Jacqueline 'Jackie' Reses / Lead Bank
Fintech Executive - Investor - Author
Chair & CEO, Lead Bank | CEO, Post House Capital
The woman who convinced the U.S. Treasury to let fintechs run PPP loans, built Square's lending arm into a multi-billion dollar business, and now runs the bank behind fintech's plumbing.
She grew up running carnival games on a Jersey Shore boardwalk with her brother, daughter of the pharmacist who owned Reses Pharmacy in Margate, New Jersey. Jacqueline "Jackie" Reses calls it "a pretty gritty childhood." It turns out that growing up hustling games of chance in Atlantic City was better preparation for Wall Street - and Silicon Valley - than most MBA programs.
Reses graduated early from the Peddie School, briefly enrolled at George Washington University, then transferred to Wharton where she earned a B.S. in Economics with honors. In 1992, Goldman Sachs got her first. She spent seven years there in mergers and acquisitions and principal investment, which meant she knew how capital moved before most of her peers had finished paying off their student loans.
What followed is a career that defies a single headline: CEO of an early real estate software startup (sold to Realeum in 2001). A decade running the U.S. media group at Apax Partners in London. Then Yahoo, where as Chief Development Officer she executed 41 transactions in three years - including a board seat at Alibaba that positioned her to help lead one of the largest IPOs in history.
"That opportunity was truly a life-altering experience."
- Jacqueline Reses, on her Alibaba board tenureThe Alibaba IPO in September 2014 raised $25 billion. Reses was on the board, co-chairing the audit committee. She also helped navigate Alibaba's relationship with ANT Financial and its international payments operations - which is to say she had a front-row seat to the biggest digital money story of the 2010s. She was still officially on Yahoo's payroll.
In 2015, Jack Dorsey called. Square was building Square Capital, a small-business lending program, and wanted someone who understood both Wall Street credit and Silicon Valley product development. Reses joined. "I went from being a corporate executive with 10,000 employees working for me to having none," she said later, "which I loved because I liked going back to my entrepreneurial roots."
She built Square Capital into a multi-billion dollar lending business. Then COVID-19 hit. In March 2020, while the country was shutting down, Reses picked up the phone and called Treasury Secretary Steve Mnuchin. Her pitch: let fintechs into the Paycheck Protection Program. He agreed. What came next was arguably the most compressed product launch in financial history - a lending platform for Main Street America built in two weeks. "It was probably one of the most intense life experiences I've ever had," she said. "We had to build a product in two weeks that was one of the biggest lending programs ever created to serve Main Street America."
Also in 2020, Square received the first FDIC Industrial Loan Company charter granted in over a decade - a regulatory milestone that Reses had been working toward. It signaled something important: the lines between fintech and banking were about to blur in ways that would create enormous opportunity. Reses had already started thinking about what came next.
In July 2022, Reses and a group of fintech investors paid $56 million for a community bank headquartered in Kansas City, Missouri. Lead Bank had roughly $778.9 million in assets and a state charter. What it did not have was a strategy for the next decade of financial infrastructure.
Reses had a thesis: every fintech company needs a bank behind it, and that bank is almost always a pain point. Integrating with legacy financial rails was the tax every startup paid just to exist. She had felt it firsthand at Square. The solution was to build a chartered bank that operated with the agility of a software company - an API-first platform offering FDIC-insured accounts, lending, card issuing, ACH payments, wire transfers, and compliance infrastructure as a service.
The market responded immediately. "Even before we owned Lead, we had instant product market fit," Reses said. "Once people knew what we were doing, we were overwhelmed with inbounds." By Q3 2023, Lead Bank was serving over one million customers, with revenue growing 9% quarter-over-quarter and net profit up 50%.
Lead Bank joined forces with Stripe and Visa to power their stablecoin-linked payment card platform - and began settling transactions with Visa in USDC over the Solana blockchain. A chartered community bank, settling with Visa in crypto. That is what first-principles thinking looks like in practice.
"Even before we owned Lead, we had instant product market fit. Once people knew what we were doing, we were overwhelmed with inbounds."
- Jackie Reses, Fintech Leaders InterviewSeries B Investors (Sept 2025)
Lead Bank Services
1992-1999
Goldman Sachs - Mergers & Acquisitions and Principal Investment Areas. Seven years learning how capital moves.
1999-2001
iBuilding, Inc. - CEO of real estate software startup. First taste of building from zero. Sold to Realeum Software.
2001-2012
Apax Partners - Partner, ran U.S. media group for one of the world's largest private equity firms, based in London.
2012-2015
Yahoo! - EVP of People & Development, then Chief Development Officer. Led 41 transactions. Authored the 2013 remote work policy that became a national conversation.
2012-2014
Alibaba Group - Board member, co-chaired audit committee. Helped lead the September 2014 IPO - at the time, the largest in history at $25 billion raised.
2015-2022
Square / Block - Built Square Capital from launch into a multi-billion dollar small-business lending program. Also served as Chief Human Resources Officer and Executive Chairman of Square Financial Services.
March 2020
COVID-19 PPP - Lobbied Treasury Secretary Mnuchin to include fintechs in PPP loan distribution. Built the product in two weeks. Secured Square's first-in-a-decade FDIC Industrial Loan Company charter.
2022
Lead Bank acquisition - Led investor group in $56M purchase of Kansas City community bank. Became Chair and CEO. Co-authored Self-Made Boss.
2025
Lead Bank Series B - $70M raised at $1.47B valuation. Stablecoin partnership with Stripe and Visa. USDC settlement on Solana. Forbes Fintech 50.
Over her career, Reses worked directly alongside three of the most distinctive operators in the global tech economy. She has spoken openly about synthesizing their styles into her own.
Jack Dorsey
Product rigor. Building things that work for millions of small businesses. The discipline of simplicity at scale.
Jack Ma
Global scaling. The Alibaba IPO as proof that non-Western financial markets could define global commerce. The art of operating inside regulatory constraints.
Masayoshi Son
"Masa would say, 'I want to know what the key principles are of this deal. That is fine. I trust that we will make this transaction happen.'" Trust-based delegation at planetary scale.
"It was probably one of the most intense life experiences I've ever had. We had to build a product in two weeks that was one of the biggest lending programs ever created to serve Main Street America."
On COVID-19 PPP loan distribution via fintechs"I went from being a corporate executive with 10,000 employees working for me to having none, which I loved because I liked going back to my entrepreneurial roots."
On joining Square from Yahoo"Even before we owned Lead, we had instant product market fit. Once people knew what we were doing, we were overwhelmed with inbounds."
On Lead Bank's early traction"I'd like to see everything boiled back to first principles and thought through in a digital-first way, so that I know what product I'm taking out."
On financial regulation"Debanking is a fiction, to some degree."
At a fintech summit, 2025, on the debanking debate"I really enjoy Kansas City and think it's a hidden treasure."
On Lead Bank's Midwestern home2024
Named to inaugural CNBC Changemakers: Women Transforming Business list
2025
Forbes Fintech 50 - Lead Bank named to annual list
2024
CNBC Disruptor 50 - Lead Bank named to annual list
2020
American Banker - Most Powerful Woman in Finance
Ongoing
Forbes Self-Made Women list
Ongoing
Fast Company - Most Creative People in Business
2020
Square received first FDIC ILC charter in over a decade under her leadership
2022
Co-authored "Self-Made Boss" with Lauren Weinberg (McGraw-Hill)
2025
Joined CNBC Changemakers Advisory Board
Reses has become one of the most vocal advocates for first-principles thinking in financial regulation. Her argument is simple: the current regulatory framework was built for a paper-based, branch-centric financial world. Layering digital products onto rules designed for a different era creates unnecessary friction - and in some cases, unintended harm.
Her example: a 400-page mortgage disclosure document. The intent is consumer protection. The effect is that consumers stop reading. The result is the opposite of the intent. Regulatory complexity, she argues, is not the same as regulatory rigor.
On stablecoins, she has been similarly clear: she wants "legislative definitions around market structure for stablecoins and cryptocurrencies" so that builders know what they're building toward. Lead Bank doesn't wait for that clarity - it builds it into the product architecture ahead of the regulation arriving.
"I'd like to see everything boiled back to first principles and thought through in a digital-first way."
- Jackie ResesSelf-Made Boss
Advice, Hacks, and Lessons from Small Business Owners
Co-authored with Lauren Weinberg (McGraw-Hill, 2022). A practical guide to building a small business from scratch - from securing startup capital to hiring, growth planning, and managing the daily weight of being your own boss.
The book grew directly out of her work at Square Capital, where she spent years talking to the small business owners who were Square's core customers.
Also noteworthy
Reses holds multiple patents in payments, credit, and cryptocurrency - not common for a bank CEO. She is both the regulator and the inventor, a combination that gives Lead Bank an unusual advantage in product development.
Lead Bank is headquartered in Kansas City, Missouri, with corporate operations in Sunnyvale, California. It holds a state charter, FDIC insurance, and the technical architecture to serve as the banking partner for fintech companies, direct-to-consumer products, and enterprise clients needing embedded financial services. In April 2025, Lead Bank joined Stripe and Visa to power stablecoin-linked payment cards - and became one of the first chartered banks in the U.S. to settle with Visa in USDC over Solana.
She ran carnival games on the Jersey Shore boardwalk as a kid. Her father owned a pharmacy. Small business was the family default - long before Square Capital.
Her brother Jacob Reses is Chief of Staff to U.S. Vice President JD Vance. Different worlds, same family.
She paid $56 million for a community bank in Kansas City in 2022. Three years later, that bank is valued at $1.47 billion. That's a 26x return on a banking acquisition - not common.
She holds patents in payments, credit, and cryptocurrency - an unusual combination for the CEO of a regulated chartered bank.
The 2013 Yahoo remote work policy that banned working from home and became a national debate? She wrote it. The rationale: Yahoo needed its employees in the same building to rebuild company culture.
Lead Bank now settles transactions with Visa in USDC over the Solana blockchain. A Midwestern community bank founded in 1919, settling with Visa in crypto. That is not a sentence anyone predicted.
Reses graduated early from the Peddie School in Highstown, New Jersey in 1988, then briefly enrolled at George Washington University before transferring to Wharton - the University of Pennsylvania's business school - where she graduated with a B.S. in Economics with honors in 1992.
Since 2015, she has served on the Wharton Board of Advisors - returning to the institution that shaped her analytical toolkit, now helping shape how the next generation of business leaders learns to think about markets.
Education Timeline
1988
Peddie School - Graduated early
1988
George Washington University - Senior year coursework
1988-1992
Wharton, University of Pennsylvania - B.S. Economics, with honors
2015-present
Wharton Board of Advisors - Elected member
SEPT 2025
$70M Series B
Lead Bank closes $70M Series B at $1.47B valuation. New investors ICONIQ and Greycroft join existing backers a16z, Ribbit, Coatue, Khosla, and Zeev Ventures.
APR 2025
Stablecoin Partnership
Lead Bank partners with Stripe and Visa for stablecoin-linked payment card platform. Begins settling Visa transactions in USDC on Solana.
NOV 2025
CNBC Advisory Board
Reses joins the CNBC Changemakers Advisory Board, adding strategic counsel to the media organization's flagship women-in-business initiative.