Episodes

In this episode, I sit down with Soraya Hatcher, SMB Sales Manager at HubSpot, to talk about how AEs can position themselves for sales leadership, build trust in a remote environment, and manage a team with more structure and...

In this episode, I sit down with Chris McLendon, Partner and Chief Revenue Officer at TidalWave, to talk about what it looks like to sell AI-native mortgage technology into an industry that is under margin pressure, skeptical...

In this episode, I sit down with Seth Haake, Strategic Sales Engineer at Total Expert, to talk about how mortgage technology companies win enterprise deals by selling outcomes instead of features. Seth breaks down how Total E...

In this episode, I sit down with Graham Young, Strategic Account Executive at Vesta, to talk about what it really takes to sell major platform change in mortgage tech, especially when buyers have been burned by software promi...

In this episode, I sit down with Raymond Griffin, Regional Sales Manager at Numa, to talk about what it actually takes to become a top producer in sales and stay there across multiple stops in automotive tech. Raymond breaks ...

In this episode, I sit down with Jordan Benjamin, CEO of My Core OS and former 6x President’s Club member at HubSpot, to talk about the mindset and psychology behind sustainable sales performance. Jordan breaks down the bigge...

In this episode, I sit down with Erica Waldron and Andrea Castelli, Account Executives at Snapdocs, to talk about their unconventional path into mortgage tech sales and how they built their way into the industry by starting t...

In this episode, I sit down with Pat Mulvey, Director of Global Business Development at Zywave, to talk about what it actually takes to reset and scale a business development team inside a changing go-to-market environment. P...

In this episode, I sit down with Craig Holbrook, Vice President of New Client Acquisition Sales at nCino, to talk about what sales leaders actually look for when hiring, coaching, and developing reps. Craig shares lessons fro...

In this episode, I sit down with Ian Grace, VP of Sales at Ocrolus, to talk about what it takes to turn a sales team around, coach reps more effectively, and build a repeatable process that actually drives revenue. Ian breaks...

In this episode, I sit down with Matt Nucifora, Senior Manager of Enterprise Sales at Dandy and former Principal Manager of Mid-Market Sales at HubSpot, to talk about what it actually takes to get promoted consistently, coach...

In this episode, I sit down with Fred Ramstedt, Business Development Executive at Wipro Gallagher Solutions and former Director of Sales at TRUE, to talk about what it really takes to sell complex mortgage technology when the...

In this episode, I sit down with David Gipson, Director of Sales Engineering at Ocrolus, to break down what it really takes to sell AI and automation into mortgage. David shares how his background as an underwriter, loan offi...

In this episode, I sit down with Suzy Djilas, Enterprise Account Executive at Arcasa and former Director of Sales at nCino, to talk about what it takes to build trust and sell effectively in the mortgage industry over the lon...

In this episode, I sit down with Robby MacAskill, Director of Business Development at Zonda, to talk about one of the biggest blind spots in mortgage sales: why lenders are often chasing the wrong builder accounts and missing...

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...