Tech Sales with Carter

Carter Armendarez

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

Jun 18

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 yearsWhy internal networking and building a strong brand can accelerate your sales careerHow to ramp quickly when joining a new company as an experienced sellerWhy specializing in one vertical can create more opportunity over timeHow to sell technology into slow-moving financial services companiesHow to tell the difference between serious AI buyers and tire kickersABOUT 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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Gong: https://www.gong.io/
Jun 18

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 salespeopleWhy repeatable success matters more than a good-looking resumeHow to know if a top sales rep is actually ready for sales leadershipWhy great salespeople need enablement, culture, and career growth to stayHow customer loyalty, NPS, retention, and referrals connect to revenue growthWhy the best sellers diagnose before they prescribe and disqualify bad deals fasterABOUT 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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about CREtelligent: https://www.cretelligent.com/
Jun 12

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 lendingHow banks and credit unions compete with faster fintech lending experiencesWhy AI products need to balance speed, risk, and regulatory requirementsWhat tech sellers get wrong about selling into lenders and financial institutionsHow to build ROI stories using the customer’s actual workflow and dataWhy risk, compliance, and operational roadblocks need to be handled early in the dealABOUT 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/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Moody’s: https://www.moodys.com/
Jun 5

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/
May 31

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/
May 27

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/
May 13

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/
May 4

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/

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

Creator

Carter Armendarez
Years Active

2026
Episodes

39
Rating

Clean
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© 2026 Tech Sales with Carter
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