Lessons from a CEO: People Love to Buy. They Hate to Be Sold | Anthony Romano (CREtelligent)

How to Go From BDR to Enterprise AE in 3.5 Years | Jolie Stern (Gong)

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 sell technology into slower-moving, highly regulated industries. Jolie shares how she thinks about change management, security and compliance objections, getting in person with customers, and how to separate serious AI buyers from prospects who are just curious. TOPICS WE COVER * How Jolie moved from BDR to Enterprise AE and RVP in less than five years * Why internal networking and building a strong brand can accelerate your sales career * How to ramp quickly when joining a new company as an experienced seller * Why specializing in one vertical can create more opportunity over time * How to sell technology into slow-moving financial services companies * How to tell the difference between serious AI buyers and tire kickers ABOUT THE GUEST Jolie Stern is an Enterprise Account Executive at Gong. She started her sales career at a full-service digital marketing agency in New York City before joining Slack as a BDR. During her time at Slack and Salesforce, she moved into enterprise sales and frontline leadership, eventually becoming an RVP. She is now based in Miami and sells Gong into financial services accounts. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ [https://www.linkedin.com/in/carter-armendarez/] Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ [https://www.techsaleswithcarter.com/newsletter/] Learn more about Gong: https://www.gong.io/ [https://www.gong.io/]

Lessons from a CEO: People Love to Buy. They Hate to Be Sold | Anthony Romano (CREtelligent)

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 behind the scenes. Anthony breaks down why top salespeople need more than a strong comp plan, how companies can retain high performers with enablement, culture, data, and career paths, and why customer loyalty is one of the strongest leading indicators of long-term growth. He also shares one of the biggest lessons he learned in sales: people love to buy, but they hate to be sold. The best sellers ask better questions, diagnose before they prescribe, and disqualify bad deals faster. TOPICS WE COVER * What CEOs look for when hiring great salespeople * Why repeatable success matters more than a good-looking resume * How to know if a top sales rep is actually ready for sales leadership * Why great salespeople need enablement, culture, and career growth to stay * How customer loyalty, NPS, retention, and referrals connect to revenue growth * Why the best sellers diagnose before they prescribe and disqualify bad deals faster ABOUT THE GUEST Anthony Romano is the CEO of CREtelligent, a commercial real estate due diligence company. CREtelligent serves around 1,100 clients across eight verticals. Anthony has spent more than 20 years building and leading sales organizations across real estate, mortgage, data, and financial technology. Before joining CREtelligent, he served as Chief Revenue Officer at First American and EVP of Global Mortgage Solutions at CoreLogic. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ [https://www.linkedin.com/in/carter-armendarez/] Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ [https://www.techsaleswithcarter.com/newsletter/] Learn more about CREtelligent: https://www.cretelligent.com/ [https://www.cretelligent.com/]

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 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 strong product demo. Tiffany explains why lenders are workflow-driven, risk-driven, and regulation-driven, and why sellers need to understand those constraints early in the deal. She shares how ROI stories become more powerful when they are built around the customer’s real data, why risk and compliance need to be involved before the end of the sales cycle, and why deals can go silent when champions are left to fight internal battles alone. TOPICS WE COVER * Why cycle time is one of the biggest pain points in home equity lending * How banks and credit unions compete with faster fintech lending experiences * Why AI products need to balance speed, risk, and regulatory requirements * What tech sellers get wrong about selling into lenders and financial institutions * How to build ROI stories using the customer’s actual workflow and data * Why risk, compliance, and operational roadblocks need to be handled early in the deal ABOUT THE GUEST Tiffany Stringfellow is the Director of Client Development at Moody’s supporting its automated property condition report solution, which is primarily used in home equity lending and capital markets. She has spent around 20 years in the mortgage industry across lending technology, capital markets, origination, and client success. Before Moody’s, Tiffany was VP of Client Success at Informative Research. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ [https://www.linkedin.com/in/carter-armendarez/] Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ [https://www.techsaleswithcarter.com/newsletter/] Learn more about Moody’s: https://www.moodys.com/ [https://www.moodys.com/]

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 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 shares how she uses conferences, in-person meetings, and vendor-only dinners to build trust, create referral relationships, and stay top of mind with lenders and other mortgage technology providers. She also explains why reputation matters so much in a small industry, why partying at conferences can damage credibility, and how she decides when a prospect is serious versus just wasting time. Amanda also shares how consistency has helped grow her personal brand over the past year. From LinkedIn to podcasts, awards, publications, and conferences, she explains why there is no single silver bullet and why showing up consistently across multiple channels is what really moves the needle. TOPICS WE COVER * Why lenders often wait until after a fraud scare to look for risk prevention tools * How Secure Insight helps mortgage lenders protect against wire and closing fraud * Why mortgage is still such a face-to-face, relationship-driven industry * How vendor-only dinners can create referral relationships and industry trust * The biggest reputation mistakes people make at mortgage conferences * Why consistency across LinkedIn, conferences, podcasts, and industry events builds a stronger personal brand ABOUT THE GUEST Amanda Padd is the Chief Revenue Officer at Secure Insight, a fintech company in the mortgage industry that helps lenders protect themselves against wire fraud, closing fraud, and third-party risk at the closing table. Amanda has been with Secure Insight for more than 10 years and has built a strong reputation in the mortgage industry through conferences, client relationships, thought leadership, and consistent personal branding. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ [https://www.linkedin.com/in/carter-armendarez/] Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ [https://www.techsaleswithcarter.com/newsletter/] Learn more about Secure Insight: https://secureinsight.com/ [https://secureinsight.com/]

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 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 reaches the post-sale team. We also talk about selling AI into legal teams, where trust, security, and expectation-setting are critical. Alexis explains why reps should never promise that AI can “do magic,” how Matey AI builds trust with litigators, firms, and government offices, and why the best customer champions are the ones who refer, expand, and bring their colleagues into the product. She also shares why “the deal is never done” and why CS teams are always selling through renewals, expansions, referrals, and stronger client relationships. TOPICS WE COVER * Why churn can start during discovery before the customer ever reaches onboarding * How delayed implementation can reveal weak urgency, weak champions, or poor qualification * What AEs should avoid promising during the sales cycle, especially with AI products * How Matey AI builds trust with legal teams handling sensitive case information * What great customer champions look like after the sale * Why the deal is never really done after the contract is signed ABOUT THE GUEST Alexis Cisneros is the Vice President of Client Success at Matey AI, an AI-native eDiscovery case intelligence platform that helps legal teams analyze, organize, review, and investigate digital discovery. Before Matey AI, Alexis was the Director of Customer Success at Dealerware. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ [https://www.linkedin.com/in/carter-armendarez/] Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ [https://www.techsaleswithcarter.com/newsletter/] Learn more about Matey AI: https://www.matey.ai/ [https://www.matey.ai/]