Leaders In Payments

Greg Myers
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May 6, 2025 • 25min

Jacob Olins, SVP & GM, Fintech at Workwave | Episode 393

Ever wondered how pest control, landscaping, and janitorial companies are being transformed through innovative financial technology? Jacob Olins, SVP & GM of Fintech at WorkWave, takes us deep into the world where field service management software meets cutting-edge financial services.WorkWave has positioned itself as the operating system for field service businesses, providing everything from customer acquisition tools to mobile apps for technicians. But what truly sets their platform apart is how they've revolutionized payments and financial services within these traditional industries. Olins walks us through their journey from payment reseller to full Payment Facilitator, giving them complete control over the customer experience and unlocking new revenue opportunities.The most fascinating aspect of our conversation reveals how embedded financial services are solving real business problems. For companies struggling with customer retention, WorkWave's card-on-file and subscription capabilities have helped transform one-off service calls into recurring revenue streams. Their consumer financing partnerships make large emergency services affordable for homeowners. Perhaps most impressive, their earned wage access feature has increased employee retention by over 30% by allowing hourly workers to access earned wages before payday.Ready to understand how the $13 trillion banking industry is being reshaped by innovative software platforms? Listen now and discover insights that might forever change how you view the intersection of software and financial services.
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May 1, 2025 • 20min

Jeff Shea, Co-Founder & CEO of Under | Episode 392

Meet Jeff Shea, the co-founder and CEO of Under who's revolutionizing how payments companies onboard merchants. Drawing from over two decades in payments and fintech, Jeff has created a digital account opening platform that's solving one of the industry's most persistent challenges.Under helps payments companies streamline merchant onboarding through integrated identity verification, automated risk assessments, and simplified application collection. Serving over 100 payments organizations across the United States, the company primarily works with wholesale ISOs, payment facilitators, payment processors, and software companies that monetize payments. Jeff explains that their platform bridges the gap between disjointed point solutions that many companies currently cobble together, creating a seamless experience from lead generation through merchant approval.The conversation takes a fascinating turn when Jeff discusses the future of payments and underwriting. He predicts continued growth in embedded and verticalized payments as more software platforms own their payment stacks. Looking further ahead, he believes payments will become increasingly commoditized, with differentiation coming from how platforms manage identity, trust, decisioning, and merchant experience. Most compellingly, Jeff references a McKinsey report predicting that traditional underwriting will disappear within a decade, replaced by artificial intelligence, deep learning, and machine learning. These technologies promise faster approvals for legitimate merchants while more effectively identifying problematic applicants.Ready to transform your merchant onboarding process? Discover how Under can help you approve the right merchants faster while reducing risk at under.io.
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Apr 29, 2025 • 23min

Brian Bailey, President of Clip | Episode 391

What happens when you combine decades of payment industry expertise with a mission to solve one of the most overlooked problems in business banking? Brian Bailey, President of Clip Money, joins us to reveal how his company is transforming the way businesses handle cash deposits.Despite the rapid growth of digital payments, cash still accounts for nearly 30% of all in-store transactions. Yet for decades, businesses have been forced to operate within an antiquated system - physically carrying cash to bank branches during limited hours, using paper deposit slips, and lacking visibility into their deposit lifecycle. With a network of 7,000 deposit locations across North America, Clip Money offers a revolutionary alternative that saves businesses 40-60% on deposit costs while providing next-business-day credit.Bailey walks us through Clip's innovative shared network model that includes smart safes in shopping malls, deposit-enabled ATMs in partnership with NCR Atleos, and over-the-counter services through Green Dot's retail network. This infrastructure allows businesses to make deposits on their schedule, closer to their locations, while gaining full digital transparency through Clip's software platform. The result is a win-win proposition - businesses improve cash flow and reduce costs, while financial institutions can move cash handling outside their branches.Drawing from his extensive background at NCR and Cardtronics, Bailey shares valuable insights about payment infrastructure evolution, regulatory challenges for fintech innovators, and the future of shared payment networks. 
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Apr 24, 2025 • 26min

Mary Kay Bowman, EVP & GM of Payments & Financial Services at BILL | Episode 390

Mary Kay Bowman takes us behind the scenes of BILL's mission to transform financial operations for small businesses through an expertly crafted blend of software and financial services. As EVP and GM of Payments and Financial Services, she brings decades of experience from pioneering roles at Amazon, Square, and Visa to tackle the challenges that interrupt the daily flow of small business finance.The conversation reveals how BILL serves as both operational software provider and financial partner to thousands of small businesses across every industry vertical. Working alongside 8,000 accounting firm partners, the platform handles everything from accounts payable and receivable to employee expense management, while supporting transactions across 130 currencies. What truly sets BILL apart is their seamless integration of workflow management with money movement – creating a system that doesn't just process payments but optimizes cash flow at every step.Looking toward the future of payments, Bowman offers a refreshing perspective on the balance between frictionless technology and necessary visibility. While consumer payments often aim to disappear into the background, B2B transactions require strategic visibility at critical moments. This nuanced understanding comes from Bowman's remarkable journey through the evolution of digital payments, beginning at the dawn of internet commerce when she volunteered to tackle the "bumpy intersection" between money movement and technology. Ready to transform your business's financial operations? Discover how BILL's intelligent platform can help your small business thrive by automating the noise and complexity of everyday finance, letting you focus on what truly matters.
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Apr 22, 2025 • 22min

AI in Payments Series: Featuring Payarc Chief Revenue Officer Dustin Siner | Episode 389

Dustin Siner, Chief Revenue Officer at Payarc, brings 27 years of payments industry expertise and a fascinating journey that began with a psychology degree and a brief stint as a rehabilitation counselor. His therapeutic background proved surprisingly valuable in navigating the complex payments landscape, where relationship building remains the cornerstone of success despite technological advances.Fresh from Payarc's recognition as ISO of the Year at the Electronic Transactions Association (ETA), Dustin reveals the secret behind their meteoric rise - "The Payarc Way." This philosophy, built on integrity, empathy, courage, knowledge, and caring, guides how the company supports its network of 1,400+ independent agents, ISOs, and ISVs who generate an impressive 95% of their business.While many competitors devalue the independent agent channel, Payarc doubles down on relationships with dedicated managers, responsive support teams, and proprietary technology platforms designed exclusively for partners. Their Partner Hub provides comprehensive tools for the entire sales process, from application to approval, while their suite of payment solutions offers partners competitive advantages in a crowded marketplace.What truly distinguishes Payarc is their approach to artificial intelligence through their PIE AI program. Rather than replacing human interaction, they enhance it - helping partners analyze statements with PIE Agent Advisor, predict customer churn with PIE Churn, and enable merchants to gain business insights through natural language queries with PIE Merchant Advisor.For agents, ISOs, and ISVs seeking a partner that values relationships as much as innovation in an increasingly consolidated market, Payarc offers a refreshing alternative where technology and humanity work together to drive mutual success.
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Apr 16, 2025 • 29min

Allen Kopelman, CEO & Founder of Nationwide Payment Systems | Episode 388

Allen Kopelman, CEO and Founder of Nationwide Payment Systems, takes us behind the curtain of the rapidly evolving payments landscape, sharing insights gained from his fascinating career transition from restaurant chef to payments industry leader. Since founding his company in 2001, Allen has navigated multiple industry transformations, positioning his business to thrive amid technological disruption.The conversation reveals a fundamental shift in merchant priorities: "Today businesses are buying tech first, merchant services second." This observation frames Allen's provocative assertion that "Software is the new ISO."Looking ahead, Allen identifies several critical trends reshaping payments: the dominance of software-driven solutions, the impact of the FTC's "click-to-cancel" rule on recurring transactions, and potential interchange fee adjustments from card networks. He offers a compelling perspective on artificial intelligence as well, revealing how his company has leveraged AI to dramatically improve SEO performance and predicting that "people who know how to use AI will replace people who don't use AI."Ready to gain insights from a payments veteran who's successfully navigated decades of industry evolution? This episode delivers practical wisdom you can apply immediately to your payments business or career.
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Apr 10, 2025 • 22min

Andrew Riabchuk, Founder & CTO of Akurateco | Episode 387

Andrew Riabchuk's journey from building a payment gateway prototype as a computer science student in Ukraine to founding Akurateco—a global payment orchestration platform—reveals how technical expertise shapes fintech innovation. During our conversation, Andrew offers a fascinating perspective on what payment orchestration truly means beyond simple transaction routing: it's about creating value, reducing complexity, and enabling businesses to scale globally with minimal friction.The technical side of payments is becoming increasingly sophisticated while consumer experiences grow more seamless. Andrew explains how Akurateco navigates this paradox by providing a platform that handles the complexity behind the scenes, allowing their clients—payment service providers, banks, and enterprise merchants—to focus on their core business. With over 50 pre-integrated financial partners accessible through a single integration point, businesses can quickly expand into new markets and offer localized payment methods without the traditional technical burden.What stands out most about Andrew's approach is the emphasis on partnership over mere service provision. Their "payment team as a service" concept reflects a deeper understanding that payments success requires both advanced technology and human expertise. As payment verticals become increasingly specialized for specific industries, and as cryptocurrency gradually moves toward mainstream adoption, Andrew's insights offer a valuable roadmap for navigating the evolving payments landscape. Want to learn more about streamlining your payment operations or explore how payment orchestration could transform your business? Connect with Andrew and the Akurateco team to discover strategies that could simplify your technical infrastructure while expanding your global reach.
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Apr 8, 2025 • 27min

Will Martino, President & Co-Founder of Kadena | Episode 386

Blockchain technology is finally crossing the threshold from speculative promise to practical implementation, and Will Martino is at the forefront of this transformation. As President and Co-Founder of Kadena, Will brings unique credentials to the blockchain space—having built JP Morgan's first blockchain payment system before leaving to solve the fundamental limitations preventing enterprise-grade adoption.The blockchain industry has struggled with a persistent trilemma: how to achieve security, decentralization, and scalability simultaneously. Kadena's breakthrough comes through its innovative ChainWeb architecture, which horizontally scales proof-of-work consensus without corresponding increases in energy consumption. "Right now we have 20 chains that are all in a single network, braided together using proof of work," Will explains. "When we go from 20 to 40, we actually increase our efficiency by 2x for basically no cost."This technical achievement arrives at a pivotal moment. Financial institutions that once insisted on private blockchains are now actively exploring public blockchain integration following BlackRock's successful SEC-approved protocol launch. This shift has created unprecedented opportunity for proof-of-work blockchains like Kadena that offer stronger security guarantees than proof-of-stake alternatives.Beyond the technical architecture, Will's team is addressing critical user experience challenges through SpireKey—a decentralized authentication system inspired by Sweden's Bank ID that transforms smartphones into hardware wallets. Having lived through the early, sometimes painful days of blockchain development (including lost wallet keys worth thousands), Will is committed to making the technology accessible to everyone.Check out kadena.io to explore how this next-generation blockchain is building the infrastructure for crypto's inevitable mainstream adoption.
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Apr 2, 2025 • 28min

Joe Mach, CEO of Castles Technology | Episode 386

Joe Mach, CEO of North America at Castles Technology, reveals how this fourth-largest player in payment terminals has captured massive market share while flying under the radar. Their secret? Over 60% of everything they sell doesn't bear their name - it's white-labeled for partners who trust them enough to put their own brands on the technology.Castles' success stems from their deep technical expertise and customer-first approach. Based in Taiwan ("Technology Island"), they innovate faster than legacy providers, delivering not just hardware but comprehensive solutions tailored to specific industry challenges. Their movement from basic terminal management to true Mobile Device Management capabilities enables remote troubleshooting, geofencing for security, and even AI-powered predictive maintenance.Looking forward, Mach identifies three transformative trends: the rising influence of specialized software vendors, seamless integration of AI with payments, and the emergence of SoftPOS technologies on consumer devices. These innovations address the expectations of younger consumers who simply won't tolerate friction in their shopping experiences.As an "accidental CEO" who rose through sales and commercial roles, Mach's leadership philosophy centers on growth - not just for shareholders, but as a vehicle to create opportunities for employees. Listen now to discover how Castles Technology is transforming the payment landscape for merchants of all sizes.
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Mar 27, 2025 • 29min

Navigating the Payments Ecosystem: Insights from MAPP Advisors | Episode 384

The payments ecosystem is evolving rapidly, creating both challenges and opportunities for every player in the industry. In this thought-provoking conversation with Alexander Renzi and Aleks Teichman of MAPP Advisors, we dive deep into how ISOs, ISVs, banks, and fintechs can navigate this changing landscape.Alexander and Aleks bring unique perspectives from their decades of experience across all facets of the payments industry. They offer invaluable insights into the practical realities of growing a payments business today. Their firm, MAPP Advisors, works collaboratively with companies across the ecosystem, providing actionable guidance rather than theoretical advice.For ISOs facing unprecedented pressure from all angles – regulatory scrutiny, processor competition, and integrated payments solutions – the message is clear: adapt or perish. The most successful ISOs are evolving beyond transaction processing, building deeper relationships with merchants through value-added services. Bank-fintech partnerships represent another critical evolution in payments. What was once a vendor-client relationship has transformed into essential collaborative partnerships. Banks are no longer just fine print on merchant applications – they're strategic partners whose sustainability and approach are key considerations for fintechs and ISOs alike.Whether you're running an ISO, developing payments technology, or working within a financial institution, this episode offers strategic insights to help you navigate growth, regulation, and partnerships in today's complex payments landscape. 

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