Explore every episode of the podcast Tech Sales with Carter
| Title | Pub. Date | Duration | |
|---|---|---|---|
| How to Coach a Sales Team Like Ted Lasso | Rodney Alcantara (Deel) | 28 Sep 2026 | 00:18:08 | |
In this episode, I sit down with Rodney Alcantara, Sales Manager Mid-Market & Enterprise NAM (Deel IT), to talk about remote sales leadership, hiring, coaching underperforming reps, developing future managers, and building high-performing teams. Rodney shares how his approach to leadership has evolved from an in-office environment to managing remotely, why understanding what motivates each individual matters, and how acts of service and intentional one-on-ones can help leaders build stronger relationships with their teams. We also talk about what Rodney looks for when hiring salespeople, why upward career progression and strong referrals stand out, and how a candidate’s follow-up after an interview can reveal how they might handle prospects. Rodney explains why he approaches underperformance with curiosity instead of judgment, how radical candor works when employees know their manager genuinely cares about their success, and why great managers have to adapt their leadership style to each person instead of managing everyone the same way. TOPICS WE COVER
ABOUT THE GUEST Rodney Alcantara leads a North American sales team for Deel IT, working across the mid-market and enterprise segments. He began his tech sales career at Yelp, where he started by making 100 cold calls a day before progressing from individual contributor into sales leadership. Throughout his career, Rodney has held sales and management roles at companies including Yelp, Uber, Kandji, and Deel. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Treat Every Call Like It’s a Six-Figure Deal | Jordyn Schiff (Salesforce) | 10 Aug 2026 | 00:16:03 | |
In this episode, I sit down with Jordyn Schiff, Regional Vice President of Sales for Southern California at Salesforce, to talk about career growth, becoming a better seller, sales leadership, hiring, and developing top-performing teams. Jordyn explains how to know when you’ve stopped growing at a company, why there is no perfect career opportunity, and how learning to execute smaller deals can prepare sellers for the biggest opportunities of their careers. We also talk about what separates Salesforce’s best sales leaders, why great managers empower their reps instead of doing the work for them, and what Jordyn looks for when hiring. She explains why unconventional backgrounds can succeed at Salesforce, how scenario-based interview questions reveal aptitude and attitude, and why investing in people’s careers is one of the best ways to retain top performers. TOPICS WE COVER
ABOUT THE GUEST Jordyn Schiff is a Regional Vice President of Sales at Salesforce, where she leads sales for Southern California within the company’s financial services practice. Since joining Salesforce, Jordyn has built a track record as a top-performing sales leader, increasing annual attainment from 103% to 127% to 153% while progressing from Regional Sales Manager to RVP. She was also selected for Salesforce’s Sales Leader Excellence Academy. Before joining Salesforce, Jordyn was an Enterprise AE and Sales Manager at Talkdesk. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Strategic Sales Is a Team Sport | Jaron Murphy (FICO) | 04 Aug 2026 | 00:24:06 | |
In this episode, I sit down with Jaron Murphy, Head of Scores Partnerships at FICO, to talk about the lessons he has learned across cold calling, enterprise sales, strategic accounts, sales leadership, and partnerships. Jaron explains how early rejection built the resilience he has carried throughout his career, why trust must be earned when selling to senior executives, and how joining FICO forced him to develop into a more strategic seller. We also talk about why selling into banks requires a different mindset, how strategic account management differs from simply being a strong closer, and what individual contributors must unlearn when they move into leadership. Jaron shares what makes a partnership generate real revenue, why curiosity is one of the most important qualities he looks for when hiring, and why ambitious sellers should stop comparing their career progress to everyone around them. TOPICS WE COVER
ABOUT THE GUEST Jaron Murphy is the Head of Scores Partnerships at FICO, where he leads the go-to-market function for strategic partners within the FICO Score business. During nearly seven years at FICO, he has sold the company’s software platform to major financial institutions, led its U.S. platform sales business, and built a new partnership team within the scores division. Before joining FICO, Jaron was an Enterprise AE at SAS. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Become an RVP at a SaaS Giant | Ben Gibson (Slack) | 03 Aug 2026 | 00:17:44 | |
In this episode, I sit down with Ben Gibson, Regional Vice President at Slack, to talk about what it takes to move from an individual contributor role into sales leadership. Ben explains why aspiring leaders need to make their ambitions known, start doing the job before they receive the title, and become the most obvious candidate when an opportunity opens. We also talk about why Ben left enablement to return to a quota-carrying role, how that experience helped him develop as a sales leader, and why he approaches career decisions through the lens of mastering his craft. Ben shares the biggest mistake he made as a new manager, how sellers should approach conversations about AI, and how ambitious goals help him prioritize his time across work, family, and physical pursuits. TOPICS WE COVER
ABOUT THE GUEST Ben Gibson leads Slack’s commercial communications, media, technology, and new-logo business. His career has included roles across sales, sales leadership, and enablement. At Slack, he helped build the company’s manager-development function before returning to the field as an Account Executive and later moving into sales leadership. His experience across those roles has shaped his approach to career development, coaching, and building high-performing sales teams. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Go From BDR to Enterprise AE in 3.5 Years | Jolie Stern (Gong) | 18 Jun 2026 | 00:16:52 | |
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
ABOUT 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/ | |||
| Lessons from a CEO: People Love to Buy. They Hate to Be Sold | Anthony Romano (CREtelligent) | 18 Jun 2026 | 00:22:37 | |
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
ABOUT 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/ | |||
| How to Sell to Banks and Lenders | Tiffany Stringfellow (Moody's Analytics) | 12 Jun 2026 | 00:18:29 | |
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
ABOUT 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/ | |||
| Every Conversation Is Worth the Conversation | Amanda Padd (Secure Insight) | 05 Jun 2026 | 00:14:34 | |
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
ABOUT 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/ | |||
| What Every AE Gets Wrong About Customer Success | Alexis Cisneros (Matey AI) | 31 May 2026 | 00:14:20 | |
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
ABOUT THE GUEST Alexis Cisneros is the Vice President of Client Success at Matey AI, an AI-native eDiscovery case intelligence platform that helps legal teams analyze, organize, review, and investigate digital discovery. Before Matey AI, Alexis was the Director of Customer Success at Dealerware. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Why Executives Ignore Your Sales Pitch | Ben Sizemore (Land Gorilla) | 27 May 2026 | 00:11:56 | |
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
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/ | |||
| How to Sell AI in the Mortgage Industry | Mike Brown (Gateless) | 13 May 2026 | 00:13:43 | |
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
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/ | |||
| How to Be the Best BDR at Your Company | Jim Robertson (CertifID) | 04 May 2026 | 00:21:03 | |
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
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/ | |||
| How to Sell Software in a Heavily Regulated Industry | Nina Hein (Homebot) | 03 May 2026 | 00:15:45 | |
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
ABOUT THE GUEST Nina Hein is the Director of Growth for the title vertical at Homebot. She has been with Homebot for eight years and has held roles across sales, customer success, strategy, leadership, and account executive functions. Before joining Homebot, Nina worked in the real estate industry in administrative and transaction coordination roles, giving her a unique perspective on the buyers, partners, and customers Homebot serves. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Lessons from a CRO: Scaling a Tech Company in 2026 | Joe Zeibert (Mortgage Cadence) | 01 May 2026 | 00:24:03 | |
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
ABOUT THE GUEST Joe Zeibert is the Chief Revenue Officer at Mortgage Cadence, where he is helping lead the company’s next chapter in mortgage technology, LOS modernization, and AI-driven workflow transformation. He brings more than 15 years of experience across mortgage, banking, capital markets, pricing, product strategy, analytics, and financial technology, with senior leadership roles at Anchor Loans, FICO, Nomis Solutions, Ally Financial, and Bank of America. His background spans mortgage and capital markets, home lending product strategy, enterprise capital management, pricing optimization, credit risk, analytics, and business intelligence, including helping launch Ally Home Loans and leading major data-driven pricing, product, and reporting initiatives across the financial services industry. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Sell Software by Asking Better Questions | Dillan Dove (JewelLink) | 30 Apr 2026 | 00:17:51 | |
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
ABOUT THE GUEST Dillan Dove is the VP of Sales at JewelLink, a software company helping jewelry stores improve sales training and performance. Before joining JewelLink, Dillan was Director of Sales at Podium. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Get Promoted at an Elite Sales Org | Soraya Hatcher (HubSpot) | 29 Apr 2026 | 00:19:19 | |
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
ABOUT THE GUEST Soraya Hatcher is an SMB Sales Manager at HubSpot, where she leads a team of eight account executives. Before moving into management, Soraya spent over three years as an AE at HubSpot, where she mentored reps, created training material, and founded the Future Leaders Program to help develop aspiring sales leaders. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Sell AI in an Industry Dominated by Legacy Tech | Chris McLendon | 27 Apr 2026 | 00:16:35 | |
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
ABOUT THE GUEST Chris McLendon is the Partner and Chief Revenue Officer at TidalWave, an AI-native mortgage technology company focused on improving the borrower and lender experience through automation at the front end of the loan process. Chris has been in the mortgage industry since 1999, starting in production as a loan officer before moving into mortgage technology. Before joining TidalWave, he spent five years at Black Knight on the Empower platform and ten years with Encompass/ICE Mortgage Technology, working across relationship management, enterprise accounts, and new logo sales. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Demo Software Without Turning It Into a Product Tour | Seth Haake | 25 Apr 2026 | 00:16:58 | |
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
ABOUT THE GUEST Seth Haake is a Strategic Sales Engineer at Total Expert, where he has spent nearly nine years helping enterprise lenders, IMBs, banks, and credit unions think through customer engagement, retention, loan officer productivity, and growth strategy. In his role, Seth works across sales, product marketing, marketing, and product to help lenders understand how to turn their customer database into a growth engine and operationalize what their best loan officers are already doing. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| You’re Not Really Selling AI. The Hard Sell Is Change. | 20 Apr 2026 | 00:12:17 | |
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
ABOUT THE GUEST Graham Young is a Strategic Account Executive at Vesta, where he works with mortgage lenders making high-stakes decisions around core technology and platform change. He was brought in to help scale the enterprise go-to-market from founder-led relationships to a repeatable, AE-led motion. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| The Magic of Thinking Big in Tech Sales | 16 Apr 2026 | 00:27:39 | |
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
ABOUT THE GUEST Raymond Griffin is a Regional Sales Manager at Numa with a long track record of success in automotive sales. Before Numa, he held sales roles across companies including Cars.com, Dealer Inspire, Tekion, and Impel, and built a reputation as a high-performing seller and sales leader in the automotive tech space. His career honors include 2024 President’s Club at Outsell/Impel AI, 2014 Rookie of the Year at Cars.com, multiple President’s Club selections, multiple Regional and Divisional Team MVP awards, and NADA Team recognition at Cars.com. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Why More Dials Won’t Fix Your Sales Problem | 16 Apr 2026 | 00:21:46 | |
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
ABOUT THE GUEST Jordan 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How Two Best Friends Built a Signing Business and Broke Into Tech Sales | 09 Apr 2026 | 00:14:44 | |
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
ABOUT THE GUESTS Erica 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Scale the BD Org of a $1B+ Tech Company | 03 Apr 2026 | 00:18:14 | |
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
ABOUT THE GUEST Pat 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Lessons from a VP: You Can't Turn a D Player Into an A Player | Craig Holbrook (nCino) | 02 Apr 2026 | 00:16:18 | |
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
ABOUT THE GUEST Craig 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to scale a sales org to $50M ARR | Ian Grace (Ocrolus) | 30 Mar 2026 | 00:18:31 | |
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
ABOUT THE GUEST Ian 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Sales Leadership Lessons No One Talks About | Matt Nucifora (Dandy) | 27 Mar 2026 | 00:19:42 | |
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
ABOUT THE GUEST Matt 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Everything you need to know about selling mortgage tech in 30 mins | Fred Ramstedt (Wipro) | 26 Mar 2026 | 00:30:03 | |
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
ABOUT THE GUEST Fred 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Sell AI to an Industry That Doesn't Trust It | David Gipson (Ocrolus) | 24 Mar 2026 | 00:21:12 | |
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
ABOUT THE GUEST David 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Why You’re Chasing the Wrong Accounts (and What to Do About It) | Robby MacAskill (Zonda) | 22 Mar 2026 | 00:21:31 | |
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
ABOUT THE GUEST Robby 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Why You Should Be Selling in Person | Suzy Djilas (Arcasa) | 22 Mar 2026 | 00:10:52 | |
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
ABOUT THE GUEST Suzy 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to break into tech sales without a perfect background | Grey Bradshaw-Mack (Default) | 13 Mar 2026 | 00:35:08 | |
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 COVER
ABOUT THE GUEST Grey 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly) | 12 Mar 2026 | 00:21:23 | |
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 COVER
ABOUT THE GUEST Zac 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Why your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet) | 11 Mar 2026 | 00:37:56 | |
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 COVER
ABOUT THE GUEST Kyle 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Pick your next sales role like a VC | Frank Pastirchak (Sales Director, Reggora) | 08 Mar 2026 | 00:15:25 | |
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 COVER
ABOUT THE GUEST Frank 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Build a Sales Team That Doesn't Need You | Tim McEuen (AppFolio) | 06 Mar 2026 | 00:19:17 | |
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 COVER
ABOUT THE GUEST Tim 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Sell Tech to an Industry That Hates Change | Dewayne Starling (nCino) | 06 Mar 2026 | 00:15:53 | |
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 COVER
ABOUT THE GUEST Dewayne 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| From Pro Mountain Biker to B2B SaaS: How to Design Your Career Around Your Life | Angie Parkhouse (Qualia) | 27 Feb 2026 | 00:21:25 | |
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 COVER
ABOUT THE GUEST Angie 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| Customer Success Secrets Every AE Needs to Know | Matt Sterenberg (Modern Campus) | 23 Feb 2026 | 00:21:13 | |
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 COVER
ABOUT THE GUEST Matt 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| 25 years of EdTech sales lessons and an $835M exit | Sean Gannon, GTMppl | 19 Feb 2026 | 00:26:39 | |
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 COVER
ABOUT THE GUEST Sean 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. LINKS Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Run a 4,500-Location Enterprise Rollout (In One Year) | Zach Larabee (Sr. Manager at Toast) | 18 Feb 2026 | 00:25:33 | |
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 COVER
ABOUT 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/ | |||
| Building a Sales Org From Scratch During COVID | Kaylin McNamara (Sr. Director, GTM at Owl Labs) | 11 Feb 2026 | 00:29:47 | |
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 COVER
ABOUT THE GUEST Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||
| How to Turn Inbound Leads into Enterprise Deals | Michael Conrad (Enterprise AE at n8n) | 10 Feb 2026 | 00:09:55 | |
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 COVER
ABOUT THE GUEST Michael 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/ | |||
| How to Get Hired as an AE at a VC-backed Startup | Matt Stinson (CRO at Starbridge) | 03 Feb 2026 | 00:20:01 | |
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 COVER
ABOUT THE GUEST Connect with me: https://www.linkedin.com/in/carter-armendarez/ | |||