Tech Sales with Carter

Tech Sales with Carter

Interviews with founders and top producers about sales.

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Recent Episodes

How to break into tech sales without a perfect background | Grey Bradshaw-Mack (Default)
March 12, 2026

How to break into tech sales without a perfect background | Grey Bradshaw-Mack (Default)

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 ...
How to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly)
March 12, 2026

How to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly)

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...
Why your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet)
March 11, 2026

Why your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet)

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 ...
Pick your next sales role like a VC | Frank Pastirchak (Sales Director, Reggora)
March 8, 2026

Pick your next sales role like a VC | Frank Pastirchak (Sales Director, Reggora)

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...
How to Build a Sales Team That Doesn't Need You | Tim McEuen (AppFolio)
March 6, 2026

How to Build a Sales Team That Doesn't Need You | Tim McEuen (AppFolio)

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...
How to Sell Tech to an Industry That Hates Change | Dewayne Starling (nCino)
March 5, 2026

How to Sell Tech to an Industry That Hates Change | Dewayne Starling (nCino)

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...