E66: Win More (by Losing Less) | Kevin Bailey, CEO @ Dreamfuel

The Most Efficient Marketing Org In The World? (35 People, $350M) | Tim Rutten, CMO @ Backbase

Tim Rutten, CMO at Backbase, runs a 35-person marketing team against a book of business north of $350 million in ARR, and joins Kyle Norton to break down the AI-native go-to-market operating model he built from the ground up. Topics include what AI-native actually means as an architecture principle, throwing out the org chart to rebuild around the real work, and building GTMOS, an in-house go-to-market operating system where 100% of the code is agent-generated. Plus, replacing a signal-engine tool like 6sense with a white-box build, scanning 3,000 target banks against a live ICP model for around $500 a week, and the "love letters" tactic that gets 40% of banking executives to respond. In short, a tactical playbook for AI-native revenue leadership. Key Takeaways: - Tim Rutten treats AI-native as an all-or-nothing bet. As the CMO at Backbase put it: "you either go all in or you don't go at all... in the middle, you're not getting the full value." That conviction let him treat the whole revenue org as an engineering problem and rebuild it around one go-to-market OS. - The competitive edge is a harness good enough to turn business leaders into builders. Tim Rutten's guidance is to "make sure you have a landing zone, a good architecture, really understand how to do this so you can make non-engineers dangerous," so the people closest to the customer can ship agents and workflows without waiting in a GTM engineering queue. - Building in-house is already pulling real cost out of the P&L. Backbase replaced 6sense with a bespoke, white-box signal engine, and Tim Rutten says "before the end of the year, we're taking out at least, at least $100K extra" in deprecated tools, calling the build "the best ROI I've seen in this full year." - One of the highest-return plays is also the lowest-tech. Tim's team writes public "love letters" that champion a target bank's executives by name, and he says "let's say 40% of the actual executives respond" because "people feel special. They feel heard. They feel seen." It gets Backbase into C-suite conversations at a fraction of the cost of a classic ABM campaign. Connect with the Hosts & Guests: Host: Kyle Norton, CRO at Owner.com - https://www.linkedin.com/in/kylecnorton/ Guest: Tim Rutten, CMO at Backbase - https://www.linkedin.com/in/timrutten/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/ Chapters: 00:00 Introducing Tim Rutten 02:57 What AI Native Actually Means 06:24 Throwing Out the Org Chart 09:21 Which GTM Roles Get Hollowed Out 12:12 Getting the Team Into Claude Code 17:45 Building the GTM Operating System 20:40 The Vercel AI-Native Stack 25:15 Cutting Tools and $100K in Costs 29:29 Making Non-Engineers Dangerous 35:00 Centralized vs Distributed AI GTM 43:00 Reorganizing the Marketing Team 46:16 Scanning 3,000 Accounts With AI 55:55 From Weeks to 15-Minute ABM 1:06:43 The Love Letters Tactic 1:13:40 Quickfire CMO Questions

E70: Manufacture Motivation, Sell More | Kevin Bailey, CEO @ Dreamfuel

Kevin Bailey, CEO of Dreamfuel, returns to The Revenue Leadership Podcast for part two of his conversation with Kyle Norton on mental performance. This time they dial in on how revenue leaders cascade these practices through their organizations. Topics include the Greenlight Guru breakthrough story (one breathwork session that converted a skeptical co-founder), the pre-call warmup protocol Kevin used during a solo enterprise sales year that doubled his close rate, and why every executive needs a "serotonin day" every two weeks to recover their dopamine system. Plus, how Owner.com keeps award-winning performers on "Get On Track" plans without spiraling identities, Jim Collins's return on luck for sales slumps, and what to track with WHOOP and Oura to make recovery a competitive advantage. Key Takeaways: - Kevin Bailey's single biggest performance unlock during his solo enterprise sales year was the pre-call warmup Hugh Jackman calls "daily design": 30 rapid belly breaths, a breath hold, fire-up music, then journaling as if the meeting is already over. As Kevin put it: "I did this for every single call. My close rate about doubled… it puts elite behaviors on autopilot. Again, why all athletes do it." The mechanism is mental contrasting: the subconscious can't fully distinguish a vividly-imagined outcome from a real one, so the dopamine and serotonin from the visualization juice neuroplasticity that reinforces hard behaviors. - Kevin's prescription for revenue leaders is one "serotonin day" every two weeks: a full day with no goals, no time pressure, and no phone. The kid-kicking-a-ball-for-the-pure-joy-of-it kind of day, rather than the soccer-with-rules kind. In the age of AI, when an executive's edge is the quality of their thinking and not their grind, the nervous-system reset is what unlocks bottom-up creative insight the rest of the week. - Kyle Norton's process-over-outcome culture at Owner.com has produced something counterintuitive: "tons of our best, very best performers at the company… award-winning performers have been on what we call Get On Track plans, which is our version of a PIP." The setup is Jim Collins's return on luck. Sales swings cut both ways, and a culture that anchors identity to inputs and process (not just W's) lets reps work through cold streaks without spiraling. Kevin's neurochemistry framing of the same idea: "If you learn how to control the dopamine of your team using tools like this, then you have control and you can push through the hard parts where your competitors will falter." - Trying to install seven new mental performance habits at once guarantees zero stick. The brain doesn't want to rewire. Kevin's image is that your brain is a giant interstate and it doesn't want you blowing up lanes to move on-ramps. Pick one practice, get serious about it for 30 days minimum, then move to the next. Connect with the Hosts & Guests: Host: Kyle Norton, CRO at Owner.com - https://www.linkedin.com/in/kylecnorton/ Guest: Kevin Bailey, CEO at Dreamfuel - https://www.linkedin.com/in/kevinjamesbailey/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/ Chapters: 00:00 Introducing Kevin Bailey 05:53 The Leader Must Embody It First 08:36 Greenlight Guru Breakthrough Story 11:30 Engineering Breakthrough Moments 15:45 Biometric Trackers and Challenges 22:29 Pick One Habit at a Time 26:32 The Pre-Call Warmup Protocol 34:14 Visualization Without the Woo 38:09 Dopamine Triggers Leaders Control 44:11 Return on Luck and PIPs 47:07 Why Every Exec Needs a Serotonin Day 53:13 Why Sitting Still Feels Threatening 58:10 Sleep, Drinking, and the HRV Test 01:05:31 Shared Language and Four Zones

E69: Stop Paying For SaaS: The AI Playbook Driving A $1B Trajectory | Ghazi Masood, CRO @ Replit

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/ [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

E68: Are You UNINVESTABLE? The New GTM Reality | Cassie Young, General Partner @ Primary Venture Partners

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

E67: Your Buyer's AI Is Pitching YOUR Product (Badly) | Adrian Rosenkranz, CRO @ Webflow

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 [https://gemini.google.com/app/3a6c37ddefd8472a] 📩 Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ [https://gemini.google.com/app/3a6c37ddefd8472a] 🤝 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 [https://gemini.google.com/app/3a6c37ddefd8472a] 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