How to Sell Software by Asking Better Questions | Dillan Dove (JewelLink)

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/]

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 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 impact, and ROI.  We also talk about what really drives lending technology purchases: operational efficiency, doing more with less, and reducing cost or manual work. Ben explains why some products become table stakes instead of delivering real ROI, how sellers should tailor their message to different executive audiences, and why he sometimes has to help vendors reshape their own pitch so they can win internal approval.  TOPICS WE COVER *  Why CIOs ignore most cold outreach unless there is already context or a relationship  *  How conferences help vendors get in front of executives more effectively than generic emails  *  Why lending technology purchases usually come down to operational efficiency and ROI  *  What makes a software salesperson credible early: facts, numbers, preparation, and intelligent answers  *  Why executives do not want to be sold — they want a real conversation about workflow, value, and fit  *  How sellers lose deals by failing to tailor the message to the buyer, audience, and approval process  ABOUT THE GUEST Ben Sizemore is the Chief Information Officer at Land Gorilla, a construction lending software company serving the mortgage industry and other industries where construction lending is involved. Ben has spent more than 35 years in technology and lending, and brings a CIO’s perspective on software buying, internal selling, vendor evaluation, and what executives need to hear before approving new technology.  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 Land Gorilla: https://landgorilla.com/ [https://landgorilla.com/]

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 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 focused on credit, income, and asset automation instead of trying to “boil the ocean.” Mike explains why buyers need to validate ROI for themselves, how Gateless has helped clients save 5–12 days between application and clear to close, and why the best salespeople are competitive, curious, willing to fail fast, and able to show a real desire to win.  TOPICS WE COVER *  How AI tools are helping smaller revenue teams do more with fewer people  *  Why mortgage AI adoption is slower because of regulation, compliance, and hallucination risk  *  How Gateless proves ROI through manual steps removed, client validation, and measurable time savings  *  Why lenders should start with one or two automation problems instead of trying to solve every edge case  *  How to separate real AI products from hype in mortgage technology  *  What Mike looks for when hiring salespeople: competitiveness, curiosity, and the will to win  ABOUT THE GUEST Mike Brown is the Chief Revenue Officer at Gateless, a mortgage technology company focused on using AI to automate key parts of the lending process, including credit, income, and asset review. Before Gateless, Mike held sales leadership roles at companies including Dark Matter, Black Knight, and ACA Group.  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 Gateless: https://gateless.com/ [https://gateless.com/]

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 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, white papers, direct mail, referrals, fraud signals, and hyper-specific follow-up to create relevant conversations with title and escrow companies. He also shares how AI has changed real estate wire fraud, why CertifID’s BDRs live “in the problem,” and how newer reps can become more effective by listening, asking better questions, and understanding the industry they sell into.  TOPICS WE COVER *  What the best BDRs do differently: active listening, curiosity, and caring about the problem  *  Why CertifID’s outreach is built around relevance, timing, and campaign-specific follow-up  *  How events, white papers, direct mail, referrals, and fraud signals turn into booked meetings  *  Why great BDRs use frameworks instead of scripts and have to “be a human”  *  How AI is increasing real estate wire fraud and changing the conversations CertifID has with prospects  *  Why BDRs need to love the problem, understand the industry, and stay curious enough to uncover real pain  ABOUT THE GUEST Jim Robertson leads the business development team at CertifID, a company helping prevent wire fraud in real estate transactions. CertifID works with title agents, escrow companies, and real estate professionals to protect buyers, sellers, and businesses from fraud attempts during high-stakes money movement. Before CertifID, Jim was a Senior Director 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 CertifID: https://www.certifid.com/ [https://www.certifid.com/]