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Interviews with founders and top producers at VC-backed startups.
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Recent Episodes
S1E37 How to Sell to Banks and Lenders | Tiffany Stringfellow (Moody's Analytics)
In this episode, I sit down with Tiffany Stringfellow, Director of Client Development at Moody’s, to talk about selling AI-powered workflow tools into lenders, banks, and credit unions. Tiffany…
S1E36 Every Conversation Is Worth the Conversation | Amanda Padd (Secure Insight)
In this episode, I sit down with Amanda Padd, Chief Revenue Officer at Secure Insight, to talk about selling fraud prevention and risk management technology into the mortgage industry. Amanda…
S1E35 What Every AE Gets Wrong About Customer Success | Alexis Cisneros (Matey AI)
In this episode, I sit down with Alexis Cisneros, Vice President of Client Success at Matey AI, to talk about what happens after the deal closes, how customer churn can start during discovery, and…
S1E34 Why Executives Ignore Your Sales Pitch | Ben Sizemore (Land Gorilla)
In this episode, I sit down with Ben Sizemore, Chief Information Officer at Land Gorilla, to talk about how technology buyers evaluate vendors, what makes salespeople credible with executives, and…
S1E33 How to Sell AI in the Mortgage Industry | Mike Brown (Gateless)
In this episode, I sit down with Mike Brown, CRO at Gateless, to talk about selling AI in the mortgage industry, building lean revenue teams, and proving ROI in a heavily regulated market. Mike…
S1E32 How to Be the Best BDR at Your Company | Jim Robertson (CertifID)
In this episode, I sit down with Jim Robertson, who leads the business development team at CertifID, to break down what separates great BDRs from average ones. Jim shares why the best reps are deeply…
S1E31 How to Sell Software in a Heavily Regulated Industry | Nina Hein (Homebot)
In this episode, I sit down with Nina Hein, Director of Growth for the title vertical at Homebot, to talk about what it actually looks like to sell technology into real estate, mortgage, and title.…
S1E30 Lessons from a CRO: Scaling a Tech Company in 2026 | Joe Zeibert (Mortgage Cadence)
In this episode, I sit down with Joe Zeibert, Chief Revenue Officer at Mortgage Cadence, to talk about what it takes to lead sales in mortgage technology at a time when the industry is under…
S1E29 How to Sell Software by Asking Better Questions | Dillan Dove (JewelLink)
In this episode, I sit down with Dillan Dove, VP of Sales at JewelLink, to talk about building a sales motion from the ground up, coaching reps hard, and turning industry knowledge into a real…
S1E28 How to Get Promoted at an Elite Sales Org | Soraya Hatcher (HubSpot)
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…
S1E27 How to Sell AI in an Industry Dominated by Legacy Tech | Chris McLendon
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…
S1E26 How to Demo Software Without Turning It Into a Product Tour | Seth Haake
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.…
S1E25 You’re Not Really Selling AI. The Hard Sell Is Change.
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…
S1E24 The Magic of Thinking Big in Tech Sales
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…
S1E23 Why More Dials Won’t Fix Your Sales Problem
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.…
S1E22 How Two Best Friends Built a Signing Business and Broke Into Tech Sales
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…
S1E21 How to Scale the BD Org of a $1B+ Tech Company
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…
S1E20 Lessons from a VP: You Can't Turn a D Player Into an A Player | Craig Holbrook (nCino)
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…
S1E19 How to scale a sales org to $50M ARR | Ian Grace (Ocrolus)
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…
S1E18 Sales Leadership Lessons No One Talks About | Matt Nucifora (Dandy)
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…
Frequently Asked Questions
Tech Sales with Carter has published 37 episodes since February 2026, covering topics in Business, Careers.
Tech Sales with Carter is currently highly active with new episodes weekly. Average episode length is 18m.
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