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

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/]

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. 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 regulated industries evaluate new software, and what reps should understand before selling into title executives. Nina also breaks down how she prepares for discovery calls, how Homebot thinks about sales cycles across individual, SMB, mid-market, and enterprise segments, and why patience matters when selling a product tied to long-term retention and relationship building. TOPICS WE COVER *  How Nina went from real estate administration to becoming Homebot’s first inside sales rep  *  Why career growth is not always a straight climb up the ladder  *  How title companies are thinking about technology, AI, fraud, compliance, and staying relevant after the closing table  *  Why the best discovery starts before the discovery call  *  How Homebot handles objections around time, data, adoption, and ROI  *  Why phrases like “say more about that” can turn a demo into a real conversation  ABOUT THE GUEST Nina Hein is the Director of Growth for the title vertical at Homebot. She has been with Homebot for eight years and has held roles across sales, customer success, strategy, leadership, and account executive functions. Before joining Homebot, Nina worked in the real estate industry in administrative and transaction coordination roles, giving her a unique perspective on the buyers, partners, and customers Homebot serves.  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 Homebot: https://homebot.ai/ [https://homebot.ai/]