Tech Sales with Carter

Carter Armendarez

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Interviews with founders and top producers at VC-backed startups.

6 days ago

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 toolsHow Secure Insight helps mortgage lenders protect against wire and closing fraudWhy mortgage is still such a face-to-face, relationship-driven industryHow vendor-only dinners can create referral relationships and industry trustThe biggest reputation mistakes people make at mortgage conferencesWhy consistency across LinkedIn, conferences, podcasts, and industry events builds a stronger personal brandABOUT 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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Secure Insight: https://secureinsight.com/

15 min
31 May

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 onboardingHow delayed implementation can reveal weak urgency, weak champions, or poor qualificationWhat AEs should avoid promising during the sales cycle, especially with AI productsHow Matey AI builds trust with legal teams handling sensitive case informationWhat great customer champions look like after the saleWhy the deal is never really done after the contract is signedABOUT 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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Matey AI: https://www.matey.ai/

14 min
27 May

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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Land Gorilla: https://landgorilla.com/

12 min
13 May

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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Gateless: https://gateless.com/

14 min
4 May

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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about CertifID: https://www.certifid.com/

21 min
3 May

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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Homebot: https://homebot.ai/

16 min
1 May

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 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 the future. We also get into why technology has failed to bring down the cost to originate, what AI could actually change in mortgage operations, and why vendors need a strong point of view instead of just building whatever customers ask for. Joe breaks down how thought leadership helps sales teams build credibility, what he learned from managing different types of performers, and why the best sales leaders need both broad industry understanding and deep expertise in a few key areas. TOPICS WE COVER What a CRO looks at in the first 90 days of a new leadership role Why understanding company history matters before changing strategy How mortgage technology has failed to lower the cost to originate Why AI should redesign mortgage workflows instead of just automating old processes How thought leadership helps sales teams build credibility and close deals faster Why future sales leaders need both broad industry knowledge and deep expertise ABOUT THE GUEST Joe Zeibert is the Chief Revenue Officer at Mortgage Cadence, where he is helping lead the company’s next chapter in mortgage technology, LOS modernization, and AI-driven workflow transformation. He brings more than 15 years of experience across mortgage, banking, capital markets, pricing, product strategy, analytics, and financial technology, with senior leadership roles at Anchor Loans, FICO, Nomis Solutions, Ally Financial, and Bank of America. His background spans mortgage and capital markets, home lending product strategy, enterprise capital management, pricing optimization, credit risk, analytics, and business intelligence, including helping launch Ally Home Loans and leading major data-driven pricing, product, and reporting initiatives across the financial services industry. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Mortgage Cadence: https://www.mortgagecadence.com/

24 min
30 Apr

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 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 when a customer is or is not a fit. We also get into sales leadership, rep development, and what separates average reps from top performers. Dillan breaks down his direct coaching style, why honest feedback only works when people know you actually care, and how one tough conversation helped turn a top rep into a much higher performer. He also shares lessons from Podium that he now applies as a VP, including why sales leaders should understand onboarding, implementation, product, and the full customer experience — not just quota and pipeline. TOPICS WE COVER How Dillan is building the early sales playbook at JewelLink, and why the foundation is asking meaningful questions instead of dumping product features Why industry knowledge only matters if it helps you understand customer pain and connect the product to a real business problem How consulting with JewelLink before joining full-time helped Dillan step into a bigger leadership role and think more like a VP What brutal but caring sales coaching looks like, including how honest feedback can unlock a rep’s next level Why stalled deals usually come back to weak discovery, unclear pain, and reps pitching every tool instead of the one that matters most The biggest lessons Dillan took from Podium, including why sales leaders should study onboarding, implementation, and the full customer journey ABOUT THE GUEST Dillan Dove is the VP of Sales at JewelLink, a software company helping jewelry stores improve sales training and performance. Before joining JewelLink, Dillan was Director of Sales at Podium. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about JewelLink: https://www.jewellink.com/

18 min

Interviews with founders and top producers at VC-backed startups.

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Carter Armendarez
Years Active

2K
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36
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Clean
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Tech Sales with Carter