Tech Sales with Carter

In this episode, I sit down with Jordan Benjamin, CEO of My Core OS and former 6x President’s Club member at HubSpot, to talk about the mindset and psychology behind sustainable sales performance. Jordan breaks down the biggest lies reps believe about success, including the idea that more hours and more dials automatically lead to better results, and explains why energy, self-awareness, and emotional resilience are often the real drivers of consistent performance. He also shares how top reps can tell whether missed quota is really a skill problem or a mindset problem, and why confidence, internal stories, and self-belief quietly shape how people show up on calls every day. 

We also get into social selling, career growth, and what reps can do when they feel stuck. Jordan explains how he built My Core OS from corporate workshops into a more direct-to-consumer coaching business, why LinkedIn has become such a powerful channel for both prospecting and brand building, and how sales reps should think about using it more like a landing page than a resume. He also shares practical advice on gratitude, imposter syndrome, asking for help, and how to structure a strong interview story around why you, why now, and why this role. 

TOPICS WE COVER

•  Why more hours and more dials are often not the real answer to better sales performance 
•  How to tell whether a rep is missing quota because of skill issues or mindset issues 
•  Why emotional intelligence, self-awareness, and confidence matter so much in sales 
•  How Jordan built My Core OS and what changed as he moved from corporate workshops to coaching individuals 
•  Why LinkedIn is such an overlooked tool for prospecting, personal brand, and social selling 
•  How to handle imposter syndrome, build better habits, and structure a stronger interview story 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about My Core OS: https://www.mycoreos.com/

In this episode, I sit down with Erica Waldron and Andrea Castelli, Account Executives at Snapdocs, to talk about their unconventional path into mortgage tech sales and how they built their way into the industry by starting their own signing service from scratch. Before joining Snapdocs, Erica and Andrea co-founded Sunny Signings LLC during COVID after seeing the surge in demand for mobile notary services, then later merged the business with First Class Signing Service. They share how they went from bartending and working in real estate-related roles to building a company together, knocking on doors at title companies, bringing flowers into offices, and figuring things out in real time with no safety net.

We also get into what made their partnership work, why merging their business ended up accelerating their growth, and how their reputation in the signing world helped create the opportunity to join Snapdocs. Erica and Andrea explain why the transition into tech sales was more natural than people might expect, how their experience on the title, notary, and signing service sides gives them credibility with clients, and what it looks like to operate as a true AE duo inside a tech company. They also share advice for people trying to break into mortgage tech sales without a traditional background and why keeping your options open can lead to opportunities you never would have planned for. 

TOPICS WE COVER

•  How Erica and Andrea went from bartending and real estate-adjacent roles to launching Sunny Signings during COVID 
•  What they learned from building a signing service from the ground up through door-to-door outreach and conferences 
•  Why merging Sunny Signings with First Class Signing Service helped them grow faster than staying independent 
•  How their industry reputation and experience using Snapdocs led to the opportunity to join the company 
•  Why the move from signing services into tech sales was more transferable than most people would expect 
•  How they function as a true AE duo at Snapdocs and why being a package deal has actually worked in their favor 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Snapdocs: https://www.snapdocs.com/

In this episode, I sit down with Pat Mulvey, Director of Global Business Development at Zywave, to talk about what it actually takes to reset and scale a business development team inside a changing go-to-market environment. Pat breaks down why you cannot just copy and paste a strategy from one company to another, even if it worked at a high level somewhere else, and explains how he thinks about diagnosing a BD org through Salesforce rigor, deal velocity, and repeatable patterns in the data. He also shares what he looks for when hiring new BDR talent, why athletes and other highly driven profiles often stand out, and how commitment, grit, and self-awareness tend to show up early in the people who go on to perform.

We also get into leadership, coaching, and the habits that separate strong reps from struggling ones. Pat explains why reps who adapt fastest to leadership change are usually the ones who ask for help early, why poor time management quietly kills performance, and how he handles underperformance before it turns into a formal process. He also talks through the shift from being a seller to becoming a manager, why new leaders often stay too attached to the rep identity, and what someone should consider before deciding they want to pursue leadership long term.

TOPICS WE COVER

•  Why you cannot just reuse the same go-to-market playbook at a new company, even after success somewhere else 
•  How Pat evaluates a BD org through Salesforce data, deal velocity, repeatability, and ICP fit 
•  What he looks for when hiring BDRs, including grit, commitment, and why athletic backgrounds can stand out 
•  Why reps who adapt fastest to leadership change usually ask for help early instead of sitting back 
•  The biggest hidden mistake BDRs make with time management and why it wrecks performance 
•  What changes when a strong rep becomes a manager, and how to know if leadership is actually the right path 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Zywave: https://www.zywave.com/

In this episode, I sit down with Craig Holbrook, Vice President of New Client Acquisition Sales at nCino, to talk about what sales leaders actually look for when hiring, coaching, and developing reps. Craig shares lessons from more than a decade in mortgage sales and leadership, including why some qualities simply cannot be coached, why you cannot turn a D player into an A player, and how strong sales leadership starts with understanding what motivates each rep differently. He also breaks down the intangibles he looks for in account executives, including work ethic, curiosity, assertiveness, and attention to detail, and explains why those traits matter more than surface-level interview polish.

We also get into coaching, management, and what it really takes for a rep to grow into a leadership role. Craig explains how he evaluates a team in the first 90 days, why he believes in giving reps freedom within a framework, and how he coaches strong performers who are still leaving money on the table because of bad habits. He also talks through how nCino is using AI in its hiring process to analyze assessments, generate probing interview questions, and help identify candidates with the right underlying traits to succeed in sales.

TOPICS WE COVER

•  Why some sales traits, like work ethic, curiosity, and assertiveness, are hard or impossible to coach 
•  Why you cannot turn a D player into an A player, and how Craig thinks about developing talent more realistically 
•  How Craig evaluates a new team in his first 90 days and sets expectations with a freedom-within-a-framework approach 
•  How to coach reps who are hitting quota but still have bad habits that are limiting their upside 
•  What separates a strong individual contributor from someone who is actually ready to lead a team 
•  How nCino is using AI in hiring to analyze assessments, generate better interview questions, and improve candidate evaluation 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about nCino: https://www.ncino.com/

In this episode, I sit down with Ian Grace, VP of Sales at Ocrolus, to talk about what it takes to turn a sales team around, coach reps more effectively, and build a repeatable process that actually drives revenue. Ian breaks down how he came into Ocrolus during a brutal stretch for the mortgage industry and helped overhaul the sales motion by implementing forecasting, deal coaching, MEDDPICC, and a blended approach built around gap selling and challenger principles. He explains why great discovery is still the foundation of winning deals, and why too many reps stop at surface-level pain instead of digging until they understand the real business impact in dollars. 

We also get tactical on pipeline management, leadership, and the use of AI inside modern sales organizations. Ian shares why thin pipeline is usually a prospecting discipline problem before it is anything else, how managers can coach reps without taking deals over for them, and what changed in his own leadership when he stopped thinking about himself and started thinking more about how to truly support his team. He also talks through how Ocrolus is experimenting with Claude and Gong to score calls, evaluate reps against sales frameworks, and create more precise coaching feedback at scale. 

TOPICS WE COVER

•  How Ian helped improve win rates at Ocrolus by implementing forecasting, deal coaching, MEDDPICC, and stronger day-to-day sales habits 
•  Why shallow discovery kills deals, and how the best reps turn pain into real dollar impact that creates urgency 
•  The most common reasons deals stall, including weak champions, lack of multithreading, and incomplete discovery 
•  Why pipeline problems usually start with prospecting discipline, and how Ian thinks about quantity before quality 
•  What strong sales coaching looks like in practice, including call review, live feedback, and helping reps improve without taking over for them 
•  How Ian is using tools like Gong and Claude to score calls, evaluate reps against sales frameworks, and create more actionable coaching feedback 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Ocrolus: https://www.ocrolus.com/

In this episode, I sit down with Matt Nucifora, Senior Manager of Enterprise Sales at Dandy and former Principal Manager of Mid-Market Sales at HubSpot, to talk about what it actually takes to get promoted consistently, coach sales reps effectively, and lead teams through more complex enterprise sales motions. Matt breaks down the difference between simply performing well in your current role and actively showing you can do the next one. He explains why strong promotion cases are built on objective performance, visible leadership behaviors, and the ability to operate at a higher level before anyone formally gives you the title. 

We also get tactical on sales coaching, deal diagnosis, and startup go-to-market. Matt shares why stalled deals usually trace back to weak discovery a few calls earlier, how to coach underperforming reps using data instead of guesswork, and why managers should focus on fixing one problem at a time instead of trying to improve everything at once. He also talks through the transition from HubSpot to Dandy, what carries over when entering a new industry, and what he has learned through Stage 2 Capital about hiring startup sales talent, building repeatable process, and helping early-stage companies move from raw potential to real revenue. 

TOPICS WE COVER

•  Why Matt got promoted so consistently at HubSpot, including the importance of objective performance and showing you can already do the next job before you get it 
•  What it looks like to enter a new industry as a sales leader, including how to learn the buyer, the language, and the business problems fast 
•  The most common reason deals get stuck, and why the real problem usually happened earlier in discovery rather than at the end of the sales process 
•  How Matt coaches underperforming reps using deal data, call review, and a one-variable-at-a-time approach to improvement 
•  What founders often get wrong when hiring startup sales talent, especially when they choose comfort over the kind of sales DNA that can actually create growth 
•  What Matt looks for when helping Stage 2 Capital portfolio companies, including where process, pipeline, urgency, and hiring can unlock outsized revenue gains 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Dandy: https://www.meetdandy.com/

In this episode, I sit down with Fred Ramstedt, Business Development Executive at Wipro Gallagher Solutions and former Director of Sales at TRUE, to talk about what it really takes to sell complex mortgage technology when the stakes are high, the sales cycles are long, and buyers are skeptical of empty ROI claims. Fred breaks down the difference between selling a point solution that improves one part of the workflow versus selling a broader platform that helps lenders rethink how the entire loan manufacturing process should work. He also explains why the best mortgage tech sellers are not just pitching features. They’re helping lenders understand operational friction, implementation risk, and what meaningful change will actually require.

We also get tactical on enterprise sales. We talk about what proof actually makes buyers believe an ROI story, what good discovery sounds like in mortgage tech, and why deals often stall even when the value seems obvious. Fred shares how to surface real urgency, why change management is often the real blocker, and what shifts when you go from selling at a fast-moving startup like TRUE to selling inside a much larger organization like Wipro. He also explains why no sale is ever easy, why large complex deals require multiple champions, and how top sellers use AI, research, and customer context to stay relevant in long enterprise cycles.

TOPICS WE COVER

•  Fred’s background in mortgage technology and how his work has evolved from document intelligence and AI at TRUE to broader platform and workflow conversations at Wipro Gallagher Solutions 
•  The difference between selling a point solution that fixes a specific operational problem and selling a platform that helps lenders redesign the full loan manufacturing process 
•  What actually makes mortgage buyers believe the ROI story, including why speed, cost, risk, and well-defined proof of concept criteria matter most 
•  What good discovery looks like in mortgage tech, including how to trace the loan process, find friction, and ask questions that expose where the real pain lives 
•  Why deals stall even when the value is obvious, and how implementation risk, competing priorities, and internal resistance often matter more than product fit 
•  What changed for Fred when he moved from TRUE to Wipro, including broader conversations, more strategic deals, longer cycles, and much more organizational firepower behind the sale 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Wipro Gallagher Solutions: https://www.wipro.com/gallagher/

In this episode, I sit down with David Gipson, Director of Sales Engineering at Ocrolus, to break down what it really takes to sell AI and automation into mortgage. David shares how his background as an underwriter, loan officer, and sales ops leader shapes the way he helps lenders evaluate new technology, and why the best sales conversations are never really about flashy features. They’re about solving real workflow pain in a way that feels practical, familiar, and easy to adopt.

We also get into how skepticism around AI has changed inside lending, why multi-persona messaging matters so much in mortgage sales, and what actually causes long deals to stall out. David explains how Ocrolus navigated the brutal mortgage downturn, why slow markets can be the best time to evaluate tech, and how reputation compounds in a tight-knit industry like mortgage. He also shares one of the most underrated ways to save a stalled deal: getting on a plane, showing up in person, and working through problems face-to-face.

TOPICS WE COVER

•  What sellers get wrong when pitching underwriting automation to lenders 
•  Why mortgage buyers care more about solving practical problems than hearing about flashy AI features 
•  How skepticism around AI is changing across executives, operators, and end users 
•  Why making automation feel familiar is critical for adoption inside mortgage teams 
•  How to demo more effectively by tailoring messaging to each lender’s mix of products and priorities 
•  How David coaches sales engineers to prepare for demos using research, AI tools, and persona-specific messaging 
•  What usually causes long mortgage tech deals to stall out or die around month six 
•  Why “time kills deals” and how unclear positioning creates paralysis by analysis 
•  How Ocrolus adjusted its sales approach during the mortgage downturn when rates rose and budgets tightened 
•  Why slow markets can be the best time for lenders to evaluate and replace technology 
•  How Ocrolus used the downturn to improve product-market fit and prepare for the rebound 
•  Why reputation compounds in the mortgage industry and drives more pipeline over time 
•  How strong implementation, support, and client success teams help build brand trust in a relationship-driven market 
•  Why in-person meetings still matter and how face-to-face collaboration can rescue or accelerate deals 
•  Why showing customers you care enough to get on a plane can change the entire sales dynamic 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Ocrolus: https://www.ocrolus.com/

In this episode, I sit down with Robby MacAskill, Director of Business Development at Zonda, to talk about one of the biggest blind spots in mortgage sales: why lenders are often chasing the wrong builder accounts and missing easier opportunities hiding in plain sight. Robby shares what he’s learned from working with lenders on builder strategy every day, including why mid-sized production builders are often a far better target than most loan officers realize and how data can reveal where the real openings are. 

We also get tactical on prospecting and sales execution. We talk about how to break into builder relationships that already seem locked up, why in-person outreach still creates a huge edge, and which loan products can open the door fastest. Robby also pulls lessons from his transition into tech sales, including the importance of repeated outreach, multi-threading, time blocking, and running sales conversations that are so valuable the buyer feels like they should have paid for them. 

TOPICS WE COVER

•  Why most lenders misunderstand the builder opportunity, and where the real opening is with mid-sized production builders rather than only chasing national accounts 
•  How to identify builders that do not have strong lender relationships, including the signals Zonda uses to find low-capture-rate accounts 
•  Why the best path into builder business is usually through the sales reps on the ground, not just the CEO or division president 
•  The power of in-person prospecting, including driving to sales offices, meeting multiple reps, and building momentum across an entire builder organization 
•  Loan products that help lenders win builder referrals, including FHA and VA manual underwrites, buy-before-you-sell programs, and forward commitments 
•  What mortgage salespeople can learn from SaaS prospecting, especially the importance of four to five outreach attempts before expecting a response 
•  Why multi-threading matters so much, including how to spread awareness inside an account and turn one meeting into multiple stakeholders and champions 
•  How to use industry events to create pipeline, including pre-event outreach, attendee research, and scheduling follow-up meetings before the conversation ends 
•  Robby’s biggest lessons from tech sales, including teaching instead of pitching, protecting time for revenue-generating activities, and building a true partnership with your SDR 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Zonda: https://zondahome.com/

In this episode, I sit down with Suzy Djilas, Enterprise Account Executive at Arcasa and former Director of Sales at nCino, to talk about what it takes to build trust and sell effectively in the mortgage industry over the long haul. Suzy shares how her 35-year career has evolved alongside the industry, from a highly manual, relationship-driven business to a more tech-enabled one, and why the fundamentals of credibility, honesty, and face-to-face connection still matter just as much as ever.

We also get tactical on sales. We talk about the difference between selling mortgage technology and selling a financing product tied directly to borrower outcomes, how to introduce a product that feels new or unconventional, and why in-person meetings still create an advantage in mortgage sales. Suzy also explains why she left leadership to go back into an individual contributor role, what she loves about winning over skeptical buyers, and the mindset that has helped her stay successful for decades.

TOPICS WE COVER

•  Suzy’s 35-year journey in mortgage, from Chase to Ellie Mae to nCino to Arcasa 
•  The difference between selling mortgage software versus selling a financing product tied directly to helping borrowers get into homes 
•  How to pitch a product that feels new or unconventional to lenders, and what has to happen for adoption to click 
•  Why Arcasa leads with down payment assistance rather than “solar,” and how Suzy reframes the conversation around borrower outcomes 
•  The role of credibility, honesty, and long-term relationships in overcoming objections and getting lenders to take a smaller company seriously 
•  Why face-to-face selling still matters so much in mortgage, including reading the room, handling doubt in real time, and building trust faster in person 
•  Why Suzy moved from a Director of Sales role back into an AE seat, and what she missed about owning the full sales process 
•  How to turn a skeptical buyer into a champion by asking better questions and staying in the conversation 
•  Suzy’s advice for salespeople on honesty, persistence, believing in your product, and treating “no” as “not yet” 
•  Why conferences are less about instant leads and more about warm introductions that open doors to the right stakeholders 

ABOUT THE 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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Arcasa: https://www.arcasa.io/