SLG (14:56) Pricing and Packaging for Enterprise Solutions (17:52) Building the Sales Team for Growth (20:52) Hiring the Right Sales Reps for Success (30:48) Understanding User Adoption and Buyer Dynamics (35:24) Team Building Strategies: Lessons from WP Engine and Canva (37:23) Key Roles in Early Team Development (42:54) Metrics for Revenue Leaders: Signals to Invest or Pull Back (45:42) Understanding Sales-Led Growth and Incremental Value (48:13) Balancing Sales and Self-Service Models (51:54) Product Differentiation for Market Segments (59:03) Aligning Sales, Marketing, and Product (01:10:02) The Disparity in Revenue Talent (01:13:00) Framework for Company Selection (01:18:26) Optimizing for Company Quality (01:21:10) What Separates Good from Great CROs? (01:23:03) Advice for Young Leaders (01:24:26) Lessons Learned in Team Dynamics (01:26:26) Insights on Mental Health and Leadership

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 highlights the need for collaboration across departments and the importance of sales reps mastering AI tools to effectively engage with prospects.  They also explore the changing role of sales development leaders, the hiring process, and the significance of compensation in retaining talent. The discussion emphasizes the need for a diverse skill set within sales teams and the importance of continuous learning and adaptation in a rapidly changing environment. New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. Your'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 Moments: (00:00) Introduction (01:49) Understanding Outbound Sales and AI's Role (08:38) Defining Signals and Intent in Sales (10:58) The Evolution of Outbound Sales: From 1.0 to 3.0 (14:47) The Profile of an Outbound 3.0 Sales Rep (32:35) Building Champions in Rev Ops (38:03) Leveraging AI for Account Insights (39:53) Human Touch in AI Outreach (45:52) Innovative Approaches to Outbound Sales (49:57) The Evolution of Networking and Referrals (01:01:59) Teaching and Sharing Insights with Prospects (01:05:04) The Role of Sales Development Leaders (01:09:53) Hiring and Developing Effective Sales Teams (01:15:08) The Importance of Compensation and Career Paths in Sales

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. Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. Your'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 Moments: (00:00) - Introduction and Podcast Overview (01:22) - Guest Introduction: Kevin Dorsey (02:00) - Diving into AI and GTM (02:51) - AI in Sales: Practical Applications (06:36) - Building AI Tools Internally (14:21) - Call Scoring and AI Coaching (20:44) - Issue Diagnosis with AI (33:08) - Leveraging AI for Documentation and Training (35:36) - Choosing Between Building and Buying AI Solutions (40:28) - The Decision to Step Away from Founding (41:01) - Challenges in Building AI Companies (42:08) - The Future of SaaS Companies (43:29) - Leveraging AI for Business Success (46:02) - Learning and Adapting with AI (46:50) - Exploring AI Tools and Resources (58:04) - Evaluating AI Vendors (01:03:04) - Personal Productivity with AI (01:13:42) - Final Thoughts and Advice

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 his diverse background and how QuotaPath navigates commission planning to ensure high performance and retention. The conversation also touches on key aspects such as measuring incrementally, balancing incentives, diagnosing ineffective plans, and trends in the current market. New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. Your'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 Moments: (01:09) - Meet Ryan Milligan: From Data Science to Sales Leadership (02:58) - The Path from Rev Ops to CRO (05:40) - Sales Commission Strategy: Ownership and Design (12:56) - Aligning Comp Plans with Business Metrics (24:01) - Designing Effective Comp Plans: A Step-by-Step Guide (33:47) - Testing and Measuring Incrementality in Comp Plans (41:32) - Building Effective Quotas (52:34) - Setting Realistic and Motivating Targets (01:02:30) - Common Pitfalls in Commission Plans (01:12:18) - Key Traits of Great Revenue Leaders (01:18:38) - Final Thoughts and Takeaways

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 a bespoke knife fight. Plus, Alex's hardest-won lessons—from equity pitfalls to why endurance separates good CROs from great ones. New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Want more from Topline? Tune into the Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. And don't forget to join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.

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 partnerships, avoiding "paper partnerships," and creating true strategic alignment. Whether you're considering technical alliances or wondering if partnerships are right for your business model, Matt provides actionable insights on when, why, and how to build alliances that deliver real revenue impact. New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Want more from Topline? Tune into the Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. And don't forget to join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.

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 is disrupting traditional go-to-market models, how Crunchbase is using predictive data to reshape its strategy, and why the GTM stack of the future might be smaller—and smarter. Thanks for tuning in! Want more content from Pavilion? New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. Your'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 Neal Patel and Crunchbase (02:28) - State of the Market and AI's Impact (11:01) - Navigating Macro Conditions as a CRO (14:26) - Crunchbase's Shift Towards Predictive Analytics (23:27) - AI's Transformative Role in Go-to-Market Strategies (30:12) - Future of GTM: Embracing AI and Relationship Building (36:18) - The Importance of Team Innovation (41:55) - Navigating Company Selection as a CRO (46:05) - Building Relationships in Leadership (52:15) - Evaluating Market Potential and Company Goals (57:05) - Understanding AI's Impact on Business Strategy (01:01:00) - Red Flags in Company Selection (01:03:51) - Key Traits of Successful CROs

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 enterprise buyers, and what revenue leaders need to consider when layering in a sales motion.   Thanks for tuning in! Want more content from Pavilion?   New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.   Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them.   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) - The Email Problem: A Universal Challenge (09:49) - Superhuman: Revolutionizing Email Productivity (19:47) - Transitioning from PLG to SLG: A New Sales Approach (30:04) - Building Blocks for Sales Success: Data and Team Dynamics (30:32) - Personalization in Sales Outreach (31:31) - Core Pillars of Sales Strategy (32:27) - Common Pitfalls in Sales-Led Growth (33:25) - Building a Sales Culture at Superhuman (37:17) - Leveraging AI in Sales Processes (42:43) - Skills for Sales Reps in the Age of AI (49:58) - Navigating AI-Generated Communication (56:39) - Lessons in Sales Leadership  

What does it take to lead revenue in a private equity-backed company? In this episode, Kyle Norton talks with Vanessa Brangwyn, CRO at Motus, about the key differences between VC and PE environments, how PE firms drive efficiency and profitability, and what revenue leaders need to succeed. She also shares insights on integrating go-to-market strategies post-acquisition and managing a PE-backed board.   Thanks for tuning in! Want more content from Pavilion?   New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.   Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them.   Your'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 Vanessa Brangwyn and Achievers' Journey (03:13) - Transitioning from VC to PE: The Achievers Experience (06:03) - Navigating Public Company Dynamics (08:56) - The Spin-Out: Achievers' New Chapter (12:06) - Exploring the Private Equity Landscape (14:56) - CRO Insights: PE vs. VC Dynamics (18:10) - Shared Learnings in Private Equity (20:46) - The Role of Structure in Team Dynamics (24:05) - Profitability vs. Growth: Understanding PE Goals (26:48) - Strategic Decision-Making in PE (29:55) - Efficiency Metrics in Private Equity (37:59) - Tactical Metrics for Sales Efficiency (40:52) - Understanding Board Engagement in PE vs VC (44:42) - Navigating Incentives and Decision-Making in Boards (47:06) - Leveraging Data for Effective Board Management (49:46) - Lessons from Private Equity for Venture-Backed CROs (51:10) - Strategic Rationale Behind Acquisitions (56:38) - Integrating Go-To-Market Strategies Post-Acquisition (01:01:11) - Customer Success Insights for CROs (01:05:42) - The Role of Authenticity in Leadership (01:10:21) - Advice for Emerging Leaders (01:12:20) - Lessons Learned from Leadership Experiences

Great revenue leaders aren't just sales experts—they're world-class problem solvers. But how do you separate signal from noise, diagnose the right issues, and make decisions that drive long-term success?    In this episode of The Revenue Leadership Podcast, Ashley Grech, CRO at Xero, joins Kyle to break down her framework for identifying, prioritizing, and solving complex revenue challenges. She shares how revenue leaders can balance instinct with data, avoid limiting beliefs that stall innovation, and use the driver tree framework to diagnose revenue bottlenecks. Ashley also explains why prioritization is the key to unlocking scale, how decision-making frameworks can accelerate growth, and what she's learned from scaling global go-to-market strategies at Xero and Square.   Thanks for tuning in! Want more content from Pavilion?   New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.   Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them.   Your'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 Problem Solving in Revenue Leadership (03:11) - The Importance of Problem Solving (06:03) - Frameworks for Problem Identification (08:56) - Utilizing Driver Trees for Diagnostics (11:55) - Data-Driven Decision Making (15:10) - Prioritization of Problems (17:57) - Balancing Urgency and Importance (20:54) - Sourcing Information from the Team (23:49) - Navigating Customer Feedback (27:08) - The Role of Data in Solutioning (30:06) - Finding the Best Solution (32:50) - Conclusion and Key Takeaways (44:18) - Principled Problem Solving (51:38) - Organizing Principles for Success (56:03) - Teaching and Scaling Principles (57:31) - Market Expansion Strategies (01:06:30) - Timing for International Expansion (01:09:17) - Channel Diversification Insights (01:12:43) - Overcoming Limiting Beliefs (01:17:14) - Qualities of a Great CRO  

How do you scale a sales organization as your company evolves from a single product to multiple business lines? In this episode of The Revenue Leadership Podcast, Jeff Perry, CRO of Carta, shares how he has built and structured Carta's go-to-market strategy to support its rapid expansion across corporations, venture capital, and private equity. He breaks down the challenges of multi-product growth, the decision-making behind sales org design, and how Carta balances specialization with cross-functional alignment. Jeff also dives into the nuances of different sales motions, marketing strategies, and customer acquisition models across Carta's distinct business units.   Are you being paid what you're worth? Help us refresh Pavilion's industry-standard compensation report for 2025 by taking our anonymous survey at joinpavilion.com/comp and get early access to the results!   Thanks for tuning in! Want more content from Pavilion?   New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.   Stay ahead with the latest industry developments, emerging go-to-market trends, and valuable benchmarking data. Subscribe to Topline Newsletter for expert insights from Asad Zaman every Thursday.   Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them.   Your'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 Jeff Perry and Carta (05:53) - Understanding Carta's Multi-Product Strategy (11:57) - Revenue Breakdown and Business Growth (18:00) - Organizational Design and Sales Strategy (24:08) - Marketing Approaches for Different Business Units (29:49) - Challenges in Managing Diverse Sales Motions (35:53) - The Importance of Customer Experience (39:03) - Leadership and Team Structure at Carta (41:26) - Understanding Private Equity Portcodes (42:39) - Career Progression and Mountain Jumping (44:48) - Sales Team Structure and Specialization (46:15) - Data-Driven Decision Making in Sales (48:58) - Sales Engineering and Cross-Training (51:49) - Organizational Design and Decision Making (55:32) - Input-Output Framework in Sales Management (56:59) - Balancing Customer and Company Needs (01:01:06) - International Sales Strategy (01:07:55) - Qualities of a Great CRO (01:11:07) - Leadership Lessons and Career Patience (01:13:23) - Performance Management and Coaching Plans (01:17:35) - Recommended Reads and Continuous Learning  

In this episode of the Revenue Leadership Podcast, host Kyle Norton sits down with Jason Gelman, Operating Partner at Primary Ventures and Co-Founder of Jump, to explore his transition from operator to VC and the lessons he's learned along the way. Jason shares insights from scaling Compass from $100M to $6B in revenue, why not every startup should raise venture funding, and how founders can navigate the challenges of go-to-market strategy. They also cover the evolving role of AI in revenue leadership, the traits that separate great CROs from the rest, and the fundamental mistakes many startups make when trying to scale.   If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast by Pavilion for new episodes every Wednesday.   Want more content from the Topline media family?   Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman.   Join the Topline Slack channel to engage with hosts, guests, and other listeners.    Subscribe to Topline Newsletter written by Asad Zaman.   Primary: https://www.primary.vc/ Jump: https://jumprevenue.com/ B&T Infra Newsletter: https://www.infranewsletter.com/ LinkedIn: https://www.linkedin.com/in/jasongelman/ Contact: [email protected] Key Chapters: (00:00) - Introduction to Jason Gelman and Primary Ventures (02:46) - The Role of an Operating Partner (06:03) - Understanding Jump: A Revenue Calendar Tool (08:53) - Navigating Venture Capital: When to Raise Funds (12:05) - The Transition from Operator to VC (15:02) - Lessons Learned as an Operating Partner (17:53) - Identifying Product-Market Fit (21:06) - The Importance of Talent in VC (23:57) - Final Thoughts and Future Aspirations (41:06) - Navigating Venture Capital Networks (44:00) - Insights from Operating as a Non-Venture Backed Company (49:40) - The 'God of Beliefs' Framework in Investment (53:01) - Mastering VC Relationships (56:27) - The Rapid Evolution of Go-To-Market Tech (01:01:09) - The Future of CRM and AI Integration (01:06:20) - The Challenge of Investing in AI Startups  (01:12:11) - Creating a Culture of AI Experimentation (01:16:26) - Defining Greatness in Revenue Leadership

In this episode of the Revenue Leadership Podcast, host Kyle Norton converses with Jordan Crawford, a GTM Data Scientist, to examine the transformative impact of AI in business. They delve into the DeepSeek AI model and its potential to revolutionize the industry while critiquing traditional sales models and emphasizing the importance of data-driven strategies. The discussion highlights how revenue leaders can integrate AI into their daily operations, utilizing tools like ChatGPT and Claude to boost productivity and learning. Jordan offers insights on crafting a strategic approach to AI implementation, underscoring the need for specialized roles and external expertise to guide organizational transformation.   If you like what you heard from Kyle today, make sure to follow The Revenue Leadership Podcast by Pavilion for new episodes every Wednesday.   Want more content from the Topline media family?   Listen to Topline Podcast with Sam Jacobs, AJ Bruno, and Asad Zaman.   Join the Topline Slack channel to engage with hosts, guests, and other listeners.  Subscribe to Topline Newsletter written by Asad Zaman.