Women Leaders in Payments: Maggie O'Toole, Chief Client Officer at Dash Solutions | Episode 410

Maggie O'Toole's remarkable journey from arriving in Chicago from Poland with just $300 to becoming Chief Client Officer at Dash Solutions exemplifies the power of mindset and determination in creating extraordinary outcomes. Her story serves as both inspiration and blueprint for anyone looking to make their mark in the payments industry.With disarming candor, Maggie shares the formative experiences that shaped her leadership philosophy – from bartending jobs in her early days to orchestrating client success strategies at a Fortune-recognized innovative company. She reveals how focusing on possibilities rather than limitations became her superpower, allowing her to navigate unfamiliar terrain without a support system and ultimately thrive professionally.At the heart of Maggie's leadership approach is a profound understanding that business success stems from human connection. "Businesses are people, and people want to do business with who they like and trust," she emphasizes, highlighting how Dash Solutions differentiates itself through exceptional service built on relationships. This philosophy drives her work transforming how companies handle payment operations across healthcare and other sectors traditionally slow to embrace digital innovation.Maggie offers a refreshingly nuanced perspective on modern leadership, advocating for situational approaches tailored to team members' growth journeys rather than one-size-fits-all management. She stresses the importance of psychological safety in fostering innovation, encouraging teams to "question everything" and imagine what might be possible if failure wasn't an option. For women navigating career advancement, her advice to "find your tribe" rather than just pursuing job titles resonates as both practical and profound.

Discover the evolution of leadership in the payments industry through the lens of someone who's lived it. Sheffali Welsh, Chief Operating Officer of The Clearing House, brings a unique perspective shaped by her unconventional journey from cognitive science studies to overseeing operations for America's only private payment network operator.The payments landscape demands a special kind of leadership – one that balances innovation with stability, risk-taking with prudence, and technical expertise with people-centered approaches. Sheffali articulates how leadership in financial services has transformed from the hierarchical, top-down model of decades past to today's collaborative, empowering style that connects employees to purpose and embraces flexibility. Her experiences navigating the 2008 financial crisis as chief of staff to Citigroup's global CFO provided invaluable lessons about leadership during turbulence that continue to shape her approach today.What sets great leaders apart? According to Sheffali, it's "grit" – that powerful combination of passion and perseverance particularly evident in women who've had to play the long game in their careers. She makes a compelling case for how this quality is perfectly suited to the payments industry, where innovations like real-time payments require both visionary thinking and patient execution. Her insights on the distinction between mentorship and sponsorship illuminate why women still need more advocates who will speak up for them when they're not in the room. Looking ahead, she's watching the emerging digital assets and stablecoin landscape as payments' next frontier.Listen now and discover why playing the long game through strategic lateral moves might be your best career strategy in the dynamic world of payments.

What happens when the primary users of an industry's products aren't well-represented in its leadership? Serena Smith, Chief Client Officer at i2c, tackles this fundamental question in a fascinating exploration of women's influence in the payments ecosystem.The stark reality? Women drive 85% of consumer purchases across categories but hold only 27% of C-suite positions in financial services. This disconnect creates a leadership opportunity that Serena has embraced throughout her remarkable career journey, which began in a bank's mailroom and led to executive roles spanning global payment operations.Serena shares the pivotal risk that transformed her career trajectory - pitching a new remittance processing business directly to FIS's executive team when her position was threatened by an acquisition. This bold move not only saved her job but catapulted her career forward, embodying her philosophy that calculated risk-taking and authentic leadership are essential for success.Her battle with cancer represents another transformative chapter, reshaping how she approaches leadership: "I'm not the same person I was before cancer. I'm stronger, wiser, more alive." This experience taught her to lead with purpose, gratitude, and a heightened awareness of what truly matters.As payments become increasingly personalized, Serena emphasizes that tomorrow's successful payment solutions must adapt to consumers rather than the reverse. At i2c, she helps clients navigate this evolution through a flexible technology stack that supports global payment processing needs across 90+ countries.For aspiring women leaders, Serena's advice is clear: own your story, recognize your unique perspective as strength, develop deep business knowledge, and both seek and provide mentorship. The future of payments needs diverse voices at the table, especially from those who understand consumer needs firsthand. 

Billi Jo Wright's unconventional journey from working in her uncle's sheet metal factory to executive leadership in payments spans nearly three decades and offers powerful lessons about persistence, adaptability, and betting on yourself. Without a college degree but armed with boundless curiosity, Billi Jo navigated through various roles across issuing and acquiring before finding her passion in risk management, where she's thrived by approaching old problems with fresh perspectives.Two pivotal moments shaped her career trajectory: first, when she returned to work after having four children in 18 months, eventually becoming her family's sole breadwinner; and second, when she left what seemed like a dream role at a large company to join a smaller startup where she could drive meaningful change. Both decisions required tremendous courage and self-confidence—qualities that continue to define her leadership approach.For Billi Jo, modern leadership centers on empowerment. She builds high-performing teams by deliberately seeking diverse perspectives and complementary skill sets, then creating high-trust environments where people can thrive. This collaborative approach has proven successful through multiple acquisitions, demonstrating that effective leadership isn't about command-and-control but about enabling others to succeed.Looking toward the future of payments, she's closely watching how artificial intelligence will transform both operational capabilities and fraud vectors. Her balanced perspective embraces innovation while remaining vigilant about emerging risks - exactly the thoughtful approach needed in today's rapidly evolving payment ecosystem.For those building careers in payments, especially women, Billi Jo emphasizes networking, finding mentors who exemplify the leadership style you aspire to, and securing sponsors who will actively advocate for your advancement. Her advice to "get uncomfortable" acknowledges that growth often happens outside our comfort zones. Ready to transform how you think about leadership and risk in payments? Listen now and discover strategies that can elevate your approach to both.

What happens when you build direct connections to over 350 real-time banks and wallets worldwide? You create what Thunes CEO Floris de Kort calls "the smart superhighway to move money around the world."The limitations of traditional cross-border payments are all too familiar for businesses operating globally. SWIFT transfers take days, lack transparency, come with hefty fees, and stop completely on weekends and holidays. Thunes is revolutionizing this outdated model by enabling real-time payments across 130 countries and 80 currencies through direct connections to financial institutions and alternative payment methods.During this revealing conversation, Floris explains how Thunes has built a powerful competitive advantage through direct integrations with payment endpoints like GCash in the Philippines and M-Pesa in Kenya. Unlike competitors who rely on chains of aggregators, these direct connections deliver higher transaction success rates, more cost-efficient processing, and faster issue resolution when problems arise.Perhaps most compelling is how Thunes' services are enabling financial inclusion in emerging markets. By facilitating immediate payments to mobile wallets, they're helping unbanked individuals participate in the global economy - like ride-share drivers in Africa who can now receive instant payment, purchase fuel, and continue earning without traditional banking infrastructure.With licenses now secured in all 50 U.S. states and a new office opening in Atlanta, Thunes is positioned for aggressive growth in American markets, particularly serving U.S. companies with global payment needs.

Step into the world of payment innovation with Pierre Aurel, Chief Product Officer, and Norman Frankel, Chief Growth Officer at Stanchion Payments as they demystify SoftPOS technology - the revolutionary software turning ordinary smartphones into powerful payment terminals.SoftPOS fundamentally transforms how merchants accept payments, enabling any NFC-capable Android or iOS device to process contactless transactions without specialized hardware. This breakthrough eliminates barriers for small businesses, sole proprietors, and mobile vendors who previously couldn't justify the expense of traditional payment terminals. As Norman reveals, one European bank reported that 25% of all their acquired transactions came from SoftPOS applications just one year after launch - a testament to the technology's rapid adoption.Security concerns have been meticulously addressed through rigorous standards including PCI MPOC, creating a protected environment for processing sensitive payment data on everyday devices. While implementation requires significant investment from software providers to meet these standards, the end result delivers enterprise-grade security with consumer-grade simplicity.The technology has found unexpected champions across diverse sectors. Churches embraced it during the pandemic for contactless donations, government mandates in countries like Romania and Greece accelerated adoption for tax compliance, and major retailers including Walmart and Decathlon deploy it for queue-busting and business continuity during outages.Looking ahead, Pierre envisions improvements in NFC antenna technology to enhance the payment experience, deeper integration into everyday applications, and the blurring of lines between e-commerce and in-person payments. For merchants considering the switch, the benefits are compelling - potential savings of $300+ compared to terminal rental costs, enhanced payment flexibility, and no more missed sales due to uncharged or malfunctioning hardware.

What happens when you combine the merchant benefits of pay-by-bank transactions with the consumer rewards typically reserved for credit cards? Matt Brennan, CEO of Spire, reveals how their groundbreaking approach is transforming everyday payments across America.Brennan walks us through Spire's innovative branded payment solution that powers merchant-specific programs like Shell's "S-Pay." By partnering with Discover Network, Spire issues 16-digit PANs linked to consumers' bank accounts - creating a hybrid payment that works on existing terminals while settling via ACH. This elegant solution eliminates the traditional hurdles that have limited pay-by-bank adoption at physical points of sale.The beauty of Spire's approach lies in its true win-win nature: merchants dramatically reduce processing costs while offering substantial rewards (like 15-20¢ off per gallon or 5% store discounts), and consumers enjoy immediate benefits without accumulating credit card debt. This value proposition has fueled remarkable growth, with Spire now accepted at 55,000 locations representing 65% of branded fuel retailers nationwide.With 750,000 bank accounts linked and transaction volumes growing 200% in just seven months, Spire is clearly tapping into unmet consumer needs. Brennan identifies two key adopter groups: tech-savvy younger consumers comfortable with alternative payment methods, and financially-conscious "savvy savers" seeking rewards without additional debt. As consumer debt concerns continue to rise and open banking makes account linking increasingly mainstream, Spire is positioned at the intersection of major financial trends.

Digital commerce security stands at a critical crossroads, with an average of 66 third-party vendors present during the typical e-commerce checkout flow. Each of these represents a potential security vulnerability that could compromise your customers' payment data. Few understand this landscape better than Rui Ribeiro, Co-Founder and CEO of Jscrambler.Ribeiro's journey began in Portugal with a computer science background that led him through the banking industry before identifying a crucial gap in 2014: client-side security. What started as a broad security mission has evolved into specialized protection for payment processes, with Jscrambler now serving major e-commerce platforms across airlines, retail, and hospitality sectors.The timing couldn't be more relevant. With the PCI Council's recent release of PCI DSS v4, client-side security has moved from a best practice to a compliance requirement. Companies must now implement strategies that protect cardholder data by securing JavaScript and payment pages while detecting unauthorized access - exactly what Jscrambler specializes in."Security should never be a barrier for innovation," Ribeiro emphasizes. His company's approach allows businesses to continue adding frictionless checkout features while ensuring third parties can't access sensitive payment information. This balance becomes increasingly challenging as merchants integrate chatbots, payment calculators, installment options, and other tools that improve customer experience but potentially expand the attack surface.

The future of payments is shifting dramatically as consumers demand more options and businesses seek better ways to assess risk. John Gordon, CEO of ValidiFI, takes us deep into how bank account behavior data is becoming the missing puzzle piece in understanding consumer reliability beyond traditional credit scores.Gordon explains how ValidiFI sits at the critical intersection of compliance and fraud prevention, helping businesses meet NACHA's WEB debit rule requirements while gaining valuable insights into consumer payment patterns. By analyzing factors like bank account changes, previous negative balances, and account relationship patterns, ValidiFI provides powerful signals that predict payment outcomes and identify potential fraud before it happens.What truly sets this conversation apart is Gordon's perspective on consumer financial empowerment. He notes how payment preferences are evolving rapidly, with account-to-account transfers growing yearly and programs like Target's RedCard demonstrating the power of bank-account-linked payment methods. The conversation explores how real-time payment networks and non-credentialed bank verification are creating new opportunities for businesses to offer seamless, secure payment experiences that consumers actually want to use. Ready to rethink how you validate customer payment information? Listen now and discover strategies that go beyond basic compliance to deliver real business value while meeting evolving consumer expectations.

Max Galash takes us on a fascinating journey through the rapidly evolving cryptocurrency landscape as CEO of Coinchange, a global crypto brokerage and asset management platform with offices in Warsaw and Toronto.Having pivoted from a direct-to-consumer approach following the collapse of major players like Celsius and BlockFi, CoinChange now focuses exclusively on B2B relationships with crypto operators, exchanges, neobanks, and payment platforms. What sets them apart in this emerging space is their multi-manager investment approach – rather than simply offering tokenized T-bills like many competitors, they employ various managers deploying different trading strategies to create customized, principle-protected structured products.The conversation provides remarkable insight into how stablecoins are revolutionizing global payments, especially in emerging markets where access to USD-denominated products is limited. "Stablecoins are a bridge between banking, trading, exchanges, crypto and remittances," Max explains, highlighting their crucial role in enabling global settlements within seconds. His prediction that blockchain will become the backbone of settlement networks rather than remaining consumer-facing technology aligns with moves by financial giants like BlackRock and JP Morgan, who are already settling billions through private blockchains.Ready to understand how cryptocurrency is reshaping global finance? Listen now to hear Max's complete insights and predictions for this transformative industry.