Jackie Reses — Leadership Lessons, Fintech Innovation, & Helping Small Businesses
Miguel Armaza sits down with Jackie Reses, former Head of Square Capital, current Chairman of the Economic Development Council of the Federal Reserve of San Francisco, board member of Affirm and Wish (Context Logic), and all-around business and fintech leader. Some of her past roles also include Chief Development Officer at Yahoo and Board member of Alibaba.
She’s also a proud alum of our very own Wharton School.
We talked about
- Jackie’s upbringing and professional background
- Why she describes Wharton and the University of Pennsylvania as a place that saved her life
- The meaningful lessons she learned while working at Goldman Sachs, Apax Partners, and Yahoo
- Key reflections from her experience as an Alibaba board-member and what we can all learn from Chinese entrepreneurs
- What drove her decision to join Square and why she fell in love with its culture
- The incredibly impactful experience of the Square Capital team navigating COVID and the complex dynamics of launching a PPP product in record-time
- Her outlook of the road ahead and what’s next for Jackie
- And a whole lot more!
Full interview → Spotify | Soundcloud | Apple
Growing up on the Jersey Shore, Jackie always aspired to run her own business and become an entrepreneur. But once she went off to Wharton for college, she realized she did not know much about running a company and didn’t think she had the tools to make good business decisions. So she decided to pause her entrepreneurial journey and instead go work at Goldman Sachs in the early 90s. She describes the University of Pennsylvania as a place that “saved her life” and allowed her to build lifelong and impactful relationships, setting her off on a path of “lifelong global exploration”.
US Finance and Chinese Entrepreneurship
Jackie joined Goldman upon graduation and credits the firm for teaching her skills around professionalism, excellence, and teamwork. She then went to on join Apax Partners, one of the largest private equity shops in the world, where she worked for a decade. But after spending two decades in the finance world, she was recruited by Marissa Meyer to Yahoo where Jackie held a number of leadership roles, including a seat on the board of their Asian assets and Alibaba from 2012–2014.
Working with Alibaba and navigating the impressive Chinese tech ecosystem taught her valuable lessons about business in China. She recalls the biggest observation from this experience was realizing that commerce just works differently in a country like China. For Americans or foreigners to succeed in this environment, they need to stop imposing their own view of how society works and recognize the Chinese system is just very different. In her own words, “It’s not better, it’s not worse, it’s just different. So when you go there, as an entrepreneur, as an executive, you have to start from a grounding that you appreciate and understand how they do business, and then build from there.”
Joining Square
When Jackie joined Square in 2015, the company had a thousand employees but was nowhere near what it is today. She jumped at the opportunity to lead Square Capital because she valued the opportunity to learn from Jack Dorsey, appreciated the culture of experimentation and learning from mistakes, and felt she was well-positioned to scale the business to new heights.
“At the time there was no market for sub-prime, small-dollar, whole loans to be marketed institutionally to a broad base, such that we thought we could sell it to anyone other than a small group of hedge funds. And so we created a lot of interesting ways of going about it (…) And so we had an unusually challenging dual path of building out both sides of the market for a lending product, and then a banking set of products for small businesses.”
COVID and the Paycheck Protection Program (PPP)
Without a doubt, the most interesting and inspiring segment of this interview was hearing Jackie describe her experience navigating COVID and the Paycheck Protection Program (PPP) created by the US government to save the economy. I encourage you to listen minute 23:03 of the episode.
“The PPP dynamics were some of the most extraordinary experiences I’ve had in my professional life. As we started to see the crisis unfold with shelter in place orders and government restrictions, our team at Square Capital tried to pivot to manage these extraordinary circumstances for the benefit of small businesses. We did not care one iota about how it was going to impact Square. First and foremost, in almost every conversation, we thought about how we were going to help save the small businesses.”
Throughout this experience, the Square team made it their mission to advocate and fight for small businesses with the most senior levels of the US Federal Government, including the Department of Treasury, members of Congress, and the Small Business Administration. Once they made the decision to build a PPP product, Jackie rallied team members from all over Square and asked for volunteers to join the PPP team for what would be long 18-hour shifts, every day of the week. The response was overwhelming and they had hundreds of people from around the company volunteering to process loans and take small businesses through the operational process to get their loans approved.
“Every day I felt I was kicked in the face”
At one point it became clear to Jackie that many small businesses really didn’t know that they had access to these funds. So she went on a very public Twitter campaign in order to help the smallest businesses gain access to insight and help. Although she is happy and proud of the work they achieved, Jackie also recognizes the product was not perfect and that they disappointed some people in the process.
“We were, 1/10th engineers, 1/10th psychiatrists, 1/10th business advisors, 1/10th tax advisors, 1/10th friends, and unfortunately, 1/10th disappointment, in some cases (…) But if you ask anyone from the Square Capital team, they will tell you it was one of the most extraordinary products that we have ever built and an extraordinary experience.”
Jackie Reses
Ms. Reses is the CEO of Post House Capital and Chairman of the Economic Advisory Council of the Federal Reserve Bank of San Francisco. She previously led Square Capital, part of Square Inc., where she built the business and transformed the ability of small businesses in the US to access credit. She was also the Executive Chairman of Square Financial Services, an FDIC-insured bank owned by Square Inc. and the first industrial bank in the US started by a technology company.
Prior to Square, Jackie was the Chief Development Officer for Yahoo and the head of the US media group at Apax Partners, one of the largest global private equity firms. Jackie also spent seven years at Goldman Sachs in mergers and acquisitions and the principal investment area.
Jackie is a member of the Board of Advisors of the Wharton School of the University of Pennsylvania and serves on the Advisory Board of Wharton’s Stevens Center for Innovation in Finance, its fintech center, which is chaired by Mr. Stevens. Jackie also serves on the boards of Affirm and Wish (Context Logic). Jackie received a bachelor’s degree in economics with honors from the Wharton School of the University of Pennsylvania.
Previous Episodes You May Enjoy:
Eyal Shinar, Co-Founder of Fundbox — Disrupting B2B Financing
Creating Pathways to Better Financial Health — Anu Shultes, CEO of LendUp
Building Unicorns and Redefining Online Banking — Renaud Laplanche, Upgrade CEO/Co-Founder
Unlocking Entrepreneurial Progress with Vanessa Colella, Head of Citi Ventures
Revolutionizing Working Capital Financing — Sandy Kemper, Founder & CEO of C2FO
Building a Global Payments Powerhouse — Kamran Zaki, COO of Adyen
Anish Acharya, General Partner at Andreessen Horowitz — Doubling Down on Fintech
Miguel Armaza is Co-Host of the Wharton Fintech Podcast and Co-Founder of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas.
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