Episodes

In this episode, I sit down with Jolie Stern, Enterprise Account Executive at Gong, to talk about how she moved from BDR to Enterprise AE and RVP in less than five years at Slack and Salesforce. Jolie breaks down why internal networking, building a strong brand, and creating impact beyond the dashboard helped her move up quickly inside a large sales organization. We also talk about what it takes to ramp fast at a new company, why she chose to stay focused on financial services, and how reps can...

In this episode, I sit down with Anthony Romano, CEO of CREtelligent, to talk about hiring, leading, and retaining great salespeople. Anthony shares what he looks for when evaluating sales candidates, including repeatable success, curiosity, presence, competitiveness, and extreme ownership. He also explains why the best individual contributor is not always the best manager, and what actually signals that a rep may be ready to lead. We also talk about what makes a great sales organization work b...

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 shares why cycle time is often the pain that gets lenders to take a conversation seriously, especially in home equity lending where fintechs can move quickly and traditional institutions need to compete without increasing risk. We also talk about why selling into financial services requires more than a s...

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 explains why many lenders only start looking for solutions after a scare, an audit finding, or an actual fraud event, and why companies need to think about wire and closing fraud before it becomes too late. We also talk about why mortgage is still such a relationship-driven, face-to-face industry. Amanda s...

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 why sales and customer success teams need to work together long before implementation begins. Alexis shares why delayed onboarding is often an early warning sign, how AEs can prevent churn by identifying real champions and power users, and why rigorous qualification matters before a customer ever reach...

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 why most software pitches fail before they ever become real conversations. Ben shares why CIOs do not want to be “sold,” why cold outreach rarely works on him unless there is already some relationship or in-person context, and why the best sales conversations are grounded in facts, numbers, workflow im...

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 shares how Gateless is using AI and automation to do more with a smaller team, why mortgage lenders are slower to adopt AI than the conference hype suggests, and why AI products in lending have to be provable, compliant, and tied to measurable business outcomes. We also talk about how Gateless stays focu...

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 curious, care about the problem they’re solving, and know how to stay human instead of sounding like they’re reading from a script. We also talk about what BDR outreach looks like in a vertical SaaS market where prospects often have very little online presence. Jim explains how his team uses events...

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. Nina shares how she went from being a Homebot user to becoming the company’s first inside sales rep, eventually moving through customer success, strategy, leadership, and now back into an AE role focused on title companies. We get into why title may be more tech-forward than people think, how regulat...

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 pressure, costs are rising, and lenders are being forced to rethink how they operate. Joe shares what he looks at first when stepping into a CRO role, why understanding a company’s history matters before making changes, and how Mortgage Cadence is thinking about redesigning LOS and workflow technology for th...

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 software sales advantage. Dillan shares how he went from selling and leading teams at Podium to helping build JewelLink’s go-to-market motion in the jewelry industry, including why the early playbook is less about pitching every feature and more about asking better questions, finding real pain, and knowing...

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 accountability. Soraya shares how she went from AE to manager at HubSpot by taking on leadership work before she had the title, including mentoring reps, creating training material, and helping build the Future Leaders Program. She explains why internal brand matters, how ...

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 of hype, and still deeply dependent on legacy systems. Chris explains why he left a much larger incumbent in ICE Mortgage Technology to join TidalWave, what made the product and team feel real, and why Diane Yu’s track record was a major part of his decision. We also get i...

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 Expert has evolved from a compliance marketing tool into a broader customer engagement platform for lenders, and why executive buyers do not want a product tour. They want to understand how the technology can drive growth, improve retention, increase lead conversion, and make...

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 promises before. Graham explains why the real challenge is usually not selling AI itself, but selling the risk and pain of change. He shares how enterprise sellers can build trust in high-stakes, long-cycle deals by understanding buyer pain deeply, reducing uncertainty, and helpi...

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 down how luck, mentorship, territory selection, and obsession all played a role in his early success at Cars.com, including the mindset shift that helped him go from near the bottom of the leaderboard to winning Rookie of the Year in a single month. He also explains why posi...

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 biggest lies reps believe about success, including the idea that more hours and more dials automatically lead to better results, and explains why energy, self-awareness, and emotional resilience are often the real drivers of consistent performance. He also shares how top reps can...

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 their own signing service from scratch. Before joining Snapdocs, Erica and Andrea co-founded Sunny Signings LLC during COVID after seeing the surge in demand for mobile notary services, then later merged the business with First Class Signing Service. They share how they went ...

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. Pat breaks down why you cannot just copy and paste a strategy from one company to another, even if it worked at a high level somewhere else, and explains how he thinks about diagnosing a BD org through Salesforce rigor, deal velocity, and repeatable patterns in the data. He a...

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 from more than a decade in mortgage sales and leadership, including why some qualities simply cannot be coached, why you cannot turn a D player into an A player, and how strong sales leadership starts with understanding what motivates each rep differently. He also breaks down t...

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 down how he came into Ocrolus during a brutal stretch for the mortgage industry and helped overhaul the sales motion by implementing forecasting, deal coaching, MEDDPICC, and a blended approach built around gap selling and challenger principles. He explains why great discov...

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 sales reps effectively, and lead teams through more complex enterprise sales motions. Matt breaks down the difference between simply performing well in your current role and actively showing you can do the next one. He explains why strong promotion cases are built on object...

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 stakes are high, the sales cycles are long, and buyers are skeptical of empty ROI claims. Fred breaks down the difference between selling a point solution that improves one part of the workflow versus selling a broader platform that helps lenders rethink how the entire loan...

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 officer, and sales ops leader shapes the way he helps lenders evaluate new technology, and why the best sales conversations are never really about flashy features. They’re about solving real workflow pain in a way that feels practical, familiar, and easy to adopt. We also get i...