Shows
Tech Sales with CarterEvery Conversation Is Worth the Conversation | Amanda Padd (Secure Insight)In this episode, I sit down with Amanda Padd, Chief Revenue Officer at Secure Insight, to talk about selling fraud prevention and risk management technology into the mortgage industry. Amanda explains why many lenders only start looking for solutions after a scare, an audit finding, or an actual fraud event, and why companies need to think about wire and closing fraud before it becomes too late.We also talk about why mortgage is still such a relationship-driven, face-to-face industry. Amanda shares how she uses conferences, in-person meetings, and vendor-only dinners to build trust, create referral relationships, and...
2026-06-0614 minTech Sales with CarterWhat Every AE Gets Wrong About Customer Success | Alexis Cisneros (Matey AI)In this episode, I sit down with Alexis Cisneros, Vice President of Client Success at Matey AI, to talk about what happens after the deal closes, how customer churn can start during discovery, and why sales and customer success teams need to work together long before implementation begins. Alexis shares why delayed onboarding is often an early warning sign, how AEs can prevent churn by identifying real champions and power users, and why rigorous qualification matters before a customer ever reaches the post-sale team.We also talk about selling AI into legal teams, where trust, security, and...
2026-05-3114 minTech Sales with CarterWhy Executives Ignore Your Sales Pitch | Ben Sizemore (Land Gorilla)In this episode, I sit down with Ben Sizemore, Chief Information Officer at Land Gorilla, to talk about how technology buyers evaluate vendors, what makes salespeople credible with executives, and why most software pitches fail before they ever become real conversations. Ben shares why CIOs do not want to be “sold,” why cold outreach rarely works on him unless there is already some relationship or in-person context, and why the best sales conversations are grounded in facts, numbers, workflow impact, and ROI. We also talk about what really drives lending technology purchases: operational efficiency, doing more with less...
2026-05-2711 minTech Sales with CarterHow to Sell AI in the Mortgage Industry | Mike Brown (Gateless)In this episode, I sit down with Mike Brown, CRO at Gateless, to talk about selling AI in the mortgage industry, building lean revenue teams, and proving ROI in a heavily regulated market. Mike shares how Gateless is using AI and automation to do more with a smaller team, why mortgage lenders are slower to adopt AI than the conference hype suggests, and why AI products in lending have to be provable, compliant, and tied to measurable business outcomes.We also talk about how Gateless stays focused on credit, income, and asset automation instead of trying to “bo...
2026-05-1313 minTech Sales with CarterHow to Be the Best BDR at Your Company | Jim Robertson (CertifID)In this episode, I sit down with Jim Robertson, who leads the business development team at CertifID, to break down what separates great BDRs from average ones. Jim shares why the best reps are deeply curious, care about the problem they’re solving, and know how to stay human instead of sounding like they’re reading from a script.We also talk about what BDR outreach looks like in a vertical SaaS market where prospects often have very little online presence. Jim explains how his team uses events, white papers, direct mail, referrals, fraud signals, and hyper-specific foll...
2026-05-0421 minTech Sales with CarterHow to Sell Software in a Heavily Regulated Industry | Nina Hein (Homebot)In this episode, I sit down with Nina Hein, Director of Growth for the title vertical at Homebot, to talk about what it actually looks like to sell technology into real estate, mortgage, and title. Nina shares how she went from being a Homebot user to becoming the company’s first inside sales rep, eventually moving through customer success, strategy, leadership, and now back into an AE role focused on title companies.We get into why title may be more tech-forward than people think, how regulated industries evaluate new software, and what reps should understand before selling in...
2026-05-0315 minTech Sales with CarterLessons from a CRO: Scaling a Tech Company in 2026 | Joe Zeibert (Mortgage Cadence)In this episode, I sit down with Joe Zeibert, Chief Revenue Officer at Mortgage Cadence, to talk about what it takes to lead sales in mortgage technology at a time when the industry is under pressure, costs are rising, and lenders are being forced to rethink how they operate. Joe shares what he looks at first when stepping into a CRO role, why understanding a company’s history matters before making changes, and how Mortgage Cadence is thinking about redesigning LOS and workflow technology for the future. We also get into why technology has failed to bring dow...
2026-05-0124 minTech Sales with CarterHow to Sell Software by Asking Better Questions | Dillan Dove (JewelLink)In this episode, I sit down with Dillan Dove, VP of Sales at JewelLink, to talk about building a sales motion from the ground up, coaching reps hard, and turning industry knowledge into a real software sales advantage. Dillan shares how he went from selling and leading teams at Podium to helping build JewelLink’s go-to-market motion in the jewelry industry, including why the early playbook is less about pitching every feature and more about asking better questions, finding real pain, and knowing when a customer is or is not a fit.We also get into sales le...
2026-04-3017 minTech Sales with CarterHow to Get Promoted at an Elite Sales Org | Soraya Hatcher (HubSpot)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...
2026-04-3019 minTech Sales with CarterHow to Sell AI in an Industry Dominated by Legacy Tech | Chris McLendonIn 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 ho...
2026-04-2716 minTech Sales with CarterHow to Demo Software Without Turning It Into a Product Tour | Seth HaakeIn 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...
2026-04-2516 minTech Sales with CarterYou’re Not Really Selling AI. The Hard Sell Is Change.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 strat...
2026-04-2012 minTech Sales with CarterThe Magic of Thinking Big in Tech SalesIn 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...
2026-04-1627 minTech Sales with CarterWhy More Dials Won’t Fix Your Sales ProblemIn 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, an...
2026-04-1621 minTech Sales with CarterHow Two Best Friends Built a Signing Business and Broke Into Tech SalesIn 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...
2026-04-0914 minTech Sales with CarterHow to Scale the BD Org of a $1B+ Tech CompanyIn 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...
2026-04-0318 minTech Sales with CarterLessons from a VP: You Can't Turn a D Player Into an A Player | Craig Holbrook (nCino)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...
2026-04-0216 minTech Sales with CarterHow to scale a sales org to $50M ARR | Ian Grace (Ocrolus)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...
2026-03-3018 minTech Sales with CarterSales Leadership Lessons No One Talks About | Matt Nucifora (Dandy)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...
2026-03-2719 minTech Sales with CarterEverything you need to know about selling mortgage tech in 30 mins | Fred Ramstedt (Wipro)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...
2026-03-2630 minTech Sales with CarterHow to Sell AI to an Industry That Doesn't Trust It | David Gipson (Ocrolus)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 ma...
2026-03-2421 minTech Sales with CarterWhy You’re Chasing the Wrong Accounts (and What to Do About It) | Robby MacAskill (Zonda)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...
2026-03-2221 minTech Sales with CarterWhy You Should Be Selling in Person | Suzy Djilas (Arcasa)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...
2026-03-2210 minTech Sales with CarterHow to break into tech sales without a perfect background | Grey Bradshaw-Mack (Default)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...
2026-03-1335 minTech Sales with CarterHow to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly)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 coun...
2026-03-1221 minTech Sales with CarterWhy your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet)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 a...
2026-03-1237 minTech Sales with CarterPick your next sales role like a VC | Frank Pastirchak (Sales Director, Reggora)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...
2026-03-0815 minTech Sales with CarterHow to Build a Sales Team That Doesn't Need You | Tim McEuen (AppFolio)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...
2026-03-0619 minTech Sales with CarterHow to Sell Tech to an Industry That Hates Change | Dewayne Starling (nCino)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 ho...
2026-03-0615 minTech Sales with CarterFrom Pro Mountain Biker to B2B SaaS: How to Design Your Career Around Your Life | Angie Parkhouse (Qualia)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...
2026-02-2721 minTech Sales with CarterCustomer Success Secrets Every AE Needs to Know | Matt Sterenberg (Modern Campus)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-t...
2026-02-2321 minTech Sales with Carter25 years of EdTech sales lessons and an $835M exit | Sean Gannon, GTMpplIn 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 avoi...
2026-02-1926 minTech Sales with CarterHow to Run a 4,500-Location Enterprise Rollout (In One Year) | Zach Larabee (Sr. Manager at Toast)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...
2026-02-1825 minTech Sales with CarterBuilding a Sales Org From Scratch During COVID | Kaylin McNamara (Sr. Director, GTM at Owl Labs)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
2026-02-1129 minTech Sales with CarterHow to Turn Inbound Leads into Enterprise Deals | Michael Conrad (Enterprise AE at n8n)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 newe...
2026-02-1009 minTech Sales with CarterHow to Get Hired as an AE at a VC-backed Startup | Matt Stinson (CRO at Starbridge)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 hiri...
2026-02-0320 min
Book Reviews for Average PeopleLife Advice From Death RowThis is the quick and dirty review of the book "Life Advice From Death Row" by Carter Armendarez.
2024-01-1505 min
The Winning Youth Coaching Podcast: Youth Sports | Coaching | Parenting | Family ResourcesWYC 145 – College Recruitment – Carter Armendarez talks college recruitment do’s and don’tsCarter Armendarez is a senior at Wesleyan University, where he's also captain of the wrestling team. Getting recruited to play sports in college is confusing to lots of athletes, but it really shouldn’t be. Carter has seen too many athletes fail to get recruited. So he made Acute Recruit’s College Recruitment Guide for Athletes so that doesn’t happen anymore.
Website: acuterecruit.com
Facebook: /Acute-Recruit-369368080173002/
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2018-03-2200 min
The Winning Youth Coaching PodcastWYC 145 – College Recruitment – Carter Armendarez - College recruitment do's and don'tsWYC 145 – College Recruitment – Carter Armendarez - College recruitment do's and don'ts Carter Armendarez is a senior at Wesleyan University, where he's also captain of the wrestling team. Getting recruited to play sports in college is confusing to lots of athletes, but it really shouldn’t be. Carter has seen too many athletes fail to get recruited. So he made Acute Recruit’s College Recruitment Guide for Athletes so that doesn’t happen anymore.
2018-03-2234 min