Episodes

In this episode, I sit down with Grey Bradshaw-Mack, GTM at Default, to talk about his unconventional path into tech sales, from starting out in nonprofit work to breaking into software sales through PitchBook and eventually ...

In this episode, I sit down with Zac Basile, Strategic Account Director at Polly, to talk about what it’s actually like to sell enterprise mortgage tech when there’s no playbook, deals take six to twelve months, and buying co...

In this episode, I sit down with Kyle Weiss, Head of Sales and Customer Success at Outbound Sales Pro and Parakeet, to break down what third-party outbound actually is, why some companies outsource it instead of building SDR ...

In this episode, I sit down with Frank Pastirchak, National Sales Director at Reggora, to break down what selling into mortgage, banking, and real estate actually looks like when deals are long, complex, and heavily relations...

In this episode, I sit down with Tim McEuen, Manager of the Enterprise BDR team at AppFolio, to break down what great sales leadership actually looks like in practice. We get into how Tim built structure across a huge year pe...

In this episode, I sit down with Dewayne Starling, Strategic Relationship Manager at nCino and a 30+ year mortgage industry veteran, to talk about what actually matters when selling technology into mortgage. We get into why m...

In this episode, I sit down with Angie Parkhouse, Sales Leader at Qualia (real estate transaction management software), to talk about what it looks like to design your career around your life and the sales fundamentals that s...

In this episode, I sit down with Matt Sterenberg, Senior Director of Customer Success at Modern Campus and a 12+ year EdTech leader with experience across customer success, sales, and customer advocacy, to unpack what custome...

In this episode, I sit down with Sean Gannon, GTM Strategy Consultant at GTMppl and a longtime EdTech revenue leader who spent 13 years at Parchment (later acquired by Instructure), to break down what it actually takes to bui...

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...

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...

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...

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...