Tech Sales with Carter

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

• How to motivate and build strong relationships with salespeople on a remote team
• What Rodney looks for when hiring, from upward career progression to referrals and interview follow-up
• How to coach an underperforming rep using curiosity, radical candor, and a team-first approach
• Why great sales leaders manage each person differently instead of using the same approach with everyone
• How to tell whether a top-performing individual contributor is actually ready to become a manager
• Why mastering the fundamentals, finding mentors, and embracing discomfort are critical for long-term career growth

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Deel: https://www.deel.com/

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

• How to know when you’ve stopped growing and it may be time to leave a company
• Why mastering smaller deals prepares sellers to win six- and seven-figure opportunities
• What separates the best sales leaders from strong individual contributors
• Why great managers empower their reps instead of stepping in and doing the work for them
• How Salesforce evaluates aptitude and attitude instead of relying only on a candidate’s resume
• Why investing in career development and recognition helps leaders retain their best salespeople

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Salesforce: https://www.salesforce.com/

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

• How cold calling builds the resilience needed to succeed throughout a sales career
• Why trust is the foundation of selling technology to banks and financial institutions
• What separates a strategic account leader from someone who is simply a strong closer
• Why new sales leaders must shift their focus from personal success to their team’s success
• How authenticity and relentless curiosity help teams build something from the ground up
• What separates revenue-producing partnerships from partnerships that only create meetings and press releases

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about FICO: https://www.fico.com/

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

• How to become the most obvious candidate for a sales leadership role
• Why building a strong internal brand matters alongside hitting your number
• Why Ben moved from sales enablement back into a quota-carrying AE role
• How “trust but verify” changed the way Ben coaches and manages sellers
• Why AI sales conversations should start with the buyer’s broader strategy—not your product
• How meaningful goals can help you prioritize your time and eliminate distractions

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Slack: https://slack.com/

In this episode, I sit down with Jolie Stern, Enterprise Account Executive at Gong, to talk about how she moved from BDR to Enterprise AE and RVP in less than five years at Slack and Salesforce. Jolie breaks down why internal networking, building a strong brand, and creating impact beyond the dashboard helped her move up quickly inside a large sales organization.

We also talk about what it takes to ramp fast at a new company, why she chose to stay focused on financial services, and how reps can sell technology into slower-moving, highly regulated industries. Jolie shares how she thinks about change management, security and compliance objections, getting in person with customers, and how to separate serious AI buyers from prospects who are just curious.

TOPICS WE COVER

• How Jolie moved from BDR to Enterprise AE and RVP in less than five years
• Why internal networking and building a strong brand can accelerate your sales career
• How to ramp quickly when joining a new company as an experienced seller
• Why specializing in one vertical can create more opportunity over time
• How to sell technology into slow-moving financial services companies
• How to tell the difference between serious AI buyers and tire kickers

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Gong: https://www.gong.io/

In this episode, I sit down with Anthony Romano, CEO of CREtelligent, to talk about hiring, leading, and retaining great salespeople. Anthony shares what he looks for when evaluating sales candidates, including repeatable success, curiosity, presence, competitiveness, and extreme ownership. He also explains why the best individual contributor is not always the best manager, and what actually signals that a rep may be ready to lead.

We also talk about what makes a great sales organization work behind the scenes. Anthony breaks down why top salespeople need more than a strong comp plan, how companies can retain high performers with enablement, culture, data, and career paths, and why customer loyalty is one of the strongest leading indicators of long-term growth. He also shares one of the biggest lessons he learned in sales: people love to buy, but they hate to be sold. The best sellers ask better questions, diagnose before they prescribe, and disqualify bad deals faster.

TOPICS WE COVER

• What CEOs look for when hiring great salespeople
• Why repeatable success matters more than a good-looking resume
• How to know if a top sales rep is actually ready for sales leadership
• Why great salespeople need enablement, culture, and career growth to stay
• How customer loyalty, NPS, retention, and referrals connect to revenue growth
• Why the best sellers diagnose before they prescribe and disqualify bad deals faster

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about CREtelligent: https://www.cretelligent.com/

In this episode, I sit down with Tiffany Stringfellow, Director of Client Development at Moody’s, to talk about selling AI-powered workflow tools into lenders, banks, and credit unions. Tiffany shares why cycle time is often the pain that gets lenders to take a conversation seriously, especially in home equity lending where fintechs can move quickly and traditional institutions need to compete without increasing risk.

We also talk about why selling into financial services requires more than a strong product demo. Tiffany explains why lenders are workflow-driven, risk-driven, and regulation-driven, and why sellers need to understand those constraints early in the deal. She shares how ROI stories become more powerful when they are built around the customer’s real data, why risk and compliance need to be involved before the end of the sales cycle, and why deals can go silent when champions are left to fight internal battles alone.

TOPICS WE COVER

• Why cycle time is one of the biggest pain points in home equity lending
• How banks and credit unions compete with faster fintech lending experiences
• Why AI products need to balance speed, risk, and regulatory requirements
• What tech sellers get wrong about selling into lenders and financial institutions
• How to build ROI stories using the customer’s actual workflow and data
• Why risk, compliance, and operational roadblocks need to be handled early in the deal

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Moody’s: https://www.moodys.com/

In this episode, I sit down with Amanda Padd, Chief Revenue Officer at Secure Insight, to talk about selling fraud prevention and risk management technology into the mortgage industry. Amanda explains why many lenders only start looking for solutions after a scare, an audit finding, or an actual fraud event, and why companies need to think about wire and closing fraud before it becomes too late.

We also talk about why mortgage is still such a relationship-driven, face-to-face industry. Amanda shares how she uses conferences, in-person meetings, and vendor-only dinners to build trust, create referral relationships, and stay top of mind with lenders and other mortgage technology providers. She also explains why reputation matters so much in a small industry, why partying at conferences can damage credibility, and how she decides when a prospect is serious versus just wasting time.

Amanda also shares how consistency has helped grow her personal brand over the past year. From LinkedIn to podcasts, awards, publications, and conferences, she explains why there is no single silver bullet and why showing up consistently across multiple channels is what really moves the needle.

TOPICS WE COVER

• Why lenders often wait until after a fraud scare to look for risk prevention tools
• How Secure Insight helps mortgage lenders protect against wire and closing fraud
• Why mortgage is still such a face-to-face, relationship-driven industry
• How vendor-only dinners can create referral relationships and industry trust
• The biggest reputation mistakes people make at mortgage conferences
• Why consistency across LinkedIn, conferences, podcasts, and industry events builds a stronger personal brand

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Secure Insight: https://secureinsight.com/

In this episode, I sit down with Alexis Cisneros, Vice President of Client Success at Matey AI, to talk about what happens after the deal closes, how customer churn can start during discovery, and why sales and customer success teams need to work together long before implementation begins. Alexis shares why delayed onboarding is often an early warning sign, how AEs can prevent churn by identifying real champions and power users, and why rigorous qualification matters before a customer ever reaches the post-sale team.

We also talk about selling AI into legal teams, where trust, security, and expectation-setting are critical. Alexis explains why reps should never promise that AI can “do magic,” how Matey AI builds trust with litigators, firms, and government offices, and why the best customer champions are the ones who refer, expand, and bring their colleagues into the product. She also shares why “the deal is never done” and why CS teams are always selling through renewals, expansions, referrals, and stronger client relationships.

TOPICS WE COVER

• Why churn can start during discovery before the customer ever reaches onboarding
• How delayed implementation can reveal weak urgency, weak champions, or poor qualification
• What AEs should avoid promising during the sales cycle, especially with AI products
• How Matey AI builds trust with legal teams handling sensitive case information
• What great customer champions look like after the sale
• Why the deal is never really done after the contract is signed

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/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Matey AI: https://www.matey.ai/

In this episode, I sit down with Ben Sizemore, Chief Information Officer at Land Gorilla, to talk about how technology buyers evaluate vendors, what makes salespeople credible with executives, and why most software pitches fail before they ever become real conversations. Ben shares why CIOs do not want to be “sold,” why cold outreach rarely works on him unless there is already some relationship or in-person context, and why the best sales conversations are grounded in facts, numbers, workflow impact, and ROI. 

We also talk about what really drives lending technology purchases: operational efficiency, doing more with less, and reducing cost or manual work. Ben explains why some products become table stakes instead of delivering real ROI, how sellers should tailor their message to different executive audiences, and why he sometimes has to help vendors reshape their own pitch so they can win internal approval. 

TOPICS WE COVER

•  Why CIOs ignore most cold outreach unless there is already context or a relationship 
•  How conferences help vendors get in front of executives more effectively than generic emails 
•  Why lending technology purchases usually come down to operational efficiency and ROI 
•  What makes a software salesperson credible early: facts, numbers, preparation, and intelligent answers 
•  Why executives do not want to be sold — they want a real conversation about workflow, value, and fit 
•  How sellers lose deals by failing to tailor the message to the buyer, audience, and approval process 

ABOUT THE GUEST

Ben Sizemore is the Chief Information Officer at Land Gorilla, a construction lending software company serving the mortgage industry and other industries where construction lending is involved. Ben has spent more than 35 years in technology and lending, and brings a CIO’s perspective on software buying, internal selling, vendor evaluation, and what executives need to hear before approving new technology. 

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Land Gorilla: https://landgorilla.com/