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24:52

SPOTLIGHT: The AI category GTM teams are about to...

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2026/07/21

A rep says "follow up on that" on a call, then buries it under five more calls and a late-night inbox. Three days later the deal's gone cold, but the CRM still says it's live. The manager forecasts off that. The CRO forecasts off the manager. The board asks the CEO if anyone actually has a grip on the number. The whole thing was built on a promise nobody kept. Adam Liska worked on the early Gemini models at Google DeepMind before leaving to close that gap. His company, airspeed, just raised a

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01:13:57

AI Marketing Master: The 'AI CMO' is a Beautiful Lie...

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2026/07/19

Marc Ferrentino, Co-Founder and CEO of Quotient and former chief technical architect at Salesforce, joins Sam Jacobs and Asad Zaman to separate AI-marketing hype from what actually works today. Marc's core claim: the 'AI CMO' is marketing fiction, and the real near-term unlock is clearing the roughly 70% of a marketer's day lost to busywork, so smaller teams can finally operate like big ones. Topics include the collapse of specialized marketing roles into cross-functional generalists, why the

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23:13

SPOTLIGHT: Why High Performers Underperform Under...

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2026/07/17

A CEO walks into a board meeting knowing exactly what to say then freezes. A sales rep doomscrolls between calls and shows up to the next one flat. A founder grinds toward the exit, only to sacrifice their relationships and themselves along the way. The problem isn't always strategy, skill, or effort. Sometimes, it's the nervous system. Kevin Bailey knows this firsthand. After building a high-growth tech company with around 100 employees, he noticed something strange: some days he was exceptionally

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01:14:37

$300M Operator: "70% Of The Executive Playbook Is...

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2026/07/12

Katie Bullard helped take DiscoverOrg from $30 million to $300 million in revenue, then served as president of A Cloud Guru and Red Canary through exits to Pluralsight and Zscaler. She joins AJ Bruno and Asad Zaman to break down what actually changes for operators in an AI-first world. From why "AI native" is not a growth strategy, to how to align the CRO, CFO, and product team around a single growth plan. Topics include building for customer value before chasing AI ARR, the move from seat-based to

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01:10:27

What It's Really Like To Scale To $1 Billion | CRO @...

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2026/07/05

Ghazi Masood, Chief Revenue Officer at Replit, joins Sam Jacobs and Asad Zaman to break down the company scaled from $2 million towards a North Star of $1 billion in revenue in about two years, with roughly 350 employees and a 75-person go-to-market team. Ghazi gets specific on the operational cadence that replaced the quarterly SaaS playbook, why more than 90% of reps overachieved in H1 and why he believes $2 million per rep still isn't the ceiling, and how Replit built its own CPQ, Clari, and

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01:15:22

The Godfather of Modern GTM: This Is How To Measure...

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2026/06/28

Mark Roberge, founding CRO at HubSpot and co-founder of Stage 2 Capital, joins Sam Jacobs and AJ Bruno to tackle the question every board is asking in 2026: how do you actually measure AI's impact on a go-to-market team? They get into the revenue velocity formula, why selling time is the one variable AI can realistically double, and the ICONIQ data showing AI lifts top-of-funnel conversion 11% while barely moving active deal cycles. Plus, a Quiz Pro Quo on Palantir's 137% rule of 40 and Twilio's

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01:16:20

The $1M Employee Is Here: Why ClickUp Replaced 22% Of...

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2026/06/21

Gaurav Agarwal, COO of ClickUp, joins Sam Jacobs, AJ Bruno, and Asad Zaman after ClickUp, a company north of $300 million in ARR, parted ways with 22% of its workforce while rolling out pay packages up to $1 million a year for the individual contributors who stay. Gaurav walks through how a central Foundry team builds the tooling while each function's top performers automate their own jobs, why he wants his org to run like a pirate ship before a naval fleet, and how a two-person marketing team now

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01:07:11

"Dead AI Startups Keep Landing On My Desk!" | CEO @...

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2026/06/14

Steve Cox, CEO of Clari + Salesloft, joins Sam Jacobs and Asad Zaman to argue that SaaS is far from dead. Steve took the CEO role in December 2025 to merge two of the biggest brands in go-to-market tech into what he calls the world's first predictive revenue system. Topics include the narrative war pushing investors to bet against SaaS-era companies, his one non-negotiable hiring trait, and how to merge two former rivals without one culture eating the other. Plus, a Quiz Pro Quo on go-to-market

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01:12:47

Exposed: The Big VC Lie of 2026 | Michael Walrath,...

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2026/06/07

Michael Walrath, Chairman and CEO of Yext, returns to break down why the market has left a profitable, $400 million mid-cap public software company trading at one times revenue, even with over $100 million in EBITDA. He joins AJ Bruno and Asad Zaman to argue that the so-called SaaS apocalypse has almost no data behind it, that most AI layoffs are really a decade of go-to-market overhiring unwinding, and that boring compounders still out-return the hypergrowth darlings. Topics include how venture

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01:06:08

Build The World Class Team That Anthropic Won't Steal...

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2026/05/31

Craig Rosenberg, Chief Platform Officer at Scale Venture Partners and co-founder of Topo, joins AJ Bruno and Asad Zaman to take on the question every founder is wrestling with: can you still build a world-class sales team when OpenAI and Anthropic are handing individual contributors $10 million equity packages? Craig argues you do not have to compete head-on, then lays out the hiring profile to chase instead, the quota-to-comp discipline that keeps packages sane, and why founder brand has become the

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01:07:09

AI "Efficiency" Is Killing Your Marketing | Kyle...

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2026/05/24

Kyle Lacy, CMO at Docebo (previously Lessonly, Seismic, Jellyfish), joins Sam Jacobs, AJ Bruno, and Asad Zaman to push back on AI-era "efficiency" gospel in marketing. Topics include why product marketing under a sales-led organization will die, and the one-page Wall Street Journal manifesto every CMO should make their CEO write. Plus, why OpenAI and Anthropic might be lost when it comes to POV...AND the $300M Windows 95 launch with Jennifer Aniston and a Polish submarine (obviously). Key Takeaways:

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01:09:31

Playbook: AI-Era Customer Success For Hyper Growth |...

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2026/05/17

Sam Slevin, Global SVP of Customer Success at AlphaSense, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the AI-era customer success playbook. Topics include why service is the differentiator over the next 2 to 3 years, the case for customer success owning a revenue number from day one, the gap between finance's productivity targets and real-life capacity. Plus, the origins of customer success, why consumption-based pricing can quickly become a trap, and a bull-versus-bear debate on whether HubSpot

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57:19

AI Cyber Exec: Vibecoding Is A Security Time Bomb |...

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2026/05/10

Ryan Burke, VP of Worldwide Sales at Crogl, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the new economics of enterprise cyber risk. Topics include Anthropic's Mythos model, AI for the security operations center, why vibe-coded apps are far more likely to have security issues, why Claude Design tanked Figma's stock, and what the Elon Musk versus OpenAI lawsuit signals for AI governance. Key takeaways: AI has crashed the cost of running sophisticated attacks, putting nation-state-grade tooling in

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01:02:22

Top Investor: AI Killed Most Moats. These 4 Still...

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2026/05/03

Stage 2 Capital General Partner Liz Christo joins the show to discuss the disconnect between venture expectations and reality in the software market. The conversation covers the hidden costs of the new build versus buy debate, the structural changes happening within modern sales organizations, and whether traditional B2B SaaS go-to-market strategies and moats still matter when AI coding tools make software replication cheaper than ever. Key Takeaways: -The shift toward building internal AI tools

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01:03:17

VC Whisperer: There Will Be No Exits For... | Peter...

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2026/04/26

Peter Walker brings Carta's proprietary private market data from 60,000 startups and 85% of US unicorns to expose the brutal realities of today's tech landscape. While Q1 saw record capital raised, the money is highly concentrated among foundation models. We review the harsh truth behind the 530,000 open tech jobs in the US and the widening talent divide separating top 10% performers from the rest of the market. The conversation covers why venture capital is squeezing operators, how private equity

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55:34

The #1 GTM Engineer In The World | Jordan Crawford,...

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2026/04/19

In this episode, Jordan Crawford outlines how revenue leaders can build an autonomous pipeline generation engine and transition away from static playbooks. The discussion covers practical methods for extracting competitor usage data, identifying segments of users who are far more likely to buy, and generally how top GTM teams are using GTM Engineering to dramatically improve their results. The hosts also evaluate how AI tools alter revenue operations, shift the traditional B2B SaaS go-to-market

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01:05:54

How Top VCs Pick Winners In 2026 | Cassie Young,...

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2026/04/12

Cassie Young, Partner at Primary Venture Partners, joins the show to break down their contrarian $625 million seed fund and the reality of the coming gross retention apocalypse for tech companies. The conversation outlines why classical venture logic is breaking and how AI-native CRMs are plotting to steal enterprise market share from legacy giants like Salesforce. The group also details why the $6 trillion white-collar labor pool is the real target for emerging AI workflows rather than traditional

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49:26

What World-Class AI in GTM Looks Like | Kyle Norton,...

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2026/04/05

Kyle Norton's AI-enabled revenue team at Owner.com has completely rewritten the economics of what's possible in sales. Kyle joins the show to share why decentralized AI rollouts fail, how to build a core intelligence engine centrally, and why early AI investments must focus on one specific area. The hosts also discuss navigating go-to-market strategy shifts, rethinking RevOps AI integration, and why sales leadership can no longer use budget constraints to delay AI adoption. Key Takeaways: -Building

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01:00:48

E152: Is This The End of Sales As We Know It? (CEO @...

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2026/03/29

Amanda Kahlow raised $30 million to build AI sales agents that improve the buying experience. As the founder of 1mind and previously 6sense, she sits at the forefront of modern go to market strategy. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman sit down with Amanda to discuss the reality of AI in the sales motion; she explains how Superhumans (1mind's AI Agents) handle everything from top of funnel enterprise pipeline generation to acting as sales engineers on live demos. The conversation

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55:13

Why Intercom Destroyed Its Predictable SaaS Revenue

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2026/03/22

Intercom gave up $60 million in contracted seat-based ARR to bet the entire company on an AI agent named Fin. The result? They passed $400 million in total ARR, with Fin driving over $100 million in revenue and 35% growth. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman break down what went into this massive turnaround. The conversation starts with the problem: the SaaS market cap dropping by $600 billion, and how this creates an urgent need for structural pivots. The hosts discuss the

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