Jackie Reses on Hiring, Banking Infrastructure and the Future of Fintech

Jackie Reses, chair and CEO of Lead Bank, tells Harry Stebbings that her team built the bank it wanted to use. Her career has included Goldman Sachs, private equity, Yahoo and Square, and she describes a recurring interest in building businesses and products in financial services.

As a child, Reses played at being a bank teller. She grew up in an entrepreneurial family, but says her home life was chaotic and she left home for boarding school at 14. She supported herself through school and college, and connects her drive for independence to that experience.

She defines grit as repeatedly picking oneself up and continuing. Her parents strongly emphasized education and expected her to attend the University of Pennsylvania; she says the school gave her important knowledge and relationships. Meeting her husband’s family also showed her a different model of long-term relationships and integrity.

For Reses, high performance is measured by meaningful outcomes and the judgment behind them, rather than activity alone. She wants to spend time with people who demonstrate instinct and deliver results, regardless of their level in an organization.

In hiring, she looks for innate strengths rather than only prior job titles. A person with strong interpersonal skills might move from sales into recruiting. She points to her own shift from finance and private equity into people leadership: assessing talent and placing people in roles were useful across both fields.

To identify a candidate’s strengths, Reses spends time with them in personal and interview settings and uses practical case studies. She asks about life goals, what they are truly good at and where they struggle, while sharing her own weaknesses to make the discussion more candid.

She says hiring for narrow domain knowledge was a mistake in some early Square banking and lending work, because the team was creating products that had not been built in the same way before. She now prioritizes intelligence, judgment, curiosity, grit and comfort with ambiguity over a prestigious résumé or experience at scale.

Reses argues that people from difficult operating environments may have learned resourcefulness that is less visible on a résumé. She cites former Yahoo colleagues as an example, contrasting their experience with workplaces where success came more easily.

Stebbings criticizes what he sees as reduced appetite for hard work. Reses describes herself as an intense worker who sends messages at all hours, and says leaders should define the culture, goals and expectations early. This is their management perspective, not evidence about an entire generation of workers.

She recalls Square’s pandemic-era Paycheck Protection Program work, when employees volunteered to review loans around the clock. In her account, a clear mission motivated people across the company. She wants teams to be inspired and challenged, with managers honest about goals and performance.

Asked why colleagues follow her, Reses says she takes a long view of their careers, even when helping someone leave for business school, another company or another department makes her immediate job harder. She also emphasizes listening, direct feedback and doing ordinary tasks herself rather than treating them as beneath her.

In negotiations, Reses tries to avoid a zero-sum mindset. Understanding the other party’s real needs—economic outcomes, timing or other priorities—can reveal trade-offs that help both sides. She warns that using every ounce of leverage can damage a relationship needed after the deal closes.

She illustrates this with Lead Bank’s investors. Reses says she could have funded the company herself but wanted investors who would challenge the team. She gave ground on some economic terms while prioritizing speed, an appropriate bank holding-company structure and an arrangement that could obtain Federal Reserve approval and remain workable over time.

Reses calls her work on Yahoo’s Alibaba holdings one of her best economic deals. She estimates the transactions generated about $50 billion of economics for Yahoo shareholders. That is her retrospective estimate in the interview, not an independently calculated realized gain or a claim that she alone created it.

She says an earlier agreement required Yahoo to give up part of its Alibaba economics at the IPO. Despite limited contractual leverage, she sought to recover some equity by rebuilding trust with Alibaba’s board and shareholders. She recalls spending every other week in China for several years and supporting their interests before renegotiating.

Working with Alibaba and Alipay also exposed her to Chinese financial-services innovation. Reses says the speed of invention and use of transaction data later inspired work at Square. She describes this as a firsthand learning experience rather than a simple transplant of a product.

On her worst personal deals, Reses says she made damaging trades amid market changes and may have waited too long to sell. Stebbings argues that deliberately reducing winners can be valuable; both distinguish decisions to enter investments from the separate discipline of managing exits.

Reses praises Philippe and Thomas Laffont at Coatue, an investor in her business, for risk management. In her view, they combine an instinct for market changes with data and are willing to sell without becoming emotionally attached. Her praise concerns people with a commercial relationship to her.

Looking across fintech, Reses says the banking market is old and concentrated, leaving room to invent. She cites roughly $23 trillion of banking assets and 41% held by the five largest banks as figures in the 2023 conversation; these are her contemporary estimates, not current statistics.

She argues that the prior decade of fintech innovation made collecting revenue much easier, citing payment companies including Square and Stripe. In her view, expense management and infrastructure are less fully solved because businesses pay suppliers, employees and other obligations through many different processes and jurisdictions.

Accounting software records part of the picture, she says, but managing a company’s expenses also involves invoices, checks, cards and payments across locations. She expects companies that simplify this fragmented work to find opportunities over the next decade. She mentions Melio and Tipalti as examples she admires.

Why do incumbents not create every new product themselves? Reses suggests established infrastructure and business models make self-disruption difficult. She predicts that older infrastructure providers may lose ground unless they invest in new products, while noting that large financial institutions have recognized the need to innovate.

She regards PayPal, Square, Adyen and Stripe as incumbents at their scale, and credits some with building new products internally. On Goldman Sachs’ consumer efforts, she says it attempted to disrupt itself in a market where it had less expertise and was then restructuring; that is her assessment at the time.

Reses argues that no product is immune to disruption. To sustain invention, she says companies should recognize outstanding individual contributors without forcing them into management, and reward leaders who leave large teams to begin a small new project. Treating headcount as the measure of power can discourage experimentation.

She disagrees with routine micromanagement, except where a specific performance problem requires it. Her preferred approach is to set direction and goals, hire entrepreneurial people and judge outcomes, allowing different working styles while still challenging the team.

On the 2023 crypto downturn, Reses welcomes a return to first principles and scrutiny of which businesses have durable use cases. She says Lead Bank has gained customers as other banks withdrew from crypto-related companies, and believes the underlying technology merits experimentation, although she says she has not yet seen a use case whose longevity she can confidently identify.

Her bank’s work with crypto companies gives her a direct commercial interest in that view. Reses calls for clearer US regulatory rules and describes uncertainty over which agency governs particular products. These comments reflect her 2023 assessment, not a current statement of law.

Drawing on eight years of involvement with the Federal Reserve and a recently ended term chairing a San Francisco economic advisory council, Reses praises regulators’ efforts to learn from industry. She says understanding modern products and their warning signs remains difficult.

At Lead Bank, she says, the team explains crypto-related products and risks openly to supervisors and invites questions about controls. She argues that the industry and regulators need to share knowledge so oversight can improve. This is her account of her bank’s practices, not an independent examination of its compliance.

Reses expects financing pressure to produce fintech sales, closures and other restructuring. Companies that raised more than their present value may seek an acquisition or shutdown when another financing would be difficult. She says Lead Bank itself was looking at acquisition opportunities, so it could benefit from such a market.

She is skeptical of consumer neobanks without a differentiated use case: a debit card and attractive design alone may not justify customer acquisition costs. Some offerings, she argues, are features better integrated into a broader product. This is her competitive assessment, not a determination about any specific company.

Stebbings asks whether specialized services for students, immigrants or other groups will unbundle consumer banking. Reses describes recurring cycles: horizontal products create room for vertical specialists, and specialists may later bundle services to increase customer lifetime value.

Reses doubts that every narrow product can become a financial super app. She points to Cash App and Nubank as examples that have shown demand across multiple uses. She knows Square from her former role and serves on Nubank’s board, making those examples connected to her professional interests.

She credits strong consumer insight and conviction to the founders behind those products. Reses recalls Jack Dorsey and engineers working intensely to add Bitcoin to Cash App, and says product teams should articulate a view of the future, then decide what they must build today if that view proves right.

Financial products can take years to launch because teams must connect infrastructure, meet compliance requirements and test demand. Reses advocates maintaining experiments at different stages and, where warranted, giving a small team four to seven years to develop a promising idea rather than treating every product like a short cycle.

At Square, Reses encountered the difficulty of connecting products to banks and helped build a bank within a technology company. With Lead Bank, she says her team wanted to combine scalable technology, product creativity and strong controls in a bank it would want to use. This is the CEO’s description of her own business.

She distinguishes banking-as-a-service middleware, technology-led bank operators and traditional banks. Middleware can help startups experiment quickly, she says, but a bank ultimately makes decisions underneath it; operating a regulated bank requires more than software. She acknowledges that different providers can fit different customers.

Reses calls banking an ‘anti-network-effects’ business: one customer’s compliance problems can lead regulators to restrict a bank in ways that affect others. She says Lead Bank must balance technology, regulatory compliance and finance, and presents its team’s combined experience as an advantage. These are her risk model and company claims.

Reses wrote Self Made Boss with Lauren Weinberg as a practical guide for small businesses, inspired by the lack of accessible information she saw during the pandemic. She calls it a love letter to small business owners.

Asked about regret, she says she has made poor personal and professional decisions but tries to treat them as lessons and improve. She also expresses curiosity about psychedelics after reading Michael Pollan, including research involving trauma and depression; she describes a personal interest, not a treatment recommendation or proof of efficacy.

On crypto and inequality, Reses says she had not yet seen a use case clearly improve or worsen income inequality, with speculation the most visible use. She believes broader access might reduce the number of underbanked people but says access can also be created without crypto. These are her observations and expectations in 2023.

Reses predicts the economy will be in a better position by the end of 2024, while acknowledging uncertainty about inflation, unemployment and recession in 2023. She says strong employment reduced her immediate concern, though credit balances, savings and auto defaults showed possible weakness. The forecast is time-bound, not a statement of subsequent results.

Her biggest lesson from working with Jack Dorsey is the power of listening and distilling a clear point of view. She also admires how he treats people with whom he disagrees.

Looking toward 2028, Reses hopes Lead Bank can become a major fintech infrastructure provider, expand across countries and offer compliance alongside core banking. Those are the CEO’s ambitions, not outcomes established by the conversation. Stebbings closes by thanking her for the interview.