Payments don’t fail as an abstract metric. They fail for a freelancer waiting to get paid, a small business trying to accept the locally normal method, or a customer who gets told “we don’t support how you pay.” That’s why our conversation with Clarice Lehman, Alternative Payments Operations Lead at DLocal, keeps landing on one theme: the future of payments has to stay human, even as the industry gets more automated, embedded, and AI-driven.

We start with Clarice’s journey from Uruguay to fintech, including a pivotal dinner-party moment that redirected her MBA path to MIT, followed by consulting at BCG, and a return to DLocal to lead strategy and operations across alternative payment methods. We unpack what “APMs” really include (instant payments, wallets, cash-based options, BNPL operations, card-present initiatives, and crypto operations) and why delivering a consistent cross-border payments experience is hard when every market’s infrastructure looks different underneath.

Then we get practical about leadership and trust: why smarter systems can’t mean more exclusion, what transparency should look like when AI makes decisions, and why reliability and accountability are non-negotiable when downtime or a wrong decline hits. Clarice also shares the trend she’s most excited about: AI-driven credit and underwriting using alternative data, and how that can expand access to capital for consumers and SMBs that traditional credit bureaus overlook.

If you care about emerging markets, payments strategy, fintech leadership, and building products that actually include people, this one is for you.

Payments are getting smarter and more automated, but the real question is simpler: are we making life easier for the humans behind every transaction? For Women Leaders in Payments Month, we’re joined by Kimling Lam, Chief Marketing Officer at Fortis, to talk about what “the future is human” actually looks like inside fintech, embedded payments, and modern go-to-market teams. Special thanks to Payroc for sponsoring this year’s series and supporting the advancement of women across the payments industry.

Kimling shares her career journey from Wellesley and broadcast journalism to TV news reporting, software sales, and leadership roles across major payments brands before stepping into her current CMO role. Along the way, we dig into how strong storytelling becomes a growth advantage in fintech marketing, why CEO sponsorship and networks can change a career trajectory, and what it really takes to turn ambiguity into strategy that drives pipeline and revenue.

We also explore the practical impact of generative AI and large language models on marketing workflows. Kimling explains why marketers are shifting from writing everything manually to orchestrating faster, more scalable work streams while protecting brand voice and applying human judgment. From there, we zoom out to B2B payments and accounts receivable, including the pain of “swivel chair accounting,” the importance of human-centered design, and why trust in payments feels invisible until something breaks.

If you care about customer experience, embedded finance, women in fintech leadership, and where AI helps or hurts, you’ll get a lot from this conversation.

Payments are getting faster and more automated, but the hardest part still isn’t the tech. It’s trust. We talk with Rachel Costello, VP of Platform Growth at Maverick, about why the future of payments is human and how leaders can keep empathy, judgment, and real partnership at the center while AI and automation reshape everything around us.

Rachel shares her career path into fintech, from early work in ad tech and e-commerce to revenue operations and growth roles, and why payments became the perfect place to combine strategy, go-to-market, and customer impact. We also dig into what she’s building today: strategic partnerships, embedded payment strategy, and the infrastructure that helps software platforms deliver seamless commerce experiences.

A big theme is embedded payments and embedded finance, and what it actually means when a software platform becomes a commerce platform. We break down the customer journey, preferred payment methods, and the practical outcomes businesses want: less friction, faster scaling, and simpler ways to get paid. Along the way, Rachel makes the case for fundamentals, customers don’t buy buzzwords like AI or APIs, they buy the results those tools deliver.

We wrap with leadership lessons, mentorship, and advice for the next generation of women in payments: raise your hand before you feel ready, get comfortable being uncomfortable, and choose a culture that fits how you work and grow.

A failed payment is never just a technical error. It’s a customer stuck at checkout, a merchant losing revenue, and a moment where trust is either reinforced or broken. We sit down with Alexandra Dolia, co-founder and COO of Akurateco, to talk about what payments leadership looks like when you refuse to treat the industry like a black box and you build teams that can explain what’s happening end to end.

Alexandra shares her path from Ukraine to a formative year in the United States as a teenage exchange student, then into fintech almost by accident through a contact center role. That early frontline experience shaped how she thinks about customer support, payment failures, and operational details that quietly define the client experience. We also unpack the leadership philosophy that came from working in a culture where knowledge is shared, not guarded, and how she’s applied it by developing people through structured internal education.

From there, we get practical about the future of payments: embedded checkout, automation, and why “the future is human” isn’t anti-technology. It’s a reminder that technology should sharpen judgment, not replace it. Alexandra breaks down how companies earn trust through transparency, honesty when things go wrong, and consistency over time, then points to a major shift reshaping global commerce: the fast-growing mix of alternative payment methods, from wallets to account-to-account and local rails, and the rising need for payment orchestration.

Payments look instant and invisible until something goes wrong. That’s when you find out whether you’re working with a faceless system or a team you can actually trust. We sit down with Alex McCandless, EVP of Marketing and Training at Payroc, to get specific about what “people powered” really means in fintech and why transparency and access to real decision makers still matter in a world of automated transactions.

Alex shares her career journey from the agency world into payment processing, plus what she learned scaling from a scrappy startup environment into a platform shaped by 27 acquisitions. We talk about the challenge of bringing many brands under one Payroc umbrella without forcing a one-size-fits-all playbook, and how culture integration requires real discovery, humility, and a willingness to borrow the best tools and processes from every team.

We also dig into the future of payments and the role of AI in fintech. Alex makes the case for AI-assisted operations, not AI-powered relationships, and connects that to embedded finance, SaaS, and the push toward more holistic experiences across card-present and card-not-present payments. On trust and security, she explains why “secure” should be baseline, why trust is earned one transaction at a time, and how the 1% edge cases can define your reputation. We close with what she’s watching next, including agentic commerce, machine-to-machine payments, and how marketing teams are adapting for LLM search and more qualified inbound leads.

Payments are getting smarter, faster, and more automated, but the stakes are still deeply human. I sit down with Gunita Bindra, CRO of Paymode New Business Development at Bottomline, to talk about what it takes to lead in fintech when AI is reshaping how decisions get made and how money moves.

Along the way, Ganita shares her path from computer science in India to roles in software engineering, solution consulting, product management, and now leading sales and partnerships in the B2B payments world.

We explore what “the future is human” means when technology can feel like it’s in the driver’s seat. Gunita lays out why leaders in payments need to embrace change while building for enduring excellence, not just short-term success. We also get practical about the customer experience behind every transaction: how product-minded empathy shows up in sales conversations, why understanding small business payment pain matters, and how transparency turns into trust when your platform can clearly explain where a payment is, why it’s there, and what happens next.

Then we look forward at agentic commerce and the idea of payments that can route themselves with humans still in the loop. Gunita offers a grounded take on job evolution, the skills that stay valuable, and the mindset shift leaders need right now. We close with direct advice for women entering payments and fintech: network early, ask for what you want, build a business case, and learn negotiation without apology.

In this milestone 500th episode of the Leaders in Payments Podcast, I bring together seven respected leaders from across the payments ecosystem for a special look at the state of the industry.

Rather than a traditional one-on-one interview, this episode features perspectives from Jim Oberman, CEO of Payroc; Kathleen Pierce-Gilmore, President of SoFi Tech Solutions at SoFi; Greg Cohen, CEO of Fortis; Alex Shtilman, CEO and Co-Founder of Rapyd; Steve Pinado, CEO of NMI; Jess Houlgrave, CEO of WalletConnect; and Derek Dean, CEO of Flute.

Each guest shares their view on three important questions: what shift they are seeing in payments right now, what is still harder than it should be, and what the industry should be preparing for over the next three to five years.

The conversation covers the continued rise of embedded payments, the role of software in reshaping distribution, the growing importance of stablecoins and real-time money movement, the impact of AI and agentic commerce, and the ongoing need to simplify the merchant experience. Guests also discuss the friction that still exists behind the scenes, from onboarding and reconciliation to fraud, false declines, global commerce, regulation, and legacy infrastructure.

Episode 500 is both a celebration of the first 500 conversations on the podcast and a forward-looking discussion about where payments is headed. It reflects how much the industry has changed, how much complexity still needs to be solved, and how much opportunity remains ahead for payments leaders, fintech innovators, software platforms, banks, and the broader commerce ecosystem.

A special "thank you" to all who have listened, watched and participated over the last 5+ years. And now on to the next 500!

Checks still power a shocking amount of insurance money movement, and that single fact creates slow claims, higher operating costs, and an open door for fraud. Greg Myers sits down with Ian Drysdale, CEO of One Inc, to talk about what it really takes to drag property and casualty insurance payments into a modern digital payments era without breaking the workflows carriers rely on.

We unpack how One Inc handles both sides of the insurance payments stack: premium payments (inbound merchant acquiring) and claims payouts (outbound disbursements). Ian shares what “scale” looks like in this vertical, from a huge vendor network that already includes the auto body shops, doctors, and lawyers insurers pay every day, to the complex edge cases that traditional payment processors rarely touch. Think mortgage endorsements after major home damage, lienholder payoffs on total-loss auto claims, and the growing need for insurer-to-insurer settlement use cases like subrogation.

Fraud is a different beast in insurance, too. The risks aren’t about someone buying a TV with a stolen card; they’re about claims fraud, identity fraud, account takeovers, and payments getting intercepted or redirected. Ian explains how data, controls, and hands-on investigation work together to make sure claims payouts land with the right person or business, especially when payouts can run through PayPal, Venmo, push to debit, Visa Direct, and Mastercard Send.

We also zoom in on the premium payment experience gap. Policyholders, especially younger ones, expect Apple Pay, Google Pay, flexible billing dates, and a frictionless mobile flow, and network tokens help reduce failed payments by keeping card credentials current behind the scenes. You’ll leave with one blunt question Ian wants the industry to face: when will insurers write their last check?