Tech Sales with Carter

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 GUESTJim 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.LINKSConnect 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 GUESTNina 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. LINKSConnect 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 GUESTJoe 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.LINKSConnect 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 GUESTDillan 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.LINKSConnect 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 GUESTSoraya 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. LINKSConnect 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 GUESTChris 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.LINKSConnect 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 GUESTSeth 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.LINKSConnect 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 GUESTGraham 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.LINKSConnect 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 GUESTRaymond 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. LINKSConnect 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/

In this episode, I sit down with Jordan Benjamin, CEO of My Core OS and former 6x President’s Club member at HubSpot, to talk about the mindset and psychology behind sustainable sales performance. Jordan breaks down the biggest lies reps believe about success, including the idea that more hours and more dials automatically lead to better results, and explains why energy, self-awareness, and emotional resilience are often the real drivers of consistent performance. He also shares how top reps can tell whether missed quota is really a skill problem or a mindset problem, and why confidence, internal stories, and self-belief quietly shape how people show up on calls every day. We also get into social selling, career growth, and what reps can do when they feel stuck. Jordan explains how he built My Core OS from corporate workshops into a more direct-to-consumer coaching business, why LinkedIn has become such a powerful channel for both prospecting and brand building, and how sales reps should think about using it more like a landing page than a resume. He also shares practical advice on gratitude, imposter syndrome, asking for help, and how to structure a strong interview story around why you, why now, and why this role. TOPICS WE COVER Why more hours and more dials are often not the real answer to better sales performance  How to tell whether a rep is missing quota because of skill issues or mindset issues  Why emotional intelligence, self-awareness, and confidence matter so much in sales  How Jordan built My Core OS and what changed as he moved from corporate workshops to coaching individuals  Why LinkedIn is such an overlooked tool for prospecting, personal brand, and social selling  How to handle imposter syndrome, build better habits, and structure a stronger interview story ABOUT THE GUESTJordan Benjamin is the CEO of My Core OS, where he helps salespeople, leaders, and teams perform at a high level without burning out. Before that, he spent about 15 years in tech sales and was a 6x President’s Club member at HubSpot. In this episode, he shares lessons from both his sales career and his work coaching sellers on mindset, psychology, and sustainable performance. LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about My Core OS: https://www.mycoreos.com/

In this episode, I sit down with Erica Waldron and Andrea Castelli, Account Executives at Snapdocs, to talk about their unconventional path into mortgage tech sales and how they built their way into the industry by starting their own signing service from scratch. Before joining Snapdocs, Erica and Andrea co-founded Sunny Signings LLC during COVID after seeing the surge in demand for mobile notary services, then later merged the business with First Class Signing Service. They share how they went from bartending and working in real estate-related roles to building a company together, knocking on doors at title companies, bringing flowers into offices, and figuring things out in real time with no safety net.We also get into what made their partnership work, why merging their business ended up accelerating their growth, and how their reputation in the signing world helped create the opportunity to join Snapdocs. Erica and Andrea explain why the transition into tech sales was more natural than people might expect, how their experience on the title, notary, and signing service sides gives them credibility with clients, and what it looks like to operate as a true AE duo inside a tech company. They also share advice for people trying to break into mortgage tech sales without a traditional background and why keeping your options open can lead to opportunities you never would have planned for. TOPICS WE COVER How Erica and Andrea went from bartending and real estate-adjacent roles to launching Sunny Signings during COVID  What they learned from building a signing service from the ground up through door-to-door outreach and conferences  Why merging Sunny Signings with First Class Signing Service helped them grow faster than staying independent  How their industry reputation and experience using Snapdocs led to the opportunity to join the company  Why the move from signing services into tech sales was more transferable than most people would expect  How they function as a true AE duo at Snapdocs and why being a package deal has actually worked in their favor ABOUT THE GUESTSErica Waldron and Andrea Castelli are Account Executives at Snapdocs, where they work on the settlement side of the business. Before joining Snapdocs, they co-founded Sunny Signings LLC, a mobile notary and signing service business they built during COVID, which later merged with First Class Signing Service. Their background spans title, real estate, notary services, and signing operations, giving them a rare perspective across multiple sides of the transaction. LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Snapdocs: https://www.snapdocs.com/

In this episode, I sit down with Pat Mulvey, Director of Global Business Development at Zywave, to talk about what it actually takes to reset and scale a business development team inside a changing go-to-market environment. Pat breaks down why you cannot just copy and paste a strategy from one company to another, even if it worked at a high level somewhere else, and explains how he thinks about diagnosing a BD org through Salesforce rigor, deal velocity, and repeatable patterns in the data. He also shares what he looks for when hiring new BDR talent, why athletes and other highly driven profiles often stand out, and how commitment, grit, and self-awareness tend to show up early in the people who go on to perform.We also get into leadership, coaching, and the habits that separate strong reps from struggling ones. Pat explains why reps who adapt fastest to leadership change are usually the ones who ask for help early, why poor time management quietly kills performance, and how he handles underperformance before it turns into a formal process. He also talks through the shift from being a seller to becoming a manager, why new leaders often stay too attached to the rep identity, and what someone should consider before deciding they want to pursue leadership long term.TOPICS WE COVER Why you cannot just reuse the same go-to-market playbook at a new company, even after success somewhere else  How Pat evaluates a BD org through Salesforce data, deal velocity, repeatability, and ICP fit  What he looks for when hiring BDRs, including grit, commitment, and why athletic backgrounds can stand out  Why reps who adapt fastest to leadership change usually ask for help early instead of sitting back  The biggest hidden mistake BDRs make with time management and why it wrecks performance  What changes when a strong rep becomes a manager, and how to know if leadership is actually the right path ABOUT THE GUESTPat Mulvey is the Director of Global Business Development at Zywave, where he was brought in to reset and scale the BD function amid rising growth targets, an evolving go-to-market strategy, and increased quota expectations. Before Zywave, he was a Senior Sales Manager at Drata, where he managed a diverse global team of 16, contributing $7m+ in global revenue during FY26.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Zywave: https://www.zywave.com/

In this episode, I sit down with Craig Holbrook, Vice President of New Client Acquisition Sales at nCino, to talk about what sales leaders actually look for when hiring, coaching, and developing reps. Craig shares lessons from more than a decade in mortgage sales and leadership, including why some qualities simply cannot be coached, why you cannot turn a D player into an A player, and how strong sales leadership starts with understanding what motivates each rep differently. He also breaks down the intangibles he looks for in account executives, including work ethic, curiosity, assertiveness, and attention to detail, and explains why those traits matter more than surface-level interview polish.We also get into coaching, management, and what it really takes for a rep to grow into a leadership role. Craig explains how he evaluates a team in the first 90 days, why he believes in giving reps freedom within a framework, and how he coaches strong performers who are still leaving money on the table because of bad habits. He also talks through how nCino is using AI in its hiring process to analyze assessments, generate probing interview questions, and help identify candidates with the right underlying traits to succeed in sales.TOPICS WE COVER Why some sales traits, like work ethic, curiosity, and assertiveness, are hard or impossible to coach  Why you cannot turn a D player into an A player, and how Craig thinks about developing talent more realistically  How Craig evaluates a new team in his first 90 days and sets expectations with a freedom-within-a-framework approach  How to coach reps who are hitting quota but still have bad habits that are limiting their upside  What separates a strong individual contributor from someone who is actually ready to lead a team  How nCino is using AI in hiring to analyze assessments, generate better interview questions, and improve candidate evaluation ABOUT THE GUESTCraig Holbrook is the Vice President of New Client Acquisition Sales at nCino, where he focuses primarily on the IMB side of the business. He has more than a decade of sales experience in the mortgage industry and has led teams ranging from small startups to large enterprise environments. Earlier in his career, he was a top-producing individual contributor for eight of his nine years in sales and has also led large business development teams across multiple industries.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about nCino: https://www.ncino.com/

In this episode, I sit down with Ian Grace, VP of Sales at Ocrolus, to talk about what it takes to turn a sales team around, coach reps more effectively, and build a repeatable process that actually drives revenue. Ian breaks down how he came into Ocrolus during a brutal stretch for the mortgage industry and helped overhaul the sales motion by implementing forecasting, deal coaching, MEDDPICC, and a blended approach built around gap selling and challenger principles. He explains why great discovery is still the foundation of winning deals, and why too many reps stop at surface-level pain instead of digging until they understand the real business impact in dollars. We also get tactical on pipeline management, leadership, and the use of AI inside modern sales organizations. Ian shares why thin pipeline is usually a prospecting discipline problem before it is anything else, how managers can coach reps without taking deals over for them, and what changed in his own leadership when he stopped thinking about himself and started thinking more about how to truly support his team. He also talks through how Ocrolus is experimenting with Claude and Gong to score calls, evaluate reps against sales frameworks, and create more precise coaching feedback at scale. TOPICS WE COVER How Ian helped improve win rates at Ocrolus by implementing forecasting, deal coaching, MEDDPICC, and stronger day-to-day sales habits  Why shallow discovery kills deals, and how the best reps turn pain into real dollar impact that creates urgency  The most common reasons deals stall, including weak champions, lack of multithreading, and incomplete discovery  Why pipeline problems usually start with prospecting discipline, and how Ian thinks about quantity before quality  What strong sales coaching looks like in practice, including call review, live feedback, and helping reps improve without taking over for them  How Ian is using tools like Gong and Claude to score calls, evaluate reps against sales frameworks, and create more actionable coaching feedback ABOUT THE GUESTIan Grace is the VP of Sales at Ocrolus, an AI analytics and decision platform that helps lenders make faster, better decisions using financial documents. He oversees the Sales Development, Inside/Mid-Market Sales, and Sales Engineering Teams. Prior to Ocrolus he was a Senior Director at automotiveMastermind Inc. and also directed branch banking, sales, and marketing operations for a $76MM credit union in an executive role.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Ocrolus: https://www.ocrolus.com/

In this episode, I sit down with Matt Nucifora, Senior Manager of Enterprise Sales at Dandy and former Principal Manager of Mid-Market Sales at HubSpot, to talk about what it actually takes to get promoted consistently, coach sales reps effectively, and lead teams through more complex enterprise sales motions. Matt breaks down the difference between simply performing well in your current role and actively showing you can do the next one. He explains why strong promotion cases are built on objective performance, visible leadership behaviors, and the ability to operate at a higher level before anyone formally gives you the title. We also get tactical on sales coaching, deal diagnosis, and startup go-to-market. Matt shares why stalled deals usually trace back to weak discovery a few calls earlier, how to coach underperforming reps using data instead of guesswork, and why managers should focus on fixing one problem at a time instead of trying to improve everything at once. He also talks through the transition from HubSpot to Dandy, what carries over when entering a new industry, and what he has learned through Stage 2 Capital about hiring startup sales talent, building repeatable process, and helping early-stage companies move from raw potential to real revenue. TOPICS WE COVER Why Matt got promoted so consistently at HubSpot, including the importance of objective performance and showing you can already do the next job before you get it  What it looks like to enter a new industry as a sales leader, including how to learn the buyer, the language, and the business problems fast  The most common reason deals get stuck, and why the real problem usually happened earlier in discovery rather than at the end of the sales process  How Matt coaches underperforming reps using deal data, call review, and a one-variable-at-a-time approach to improvement  What founders often get wrong when hiring startup sales talent, especially when they choose comfort over the kind of sales DNA that can actually create growth  What Matt looks for when helping Stage 2 Capital portfolio companies, including where process, pipeline, urgency, and hiring can unlock outsized revenue gains ABOUT THE GUESTMatt Nucifora is Senior Manager of Enterprise Sales at Dandy, where he recently joined after spending 11 years at HubSpot. During his time at HubSpot, he spent nearly six years in sales leadership roles, helping scale teams, coach reps, and develop talent across increasingly complex sales environments. In this conversation, he shares lessons from that run of promotions, what separates strong managers from average ones, and how great coaching actually works inside a high-performance sales organization. Matt is also a Limited Partner at Stage 2 Capital, where he works with early-stage portfolio companies on go-to-market strategy, sales hiring, and process design. Across both startup and scaled environments, his focus is on helping teams create better pipeline, run stronger discovery, close with more urgency, and build repeatable systems that support long-term growth. LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Dandy: https://www.meetdandy.com/

In this episode, I sit down with Fred Ramstedt, Business Development Executive at Wipro Gallagher Solutions and former Director of Sales at TRUE, to talk about what it really takes to sell complex mortgage technology when the stakes are high, the sales cycles are long, and buyers are skeptical of empty ROI claims. Fred breaks down the difference between selling a point solution that improves one part of the workflow versus selling a broader platform that helps lenders rethink how the entire loan manufacturing process should work. He also explains why the best mortgage tech sellers are not just pitching features. They’re helping lenders understand operational friction, implementation risk, and what meaningful change will actually require.We also get tactical on enterprise sales. We talk about what proof actually makes buyers believe an ROI story, what good discovery sounds like in mortgage tech, and why deals often stall even when the value seems obvious. Fred shares how to surface real urgency, why change management is often the real blocker, and what shifts when you go from selling at a fast-moving startup like TRUE to selling inside a much larger organization like Wipro. He also explains why no sale is ever easy, why large complex deals require multiple champions, and how top sellers use AI, research, and customer context to stay relevant in long enterprise cycles.TOPICS WE COVER Fred’s background in mortgage technology and how his work has evolved from document intelligence and AI at TRUE to broader platform and workflow conversations at Wipro Gallagher Solutions  The difference between selling a point solution that fixes a specific operational problem and selling a platform that helps lenders redesign the full loan manufacturing process  What actually makes mortgage buyers believe the ROI story, including why speed, cost, risk, and well-defined proof of concept criteria matter most  What good discovery looks like in mortgage tech, including how to trace the loan process, find friction, and ask questions that expose where the real pain lives  Why deals stall even when the value is obvious, and how implementation risk, competing priorities, and internal resistance often matter more than product fit  What changed for Fred when he moved from TRUE to Wipro, including broader conversations, more strategic deals, longer cycles, and much more organizational firepower behind the sale ABOUT THE GUESTFred Ramstedt is a Business Development Executive at Wipro Gallagher Solutions. Prior to that, he was Director of Sales at TRUE, where he sold AI-driven document intelligence solutions into mortgage, mortgage insurance, servicing, and related workflows. Across more than 20 years in enterprise sales, financial services, and mortgage technology, Fred has focused on helping lenders improve speed, lower cost, manage risk, and modernize how loans move through complex systems. He brings experience selling both highly targeted workflow solutions and broader enterprise platforms, with deep expertise in multi-stakeholder deals, operational ROI, and the practical realities of selling AI and workflow change into mortgage.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Wipro Gallagher Solutions: https://www.wipro.com/gallagher/

In this episode, I sit down with David Gipson, Director of Sales Engineering at Ocrolus, to break down what it really takes to sell AI and automation into mortgage. David shares how his background as an underwriter, loan officer, and sales ops leader shapes the way he helps lenders evaluate new technology, and why the best sales conversations are never really about flashy features. They’re about solving real workflow pain in a way that feels practical, familiar, and easy to adopt.We also get into how skepticism around AI has changed inside lending, why multi-persona messaging matters so much in mortgage sales, and what actually causes long deals to stall out. David explains how Ocrolus navigated the brutal mortgage downturn, why slow markets can be the best time to evaluate tech, and how reputation compounds in a tight-knit industry like mortgage. He also shares one of the most underrated ways to save a stalled deal: getting on a plane, showing up in person, and working through problems face-to-face.TOPICS WE COVER What sellers get wrong when pitching underwriting automation to lenders  Why mortgage buyers care more about solving practical problems than hearing about flashy AI features  How skepticism around AI is changing across executives, operators, and end users  Why making automation feel familiar is critical for adoption inside mortgage teams  How to demo more effectively by tailoring messaging to each lender’s mix of products and priorities  How David coaches sales engineers to prepare for demos using research, AI tools, and persona-specific messaging  What usually causes long mortgage tech deals to stall out or die around month six  Why “time kills deals” and how unclear positioning creates paralysis by analysis  How Ocrolus adjusted its sales approach during the mortgage downturn when rates rose and budgets tightened  Why slow markets can be the best time for lenders to evaluate and replace technology  How Ocrolus used the downturn to improve product-market fit and prepare for the rebound  Why reputation compounds in the mortgage industry and drives more pipeline over time  How strong implementation, support, and client success teams help build brand trust in a relationship-driven market  Why in-person meetings still matter and how face-to-face collaboration can rescue or accelerate deals  Why showing customers you care enough to get on a plane can change the entire sales dynamic ABOUT THE GUESTDavid Gipson is the Director of Sales Engineering at Ocrolus, an AI infrastructure and automation platform for lenders. He has been with the company for more than four years and works closely with Ocrolus’ mortgage team. Before moving into sales engineering, David spent more than a decade in mortgage, with experience in underwriting, loan origination, sales operations, and other roles across the lending process.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Ocrolus: https://www.ocrolus.com/

In this episode, I sit down with Robby MacAskill, Director of Business Development at Zonda, to talk about one of the biggest blind spots in mortgage sales: why lenders are often chasing the wrong builder accounts and missing easier opportunities hiding in plain sight. Robby shares what he’s learned from working with lenders on builder strategy every day, including why mid-sized production builders are often a far better target than most loan officers realize and how data can reveal where the real openings are. We also get tactical on prospecting and sales execution. We talk about how to break into builder relationships that already seem locked up, why in-person outreach still creates a huge edge, and which loan products can open the door fastest. Robby also pulls lessons from his transition into tech sales, including the importance of repeated outreach, multi-threading, time blocking, and running sales conversations that are so valuable the buyer feels like they should have paid for them. TOPICS WE COVER Why most lenders misunderstand the builder opportunity, and where the real opening is with mid-sized production builders rather than only chasing national accounts  How to identify builders that do not have strong lender relationships, including the signals Zonda uses to find low-capture-rate accounts  Why the best path into builder business is usually through the sales reps on the ground, not just the CEO or division president  The power of in-person prospecting, including driving to sales offices, meeting multiple reps, and building momentum across an entire builder organization  Loan products that help lenders win builder referrals, including FHA and VA manual underwrites, buy-before-you-sell programs, and forward commitments  What mortgage salespeople can learn from SaaS prospecting, especially the importance of four to five outreach attempts before expecting a response  Why multi-threading matters so much, including how to spread awareness inside an account and turn one meeting into multiple stakeholders and champions  How to use industry events to create pipeline, including pre-event outreach, attendee research, and scheduling follow-up meetings before the conversation ends  Robby’s biggest lessons from tech sales, including teaching instead of pitching, protecting time for revenue-generating activities, and building a true partnership with your SDR ABOUT THE GUESTRobby MacAskill is the Director of Business Development at Zonda. He began his career in mortgage lending at Lower.com, where he became a top producer, earned President’s Club recognition, and stepped into leadership as an AVP managing a team of MLOs. He later moved into tech sales at Terradepth, where he helped build outbound strategy and the full SaaS sales cycle for Absolute Ocean before becoming a team lead. Today at Zonda, Robby combines his mortgage and technology background to help lenders use builder data and strategy to win more business with home builders.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Zonda: https://zondahome.com/

In this episode, I sit down with Suzy Djilas, Enterprise Account Executive at Arcasa and former Director of Sales at nCino, to talk about what it takes to build trust and sell effectively in the mortgage industry over the long haul. Suzy shares how her 35-year career has evolved alongside the industry, from a highly manual, relationship-driven business to a more tech-enabled one, and why the fundamentals of credibility, honesty, and face-to-face connection still matter just as much as ever.We also get tactical on sales. We talk about the difference between selling mortgage technology and selling a financing product tied directly to borrower outcomes, how to introduce a product that feels new or unconventional, and why in-person meetings still create an advantage in mortgage sales. Suzy also explains why she left leadership to go back into an individual contributor role, what she loves about winning over skeptical buyers, and the mindset that has helped her stay successful for decades.TOPICS WE COVER Suzy’s 35-year journey in mortgage, from Chase to Ellie Mae to nCino to Arcasa  The difference between selling mortgage software versus selling a financing product tied directly to helping borrowers get into homes  How to pitch a product that feels new or unconventional to lenders, and what has to happen for adoption to click  Why Arcasa leads with down payment assistance rather than “solar,” and how Suzy reframes the conversation around borrower outcomes  The role of credibility, honesty, and long-term relationships in overcoming objections and getting lenders to take a smaller company seriously  Why face-to-face selling still matters so much in mortgage, including reading the room, handling doubt in real time, and building trust faster in person  Why Suzy moved from a Director of Sales role back into an AE seat, and what she missed about owning the full sales process  How to turn a skeptical buyer into a champion by asking better questions and staying in the conversation  Suzy’s advice for salespeople on honesty, persistence, believing in your product, and treating “no” as “not yet”  Why conferences are less about instant leads and more about warm introductions that open doors to the right stakeholders ABOUT THE GUESTSuzy Djilas is an Enterprise Account Executive at Arcasa. Prior to that, she was Director of Sales at nCino and has spent more than 35 years in mortgage technology and lending, with prior experience at companies including Ellie Mae and SimpleNexus. Throughout her career, she has focused on helping lenders improve performance through technology, process optimization, and borrower-focused programs that expand access to homeownership. She is known for her deep industry relationships, strong sales leadership background, and track record of driving growth, adoption, and trust across the mortgage ecosystem.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Arcasa: https://www.arcasa.io/

In this episode, I sit down with Grey Bradshaw-Mack, GTM at Default, to talk about his unconventional path into tech sales, from starting out in nonprofit work to breaking into software sales through PitchBook and eventually moving into early-stage startup roles. Grey shares how a major skiing accident forced him to relearn how to walk, created a difficult gap in his resume, and ultimately shaped the way he thinks about resilience, discipline, and telling a compelling story in the job market. He also explains what he learned at PitchBook, why that experience gave him such a strong foundation in sales, and why he was drawn to startups over larger, more established companies.We also get into how Grey landed roles at Sunset and Default, why networking and staying close to people over time mattered more than simply sending cold applications, and what candidates should actually look for when evaluating a startup. Grey breaks down the appeal of joining an early team, the tradeoffs of startup life, and some of the most common reasons startups fail, from founder conflict and poor capital management to losing touch with the customer. He also shares why candidates should backchannel current reps, ask much tougher questions in interviews, and treat the interview process as a two-way vetting process instead of just trying to prove they deserve the job.TOPICS WE COVERGrey’s path from nonprofit work into tech sales and why his career path was anything but linearHow a major injury and long recovery created a resume gap and changed his perspective on workWhat Grey learned at PitchBook about discovery, product positioning, customer curiosity, and outboundWhy startup sales appealed to him more than staying at a larger companyHow Sunset first became a prospect and later turned into a career opportunityHow Grey got his role at Default through networking and relationship-building over timeWhy LinkedIn DMs, networking events, and staying in touch can create real job opportunitiesWhat to look for when evaluating whether an early-stage startup is actually worth joiningCommon reasons startups fail, including founder disputes, careless spending, and weak customer feedback loopsWhy job seekers should ask harder questions, talk to current reps, and treat interviews like a two-way evaluationABOUT THE GUESTGrey Bradshaw-Mack is on the GTM team at Default, a New York-based startup, and previously worked in sales at Sunset and PitchBook. Before entering tech sales, he worked in the nonprofit world, giving him a nontraditional path into software sales. He's also an investor in Mercor.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Default: https://www.default.com/

In this episode, I sit down with Zac Basile, Strategic Account Director at Polly, to talk about what it’s actually like to sell enterprise mortgage tech when there’s no playbook, deals take six to twelve months, and buying committees can range from a handful of stakeholders to dozens of people across the organization. Zac shares how he went from Polly’s founding AE to a sales leadership role, what it took to help build the company’s sales process from scratch, and how constant iteration shaped the way Polly sells into some of the largest lenders in the country.We also get into how long, complex deals really move forward, from early discovery and deal mapping to validating value across stakeholders and navigating late-stage redlines, negotiation, and procurement. Zac explains why time is the biggest killer of enterprise deals, why indecision is often just a slower version of no, and how he uses urgency, access, and expectation-setting to keep opportunities from stalling out. He also shares how his approach changed once the mortgage market turned, why he leaned more heavily into top-down selling during tighter market conditions, and what he now looks for when coaching AEs through stuck deals, including multi-threading, influence mapping, and figuring out who actually has decision power inside an account.TOPICS WE COVERWhat it was like being Polly’s founding AE and helping build a sales process without an established playbookHow Zac used constant iteration and customer feedback to shape the sales motion over timeWhy resilience and adaptability matter when products, messaging, and objections keep changingWhat the first 30 days of a six-to-twelve-month enterprise deal typically look likeHow Polly handles discovery, deal architecture, validation, demos, negotiation, and closingHow many stakeholders can get involved in large mortgage tech deals and why that complicates the processWhy time and indecision kill more deals than pricing or contract negotiationsHow Zac uses expectation-setting and urgency to prevent deals from quietly stalling outWhy giving prospects an easy out can be more effective than chasing dead opportunitiesABOUT THE GUESTZac Basile is the Strategic Account Director at Polly, where he focuses on strategic mortgage lender accounts and also helps lead and coach Account Executives across the organization. He was Polly’s founding AE and has spent the past five years helping build the company’s enterprise sales motion, manage complex deals, and shape go-to-market strategy in a highly relationship-driven market.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Polly: https://polly.io/

In this episode, I sit down with Kyle Weiss, Head of Sales and Customer Success at Outbound Sales Pro and Parakeet, to break down what third-party outbound actually is, why some companies outsource it instead of building SDR teams in-house, and what’s still working in outbound right now when everyone’s inbox is flooded with the same tired sales messages. Kyle explains the three main types of companies that hire outside outbound teams, from founder-led startups trying to minimize risk to larger venture-backed companies looking to scale pipeline fast without adding a ton of internal headcount.We also get into Kyle’s current thinking on cold email, including why the classic “pain + value + CTA” structure has gotten easier and easier to ignore, how subject lines should create just enough curiosity or doubt to earn an open, and why his team now often starts with a simple “heartbeat check” email before trying to pitch anything. Kyle shares why phone calls still outperform everything else, how he thinks about call backs after the “send me more info” objection, and the cold call structure his team uses to get prospects talking instead of shutting down.TOPICS WE COVERWhat third-party outbound is and why companies outsource SDR work instead of building everything in-houseThe three main client buckets Kyle sees, from founder-led startups to large companies with internal SDR teamsWhy consistency in outbound matters and why full-cycle reps often struggle to prospect consistentlyWhy the old cold email formula stopped working even for highly valuable productsKyle’s philosophy on subject lines and how to create curiosity without being overly deceptiveThe “heartbeat check” email approach and why a simple question can outperform a polished pitchWhat patterns instantly make a cold email feel like obvious spamWhy phone calls still drive the majority of meetings, even in modern outboundHow to handle “send me more info” without relying on the prospect to replyKyle’s cold call framework, including the permission-based opener, quick value statement, and question-driven approachABOUT THE GUESTKyle Weiss is the Head of Sales and Customer Success at Outbound Sales Pro and Parakeet. He helps companies build outbound pipeline through a mix of outsourced sales development, cold email, LinkedIn outreach, and phone-based prospecting. Over the past several years, he has worked with a wide range of clients, from founder-led startups testing go-to-market motion for the first time to larger companies looking to scale outbound faster.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Parakeet: https://www.parakeet.io/ Learn more about Outbound Sales Pro: http://outboundsalespro.com

In this episode, I sit down with Frank Pastirchak, National Sales Director at Reggora, to break down what selling into mortgage, banking, and real estate actually looks like when deals are long, complex, and heavily relationship-driven. We get into how Frank thinks about timing in volatile markets, what changes when budgets freeze, and why the best reps in proptech don’t just sell well, they evaluate companies and career moves like investors.We also talk about how Frank vets startups before joining them, why he brings trusted customers into the interview process to test whether a product is real or just “smoke and mirrors,” and how relationships compound over time inside one vertical. Frank shares why he rarely has to apply for jobs, what he looks for in his first 90 days at a new company, and how small thoughtful gestures inside an organization can make a huge difference when it comes to getting deals done.TOPICS WE COVERWhat mortgage and proptech sales cycles actually look like, including deal length, buyer personas, and stakeholder complexityHow Frank evaluates new sales roles like a VC or private equity investorWhat to ask in interviews to figure out whether a startup really has product-market fitThe biggest career mistake AEs make: making emotional decisions too quicklyHow downturn selling changes when budgets freeze and ROI becomes the whole pitchWhy a downturn can actually be the best time for a company to replace technology and take market shareHow strong relationships in one niche can lead to opportunities without ever applying for jobsABOUT THE GUESTFrank Pastirchak is the National Sales Director at Reggora. He has spent the past seven years selling in fintech and proptech, including roles as an Account Executive at Reggora and SimpleNexus (now part of nCino). Frank originally started as a BDR at Reggora and is now returning to the company after several high level sales roles across the space.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Reggora: https://www.reggora.com/

In this episode, I sit down with Tim McEuen, Manager of the Enterprise BDR team at AppFolio, to break down what great sales leadership actually looks like in practice. We get into how Tim built structure across a huge year personally and professionally, why he focuses more on removing friction than rigid time blocking, and how that same mindset shows up in the way he leads his team.We also talk about the kind of culture Tim believes creates great sales organizations: one built around collaboration, shared success, and helping reps get into the zone rather than obsessing over raw KPIs. Tim explains how he coaches underperforming reps, why leaders should speak last in meetings, how adult learning theory shapes his coaching style, and why aspiring sales leaders should learn the full sales cycle before moving into management.TOPICS WE COVERWhy Tim’s real estate background helped him land at AppFolio and better understand customersHow he managed a massive 2025 by focusing on tailwinds and removing frictionWhy great managers create environments, not just accountabilityHow Tim thinks about helping reps “get into the zone” instead of just chasing KPIsWhat AppFolio’s “paddle” culture means and why collaboration matters in salesThe “ship, shipmate, self” framework for making better team decisionsWhy leaders should talk last and create room for reps to leadHow Tim coaches underperformers by separating skill gaps from motivation issuesHow adult learning theory applies to sales coaching and skill developmentWhy future sales leaders should master the full sales cycle before moving into managementABOUT THE GUESTTim McEuen is the Manager of the Enterprise BDR team at AppFolio. He’s spent about 15 years across tech sales, logistics, and sales leadership, with experience managing both AEs and BDRs. Alongside his work in tech, he also built a real estate business, giving him firsthand insight into the customers and industry AppFolio serves.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about AppFolio: https://www.appfolio.com/

In this episode, I sit down with Dewayne Starling, Strategic Relationship Manager at nCino and a 30+ year mortgage industry veteran, to talk about what actually matters when selling technology into mortgage. We get into why mortgage domain knowledge still gives sellers a major edge, what pure tech reps often get wrong when they try to sell to lenders, and why mortgage remains one of the hardest industries to change.We also break down where AI is actually creating value in lending versus where there’s still hype, why the cost to originate has risen so sharply, and how lenders can use technology to reduce friction without removing the human element borrowers still want. We close with Dewayne’s advice for mortgage bankers looking to break into fintech, plus why relationships and long-term industry compounding matter more than ever.TOPICS WE COVERWhy mortgage domain expertise gives sellers an advantage in mortgage techWhat pure tech reps often get wrong when selling to lendersWhy mortgage has historically been slow to adopt new technologyHow borrower expectations are changing the loan experienceWhy the cost to originate has risen so much over timeWhere AI is actually helping lenders today and where there’s still hypeHow to balance automation with the human side of the mortgage processAdvice for mortgage bankers trying to break into mortgage techWhy relationships compound over a long career in one industryABOUT THE GUESTDewayne Starling is a Strategic Relationship Manager at nCino, where he works with many of the top independent mortgage banking customers in the industry. He has spent more than 30 years in mortgage, with experience spanning loan origination, wholesale and correspondent lending, and mortgage technology.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about nCino: https://www.ncino.com/

In this episode, I sit down with Angie Parkhouse, Sales Leader at Qualia (real estate transaction management software), to talk about what it looks like to design your career around your life and the sales fundamentals that still matter in a world drowning in AI spam. Angie shares her unconventional path from B2B sales and 13 years in medical devices to taking a sabbatical to race mountain bikes, living the van life adventure, and ultimately pivoting into SaaS so she could build a career that supported the lifestyle she wanted.We also get tactical on selling. We talk about why vertical SaaS matters and why some buyers actually pick up the phone, how to cold call without commission breath, and what it takes to sell change to customers who did not ask for it. Angie breaks down how Qualia handles reputation-based objections, why empathy is the fastest path to trust, and how her team is guiding customers through major transitions after acquisitions.TOPICS WE COVERAngie’s pivot from medical device sales to SaaS, and how she designed her career around lifestyle and freedomThe mountain bike sabbatical and van life chapter that forced a reset and led her to softwareWhy vertical SaaS matters, including choosing industries where buyers actually answer callsCold calling fundamentals that still win, including discovery first and never pitching without painWhy AI spam is hurting outreach, and how to stand out by selling like a humanHow to sell change when customers are resistant, including handling Qualia reputation objections and leading with empathyABOUT THE GUESTAngie Parkhouse is the Transition Team Sales Leader at Qualia. She previously spent 13 years in medical device sales, then took a career sabbatical to compete as a Sponsored Professional Women’s Enduro mountain bike racer. She later pivoted into SaaS to build a career aligned with her lifestyle, and now leads teams helping customers navigate major software transitions and modernize the closing process.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Qualia: https://www.qualia.com/

In this episode, I sit down with Matt Sterenberg, Senior Director of Customer Success at Modern Campus and a 12+ year EdTech leader with experience across customer success, sales, and customer advocacy, to unpack what customer success teams wish every AE understood. We get into how the higher ed ROI debate is changing buying behavior, why “time saved” isn’t a strong value prop unless you can tie it to outcomes, and what it really takes to build trust that turns customers into long-term champions.We also break down the churn equation: the metrics that actually matter (implementation, time-to-value, usage, sentiment), the hidden risk of “hostage” customers, and the simple pre-close habits that make CS infinitely easier on day one. We close with Matt’s rapid-fire sales advice on why listening is the real superpower, and how a few well-timed questions can save you months of wasted deal cycles.TOPICS WE COVERWhy higher ed is more ROI-driven and how that’s changing buying behaviorSelling value in higher ed: going beyond “time saved” to “to what end?” outcomesWhat creates customer champions, and the fastest ways to lose advocatesEarly warning signs of churn: implementation, time-to-value, usage, sentiment, and champion riskThe “hostage customer” problem: high usage, low satisfactionWhat AEs should document before close: key stakeholders + pain + success metricsABOUT THE GUESTMatt Sterenberg is the Senior Director of Customer Success at Modern Campus. He’s spent 12+ years in EdTech across customer success, sales, and customer advocacy, including leadership roles at Parchment and Instructure.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/Learn more about Modern Campus: https://moderncampus.com/

In this episode, I sit down with Sean Gannon, GTM Strategy Consultant at GTMppl and a longtime EdTech revenue leader who spent 13 years at Parchment (later acquired by Instructure), to break down what it actually takes to build predictable pipeline in EdTech and SaaS. Sean shares why most teams start in the wrong place, how to think about data and intent signals in a finite market, and what “getting your data house in order” really means if you want sustainable growth.We also dig into the selling side: the most common deal killers reps underestimate, how to avoid getting treated like a vendor, and why the best sellers lead with curiosity and equal business stature. We close with Sean’s simple 90-day GTM priorities for any $5–20M ARR leader trying to scale without adding chaos.TOPICS WE COVERSean’s background and why he moved into GTM advisingLessons from 13 years at Parchment and what it taught him about scaling in EdTechThe biggest lesson for predictable pipeline: start with data, not opinionsHow intent signals and targeting help you win in a finite marketThe most common deal killer: not listening and selling with “commission breath”How to stop being viewed as a vendor and sell as a true partnerWhy buyers are far along before they talk to sales, and what that changesThe shift from gated content to answer engine visibility in an AI worldSean’s 90-day GTM priorities for $5–20M ARR teams: data, speed to lead, experimentationABOUT THE GUESTSean Gannon is a GTM Strategy Consultant at GTMppl. He helps SaaS and EdTech companies design and execute go-to-market strategies that drive predictable pipeline, increase win rates, and turn customers into advocates. Drawing on 20+ years as a revenue leader, including 13 years at Parchment (later acquired by Instructure), Sean partners with executives and their teams to align marketing, sales, and customer success to build growth that lasts.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/Learn more about GTMppl: https://www.gtmppl.com/

In this episode, I sit down with Zach Larabee, Sr. Manager of the Enterprise Sales Coordinator Team at Toast, to break down what actually happens after an enterprise deal signs, how large brands get rolled out across hundreds (or thousands) of franchise locations, and why implementations stall when expectations aren’t set upfront.Zach explains why franchisee autonomy is the #1 variable that slows rollouts, what sellers should uncover before closing (tech stack, decision rights, and standardization), and how to create urgency with operators who don’t want to be told what to do. We also get into how he won Toast’s Employee of the Year in 2020 by taking initiative during COVID, documenting the process end-to-end, making downstream teams’ lives easier, and building cross-functional trust.TOPICS WE COVERWhat Enterprise Sales Coordinators do at Toast (the “hybrid” of onboarding + sales)How rollouts work when you’re dealing with corporate and individual franchiseesThe #1 factor that determines rollout speed: franchisee autonomy vs corporate standardizationWhy rollouts get delayed at scale (1,000 locations = 1,000 different conversations)The best-case scenario: the “standard package” rollout (100 locations in a month)What’s often missing at handoff, and what sellers should ask before closingWhy identifying the customer’s tech stack early prevents onboarding surprisesWho really derails rollouts (and why it’s usually franchisees, not finance/IT)How to create urgency and excitement so owners don’t “stick their feet in the mud”Messaging that makes rollouts smoother: finding the operator’s “why” (money, experience, autonomy)Handling competitors who try to undercut pricing, and why corporate alignment mattersHow Zach won Employee of the Year: initiative, process documentation, and helping downstream teamsABOUT THE GUEST Zach Larabee is the Senior Manager of the Enterprise Sales Coordinator Team at Toast, where he leads a team that manages large-scale enterprise and mid-market rollouts across franchise brands. He’s been at Toast for 9 years, helped scale the rollout motion from the early days, and won Toast’s Employee of the Year in 2020 for his initiative and cross-functional impact during COVID.Connect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Toast: https://pos.toasttab.com/

In this episode, I sit down with Kaylin McNamara, Sr. Director of GTM Operations at Owl Labs, to break down what it really takes to build and scale a sales org from scratch, especially when the market is changing fast.Kaylin walks through how Owl Labs went from an e-comm led motion to a true sales org during COVID, what she prioritized first (data + process before “playbooks”), how they segmented direct vs channel vs SMB, and the leadership principles that helped her earn trust and keep teams aligned through constant change.TOPICS WE COVERWhat Kaylin did in the first 60 days to stand up sales from scratchWhy you can’t build a “playbook” until the data foundation existsHow Owl Labs split direct sales vs channel to avoid self-competitionThe “Swiss Army knife” seller profile for fast, high-volume cyclesHow they handled SMB (BDRs running full-cycle under 200 employees)The hardest part of scaling: change moving faster than documentationHow to earn promotions without politics: reputation + cross-functional trustKaylin’s leadership rule: lead with the why + set clear expectationsHow to raise concerns without killing morale (bring solutions)ABOUT THE GUEST Kaylin McNamara is the Senior Director of GTM Operations at Owl Labs, a Boston-based hardware technology company building video conferencing tools for hybrid work. She joined during the early days of Owl’s growth and helped build and scale the go-to-market motion across direct sales, channel partnerships, and international expansion.Connect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Owl Labs: https://owllabs.com/

In this episode, I sit down with Michael Conrad, Senior Account Executive at n8n, to break down how enterprise AEs multi-thread deals, pull executive buyers in early, and keep momentum without annoying their champion.Michael walks through the exact assets he built in his first 30 days to drive pipeline: a “land bigger” talk track to increase ASP, LinkedIn org-charting lists to multi-thread with intent, and a follow-up email framework that keeps customers accountable. We also dig into n8n’s inbound-led motion, what they call warm-bound, and how to handle common objections when you are selling a newer platform.TOPICS WE COVERThe 3 assets Michael built in his first 30 days that drove pipeline and closesThe “land bigger” talk track and how to steer deals away from small pilots and increase ASPLinkedIn org-charting and how to identify the right personas and multi-thread with intentThe exact move after Call 1 to create 2 to 3 new threads without burning your championWhy the executive buyer should be your first persona, even in inbound-led motionsWarm-bound and why it works for accounts that already have contextThe hardest objections, including technical clarity and budget, and how Michael handles themRapid-fire tips for enterprise sellers: be bold in discovery and uncover your champion’s personal winABOUT THE GUESTMichael Conrad is a Senior Account Executive at n8n. He sells into mid-market and enterprise accounts and focuses on executive-level deal process, multi-threading strategy, and follow-up systems that drive larger outcomes.Connect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about n8n: https://n8n.io/

In this episode, I sit down with Matt Stinson, CRO at Starbridge, to talk about what top performing startups look for when hiring AEs, and how candidates can stand out fast.Matt breaks down how Starbridge is scaling their sales team, why they care so much about ramp speed, and what signals tell him someone will thrive in an early stage environment. We also get tactical on references, back channel diligence, and the exact questions he asks to find the truth behind a resume.TOPICS WE COVERWhat “ramp fast” actually means and how hiring managers judge itThe biggest hiring signals for early stage AEsHow to use references the right way, including back channelThe best reference question: “If I call you in 6 months and they failed, why?”Red flags like the “lone wolf” rep and why that mattersHow candidates should treat interviews like a sales processABOUT THE GUEST Matt Stinson is the Chief Revenue Officer at Starbridge. He has sold into and led teams across government and education markets, including K 12 and higher education. At Starbridge, the team is building tools that help sellers identify the right accounts to reach out to, when to reach out, and what messaging to use to generate more pipeline.Connect with me: https://www.linkedin.com/in/carter-armendarez/Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/Learn more about Starbridge: https://starbridge.ai/