Tech Sales with Carter

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/

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/

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/

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/

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/

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 to differentiate yourself in a competitive promotion process, and why aspiring managers need to treat the interview like a real sales cycle.

We also get into how she runs her team today, from deal reviews and weekly standups to pipeline coaching and skill development. Soraya breaks down how she diagnoses weak pipeline, how she coaches reps through common SMB objections like cost, competitors, and timeline, and why managers should help reps build their own plan instead of just telling them what to do. 

TOPICS WE COVER

•  How Soraya went from AE to SMB Sales Manager at HubSpot 
•  Why taking on leadership work before the title helped her stand out 
•  How to build trust and culture as a remote sales manager 
•  The weekly cadence Soraya uses for deal reviews, team meetings, and pipeline accountability 
•  How she coaches reps through cost, competitor, and timeline objections 
•  Why aspiring sales leaders should treat promotion like a sales process 

ABOUT THE GUEST

Soraya Hatcher is an SMB Sales Manager at HubSpot, where she leads a team of eight account executives. Before moving into management, Soraya spent over three years as an AE at HubSpot, where she mentored reps, created training material, and founded the Future Leaders Program to help develop aspiring sales leaders. 

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about HubSpot: https://www.hubspot.com/

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 into how lenders evaluate AI, why independent benchmarks matter, and how TidalWave uses its Columbia study showing strong compliance-check performance against Claude 4.5 in the sales process. Chris breaks down why the biggest opportunity is not just adding AI point solutions, but rethinking the borrower and lender experience from the front end. He also shares how startups can compete against large incumbents, why speed is a real advantage, and why reputation matters so much in a small industry where “you really only get one name.” 

TOPICS WE COVER

•  Why Chris left ICE Mortgage Technology/Encompass for TidalWave and what made the team feel different 
•  How TidalWave uses its Columbia benchmark study to build credibility with lenders evaluating AI 
•  Why many AI tools in mortgage are still point solutions, and how TidalWave is approaching the borrower experience differently 
•  How lender conversations around AI have shifted from “show me” to “how fast can we go live?” 
•  What startups have to do better than incumbents when selling into mortgage technology 
•  Why reputation, trust, and knowing early adopters matter so much in a relationship-driven industry 

ABOUT THE GUEST

Chris McLendon is the Partner and Chief Revenue Officer at TidalWave, an AI-native mortgage technology company focused on improving the borrower and lender experience through automation at the front end of the loan process. Chris has been in the mortgage industry since 1999, starting in production as a loan officer before moving into mortgage technology. Before joining TidalWave, he spent five years at Black Knight on the Empower platform and ten years with Encompass/ICE Mortgage Technology, working across relationship management, enterprise accounts, and new logo sales.

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about TidalWave: https://www.tidalwave.ai/

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 loan officers more productive.

We also get into what makes AI valuable in a real lending environment instead of just another buzzword. Seth explains how Total Expert’s AI Sales Assistant helps loan officers avoid living inside a CRM all day by engaging leads, following up repeatedly, collecting information, and surfacing stronger opportunities. He also shares why reputation matters so much in mortgage tech, how lenders evaluate new technology, and why enterprise deals often stall when sales, marketing, executives, and procurement are not aligned around a clear business outcome and mutual action plan. 

TOPICS WE COVER

•  Why software demos fail when they become feature tours instead of outcome-driven stories 
•  How Total Expert evolved from compliance marketing into a broader growth and retention platform 
•  Why executive buyers care about retention, lead conversion, loan officer productivity, and measurable business impact 
•  How AI Sales Assistant helps loan officers follow up with leads without living inside a CRM all day 
•  Why reputation and partnership matter so much when selling technology into mortgage lenders 
•  What causes enterprise deals to stall, and how mutual action plans create alignment across buying committees 

ABOUT THE GUEST

Seth Haake is a Strategic Sales Engineer at Total Expert, where he has spent nearly nine years helping enterprise lenders, IMBs, banks, and credit unions think through customer engagement, retention, loan officer productivity, and growth strategy. In his role, Seth works across sales, product marketing, marketing, and product to help lenders understand how to turn their customer database into a growth engine and operationalize what their best loan officers are already doing.

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Total Expert: https://totalexpert.com/

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 helping customers navigate change that can feel as disruptive as “heart surgery.” 

We also get into enterprise deal strategy, internal alignment, and what actually improves sales performance in hard markets. Graham talks through why domain knowledge matters only when it helps you tell a better story around pain, how missed deal risks often show up at the very beginning of a sales cycle, and why cross-functional coordination with product, engineering, and implementation is one of the most high-leverage skills an AE can build. He also shares lessons from selling through a brutal mortgage downturn, why there is no magic script for tough sales environments, and how communication across every stage of a deal is what ultimately separates average sellers from great ones. 

TOPICS WE COVER

•  Why selling AI in mortgage is really about selling change, and why buyers are often more afraid of a painful platform transition than unconvinced by the technology itself 
•  How Graham thinks about founder-led sales playbooks, including how to reverse engineer what works and turn informal selling patterns into a repeatable AE-led motion 
•  Why true domain expertise starts with understanding customer pain, not just memorizing industry facts or trends 
•  What kills large enterprise deals deep into the sales cycle, including missed buying process steps, weak champion enablement, and lack of executive commitment 
•  How strong AEs align product, engineering, and implementation teams, and why poor internal coordination can ruin both the deal and the customer outcome 
•  What selling through a down market teaches you, including why the fundamentals matter even more when budgets get tighter and buyers scrutinize ROI harder 

ABOUT THE GUEST

Graham Young is a Strategic Account Executive at Vesta, where he works with mortgage lenders making high-stakes decisions around core technology and platform change. He was brought in to help scale the enterprise go-to-market from founder-led relationships to a repeatable, AE-led motion.

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Vesta: https://www.usevesta.com/

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 positive thinking only matters if it is paired with relentless action, daily habits, and a clear plan for how you are actually going to reach the goal you say you want. 

We also get into career moves, leadership, and how strong sellers think about preparation, urgency, and coaching. Raymond shares how he evaluates whether it is time to leave a company, why financial independence gives you leverage in your career, and what he notices first when a rep starts slipping. He also explains how he cuts through AI noise in dealer conversations by knowing the customer deeply, speaking to real operational pain, and asking better questions instead of relying on a generic pitch. Toward the end, he lays out his philosophy on President’s Club-level performance, including the role of curiosity, urgency, discipline, and how badly you actually have to want it if you expect to separate yourself. 

TOPICS WE COVER

•  How Raymond went from near the bottom of the leaderboard to winning Rookie of the Year through obsession, visualization, and execution 
•  Why positive thinking only matters if it is paired with daily action, process, and working backwards from the goal 
•  How to know when it is time to leave a company and why saving money gives you more career leverage 
•  What Raymond notices first when a rep starts underperforming and how he approaches coaching early 
•  How he cuts through AI noise with dealers by knowing the customer, finding real pain, and asking better questions 
•  What it really takes to hit President’s Club, including curiosity, discipline, preparation, and how badly you want it 

ABOUT THE GUEST

Raymond Griffin is a Regional Sales Manager at Numa with a long track record of success in automotive sales. Before Numa, he held sales roles across companies including Cars.com, Dealer Inspire, Tekion, and Impel, and built a reputation as a high-performing seller and sales leader in the automotive tech space. His career honors include 2024 President’s Club at Outsell/Impel AI, 2014 Rookie of the Year at Cars.com, multiple President’s Club selections, multiple Regional and Divisional Team MVP awards, and NADA Team recognition at Cars.com. 

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Numa: https://www.numa.com/