E28: Interns to Enterprise: How Cresta’s CRO Built a Category Leader
The Revenue Leadership Podcast with Kyle Norton
Release Date: 04/09/2025
$40M ARR with 50‑Person Team (in less than a year) - Bryan Adams, VP Sales at bolt.new
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. , the #1 podcast for founders,...
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E53: Sales Capacity Planning That Doesn’t Suck (Jenny Dingus, SVP Global Sales @ Clio)
The Revenue Leadership Podcast with Kyle Norton
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. to...
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E52: Winning in Crowded Markets - The CRO Playbook (Jonathan Leaf, CRO @ BambooHR)
The Revenue Leadership Podcast with Kyle Norton
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...
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E51: How Lightspeed Commerce Built a $1B+ Sales Engine - JD Saint-Martin, President @ Lightspeed Commerce
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to...
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E50: The Secret to High-Trust, High-Performance GTM Teams - CRO @ Houzz, Tara DiCristo-Schmitt
The Revenue Leadership Podcast with Kyle Norton
Tara DiCristo-Schmitt (CRO at Houzz) joins host Kyle Norton (CRO at ), 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. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect with 600+...
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E49: All about AI and GTM at Clay - Round Two with Everett Berry
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. 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...
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E48: Work Sprawl and the Future of Marketing with Global VP Marketing @ ClickUp, Kyle Coleman
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. , the #1 podcast for founders, operators, and investors in B2B tech. to connect...
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E47: Kyle Norton’s Bets for GTM Domination (While Building a Generational Tech Company) - CRO @ Owner.com
The Revenue Leadership Podcast with Kyle Norton
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...
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E46: The RevOps Mind Behind Owner.com’s Billion-Dollar Valuation: Steve Dinner
The Revenue Leadership Podcast with Kyle Norton
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...
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E45: The inside scoop on GTM engineering with Clay’s Everett Berry
The Revenue Leadership Podcast with Kyle Norton
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. to Topline Newsletter. ,...
info_outlineWhat 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.
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