Episodes

How to Run a 4,500-Location Enterprise Rollout (In One Year) | Zach Larabee (Sr. Manager at Toast)
Feb. 18, 2026

How to Run a 4,500-Location Enterprise Rollout (In One Year) | Zach L…

In this episode, I sit down with Zach Larabee, Sr. Manager of the Enterprise Sales Coordinator Team at Toast, to break down what actually happens after an enterprise deal signs, how large brands get rolled out across hundreds...

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Building a Sales Org From Scratch During COVID | Kaylin McNamara (Sr. Director, GTM at Owl Labs)
Feb. 11, 2026

Building a Sales Org From Scratch During COVID | Kaylin McNamara (Sr.…

In this episode, I sit down with Kaylin McNamara, Sr. Director of GTM Operations at Owl Labs, to break down what it really takes to build and scale a sales org from scratch, especially when the market is changing fast. Kaylin...

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How to Turn Inbound Leads into Enterprise Deals | Michael Conrad (Enterprise AE at n8n)
Feb. 10, 2026

How to Turn Inbound Leads into Enterprise Deals | Michael Conrad (Ent…

In this episode, I sit down with Michael Conrad, Senior Account Executive at n8n, to break down how enterprise AEs multi-thread deals, pull executive buyers in early, and keep momentum without annoying their champion. Michael...

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How to get hired as an AE at a VC-backed startup | Matt Stinson (CRO at Starbridge)
Feb. 3, 2026

How to get hired as an AE at a VC-backed startup | Matt Stinson (CRO …

In this episode, I sit down with Matt Stinson, CRO at Starbridge, to talk about what top performing startups look for when hiring AEs, and how candidates can stand out fast. Matt breaks down how Starbridge is scaling their sa...

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